- Anticancer activity of some newly synthesized pyrano[2,3-d][1,2,3]triazine derivatives using 1-(7-hydroxy-2,2-dimethylchroman-6-yl)ethanone as synthon
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A series of the newly substituted pyrano[1,2,3]triazine derivatives 3-14 were synthesized using compounds 1 and 2 as starting materials. Compound 2 was methylated using methyl iodide to compound 3, which was treated with aromatic aldehydes to give acryloyl derivatives 4a-c. Compounds 4a,b were reacted with ethyl cyano-acetate to give pyran-3-carboxylates 5a,b which were reacted with ethyl glycinate hydrochloride to give 6a,b. Treatment of 6a,b with hydrazine hydrate gives acid hydrazides 7a,b, which were reacted with 5,5-dimethyl-1,3-cyclohexanedione to give acetohydrazides 8a,b. Cyclization of 8b with 2-(4-nitrobenzylidene)malononitrile afforded hexahydroquinoline 9. However, the acridindione 10 was synthesized by heating of 8b with 2-(4-nitrobenzylidene)malononitrile in acetic acid containing few drops of triethylamine. Treatment of 7a,b with phenyl isothiocyanate or 2,5-hexanedione or phthalic anhydride gave compounds 11a,b, 13a,b and 14a,b, respectively. In the present work, all the selected pyrano[1,2,3]trizine derivatives were soluble in DMSO at concentrations high enough to allow cell experiments, and the in vitro biological activity of these compounds was evaluated by their growth inhibitory potency in liver HEPG2 cancer cell lines. The cytotoxic potency of compounds 3-14 was studied in comparison to the known anticancer drugs 5-fluorouracil and doxorubicin.
- Ouf, Nabil H.,Amr, Abd El-Galil E.,Sakran, Mohamed I.
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Read Online
- Design, synthesis, and physicochemical characterization of new aminothiohydantoin Schiff base complexes for cancer chemotherapy
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A novel aminothiohydantoin Schiff base (ATHSB) ligand and its complexes {M(II)ATHSB; M = Mn(II), Cu(II), Zn(II)} have been successfully synthesized. The coordination modes, stoichiometry, geometry, thermal stability, and morphology of M(II)ATHSB were deduced based upon the outputs of different physicochemical, spectroscopic, and microscopic techniques. The comparative in-vitro anticancer studies revealed that all complexes are more cytotoxic than the parent ligands against human cancer cell lines (liver carcinoma (HepG2), colon carcinoma (HCT116)), whereas, they exhibited lower toxicity as compared to the free ligand against normal liver cells (HL7702). Complex Zn(II)ATHSB seems to be a superlative candidate; as it is the most cytotoxic one against HepG2 concomitantly with lowest toxicity toward the normal human liver cells (HL7702), thus may offering a potential alternative for conventional cancer chemotherapeutic agents.
- Alfaifi, Mohammad Y.,El-Gareb, Mohamed S.,Elshaarawy, Reda F. M.,Farouk, Nessma,Mahdy, Ahmed R. E.
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- Photoluminescence performance of green light emitting terbium (III) complexes with β-hydroxy ketone and nitrogen donor ancillary ligands
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An efficient and cost-effective technique, solution precipitation approach is adopted to synthesize five bright green luminescent terbium (III) complexes by employing the main β-hydroxy ketone ligand, 2-hydroxy-4-ethoxyacetophenone, and ancillary ligands like bathophenanthroline, 5,6-dimethyl-1,10-phenanthroline, 1,10-phenanthroline, and 2,2-bipyridyl. The elemental compositions and binding mode of ligand to terbium (III) ion can be validated by using energy dispersive X-ray analysis, elemental analysis, Fourier transform infrared, and proton nuclear magnetic resonance spectroscopy. The complexes are thermally stable up to 158°C and possess the cubic shaped particles as confirmed by thermogravimetric analysis and scanning electron microscopic study, respectively. The band-gap energy (3.02–2.92 eV) of complexes is reckoned through diffuse reflectance spectra, which tailors them as potential candidates in the field of military radars. The photoluminescence studies unveil that the complexes exhibit the bright green luminescence corresponding to 5D4 → 7F5 transition of Tb3+ ion (548 nm) under the excitation wavelength of 395 or 397 nm. The Commission International de I’Eclairage chromaticity coordinates (x, y) and color purity substantiates the green emission of complexes. The energy transfer mechanism elucidates that the main ligand and ancillary ligands sensitize Tb3+ ion, which in turn enhances the luminescence efficiency of the emissive layer of white organic light emitting diodes. The results reveal that the complexes are considered as good contenders in the field of display devices and laser technology. Lastly, in vitro antimicrobial and antioxidant activity proclaim the potent antimicrobial and antioxidant actions of complexes via tube dilution and 2, 2-diphenyl-1-picrylhydrazyl assays, respectively.
- Khanagwal, Jyoti,Kumar, Rajesh,Devi, Rekha,Bala, Manju,Sehrawat, Priyanka,Khatkar,Taxak
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p. 742 - 754
(2021/01/18)
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- Designing of luminescent complexes of europium(III) ion with hydroxyl ketone and nitrogen donor secondary ligands for improving the luminescence performance and biological actions
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Europium based five luminescent europium(III) complexes with 2-hydroxy-4-ethoxyacetophenone (main ligand) and second chromophores, bathophenanthroline, 5,6-dimethyl-1,10-phenanthroline, 1,10-phenanthroline and 2,2-bipyridyl have been prepared by employing cost-effective solution precipitation method. The various advanced techniques are employed to investigate the structural information. Thermal study proclaims the thermal stability of complexes up to 155 °C. The analyzed band-gap for complexes opens the application of these complexes in laser system. The photoluminescent properties of complexes under ultraviolet light clearly reveal the presence of prominent emission peak (5D0→7F2 transition) centered at 611 nm responsible for intense red emission of complexes, which highlights the applicability of these complexes in advanced optoelectronic devices. Judd-Ofelt intensity parameters, internal quantum efficiency and sensitization mechanism confirm the luminescence efficiency of complexes. The complexes display the excellent antimicrobial and antioxidant features.
- Hooda, Pooja,Khanagwal, Jyoti,Khatkar, S. P.,Kumar, Rajesh,Poonam,Taxak, V. B.
