- 1,3-dipolar cycloaddition reactions of the compound obtaining from cyclopentadiene-PTAD and biological activities of adducts formed selectively
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After known adduct (4) was synthesized by cycloaddition reaction of cyclopentadiene with 4-phenyl-1,2,4-triazoline-3,5-dione, seven new isoxazoline derivatives were synthesized from reactions of 4 with corresponding oximes prepared from benzaldehyde derivatives in the existence of the aqueous NaOCl in CH2Cl2 at 0°C—RT via nitrile oxides. Four new pyrazoline derivatives were also synthesized from reactions of 4 with corresponding prepared reagents via nitrile imines. Selectively, each of all isoxazole and pyrazoline derivatives was synthesized by 1,3-dipolar cycloaddition reactions of compound 4 with the corresponding reagents. Based on the results of their biological activity analyses, Ki values for acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and alpha-glucosidase (α-Gly) enzymes were obtained in this range 32.15 ± 5.73–107.44 ± 19.52 22.57 ± 4.30–186.07 ± 23.51, and 69.08 ± 8.54–528.07 ± 38.46 nM, respectively. Besides that, these compounds were subjected to molecular docking to describe the interaction against AChE, BChE, and α-Gly enzymes in which important interactions were visualized and evaluated with residues of the binding region in each target enzyme.
- Bayrak, Cetin,Menzek, Abdullah,Taskin-Tok, Tugba,Taslimi, Parham,Yavari, Mirali Akbar
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- Design, synthesis and biological evaluation of novel indanone containing spiroisoxazoline derivatives with selective COX-2 inhibition as anticancer agents
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Objective: A new family of 3′-(Mono, di or tri-substituted phenyl)-4′-(4-(methylsulfonyl) phenyl) spiroisoxazoline derivatives containing indanone spirobridge was designed, synthesized, and evaluated for their selective COX-2 inhibitory potency and cytotoxicity on different cell lines. Methods: A synthetic reaction based on 1,3-dipolar cycloaddition mechanism was applied for the regiospecific formation of various spiroisoxazolines. The activity of the newly synthesized compounds was determined using in vitro cyclooxygenase inhibition assay. The toxicity of the compounds was evaluated by MTT assay. In addition, induction of apoptosis, and expression levels of Bax, Bcl-2 and caspase-3 mRNA in MCF-7 cells were evaluated following exposure to compound 9f. The docking calculations and molecular dynamics simulation were performed to study the most probable modes of interactions of compound 9f upon binding to COX-2 enzyme. Results: The docking results showed that the synthesized compounds were able to form hydrogen bonds with COX-2 involving methyl sulfonyl, spiroisoxazoline, meta-methoxy and fluoro functional groups. Spiroisoxazoline derivatives containing methoxy group at the C-3′ phenyl ring meta position (9f and 9g) showed superior selectivity with higher potency of inhibiting COX-2 enzyme. Furthermore, compound 9f, which possesses 3,4-dimethoxyphenyl on C-3′ carbon atom of isoxazoline ring, exhibited the highest COX-2 inhibitory activity, and also displayed the most potent cytotoxicity on MCF-7 cells with an IC50 value of 0.03 ± 0.01 μM, comparable with that of doxorubicin (IC50 of 0.062 ± 0.012 μM). The results indicated that compound 9f could promote apoptosis. Also, compared to the control group, the mRNA expression of Bax and caspase-3 significantly increased, while that of Bcl-2 significantly decreased upon exposure to compound 9f which may propose the activation of mitochondrial-associated pathway as the mechanism of observed apoptosis. Conclusion: In vitro biological evaluations accompanied with in silico studies revealed that indanone tricyclic spiroisoxazoline derivatives are good candidates for the development of new anti-inflammatory and anticancer (colorectal and breast) agents.
- Abolhasani, Hoda,Zarghi, Afshin,Komeili Movahhed, Tahereh,Abolhasani, Ahmad,Daraei, Bahram,Dastmalchi, Siavoush
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- The local and natural sources in synthetic methods: the practical synthesis of aryl oximes from aryl aldehydes under catalyst-free conditions in mineral water
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The synthesis of oximes from aryl aldehydes was prepared using hydroxylamine hydrochloride. The obtained oxime compounds were synthesized at maximum efficiency in mineral water at room temperature. The developed method is economical, practical and environmentally friendly. All of the aldehydes were converted the oxime a method using local sources and useful for industrial applications is introduced in the literature. Graphic abstract: In this study, addition elimination reaction, one of the important reactions of organic chemistry, was carried out using local sources. With this reaction, aryl oximes were obtained from aryl aldehydes in mineral water under catalyst-free conditions.[Figure not available: see fulltext.]
- Goksu, H.,Orhan, E.
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- HCl-mediated cascade cyclocondensation of oxygenated arylacetic acids with arylaldehydes: one-pot synthesis of 1-arylisoquinolines
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In this paper, a concise, open-vessel synthesis of 1-arylisoquinolines is describedviaHCl-mediated intermolecular cyclocondensation of oxygenated arylacetic acids with arylaldehydes in the presence of NH2OH and alcoholic solvents under mild and one-pot reaction conditions. A plausible mechanism is proposed and discussed herein. In the overall reaction process, only water was generated as the byproduct. Various environmentally friendly reaction conditions are investigated for convenient transformationviathe (4C + 1C + 1N) annulation. This protocol provides a highly effective ring closureviathe formations of one carbon-carbon (C-C) bond, two carbon-nitrogen (C-N) bonds and one carbon-oxygen (C-O) bond.