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- EGFR/VEGFR-2 dual inhibitor and apoptotic inducer: Design, synthesis, anticancer activity and docking study of new 2-thioxoimidazolidin-4one derivatives
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Aims: EGFR and VEGFR-2 have emerged as promising targets for cancer management as they play a crucial role in tumor growth, angiogenesis and metastasis. A novel series of 2-thioxoimidazolidin-4-one derivatives were synthesized and evaluated as apoptotic inducers and EGFR/VEGFR-2 dual inhibitors. Main methods: The cytotoxic activities of all synthesized compounds were tested against MCF-7, HepG2 and A549 cell lines. The molecular mechanism of the most promising cytotoxic compounds was investigated via a series of assays including in vitro EGFR and VEGFR-2 inhibitory activity in MCF-7 cell line. Additionally, levels of p53, Bax, Bcl-2, caspase 7, 9 as well as cell cycle analysis were assessed in MCF-7 cell line to gain better understanding of their apoptotic activity. Molecular docking study was carried out to predict binding pattern of these compounds with EGFR and VEGFR-2 active sites. Finally, in silico ADME and drug-likeness profiling were calculated. Key findings: Compounds 6 and 8a exhibited superior cytotoxic activity compared to sorafenib and erlotinib, against the three tested cell lines. In the same context, 6 and 8a showed better EGFR and VEGFR-2 inhibitory activity compared to the reference compounds. The later effect was further supported by the docking study. Furthermore, these compounds displayed potent apoptotic activity as evident by cell accumulation at pre-G1 phase and cell cycle arrest at G2/M phase together with increased p53, caspae-7 and caspase-9 levels and Bax/Bcl-2 ratio. Finally, synthesized compounds have acceptable drug likeness. Significance: Compounds 6 and 8a act as potent dual EGFR/VEGFR-2 inhibitors with evident apoptotic activity.
- Mourad, Ahmed A.E.,Farouk,El-Sayed, El-Sherbiny H.,Mahdy, Ahmed R.E.
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- Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones
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American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.
- Escobar, Gustavo,González, Luis A.,Qui?ones, Wiston,Robledo, Sara,Upegui, Yulieth
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- Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide
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Chlorine is the 20th most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst, selective oxidation over chlorination of primary and secondary alcohols and their ethers with electron-donating substituents was achieved. The reagent precursor of NCBSI was recovered quantitatively and can be reused for synthesizing NCBSI.
- Badani, Purav,Chaturbhuj, Ganesh,Ganwir, Prerna,Misal, Balu,Palav, Amey
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supporting information
(2021/06/03)
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- New Seco-DSP derivatives as potent chemosensitizers
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Thirty-four seco-3′R,4′R-disubstituted-2′,2′-dimethyldihydropyrano[2,3-f]chromone (seco-DSP) derivatives were designed, synthesized and evaluated for chemo-reversal activity when combined with paclitaxel or vincristine in P-gp overexpressing A2780/T and KB-VIN drug-resistant cancer cell lines. Most of the compounds displayed moderate to significant MDR reversal activities. Compound 7e showed the most potent chemo-sensitization activity with more than 1471 reversal ratio at a concentration of 10 μM, which was higher than verapamil (VRP) (212-fold). Unexpectedly the newly synthesized compounds did not show chemosensitization activities in a non-P-gp overexpressing cisplatin resistant human ovarian cancer cell line (A2780/CDDP), implying that the MDR reversal effects might be associated with P-gp overexpression. Moreover, the compounds did not exhibit significant anti-proliferative activities against non-tumorigenic cell lines (HUVEC, HOSEC and T29) compared to VRP at the tested concentration and might be safer than VRP. In preliminary pharmacological mechanism studies, the compounds increased accumulation of DOX and promoted P-gp ATPase activity in A2780/T cell lines. Western blot analysis indicated they did not affect the expression level of P-gp in the tested MDR cell lines. Thus, further studies on these seco-DSP derivatives are merited with the goal of developing a desirable chemosensitizer drug candidate.
- Wan, Qi,Jin, Xin,Guo, Yalan,Yu, Zhihui,Guo, Shiqi,Morris-Natschke, Susan,Lee, Kuo-Hsiung,Liu, Hongrui,Chen, Ying
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- Ferulin C triggers potent PAK1 and p21-mediated anti-tumor effects in breast cancer by inhibiting Tubulin polymerization in vitro and in vivo
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Ferulin C, a natural sesquiterpene coumarin, isolated from the roots of Ferula ferulaeoides (Steud.) Korov, displaying potent antiproliferatory activity against breast cancer cells. This study aimed to elucidate the underlying molecular mechanisms of Ferulin C-induced breast cancer cells death in vitro and in vivo. Ferulin C presented potent antiproliferatory activity against MCF-7 and MDA-MB-231 cells and remarkable tubulin polymerization inhibitory activity (IC50 = 9.2 μM). Meanwhile, we predicted Ferulin C bind to the Colchicine site of tubulin through CETSA assay, molecular docking and molecular dynamics (MD) simulations. In immunofluorescence assay, Ferulin C disturbed the microtubule integrity and structure. Furthermore, Ferulin C stimulated significant cell cycle arrest in the G1/S period via p21Cip1/Waf1 - CDK2 signaling, induced classic cell apoptosis, impaired metastasis via down-regulating Ras-Raf-ERK and AKT-mTOR signaling. Intriguingly, Ferulin C treatment induced autophagy by ULK1 signaling to synergize with the inhibition of proliferation and metastasis. Based upon the RNAseq analysis, PAK1, as a novel essential modulator, was involved in the signaling regulated by Ferulin C -induced α/β-tubulin depolymerization. Additionally, Ferulin C displayed an acceptable antiproliferatory activity in an MCF-7 xenograft model without inducing obvious weight loss in the Ferulin C treated mice. Summarily, our findings substantiated that Ferulin C was a potent, colchicine site binding microtubule-destabilizing agent with anti-proliferation and anti-metastasis activity via PAK1 and p21-mediated signaling in breast cancer cells.
- He, Zhendan,Huang, Jian,Pan, Dabo,Wang, Jinhui,Yao, Dahong,Zhang, Jin,Zhen, Yongqi
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- Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies
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Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.
- Bhatia, Richa Kaur,Coutinho, Evans C.,Garg, Ruchika,Kancherla, Satyavathi,Kaur, Maninder,Madan, Jitender,Pissurlenkar, Raghuvir R. S.,Singh, Lakhwinder,Yadav, Manmohan
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p. 212 - 228
(2020/03/10)
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- Synthesis and studies of flavone and bis-flavone derivatives
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Flavonoids are widely occurring polyphenols of plant origin and well explored in the field of pharmacological activities. Recent studies showed this scaffold to be more dynamic as fluorescent probe. Very rare reports are there in literature on flavones as liquid crystals, for the first time we have synthesized and characterized flavone and bis-flavone derivatives for mesomorphic properties. Compounds 9a–d and 13a–d were studied for liquid crystalline properties by Differential scanning calorimetry (DSC) and Polarizing optical microscopy (POM) studies. The compounds 8, 9a–d, 12, and 13a–d were also studied for antioxidant property by DPPH assay.
- Durgapal, Sunil Dutt,Soman, Shubhangi S.,Umar, Shweta,Balakrishnan, Suresh
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p. 2502 - 2510
(2020/07/07)
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- Benzonate derivatives of acetophenone as potent α-glucosidase inhibitors: synthesis, structure–activity relationship and mechanism
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In this article, 23 compounds (6 and 7a–7v) were prepared and evaluated for their in vitro α-glucosidase inhibitory activity. The compounds 7d, 7f, 7i, 7n, 7o, 7r, 7s, 7u, and 7v displayed the α-glucosidase inhibition activity with IC50 values ranging from 1.68 to 7.88 μM. Among all tested compounds, 7u was found to be the most efficient, being 32-fold more active than the standard drug acarbose, which significantly attenuated postprandial blood glucose in mice. In addition, the compound 7u also induced the fluorescence quenching and conformational changes of enzyme, by forming α-glucosidase–7u complex in a mixed inhibition type. The thermodynamic constants recognised the interaction between 7u and α-glucosidase and was an enthalpy-driven spontaneous exothermic reaction. The synchronous fluorescence and CD spectra also indicate that the compound 7u changed the enzyme conformation. The findings identify the binding interactions between new ligands and α-glucosidase and reveal the compound 7u as a potent α-glucosidase inhibitor.
- Dan, Wen-Jia,Zhang, Qiang,Zhang, Fan,Wang, Wei-Wei,Gao, Jin-Ming
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p. 937 - 945
(2019/05/21)
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- Synthesis and evaluation of the in vitro antimicrobial activity of triazoles, morpholines and thiosemicarbazones
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Background: Microbial infections is a global public health problem. The aim of this work was to synthesize and evaluate the antimicrobial activity of novel triazoles, morpholines and thiosemicarbazones. Methods: Compounds were synthesized using 2,4-Dihydroxyacetophenone and 4-hydroxybenzaldehyde as starting materials. The antimicrobial activity of these compounds against bacteria and yeast was evaluated by the broth microdilution method. Results: The proposed route for synthesis gave high to moderate yields, moreover these compounds were successfully characterized by 1H NMR, 13C NMR and LC-MS. Antimicrobial testing indicated that the thiosemicarbazone and morphine derivatives had the best antimicrobial activity against the microorganisms tested with minimum inhibitory concentrations (MIC) between 0.29 and 5.30 μM. Thiosemicarbazone derivative (12) was able to inhibit the growth of C. tropicalis, with minimum fungicidal concentration (MFC) of 0.55 μM. In addition, this compound was active against E. coli, S. aureus and S. epidermidis, with MIC values ranging from 0.29 to 1.11 μM. Moreover, the morpholine derivative (15) had an MIC value of 0.83 μM against C. albicans and E. coli. Conclusion: We have efficiently synthesized a series of eleven novel triazoles, thiosemicarbazones and morpholine derivatives using 2,4-Dihydroxyacetophenone and 4-hydroxybenzaldehyde as starting materials. Thiosemicarbazone derivative (12) showed promising antifungal and antibacterial activity and these findings suggest that this compound can be used as scaffolds to design new antimicrobial drugs.
- Andradeb, Jéssica T.,Araújoc, Marcelo G. F.,Carmo, Lucas F.,Fernandesa, Joice S.,Ferreirab, Jaqueline M. S.,Santosa, Felipe R. S.,Sousab, Carla D. F.,Villar, José A. F. P.
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- Synthesis and biological evaluation of flavone-8-acrylamide derivatives as potential multi-target-directed anti Alzheimer agents and investigation of binding mechanism with acetylcholinesterase
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In a search for novel multifunctional anti-Alzheimer agents, a congeneric set of seventeen flavone-8-acrylamide derivatives (8a─q)were synthesized and evaluated for their cholinesterase inhibitory, antioxidant, neuroprotective and modulation of Aβ aggregation activities. The target compounds showed effective and selective inhibitory activity against the AChE over BuChE. In addition, the target compounds also showed moderate anti-oxidant activity and strong neuroprotective capacities, and accelerated dosage-dependently the Aβ aggregation. Also, we presented here a complete study on the interaction of 8a, 8d, 8e, 8h and 8i with AChE. Through fluorescence emission studies, the binding sites number found to be 1, binding constants were calculated as 2.04 × 104, 2.22 × 104, 1.18 × 104, 9.8 × 103 and 3.2 × 104 M?1 and free energy change as ?5.83, ?5.91, ?5.51, ?5.41 and ?6.12 kcal M?1 at 25 °C which were well agreed with the computational calculations indicating a strong binding affinity of flavones and AChE. Furthermore, the CD studies revealed that the secondary structure of AChE became partly unfolded upon binding with 8a, 8d, 8e, 8h and 8i.
- Shaik, Jeelan Basha,Yeggoni, Daniel Pushparaju,Kandrakonda, Yelamanda Rao,Penumala, Mohan,Zinka, Raveendra Babu,Kotapati, Kasi Viswanath,Darla, Mark Manidhar,Ampasala, Dinakara Rao,Subramanyam, Rajagopal,Amooru, Damu Gangaiah
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- Structure and Catalytic Mechanism of a Bacterial Friedel–Crafts Acylase
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C?C bond-forming reactions are key transformations for setting up the carbon frameworks of organic compounds. In this context, Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, which are common motifs in many fine chemicals and natural products. A bacterial multicomponent acyltransferase from Pseudomonas protegens (PpATase) catalyzes such Friedel–Crafts C-acylation of phenolic substrates in aqueous solution, reaching up to >99 % conversion without the need for CoA-activated reagents. We determined X-ray crystal structures of the native and ligand-bound complexes. This multimeric enzyme consists of three subunits: PhlA, PhlB, and PhlC, arranged in a Phl(A2C2)2B4 composition. The structure of a reaction intermediate obtained from crystals soaked with the natural substrate 1-(2,4,6-trihydroxyphenyl)ethanone together with site-directed mutagenesis studies revealed that only residues from the PhlC subunits are involved in the acyl transfer reaction, with Cys88 very likely playing a significant role during catalysis. These structural and mechanistic insights form the basis of further enzyme engineering efforts directed towards enhancing the substrate scope of this enzyme.
- Pavkov-Keller, Tea,Schmidt, Nina G.,??d?o-Dobrowolska, Anna,Kroutil, Wolfgang,Gruber, Karl
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- Thioesters as Acyl Donors in Biocatalytic Friedel-Crafts-type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens
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Functionalization of aromatic compounds by acylation has considerable significance in synthetic organic chemistry. As an alternative to chemical Friedel-Crafts acylation, the C-acyltransferase from Pseudomonas protegens has been found to catalyze C?C bond formation with non-natural resorcinol substrates. Extending the scope of acyl donors, it is now shown that the enzyme is also able to catalyze C?S bond cleavage prior to C?C bond formation, thus aliphatic and aromatic thioesters can be used as acyl donors. It is worth to mention that this reaction can be performed in aqueous buffer. Identifying ethyl thioacetate as the most suitable acetyl donor, the products were obtained with up to >99 % conversion and up to 88 % isolated yield without using additional base additives; this represents a significant advancement to prior protocols.