- Hsueh, Nai-Chen,Chen, Shin-Mei,Lin, Chun-Yi,Chang, Meng-Yang
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p. 1047 - 1059
(2021/02/16)
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- Adhesive functionalized ascorbic acid on CoFe2O4: A core-shell nanomagnetic heterostructure for the synthesis of aldoximes and amines
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This paper reports on the simple synthesis of novel green magnetic nanoparticles (MNPs) with effective catalytic properties and reusability. These heterogeneous nanocatalysts were prepared by the anchoring of Co and V on the surface of CoFe2O4 nanoparticles coated with ascorbic acid (AA) as a green linker. The prepared nanocatalysts have been identified by scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, X-ray atomic mapping, thermogravimetric analysis, X-ray powder diffraction, vibrating sample magnetometer analysis, coupled plasma optical emission spectrometry and Fourier transform infrared spectroscopy. The impact of CoFe2O4@AA-M (Co, V) was carefully examined for NH2OH·HCl oximation of aldehyde derivatives first and then for the reduction of diverse nitro compounds with sodium borohydride (NaBH4) to the corresponding amines under green conditions. The catalytic efficiency of magnetic CoFe2O4@AA-M (Co, V) nanocatalysts was investigated in production of different aldoximes and amines with high turnover numbers (TON) and turnover frequencies (TOF) through oximation and reduction reactions respectively. Furthermore, the developed environment-friendly method offers a number of advantages such as high turnover frequency, mild reaction conditions, high activity, simple procedure, low cost and easy isolation of the products from the reaction mixture by an external magnetic field and the catalyst can be reused for several consecutive runs without any remarkable decrease in catalytic efficiency.
- Sorkhabi, Serve,Ghadermazi, Mohammad,Mozafari, Roya
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p. 41336 - 41352
(2020/11/30)
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- A Synergic Activity of Urea/Butyl Imidazolium Ionic Liquid Supported on UiO-66-NH2 Metal–Organic Framework for Synthesis of Oximes
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An efficient supported ionic liquid catalyst is designed for condensation reaction of aldehydes and ketones. The Zr-based metal–organic framework (MOF), UiO-66-NH2, was initially functionalized with N,N′-dibutyl imidazolium ionic liquid (UiO-66-NH2-ILBr–), and then urea was attached to the ionic liquid (IL) to form a task-specific IL. Bromide was exchanged with tetrafluoroborate and the catalyst exhibits excellent performance for the synthesis of oximes. The ionic liquid/urea coupling showed a synergistic effect on the efficiency of the reaction. The supported catalyst system was recycled simply by filtration and reused for five times without significant decrease in its activity. The catalyst was characterized with PXRD, FTIR, TGA, XPS, BET, FE-SEM, EDS, elemental mapping and elemental analysis (CHN). Graphic Abstract: MOF/IL/urea catalytic system was used for the synthesis of oximes[Figure not available: see fulltext.].
- Askari, Saeed,Jafarzadeh, Mohammad,Christensen, David Benjamin,Kegn?s, S?ren
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p. 3159 - 3173
(2020/04/21)
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- Facile synthesis and docking studies of 7-hydroxyflavanone isoxazoles and acrylates as potential anti-microbial agents
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The present study is aimed to synthesize the novel 7-hydroxyflavanone derived compounds and to assess their biological activity. Two series of compounds such as 2-phenyl-7-((3-phenylisoxazol-5-yl)methoxy)chroman-4-ones (6a–h) and 4-oxo-2-phenylchroman-7-yl acrylates (8a–k) were synthesized from 7-hydroxyflavanone. All the compounds were subjected to anti-microbial activity and molecular docking studies. The results showed that the compounds 6e, 6g–h, 8h–i and 8k were exhibited most potent anti-microbial activity when compared with the standard drugs. Further, the docking studies revealed that the compounds 6a and 8h have the highest binding affinity score of sterol 14-α demethylase and DNA gyrase B respectively. This is the first report assigning unique synthesis of 7-hydroxyflavanone derivatives and their anti-microbial activity proved with in silico studies. Furthermore, the present study is useful for constructive research to synthesize novel compounds along with their biological activity. [Figure not available: see fulltext.].
- Asha Bhanu,China Raju,Jayavardhana Rao,Narasimha,Kesava Rao
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p. 217 - 228
(2019/11/28)
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- Tetrahydroquinoline-isoxazole/isoxazoline hybrid compounds as potential cholinesterases inhibitors: Synthesis, enzyme inhibition assays, and molecular modeling studies
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A series of 44 hybrid compounds that included in their structure tetrahydroquinoline (THQ) and isoxazole/isoxazoline moieties were synthesized through the 1,3-dipolar cycloaddition reaction (1,3-DC) from the corresponding N-allyl/propargyl THQs, previously obtained via cationic Povarov reaction. In vitro cholinergic enzymes inhibition potential of all compounds was tested. Enzyme inhibition assays showed that some hybrids exhibited significant potency to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Especially, the hybrid compound 5n presented the more effective inhibition against AChE (4.24 μM) with an acceptable selectivity index versus BChE (SI: 5.19), while compound 6aa exhibited the greatest inhibition activity on BChE (3.97 μM) and a significant selectivity index against AChE (SI: 0.04). Kinetic studies were carried out for compounds with greater inhibitory activity of cholinesterases. Structure–activity relationships of the molecular hybrids were analyzed, through computational models using a molecular cross-docking algorithm and Molecular Mechanics/Generalized Born Surface Area(MM/GBSA) binding free energy approach, which indicated a good correlation between the experimental inhibition values and the predicted free binding energy.