- ??d?o-Dobrowolska, Anna,Schmidt, Nina G.,Kroutil, Wolfgang
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p. 1064 - 1068
(2019/01/14)
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- New Flavone-Cyanoacetamide Hybrids with a Combination of Cholinergic, Antioxidant, Modulation of β-Amyloid Aggregation, and Neuroprotection Properties as Innovative Multifunctional Therapeutic Candidates for Alzheimer's Disease and Unraveling Their Mechanism of Action with Acetylcholinesterase
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In line with the modern multi-target-directed ligand paradigm of Alzheimer's disease (AD), a series of 19 compounds composed of flavone and cyanoacetamide groups have been synthesized and evaluated as multifunctional agents against AD. Biological evaluation demonstrated that compounds 7j, 7n, 7o, 7r, and 7s exhibited excellent inhibitory potency (AChE, IC50 of 0.271 ± 0.012 to 1.006 ± 0.075 μM) and good selectivity toward acetylcholinesterase, significant antioxidant activity, good modulation effects on self-induced Aβ aggregation, low cytotoxicity, and neuroprotection in human neuroblastoma SK-N-SH cells. Further, an inclusive study on the interaction of 7j, 7n, 7o, 7r, and 7s with AChE at physiological pH 7.2 using fluorescence, circular dichroism, and molecular docking methods suggested that these derivatives bind strongly to the peripheral anionic site of AChE mostly through hydrophobic interactions. Overall, the multifunctional profiles and strong AChE binding affinity highlight these compounds as promising prototypes for further pursuit of innovative multifunctional drugs for AD.
- Basha, Shaik Jeelan,Mohan, Penumala,Yeggoni, Daniel Pushparaju,Babu, Zinka Raveendra,Kumar, Palaka Bhagath,Rao, Ampasala Dinakara,Subramanyam, Rajagopal,Damu, Amooru Gangaiah
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p. 2206 - 2223
(2018/05/23)
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- Synthesis and Antibacterial Evaluation of Benzofuran Based Di-1,2,3-triazoles
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A series of novel benzofuran-1,2,3-triazole hybrid molecules are synthesized using the click chemistry approach. Structures of the synthesized compounds were assessed by IR, NMR, and mass spectroscopy. The tests of final products 10a–10l for their antibacterial activity demonstrate excellent to good activity against gram-positive and gram-negative bacteria.
- Sunitha,Kumar, A. Kishore,Shankaraiah,Jalapathi,Lincoln, Ch. A.
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p. 1515 - 1524
(2018/09/10)
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- Synthesis and Antimicrobial Evaluation of Bis-3,5-disubstituted Isoxazoles Based Chalcones
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A series of bis-isoxazoles blended chalcones 7a–7j are synthesized in high yields. The combination of three pharmacologically active moieties in a single scaffold results in the synergistic effect in their bioactivity. All the newly synthesized compounds are characterized by IR, NMR and Mass spectroscopy. The target compounds 7a–7j are assessed for their antimicrobial activity and these demonstrate high to excellent activity against tested bacterial and fungal strains. The products 7f, 7h, 7j, and 7i demonstrate potent antimicrobial activity at concentrations 75 and 100 μg/mL.
- Sunitha,Kumar, A. Kishore,Mahesh,Shankaraiah,Jalapathi,Lincoln, Ch. Abraham
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p. 1904 - 1911
(2018/11/24)
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- Synthesis and Antibacterial Activity of Some {6-[(1H-1,2,3-Triazol-4-yl)methoxy]-3-methylbenzofuran-2-yl}(4-bromophenyl)methanone Derivatives
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A series of novel benzofuran?1,2,3-triazole hybrid heterocyclic molecules were synthesized using a click chemistry approach. The structure of the synthesized compounds was assessed by IR and NMR spectroscopy and mass spectrometry. The products showed moderate to high activity against gram-positive and gram-negative bacteria.
- Kishore Kumar,Sunitha,Shankaraiah,Siddhartha,Jalapathi
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p. 789 - 796
(2018/06/14)
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- 2-Acetyl-4-aminoresorcinol derivatives: synthesis, antioxidant activity and molecular docking studies
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In this study, we synthesized new phenolic compounds that have the potential to serve as antioxidants and slow the effects of free radicals and oxidizing agents, which is beneficial for human health. Three resorcinol derivatives (new amide compounds) were generated by acetylation, nitration, and reduction. The structures of the products were determined by spectroscopic methods. The antioxidant activities of the new compounds were evaluated in vitro by redox reactions with the free radicals of the diammonium salt of 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS+●) and 1,1-diphenyl-2-picrylhydrazyl (DPPH●). The tested compounds showed antioxidant activities similar to that of resveratrol, a natural product known to affect a wide range of intracellular mediators. These derivatives were also submitted to docking simulations to evaluate their possible interactions with the enzyme myeloperoxidase. This analysis showed potential interactions with pockets “A” and “B” in the enzyme, and the best interaction was detected between succinic-amide (4) and pocket A.
- Guerra-Vargas, María A.,Rosales-Hernández, Martha C.,Martínez-Fonseca, Nadhynee,Padilla-Martínez, Itzia,Fonseca-Sabater, Yadira,Martínez-Ramos, Federico
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p. 1186 - 1197
(2018/02/12)
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- Novel Nitric Oxide Donors of Phenylsulfonylfuroxan and 3-Benzyl Coumarin Derivatives as Potent Antitumor Agents
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In this work, five new hybrids of phenylsulfonylfuroxan merging 3-benzyl coumarin and their seco-B-ring derivatives 2-6 were designed and synthesized. Among them, compound 3 showed the most potent antiproliferation activities with IC50 values range from 0.5 to 143 nM against nine drug-sensitive and four drug-resistant cancer cell lines. Preliminary pharmacologic studies showed that these compounds displayed lower toxicities than that of lead compound 1. Compound 3 obviously induced the early apoptosis and hardly affected the cell cycle of A2780, which was significantly different from compound 1. Especially, it gave 559- and 294-fold selectivity antiproliferation activity in P-gp overexpressed drug-resistant cancer cell lines MCF-7/ADR and KB-V compared to their drug-sensitive ones MCF-7 and KB, implying that compounds 2-6 might have an extra mechanism of anti-MDR-cancer with P-gp overexpression.