- Rodríguez Nú?ez, Yeray A.,Gutíerrez, Margarita,Alzate-Morales, Jans,Adasme-Carre?o, Francisco,Güiza, Fausto M.,Bernal, Cristian C.,Romero Bohórquez, Arnold R.
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- Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes: Total Synthesis of N-Me-Euphococcine
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O-Unprotected keto-and aldoximes are readily C-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly substituted N-α-secondary and tertiary homoallylic hydroxylamines. The method was used in the total synthesis of the trace alkaloid N-Me-Euphococcine.
- Kürti, László,Kattamuri, Padmanabha V.,Siitonen, Juha H.,Yousufuddin, Muhammed
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supporting information
(2020/03/24)
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- Exploring isoxazoles and pyrrolidinones decorated with the 4,6-dimethoxy-1,3,5-triazine unit as human farnesyltransferase inhibitors
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Unprecedented triazinyl-isoxazoles were afforded via an effective cycloaddition reaction between nitrile oxides and the scarcely described 2-ethynyl-4,6-dimethoxy-1,3,5-triazine as dipolarophile. The biological evaluation of the newly synthesized compounds showed that the inhibition of human farnesyltransferase by zinc complexation could be improved with triazine-isoxazole moieties. The replacement of the isoxazole unit by a pyrrolidin-2-one was detrimental to the inhibitory activity while the pyrrolidin-2-thione derivatives conserved the biological potential. The potential of selected compounds to disrupt protein farnesylation in Chinese hamster ovary (CHO) cells transfected with pEGFP-CAAX was also evaluated.
- Lucescu, Liliana,Ghinet, Alina,Shova, Sergiu,Magnez, Romain,Thuru, Xavier,Farce, Amaury,Rigo, Beno?t,Belei, Dalila,Dubois, Jo?lle,B?cu, Elena
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- Design, Synthesis and Anticancer Evaluation of New Substituted Thiophene-Quinoline Derivatives
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A series of new isoxazolyl, triazolyl and phenyl based 3-thiophen-2-yl-quinoline derivatives were synthesized adopting click chemistry approach. In addition, the synthesis of new useful synthon, (2-chloroquinolin-3-yl) (thiophen-2-yl) methanol, is reported. The obtained compounds were characterized by spectral data analysis and evaluated for their anticancer activity. All the derivatives were subjected to in vitro MTT cytotoxicity screening assay against a panel of four different human cancer cell lines, liver (HepG-2), colon (HCT-116), human cervical cancer (HeLa) and breast (MCF-7). Out of a library of 17 compounds, two compounds have been identified as potent and selective cytotoxic agents against HeLa and MCF-7 cell lines. SAR studies for such hybridized analogues were investigated and phenyl derivatives were proved to be more potent than isoxazole and triazole derivatives. Furthermore, the promising compounds were selected for in vitro inhibition of EGFR-TK and Topo II enzymes. Also, they were subjected to cell cycle arrest analysis and apoptosis assay on MCF-7 cells. Our recent finding highlights these thiophene-quinoline analogues as a promising class of compounds for further studies concerning new anticancer therapies.
- Othman, Dina I.A.,Selim, Khalid B.,El-Sayed, Magda A.-A.,Tantawy, Atif S.,Amen, Yhiya,Shimizu, Kuniyoshi,Okauchi, Tatsuo,Kitamura, Mitsuru
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- SO 2 F 2 -Promoted Dehydration of Aldoximes: A Rapid and Simple Access to Nitriles
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A rapid, simple and mild process for the dehydration of aldoximes to give the corresponding nitriles, which utilizes SO 2 F 2 as an efficient reagent, has been developed. A variety of (hetero)arene, alkene, alkyne and aliphatic aldoximes proceeded with high efficiency to afford nitriles in excellent to quantitative yields with great functional group compatibilities in acetonitrile under ambient conditions. Furthermore, an eco-friendly synthetic protocol to access nitriles from aldehydes with ortho -, meta - and para -nitrile groups was also described in aqueous methanol by using inorganic base Na 2 CO 3, and a one-pot synthetic strategy to generate nitriles from aldehydes was proved to be feasible.