- Guo, Yalan,Wang, Yujie,Li, Haihong,Wang, Ke,Wan, Qi,Li, Jia,Zhou, Yubo,Chen, Ying
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p. 502 - 506
(2018/05/14)
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- Preparation method of chalcone, dihydrochlcone and flavone compound and application
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The invention discloses a preparation method of chalcone, dihydrochlcone and flavone compound and an application. The preparation method and application disclosed by the invention have the beneficialeffects that 3,4',6'-trihydroxy-4-methoxychalcone has stronger inhibiting effect to a-glucosidase and can be used for reducing postprandial hyperglycemia; 4-dimethylaminochalcone, 4-hydroxychalcone, 3-hydroxy-4-methoxychalcone and 3,4',6'-trihydroxy-4-methoxychalcone have more obvious inhibiting effect to nonenzymatic glycation and can be used for treating diabetes and atherosclerosis.
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Paragraph 0016
(2019/01/08)
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- Molecular cloning, expression, and characterization of acyltransferase from Pseudomonas protegens
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The formation of C-C bonds by using CoA independent acyltransferases may have significant impact for novel methods for biotechnology. We report the identification of Pseudomonas strains with CoA-independent acyltransferase activity as well as the heterolo
- Schmidt, Nina G.,??d?o-Dobrowolska, Anna,Ruppert, Valerie,H?flehner, Christian,Wiltschi, Birgit,Kroutil, Wolfgang
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p. 6057 - 6068
(2018/05/16)
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- Preliminary quality evaluation and characterization of phenolic constituents in cynanchi wilfordii radix
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A new phenolic compound, 2-O-β-laminaribiosyl-4-hydroxyacetophenone (1), was isolated from Cynanchi Wilfordii Radix (CWR, the root of Cynanchum wilfordii Hemsley), along with 10 known aromatic compounds, including cynandione A (2), bungeisides-C (7) and –D (8), p-hydroxyacetophenone (9), 2,5-dihydroxyacetophenone (10), and 2,4-dihydroxyacetophenone (11). The structure of the new compound (1) was elucidated using spectroscopic methods and chemical methods. The structure of cynandione A (2), including a linkage mode of the biphenyl parts that remained uncertain, was unambiguously confirmed using the 2D13C–13C incredible natural abundance double quantum transfer experiment (INADEQUATE) spectrum. Additionally, health issues related to the use of Cynanchi Auriculati Radix (CAR, the root of Cynanchum auriculatum Royle ex Wight) instead of CWR have emerged. Therefore, constituents present in methanolic extracts of commercially available CWRs and CARs were examined using UV-sensitive high-performance liquid chromatography (HPLC), resulting in common detection of three major peaks ascribed to cynandione A (2), p-hydroxyacetophenone (9), and 2,4-dihydroxyacetophenone (11). Thus, to distinguish between these ingredients, a thin-layer chromatography (TLC) method, combined with only UV irradiation detection, focusing on wilfosides C1N (12) and K1N (13) as marker compounds characteristic of CAR, was performed. Furthermore, we propose this method as a simple and convenient strategy for the preliminary distinction of CWR and CAR to ensure the quality and safety of their crude drugs.
- Uchikura, Takashi,Tanaka, Hiroaki,Sugiwaki, Hidemi,Yoshimura, Morio,Sato-Masumoto, Naoko,Tsujimoto, Takashi,Uchiyama, Nahoko,Hakamatsuka, Takashi,Amakura, Yoshiaki
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- Panel of New Thermostable CYP116B Self-Sufficient Cytochrome P450 Monooxygenases that Catalyze C?H Activation with a Diverse Substrate Scope
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The ability of cytochrome P450 monooxygenases to catalyse a wide variety of synthetically challenging C?H activation reactions makes them highly desirable biocatalysts both for the synthesis of chiral intermediates and for late-stage functionalisations. However, P450s are plagued by issues associated with poor expression, solubility and stability. Catalytically self-sufficient P450s, in which the haem and reductase domains are fused in a single protein, obviate the need for additional redox partners and are attractive as biocatalysts. Here we present a panel of natural self-sufficient P450s from thermophilic organisms (CYP116B65 from A. thermoflava, CYP116B64 from A. xiamenense, CYP116B63 from J. thermophila, CYP116B29 from T. bispora and CYP116B46 from T. thermophilus). These P450s display enhanced expression and stability over their mesophilic homologues. Activity profiling of these enzymes revealed that each P450 displayed a different fingerprint in terms of substrate range and reactivity that cover reactions as diverse as hydroxylation, demethylation, epoxidation and sulfoxidation. The productivity of the bio-transformation of diclofenac to produce the 5-hydroxy metabolite increased 42-fold using the thermostable P450-AX (>0.5 g L?1 h?1) compared to the P450-RhF system reported previously. In conclusion, we have generated a toolkit of thermostable self-sufficient P450 biocatalysts with a broad substrate range and reactivity.
- Tavanti, Michele,Porter, Joanne L.,Sabatini, Selina,Turner, Nicholas J.,Flitsch, Sabine L.
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p. 1042 - 1051
(2018/03/21)
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- Acyl Donors and Additives for the Biocatalytic Friedel–Crafts Acylation
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The Friedel–Crafts acylation is a broadly applied reaction that can be conducted using various types of catalyst. However, a biocatalytic alternative has only been reported recently. In this study, the scope of acetyl donors is described, showing that, in addition to vinyl acetate derivatives, phenyl esters are also suitable donors. Furthermore, it was found that various amines enhance the reaction, whereby the effect do not seem to be correlated to the pH but to the structure of the donor. For instance, 1,4-diazabicyclo[2.2.2]octane (DABCO) turned out to be a viable alternative to imidazole; however the former performed best at pH 9.85, whereas the latter performed best at pH 8.3.
- Schmidt, Nina G.,Kroutil, Wolfgang
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p. 5865 - 5871
(2017/10/07)
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- Synthesis and antimicrobial activity of some novel benzofuran based 1,2,3-triazoles
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In the present study, a series of novel {6-[(1H-1,2,3-triazol-4-yl)methoxy]-3-methylbenzofuran-2-yl}(phenyl)methanones (7a–7o) have been synthesized using click chemistry approach. The structures of all newly synthesized compounds were characterized by FT-IR, 1H and 13C NMR, and MASS spectral data. Most of products demonstrated high antimicrobial activity.
- Sunitha,Kishore Kumar,Shankar,Anil Kumar,Krishna,Lincoln, Ch. A.,Pochampalli
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p. 322 - 330
(2017/04/13)
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- Primulin derivative as well as synthesis method and application of primulin derivative
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The invention discloses a primulin derivative with antibacterial activity shown as the structural general formula (I), wherein R is selected from C2-C20 alkyls. The primulin derivative is prepared from raw materials including m-dihydroxybenzene and a fatty acid derivative by the steps: carrying out Friedel-Crafts acylation and methylation to synthesize a paeonol derivative, and carrying out oxidization after carrying out carbonyl reduction. The primulin derivative has good antibacterial activity and can be used as a potential antibacterial agent.