- Ding, Chengrong,Mei, Guangyao,Wang, Haibo,Zhang, Guofu,Zhao, Yiyong
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supporting information
p. 1484 - 1488
(2019/07/15)
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- Structural and morphological aspects of small 3,5-disubstituted isoxazoles
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The structural and morphological features of small 3,5-disubstituted isoxazoles/isoxazolines are presented and discussed in the light of thermal analysis by differential scanning calorimetry (DSC), polarized optical microscopy (POM) technique, combined with single crystal X-ray diffraction and molecular modeling. The title compounds obtained were also characterized by 1H, 13C and 19F NMR. Two of the 3,5-diarylisoxazoles reported here contain totally hydrogenated or fluorinated benzene rings on both sides of the heterocycle. Partially hydrogenated and fluorinated molecules were prepared alternating the position of the benzene rings on 3- and 5-position of the isoxazoles. Other isoxazoles were synthesized to compare the influence of fluorine atoms on the transitional properties. They were synthesized in two steps, starting from [3 + 2] 1,3-dipolar cycloaddition reaction of nitrile oxides with alkenes to yield the isoxazolines and subsequent MnO2-oxidation process to reach the final isoxazoles.
- Lopes, Luana D.,Bortoluzzi, Adailton J.,Prampolini, Giacomo,dos Santos, Francisco P.,Livotto, Paolo R.,Merlo, Aloir A.
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- Design, synthesis and structure-based optimization of novel isoxazole-containing benzamide derivatives as FtsZ modulators
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Antibiotic resistance among clinically significant bacterial pathogens is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. Utilizing computational docking method and structure-based optimization strategy, we rationally designed and synthesized two series of isoxazol-3-yl- and isoxazol-5-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compounds B14 and B16 that possessed the isoxazol-5-yl group showed strong antibacterial activity against various testing strains, including methicillin-resistant Staphylococcus aureus and penicillin-resistant S. aureus. Further molecular biological studies and docking analyses proved that the compound functioned as an effective inhibitor to alter the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which finally terminated the cell division and caused cell death. Taken together, these results could suggest a promising chemotype for development of new FtsZ-targeting bactericidal agent.
- Bi, Fangchao,Song, Di,Zhang, Nan,Liu, Zhiyang,Gu, Xinjie,Hu, Chaoyu,Cai, Xiaokang,Venter, Henrietta,Ma, Shutao
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- Synthesis of new coumarin tethered isoxazolines as potential anticancer agents
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A series of new coumarin tethered isoxazolines (7a-l) were synthesized and evaluated for their cytotoxic potency against human melanoma cancer cell line (UACC 903) as well as fibroblast normal cell line (FF2441). Preliminary results revealed that some of these coumarin tethered isoxazolines 7b, 7c, 7f and 7j exhibited significant antiproliferative effect against human melanoma cancer (UACC 903) with IC50 values of 8.8, 10.5, 9.2 and 4.5 μM respectively. However, compound 7c was non-toxic to normal human cells at the tested concentration. Further, we have chosen compound 7c to check its efficacy in Ehrlich Ascites Carcinoma animal model in-vivo for its antitumor and antiangiogenic properties. Our lead compound significantly reduced the cell viability, body weight, ascites volume and downregulated the formation of neovasculature such as regression of tumor volume. The present study indicates the scope of developing into potent anticancer drug in near future.
- Lingaraju, Gejjalagere S.,Balaji, Kyathegowdanadoddi S.,Jayarama, Shankar,Anil, Seegehalli M.,Kiran, Kuppalli R.,Sadashiva, Maralinganadoddi P.
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supporting information
p. 3606 - 3612
(2018/11/06)
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- Design and Synthesis of Marine Phidianidine Derivatives as Potential Immunosuppressive Agents
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A series of novel marine phidianidine derivatives were designed, synthesized, and evaluated for their immunosuppressive activities during our search of potential immunosuppressive agents with high efficacy and low toxicity from marine sources. These compounds were tested for their inhibitory activity on Con A-induced T cell and lipopolysaccharide-induced B cell proliferation. Compounds 14a and 18c, displaying the most promising inhibitory effects and low toxicities, were further found to possess immune-regulatory activities upon cross-linking of T cell receptor (TCR) and B cell receptor (BCR) on purified T and B cells, respectively.
- Liu, Jin,Li, Heng,Chen, Kai-Xian,Zuo, Jian-Ping,Guo, Yue-Wei,Tang, Wei,Li, Xu-Wen
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p. 11298 - 11308
(2019/01/04)
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- Synthesis of novel 2H-chromene-3-carboxylate isoxazole/isoxazoline derivatives via 1,3-dipolar cycloaddition reaction (NOAC)
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Synthesis of novel (3-phenylisoxazol-5-yl)methyl-2H-chromene-3-carboxylates (7a–7d) and (3-phenyl-4,5-dihydroisoxazol-5-yl)methyl-2H-chromene-3-carboxylates (8a–8p) by 1,3-dipolar cycloaddition, and nitrile oxide and alkyne cycloaddition (NOAC) is presented. The products are characterised by IR, 1H and 13C NMR, and ESI-MS data.
- Srinivas,Krupadanam
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p. 331 - 339
(2017/04/13)
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- Design and synthesis of neolamellarin a derivatives targeting heat shock protein 90
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In this study, we designed and synthesized a novel family of neolamellarin A derivatives that showed high inhibitory activity toward heat shock protein 90 (Hsp90), a kinase associated with cell proliferation. The 3,4-bis(catechol)pyrrole scaffold and the benzyl group with methoxy modification at N position of pyrrole are essential to the Hsp90 inhibitory activity and cytotoxicity of these compounds. Western blot analysis demonstrated that these compounds induced dramatic depletion of the examined client proteins of Hsp90, and accelerated cancer cell apoptosis. Docking simulations suggested that the binding mode of 9p was similar to that of the VER49009, a potent inhibitor of Hsp90. Further molecular dynamics simulation indicated that the hydrophobic interactions as well as the hydrogen bonds contributed to the high affinity of 9p to Hsp90.
- Jiang, Long,Yin, Ruijuan,Wang, Xueting,Dai, Jiajia,Li, Jing,Jiang, Tao,Yu, Rilei
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supporting information
p. 24 - 33
(2017/04/21)
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- Asymmetric Nitrone Synthesis via Ligand-Enabled Copper-Catalyzed Cope-Type Hydroamination of Cyclopropene with Oxime
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We report realization of the first enantioselective Cope-type hydroamination of oximes for asymmetric nitrone synthesis. The ligand promoted asymmetric cyclopropene "hydronitronylation" process employs a Cu-based catalytic system and readily available starting materials, operates under mild conditions and displays broad scope and exceptionally high enantio- and diastereocontrol. Preliminary mechanistic studies corroborate a CuI-catalytic profile featuring an olefin metalla-retro-Cope aminocupration process as the key C-N bond forming event. This conceptually novel reactivity enables the first example of highly enantioselective catalytic nitrone formation process and will likely spur further developments that may significantly expedite chiral nitrone synthesis.
- Li, Zhanyu,Zhao, Jinbo,Sun, Baozhen,Zhou, Tingting,Liu, Mingzhu,Liu, Shuang,Zhang, Mengru,Zhang, Qian
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supporting information
p. 11702 - 11705
(2017/09/07)
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- Design, synthesis, molecular docking studies and anti-HBV activity of phenylpropanoid derivatives
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In this work, a series of phenylpropanoid derivatives were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated. Most of the synthesized derivatives showed effective anti-HBV activity. And compound 4d-3 showed the most effective anti-HBV activity, performing strong potent inhibitory not only on the secretion of HBsAg (IC50 = 58.28 μM, SI = 23.26) and HBeAg (IC50 = 97.21 μM, SI = 13.95), but also on the HBV DNA replication (IC50 = 42.28 μM, SI = 32.06). The structure-activity relationships (SARs) of the derivatives had been discussed, which were useful for developing phenylpropanoid derivatives as novel anti-HBV agents. Moreover, the docking study of all synthesized compounds inside the HLA-A protein (PDB ID: 3OX8) active site was carried out to explore the molecular interactions and a molecular target for activity and a modified assay method measuring the interaction between our derivatives and HBcAg was investigated, indicating that the HBV core protein might be their potential target for anti-HBV. This study identified a new class of potent non-nucleoside anti-HBV agents.
- Liu, Sheng,Li, Yubin,Wei, Wanxing,Wang, Kuiwu,Wang, Lisheng,Wang, Jianyi
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- Synthesis and antiproliferative properties of isoxazole analogs containing dibenzosuberane moiety
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A series of twelve novel isoxazole analogs containing dibenzosuberane moiety were synthesized using convergent synthesis approach. Newly synthesized compounds were well characterized by mass spectroscopy, IR and NMR spectroscopy. All the compounds were screened for their antiproliferative property against HepG2 and HeLa cell lines. Among them, compounds 7a, 7b, 7c, 7g and 7h were found active against both HepG2 and HeLa cell lines. Graphical Abstract: Twelve analogs of isoxazole containing dibenzosuberane moiety (7a-l) were synthesized, characterized and evaluated for their antiproliferative activity. [Figure not available: see fulltext.]
- Moger, Manjunath,Pradhan, Ashok,Singh, Apoorva,Govindaraju, Darshan Raj Chenna,Hindupur, Rama Mohan,Pati, Hari N.
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p. 449 - 455
(2016/02/19)
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- Copper(ii)-promoted direct conversion of methylarenes into aromatic oximes
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A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
- Yu, Jiatao,Lu, Ming
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supporting information
p. 7397 - 7401
(2015/07/15)
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- Copper(II)-promoted direct conversion of methylarenes into aromatic oximes
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A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
- Yu, Jiatao,Lu, Ming
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supporting information
p. 7397 - 7401
(2015/11/27)
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- Synthesis and structure-activity relationships of pyridinyl-1 H -1,2,3-triazolyldihydroisoxazoles as potent inhibitors of tubulin polymerization
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Three series of compounds; pyridinyl-1H-1,2,3-triazoles, pyridinyl-1H-1,2,3-triazolylisoxazoles and pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles with TMP moiety were designed, synthesized and screened for their anti-cancer and anti-tubulin properties. By sequentially designing three series of compounds comprising of dihydroisoxazole in the linker, a small substituent like chlorine on one side (R1) and aromatic group (R) on the pyridine ring, we have optimized the anti-cancer as well as anti-tubulin activity. Pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles 28b and 28c were found to be potent anti-cancer agents against all the cell lines tested with a concomitant accumulation of cells in the G2/M phase of the cell cycle. Molecular modeling suggests that the trimethoxyphenyl ring in 28b and 28c occupies the cholchicine binding domain of β-tubulin, whereas, the dihydroisoxazole extends towards the interface of α/β-tubulin.