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Paragraph 0019
(2018/01/11)
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- Synthesis of 2, 4 - dihydroxy acetophenone and waste water recycling method
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The present invention discloses a method for synthesizing 2,4-dihydroxyacetophenone and recycling and reusing wastewater. The synthesis method is as follows: reacting resorcinol as a starting material with anhydrous zinc chloride as a catalyst under the action of an acylating agent to generate 2,4-dihydroxyacetophenone. The wastewater treatment comprises the steps of: conducting concentration under reduced pressure to recover an aqueous solution of acetic acid; neutralizing the concentrated residue with aqueous solution of sodium hydroxide; centrifuging to obtain a basic zinc chloride crude product, wherein the mother liquors mainly contains phenol compounds; precipitating the phenol-formaldehyde polymer formed by polymerization of phenolic compound and formaldehyde from the mother liquor by a phenol-formaldehyde polymerization method; centrifuging to obtain the phenol-formaldehyde polymer and mother liquor reaching biochemical treatment standards; and then carrying out an activated sludge biological treatment to reach national emission standards. The invention not only optimizes the synthetic process of 2,4-dihydroxyacetophenone but also conducts in-depth study on the recovery and reuse of wastewater to reach the biochemical treatment standards and reduce the environment hazards of production wastewater.
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Paragraph 0044; 0067; 0068-0069; 0071
(2017/10/07)
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- Biocatalytic Friedel–Crafts Acylation and Fries Reaction
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The Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel–Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries rearrangement-like reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C?C bond formation methods.
- Schmidt, Nina G.,Pavkov-Keller, Tea,Richter, Nina,Wiltschi, Birgit,Gruber, Karl,Kroutil, Wolfgang
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p. 7615 - 7619
(2017/06/13)
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- A rapid, solvent-free deprotection of methoxymethyl (MOM) ethers by pTSA; An eco-friendly approach
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Background: Ease of preparation and alkaline stability of methoxymethyl (MOM) makes it an important hydroxyl protecting group. A number of methods are available for the deprotection of MOM. Though the methods are good in general, they use solvents, require prolonged reaction time and tedious work up. A solvent free, solid phase, fast deprotection of MOM has been developed and is the major theme of this paper. Methods: A mixture of MOM protected compounds and pTSA is triturated in a mortar (5 min) and left at room temperature for 30 min. On addition of water (4°C), pTSA, methanol and formaldehyde dissolved leaving the products as precipitates. Results: A series of different MOM ethers were deprotected by this method in good to excellent yield (85-98%). The compatibility of MOM in the presence of other protections such as methoxyl, benzyl, ester, amide, allyl and lactone was also established. Acetate protection is not stable under these conditions. Conclusion: An efficient, selective and high yielding deprotection MOM groups by pTSA under solvent free condition is described. The process is environment friendly since no solvent was used in the deprotection process. The reaction conditions are mild and should be useful for the deprotection of MOM derivatives of complex and labile molecules.
- Pandurangan, Nanjan
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p. 231 - 235
(2017/07/15)
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- 4 - aromatic amine - coumarin derivatives and its preparation method and medical use (by machine translation)
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The invention relates to the field of pharmaceutical chemistry, in particular relates to a series of 4?Aromatic amine?Coumarin derivatives, method for their preparation and use in medicine, in particular for the treatment of tumor, such as breast cancer, and the like. The present invention relates to compounds of the general structure is as follows, each group in the formula is defined in the specification. (by machine translation)
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Paragraph 0036; 0047; 0048; 0049
(2016/11/21)
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- Microwave-promoted Synthesis of Novel Fused Osthole Analogues
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Osthole is a natural coumarin derivative and has a broad scope of biological activities. Two series of novel fused osthole analogues were designed, and synthesized through a highly efficient microwave-promoted synthetic protocol via the reaction of 4-hydroxycoumarins and β-ketoesters. The reaction conditions including solvent, catalyst, microwave power and irradiation time were also optimized. The pyrano[3,2-c]chromene-2,5-diones and furo[3,2-c]coumarins were obtained through two distinct intramolecular cyclization processes, and the proposed mechanism was also discussed.
- Zhang, Mingzhi,Zhang, Rongrong,Wang, Jiaqun,Yu, Xiang,Zhang, Yaling,Wang, Qingqing,Zhang, Weihua
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p. 1344 - 1352
(2016/12/27)
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- Microwave-assisted synthesis and antifungal activity of novel coumarin derivatives: Pyrano[3,2-c]chromene-2,5-diones
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A series of novel fused coumarin analogues pyrano[3,2-c]chromene-2,5-diones have been synthesized through an optimized microwave-assisted protocol. All target compounds were tested and evaluated for their antifungal activity against Botrytis cinerea, Colletotrichum copsica, Alternaria solani, Gibberella zeae and Rhizoctorzia solani. The bioassay results indicated that some of the compounds exhibited potent antifungal activities at concentration less than 50 ppm. For the compounds 5d, 6c and 7b, EC50 values against B. cinerea were as low as 0.141, 0.082 and 0.091 μM, respectively, which represents better antifungal activity than that of the commonly used fungicide Azoxystrobin. Compounds 5d (57%) and 6c (55%) also exhibited more effective control than Azoxystrobin (44%) against Colletotrichum capsica.
- Zhang, Rong-Rong,Liu, Jia,Zhang, Yu,Hou, Meng-Qing,Zhang, Ming-Zhi,Zhou, Fenger,Zhang, Wei-Hua
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- Microwave-assisted synthesis and antifungal activity of novel fused Osthole derivatives
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Based on the microwave-assisted synthetic protocol developed in our previous work, we have synthesized a series of novel furo[3,2-c]coumarins as fused Osthole derivatives, via the reaction of 4-hydroxycoumarins and β-ketoesters catalyzed by DMAP. All the target compounds were evaluated in?vitro for their antifungal activity against six phytopathogenic fungi, some compounds exhibited potential activity in the primary assays. Especially compounds 6c, 7b, 8b and 8c (shown in Fig.?1) were the most active ones, EC50values of these four compounds against Colletotrichum capsica, Botrytis cinerea and Rhizoctonia solani were further investigated. 6c was identified as the most promising candidate with the EC50value at 0.110?μM against Botrytis cinerea and 0.040?μM against Colletotrichum capsica, respectively, representing better antifungal activity than that of the commonly used fungicide Azoxystrobin.