- Suman,Murthy, T. Ramalinga,Rajkumar,Srikanth,Dayakar,Kishor, Chandan,Addlagatta, Anthony,Kalivendi, Shasi V.,Raju, B. China
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p. 603 - 619
(2015/02/19)
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- Oxime carbamates as potential insecticidal agents: Design, synthesis and biological evaluation
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A series of oxime carbamates derivatives were designed and synthesized as a part of our ongoing search for novel high potential agrochemicals. Their structures were confirmed by 1H NMR, 13C NMR and elemental analysis. The bioassays results indicated that some of the obtained compounds exhibited good insecticidal activity against Heliothis armigera and Plutella xylostella.
- Ke, Shaoyong,Yang, Ziwen,Shi, Liqiao,Liu, Manli,Liang, Ying,Wang, Kaimei,Long, Tong,Jiang, Aibing,Zhang, Zhigang
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p. 771 - 777
(2015/10/05)
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- Iron-Catalyzed C-N Bond Formation via the Beckmann Rearrangement
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A simple, iron-based catalytic system allows for facile Beckmann rearrangement of various oximes. The mild conditions avoid the use of harsh or expensive acids, and the reactions do not require an inert atmosphere. Additionally, a range of amides can be accessed through this transformation.
- Jefferies, Latisha R.,Weber, Savannah R.,Cook, Silas P.
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supporting information
p. 331 - 334
(2015/02/19)
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- APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT
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PROBLEM TO BE SOLVED: To prepare analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. SOLUTION: The present invention relates to an N6-substituted adenosine derivative and an N6-substituted adenine derivative selected from the group consisting of specific compounds. The present invention also relates to a pharmaceutical composition at least comprising a therapeutically effective amount of the compounds and a pharmaceutically acceptable carrier. The invention further relates to the compounds used in preparation of analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0129
(2018/10/27)
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- 3-methyl-4-oxa-5-azahomoadamantane as an organocatalyst for the aerobic oxidation of primary amines to oximes in water
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A simple and efficient catalytic system for the aerobic oxidation of primary amines into corresponding oximes has been developed, with 3-methyl-4-oxa-5-azahomoadamantane as catalyst, acetaldoxime as co-catalyst and water as solvent. This process, which uses oxygen (O2) as an economic and green oxidant and water as a green solvent, tolerates a wide range of substrates, affording the target oximes in moderate to excellent yields. It was found that high selectivity was achieved when 3-methyl-4-oxa-5-azahomoadamantane was used, and E-type oximes were the only detected products. A possible mechanism for this catalytic process is proposed.
- Yu, Jiatao,Jin, Yong,Lu, Ming
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supporting information
p. 1175 - 1180
(2015/04/22)
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- Design, synthesis and in vitro cytotoxicity evaluation of new 3',4'-bis (3,4,5-trisubstituted)-4'H-spiro[indene-2,5'-isoxazol]-1(3H)-one derivatives as promising anticancer agents
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A new series of 3',4'-bis(3,4,5-trimethoxyphenyl)-4'H-spiro[indene-2,5'-isoxazol]-1(3H)-one derivatives was designed and synthesized. The cytotoxic effects of the synthesized compounds were evaluated on several different human cancer cells. Among them, compound 9e displayed the most potent in vitro antiproliferative activity with IC50 values of 0.07±0.01 μM on T47D cells. Another potent derivative 9h displayed an IC50 value of 0.12±0.07 μM against T47D cells, comparable to that of the positive controls (Colchicine' Cisplatin' Vincristine' Vinblastine' Doxorubicin' Celecoxib). The structure-activity relationships were discussed and both anti-tubulin and COX-2 inhibitory effects were proposed for the developed compounds
- Abolhasani, Hoda,Zarghi, Afshin,Abolhasani, Ahmad,Hamzeh-Mivehroud, Maryam,Bargahi, Nasrin,Notash, Behrouz,Mojarrad, Javid Shahbazi,Dastmalchi, Siavoush
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p. 1149 - 1161
(2015/03/31)
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- Metal-Free: A novel and efficient aerobic oxidation of primary amines to oximes using N, N', N''-trihydroxyisocyanuric acid and acetaldoxime as catalysts in water
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A general, efficient, and metal-free method for aerobic oxidation of aromatic primary amines to the corresponding oximes catalyzed by N,N',N''-trihydroxyisocyanuric acid and acetaldoxime with water as solvent is described. This practical method can use air as economic and green oxidant, water as green solvent, and tolerates a wide range of substrates, which can afford the target oximes in moderate to good yields. Georg Thieme Verlag Stuttgart. New York.
- Yu, Jiatao,Lu, Ming
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p. 1873 - 1878
(2014/08/18)
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- Sodium nitrite-catalyzed aerobic oxidative Csp2-Csp3 coupling: Direct construction of the 4-aryldihydroisoquinolinone moiety
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A bioinspired approach for the construction of the 4- aryldihydroisoquinolinone moiety via direct oxidative Csp2-Csp 3 coupling has been developed, which uses inexpensive sodium nitrite as catalyst and environmentally benign oxygen in the air as terminal oxidant.
- Su, Bo,Deng, Meng,Wang, Qingmin
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supporting information
p. 977 - 981
(2014/04/03)
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- A novel and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to oximes
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A simple and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to corresponding oximes by using toluene as the solvent is described. This practical method can use O2 as the economic and green oxidant, tolerate a wide range of substrates, which can afford the target oximes in moderate to excellent yields.
- Yu, Jiatao,Cao, Xiaohua,Lu, Ming
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supporting information
p. 5751 - 5755
(2015/02/02)
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- Iodine(III)-Mediated [3 + 2] cyclization for one-pot synthesis of benzo[ d ]isoxazole-4,7-diols in aqueous medium
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A one-pot [3 + 2] cycloadditive synthesis of benzo[d]isoxazole-4,7-diols in aqueous medium was carried out via nitrile oxides and benzoquinone intermediates by taking advantage of iodobenzene diacetate as an oxidant. This method can also be used to synthesize benzodiisoxazole-4,8-diols, isoxazolo[5,4-a]phenazines, and indazole-4,7-diols, which are difficult to obtain by classical methods.
- Hou, Yingwei,Lu, Shichao,Liu, Gang
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p. 8386 - 8395
(2013/09/24)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Paragraph 0208
(2013/03/26)
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- Amidobenzothiazoles And Process For The Preparation Thereof
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The present invention provides a compound of general formulae A useful as potential anti-cancer agents against human cancer cell lines and a process for the preparation thereof. Where in R, R1, R2═H, alkyl, alkoxy, halo, haloalkyl, halomethoxy, nitro and G= Where in R, R1, R2═H, alkyl, alkoxy, halo, haloalkyl, halomethoxy, nitro and G=
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- Synthesis of podophyllotoxin and its derivatives via nicl2/nabh4 reduction of isoxazoline ring
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A novel synthesis of podophyllotoxin was carried out in four steps. The key step was reduction of isoxazoline ring followed by diazotization and the resultant alkene was treated with Mn(OAc)3/CH3COOK to form podophyllotoxin.
- Babu, Meduri Suresh,Rai, Kuria Madhavu Lokanatha
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p. 9555 - 9557
(2014/01/06)
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- Anthranilic acid-based diamides derivatives incorporating aryl-isoxazoline pharmacophore as potential anticancer agents: Design, synthesis and biological evaluation
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A series of novel anthranilic diamides derivatives containing aryl-isoxazoline moiety were designed and synthesized as a part of our ongoing search for potential anticancer agents. Their structures were confirmed by 1H NMR, 13C NMR and ESI-MS analyses. The preliminary assays showed that some of the compounds displayed moderate to good antitumor activities against human lung cancer (NCI-H460), hepatocellular liver carcinoma (HepG2), gastric cancer (SGC-7901 and BGC-823) and breast epithelial adenocarcinoma (MCF-7) cell lines at μM level, which might be developed as novel lead scaffold for potential anticancer agents.
- Shi, Liqiao,Hu, Rui,Wei, Yanhong,Liang, Ying,Yang, Ziwen,Ke, Shaoyong
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experimental part
p. 549 - 556
(2012/09/07)
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- Synthesis and evaluation of indole-containing 3,5-diarylisoxazoles as potential pro-apoptotic antitumour agents
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A series of novel indole-containing diarylisoxazoles has been synthesised, based on our previous work on the synthesis and pro-apoptotic antitumour activity of indole-based diaryl 1,2,4-oxadiazoles. Concise synthetic routes to both 3-(indol-2-yl)-5-phenylisoxazoles and 5-(indol-2-yl)-3-phenylisoxazoles have been developed with full regiochemical control, bearing substituents on the indole ring, indole nitrogen, and/or phenyl group. Additionally a series of the related 5-(1H-indol-5-yl)-3-phenylisoxazoles has been prepared. In vitro evaluation in human cancer cell lines Colo320 (colon) and Calu-3 (lung) revealed preferential antiproliferative activity within the 5-(indol-5-yl)-3- phenylisoxazole series (low micromolar IC50). Further analysis revealed the ability of the indol-5-yl series to induce expression of effector caspases-3 and -7, and retention of viability of the human bronchial smooth muscle cell (BSMC) control cell population (particularly for compounds 18c and 18e).
- Md Tohid, Siti Farah,Ziedan, Noha I.,Stefanelli, Fabio,Fogli, Stefano,Westwell, Andrew D.
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p. 263 - 270
(2013/01/15)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES, N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Page/Page column 58
(2012/11/06)
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- Synthesis and biological evaluation of 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydroquinazolinone hybrids as anticancer agents
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A series of new 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydro quinazolinone hybrids with different linker architectures have been designed and synthesized. These compounds have been evaluated for their anticancer activity. One of the compounds 4c amongst this series has shown promising anticancer activity. Further some detailed biological assays relating to the cell cycle aspects and tubulin depolymerization activity have been examined with a view to understand the mechanism of action of this conjugate.