- Zhang, Ming-Zhi,Zhang, Rong-Rong,Wang, Jia-Qun,Yu, Xiang,Zhang, Ya-Ling,Wang, Qing-Qing,Zhang, Wei-Hua
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- Natural products as sources of new fungicides (II): antiphytopathogenic activity of 2,4-dihydroxyphenyl ethanone derivatives
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A series of 17 simple 1-(2,4-dihydroxyphenyl) ethanones were synthesised, and their structures characterised by 1H, 13C NMR and ESI-MS. Their in vitro antifungal activities were evaluated against five phytopathogenic fungi including Glomerella cingulate, Botrytis cirerea, Fusarium graminearum, Curvularia lunata and Fusarium oxysporum f. sp. vasinfectum by the mycelial growth inhibition assay. Compounds 2g and 2h exhibited broad-spectrum inhibitory activity against the mycelial growth of the tested pathogens with IC50 values in the range of 16-36 g/mL, and in particular being more active to G. cingulate, with IC50 values of 16.50 and 19.25 g/mL, respectively, than the other pathogens. Preliminary SAR indicated that an α,β-unsaturated ketone unit of the alkyl chain of the compounds is the structure requirement for fungicidal action. The results suggested that 2g and 2h may be promising leads in the development of new antifungal agents.
- Nandinsuren, Tseden,Shi, Wei,Zhang, An-Ling,Bai, Yu-Bin,Gao, Jin-Ming
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supporting information
p. 1166 - 1169
(2016/04/20)
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- 2-substituted benzopyran-4-one compounds and application thereof
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The invention relates to the technical field of medicine and discloses 2-substituted benzopyran-4-one compounds with a structure shown in general formula I and an application of the compounds in preparation of antifungal drugs and synergistic antifungal drugs. The compounds can be jointly used with azole antifungal drugs, can improve sensibility of drug-resistance bacteria to the azole drugs, reverses drug resistance and produces a synergistic antifungal function.
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Paragraph 0197
(2016/10/08)
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- Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
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Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ~ 205.19, λab ~ 350 nm, λem ~ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is
- Miao, Jianzhuang,Cui, Huaqing,Jin, Jing,Lai, Fangfang,Wen, Hui,Zhang, Xiang,Ruda, Gian Filippo,Chen, Xiaoguang,Yin, Dali
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supporting information
p. 881 - 884
(2015/02/19)
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- Synthesis and DNA Binding Affinity of Some New 7-Hydroxy-3-Carbaldehyde Chromones
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Two novel ligands, 7-methoxy chromone-3-carbaldehyde-salicylyl hydrazone and 7-hydroxy chromone-3-carbaldehyde-salicylyl hydrazone, were prepared by resorcinol their respective Eu (III) complexes had been synthesized and characterized on the base of elemental analyses, molar conductivities, IR spectra, mass spectra, UV-Vis spectra, and fluorescence studies the interactions of the Eu (III) complexes and their ligands with calf-thymus DNA were investigated, which were found that both two ligands and their rare earth complexes could strongly bind with calf-thymus DNA via an intercalation mechanism.
- Wang, Qian,Chen, Liang
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p. 196 - 202
(2015/08/06)
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- Divergent and concise total syntheses of dihydrochalcones and 5-deoxyflavones recently isolated from Tacca species and Mimosa diplotricha
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Dihydrochalcones and 5-deoxyflavones are types of compounds possessing various biologically interesting properties. Herein, we report the concise and divergent total syntheses of several naturally occurring dihydrochalcones and 5-deoxyflavones from readily available starting materials. The divergent strategy is based around manipulation of a common chalcone scaffold and features application of Algar-Flynn-Oyamada oxidation and benzoquinone C-H activation methodologies. These are the first reported total syntheses of these biologically interesting compounds and the concise and flexible route should be readily amenable to future analogue generation. Furthermore, this work provides an illustration of the utility of divergent synthesis for the expedient and step-economical preparation of natural product libraries.
- Sum, Tze Han,Sum, Tze Jing,Stokes, Jamie E.,Galloway, Warren R.J.D.,Spring, David R.
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p. 4557 - 4564
(2015/06/08)
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- Synthesis and biological evaluation of benzo[b]furans as inhibitors of tubulin polymerization and inducers of apoptosis
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A series of benzo[b]furans was synthesized with modification at the 5-position of the benzene ring by introducing C-linked substituents (aryl, alkenyl, alkynyl, etc.). These compounds were evaluated for their antiproliferative activities, inhibition of tubulin polymerization, and cell-cycle effects. Some compounds in this series displayed excellent activity in the nanomolar range against lung cancer (A549) and renal cell carcinoma (ACHN) cancer cell lines. (6-Methoxy-5-((4-methoxyphenyl)ethynyl)-3- methylbenzofuran-2-yl)(3,4,5-trimethoxyphenyl)methanone (26) and (E)-3-(6-methoxy-3-methyl-2-(1-(3,4,5-trimethoxyphenyl)vinyl)benzofuran-5-yl) prop-2-en-1-ol (36) showed significant activity in the A549 cell line, with IC50 values of 0.08 and 0.06 μM, respectively. G2/M cell-cycle arrest and subsequent apoptosis was observed in the A549 cell line after treatment with these compounds. The most active compound in this series, 36, also inhibited tubulin polymerization with a value similar to that of combretastatin A-4 (1.95 and 1.86 μM, respectively). Furthermore, detailed biological studies such as Hoechst 33258 staining, DNA fragmentation and caspase-3 assays, and western blot analyses with the pro-apoptotic protein Bax and the anti-apoptotic protein Bcl-2 also suggested that these compounds induce cell death by apoptosis. Molecular docking studies indicated that compound 36 interacts and binds efficiently with the tubulin protein. Antiproliferation additions: A series of benzo[b]furans with C-linked substituents was synthesized and evaluated for anticancer potential against five human cancer cell lines. Some of the compounds (representative shown) displayed good antiproliferative activity in the nanomolar range against the A549 cell line by inhibition of tubulin polymerization (ITP). Copyright
- Kamal, Ahmed,Reddy, N. V. Subba,Nayak, V. Lakshma,Reddy, V. Saidi,Prasad,Nimbarte, Vijaykumar D.,Srinivasulu, Vunnam,Vishnuvardhan,Reddy, C. Suresh
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p. 117 - 128
(2014/01/17)
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- A new method for the facile synthesis of hydroxylated flavones by using allyl protection
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The iodine-induced oxidative cyclization of 2′-hydroxychalcones provides a simple, highly efficient approach to various hydroxy flavones and analogues. This process is run under mild conditions, tolerates various functional groups, and provides hydroxy flavones in good to excellent yield. The allyl-protected acetophenones and benzaldehydes were smoothly deallylated under similar conditions.