- Kamal, Ahmed,Bharathi, E. Vijaya,Reddy, J. Surendranadha,Ramaiah, M. Janaki,Dastagiri,Reddy, M. Kashi,Viswanath,Reddy, T. Lakshminarayan,Shaik, T. Basha,Pushpavalli,Bhadra, Manika Pal
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experimental part
p. 691 - 703
(2011/03/22)
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- Design, synthesis and biological evaluation of 3,5-diaryl-isoxazoline/ isoxazole-pyrrolobenzodiazepine conjugates as potential anticancer agents
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A series of 3,5-diaryl-isoxazoline/isoxazole linked pyrrolo[2,1-c][1,4] benzodiazepine (PBD) conjugates were prepared. These conjugates showed potent anticancer activity with GI50 values in the range of 0.1-3.6 μM. Some of these PBD conjugates (6a-c) with promising anticancer activity were further investigated on the cell cycle distribution. Moreover, these PBD conjugates exhibited G0/G1 arrest, enhancement in the levels of p53 protein as well as mitochondrial-mediated intrinsic pathway, leading to release of cytochrome c, activation of caspase-3, cleavage of PARP and subsequent apoptotic cell death. Hence these PBD conjugates with 6a being the most potent one could be be taken up for preclinical studies either alone or in combination with existing therapies. New class of 3,5-diaryl-isoxazoline/isoxazole- pyrrolobenzodiazepine conjugates were prepared and evaluated for their anticancer activity. Further, some of the biological assays related to mechanism aspects were also carried out.
- Kamal, Ahmed,Surendranadha Reddy,Janaki Ramaiah,Dastagiri,Vijaya Bharathi,Ameruddin Azhar,Sultana, Farheen,Pushpavalli,Pal-Bhadra, Manika,Juvekar, Aarti,Sen, Subrata,Zingde, Surekha
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scheme or table
p. 3924 - 3937
(2010/09/11)
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- A simple and effective glycine-catalysed procedure for the preparation of oximes
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Ketoximes and aldoximes are expeditiously prepared by the reaction of the corresponding carbonyl compound with hydroxylamine hydrochloride in dimethylformamide, in the presence of a sub-stoichiometric quantity of glycine at room temperature. Mild (non-hydroxylic) conditions, simple workup and high yield characterise the methodology.
- Maheswara, Muchchintala,Siddaiah, Vidavalur,Gopalaiah, Kovuru,Rao, Vallabhaneni Madhava,Rao, Chunduri Venkata
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p. 362 - 363
(2007/10/03)
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- Heterocyclic and phenyl double-bond-locked combretastatin analogues possessing potent apoptosis-inducing activity in HL60 and in MDR cell lines
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Two new series of combretastatin (CA-4) analogues have been prepared. The alkenyl motif of CA-4 was replaced either by a five-membered heterocyclic (isoxazoline or isoxazole) or by a six-membered ring (pyridine or benzene). The new compounds have been evaluated for their effects on tubulin assembly and for cytotoxic and apoptotic activities. Five compounds (18b, 20a, 21a, 34b, and 35b) demonstrated an attractive profile of cytotoxicity (IC50 1 μM) and apoptosis-inducing activity but poor antitubulin activity. The isoxazoline derivatives 18b, 20a, and 21a, demonstrated potent apoptotic activity different from that of natural CA-4. Their ability to block most cells in the G2 phase suggests that these compounds could act on targets different from the mitotic spindle. This would indicate activation of both the intrinsic and the extrinsic apoptotic pathways. The data suggest unambiguously that structural alteration of the stilbene motif of CA-4 can be extremely effective in producing potent apoptosis-inducing agents.
- Simoni, Daniele,Grisolia, Giuseppina,Giannini, Giuseppe,Roberti, Marinella,Rondanin, Riccardo,Piccagli, Laura,Baruchello, Riccardo,Rossi, Marcello,Romagnoli, Romeo,Invidiata, Francesco Paolo,Grimaudo, Stefania,Jung, M. Katherine,Hamel, Ernest,Gebbia, Nicola,Crosta, Lucia,Abbadessa, Vincenzo,Di Cristina, Antonietta,Dusonchet, Luisa,Meli, Maria,Tolomeo, Manlio
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p. 723 - 736
(2007/10/03)
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- One-pot oxidation of azomethine compounds into arenecarboxylic acids
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Aromatic azomethine compounds, such as aldazines 1, aldoximes 7 and tosylhydrazones 8 oxidized with 30% hydrogen peroxide in the presence of poly(bis-1,2-phenylene) diselenide (6) as catalyst produce arenecarboxylic acids 2 mostly in high to excellent yields. The presented one-pot procedure has a synthetic value.
- Giurg,Said,Syper,Mlochowski
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p. 3151 - 3159
(2007/10/03)
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- Synthesis and Antitubercular Activity of 4-(5-Nitro-2-furyl/2-pyrazinyl/1-adamantyl)-2-(alkyl/aryl/arylamino)thiazoles
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The reaction of haloketones, obtained from Arndt-Eistert reaction on the acid chlorides of 1-adamantane, 5-nitrofuroic acid and pyrazine-2-carboxylic acid, with different thioamides and thioureas affords the title thiazoles (I-III).Some of them exhibit interesting antitubercular activity at 6.25 to 0.38 μg/ml concentration against H37Rv strain of M. tubercolosis in vitro testing.The structure activity relationship (SAR) has also been discussed.
- Khadse, B. G.,Lokhande, S. R.,Bhamaria, R. P.,Prabhu, S. R.
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p. 856 - 860
(2007/10/02)
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