- Nawghare,Sakate,Lokhande
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p. 291 - 302
(2014/04/17)
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- Pd-catalyzed allylic alkylation cascade with dihydropyrans: Regioselective synthesis of furo[3,2- c ]pyrans
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A regioselective palladium-catalyzed allylic alkylation cascade forms furo[3,2-c]pyrans from various cyclic β-dicarbonyl bis-nucleophiles and 3,6-dihydro-2H-pyran bis-electrophiles. The combination of allylic carbonate and anomeric siloxy leaving groups in the dihydropyran substrate allows control of the many regiochemical possibilities in this reaction. Annulation proceeds stereoconvergently to give cis-fused furopyrans from either cis- or trans-substituted starting material.
- Bartlett, Mark J.,Turner, Claire A.,Harvey, Joanne E.
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supporting information
p. 2430 - 2433
(2013/07/05)
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- Studies on the chemical behavior of the novel 6,8-dibromo-7- hydroxychromone-3-carboxaldehyde towards some carbon nucleophilic reagents
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A novel 6,8-dibromo-7-hydroxychromone-3-carboxaldehyde (4) was prepared by the Vilsemier-Haack formylation of 3,5-dibromo-2,4-dihydroxy acetophenone (3). The chemical reactivity of carboxaldehyde 4 was studied towards some carbon nucleophiles as cyclic and acyclic active methylene nucleophiles and also 1,3-C,N- and 1,3-C,C-binucleophiles as a route to achieve ring transformation to produce a variety of heterocyclic systems. Structures of the newly synthesized products have been deduced on the basis of elemental analysis and spectral data.
- Ibrahim, Magdy A.,Ali, Tarik E.,El-Kazak, Azza M.,Mohamed, Amira M.
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p. 1075 - 1086
(2013/06/05)
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- Synthesis, characterization and crystallographic studies of 4-{(1E)-1-[(2E)-{[4-(dimethylamino)phenyl] methylidene}hydrazono]ethyl}benzene- 1,3-diol
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The title compound 4-{(1E)-1-[(2E)-{[4-(dimethylamino)phenyl]methylidene} hydrazono]ethyl}benzene-1,3-diol (1) which is an azine moiety, has been synthesized by microwave irradiation technique. The characterization by IR and mass spectroscopy confirms the structure of (1). The crystal system, lattice parameters and molecular structure of (1) has been determined by single crystal X-ray diffraction technique. The crystallographic data for the compound (1) is being reported for the first time. Studies reveal that the compound exhibits intermolecular and intramolecular hydrogen bonding interactions in its crystal structure. The compound crystallizes in the monoclinic space group P21/n with unit cell dimensions a = 11.8734(7) A; b = 9.6194(6) A; c = 27.2410(16) A; β = 96.435(3) A; V = 3091.7(3) A3 and D calc = 1.278 Mg/m3 for Z = 8. The surface morphology of the crystalline compound has been studied by SEM analysis. SEM reveals the microcrystalline features of the compound under study.
- Kurian, Thomas O.,Sadaphale, Pranita,Paliwal,Pandey,Bagade
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p. 455 - 462
(2013/09/12)
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- Highly efficient and selective deprotection method for prenyl, geranyl, and phytyl ethers and esters using borontrifluoride-etherate
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An efficient, simple, and practical method has been developed for the deprotection of prenyl, geranyl, and phytyl ethers and esters of aromatic and aliphatic compounds using borontrifluoride-etherate (BF3· OEt2) at room temperature in good to excellent yields for the first time. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Narender,Venkateswarlu,Madhur,Reddy, K. Papi
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- Arylalkyl ketones, benzophenones, desoxybenzoins and chalcones inhibit TNF-α induced expression of ICAM-1: Structure-activity analysis
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The interaction between leukocytes and the vascular endothelial cells (EC) via cellular adhesion molecules plays an important role in the pathogenesis of various inflammatory and autoimmune diseases. Small molecules that block these interactions have been targeted as potential therapeutic agents against acute and chronic inflammatory diseases. In an effort to identify potent intercellular cell adhesion molecule-1 (ICAM-1) inhibitors, a large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones and their analogs (54 in total) have been synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated the possible mechanism for their ICAM-1 inhibitory activities. The most active compound was found to be 79. A large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones as well as their analogs (54 in total) were synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated a possible mechanism of their ICAM-1 inhibitory activities. The most active compound was found to be 79. Copyright
- Kumar, Sarvesh,Reddy L, Chandra Shekhar,Kumar, Yogesh,Kumar, Amit,Singh, Brajendra K.,Kumar, Vineet,Malhotra, Shashwat,Pandey, Mukesh K.,Jain, Rajni,Thimmulappa, Rajesh,Sharma, Sunil K.,Prasad, Ashok K.,Biswal, Shyam,Van Der Eycken, Erik,Depass, Anthony L.,Malhotra, Sanjay V.,Ghosh, Balaram,Parmar, Virinder S.
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experimental part
p. 368 - 377
(2012/07/31)
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- Highly regioselective synthesis of novel 4-O-phosphorylated paeonol analogs
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4-O-phosphorylated paeonol derivatives were conveniently prepared by a facile method. Resacetophenone was prepared by the Friedel-Crafts acylation reaction of acetic acid with resorcinol. It was then phosphorylated regioselectively at the 4-O position using the Atherton-Todd reaction. An efficient, highly regioselective method to synthesize 4-O-phosphorylated paeonol derivatives is provided, and the approach has the merits of mild reaction conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor and Francis Group, LLC 2012.
- Ju, Zhiyu,Li, Gongchun,Wang, Jie,Ye, Yong,Yang, Fengling,Zhao, Yufen
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experimental part
p. 859 - 863
(2012/07/31)
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- 3,5,2′,4′-Tetrahydroxychalcone, a new non-purine xanthine oxidase inhibitor
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Xanthine oxidase is a key enzyme that catalyses hypoxanthine and xanthine to uric acid and the overproduction of uric acid will lead to hyperuricemia which is an important cause of gout. In the present study, three chalcone derivatives were synthesized and evaluated for inhibitory activity against xanthine oxidase in vitro. Of the compounds, only Compound 1, 3,5,2′,4′-tetrahydroxychalcone, exhibited a significant inhibitory activity on xanthine oxidase with an IC50 value of 22.5 μM. Lineweaver-Burk transformation of the inhibition kinetics data demonstrated that it was a competitive inhibitor of xanthine oxidase and Ki value was 17.4 μM. In vivo, intragastric administration of Compound 1 was able to significantly reduce serum uric acid levels and inhibited hepatic xanthine oxidase activities of hyperuricemic mice in a dose-dependent manner. Acute toxicity study in mice showed that Compound 1 was very safe at a dose of up to 5 g/kg. These results suggest that Compound 1 is a novel competitive xanthine oxidase inhibitor and is worthy of further development.
- Niu, Yanfen,Zhu, Huajie,Liu, Jia,Fan, Huafang,Sun, Ling,Lu, Wei,Liu, Xu,Li, Ling
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scheme or table
p. 161 - 166
(2012/01/11)
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