- A Facile Synthesis of 2-Aminopropane-1,2,3-tricarboxylic Acid and Its Symmetrical Dimethyl Ester
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A new convenient synthetic route to 2-aminopropane-1,2,3-tricarboxylic acid is described. The first two stages of the threestep synthesis are performed in a one-pot procedure and include the cyclization of hippuric acid with DCC followed by treatment with methyl bromoacetate to yield an alkylated oxazolone. Its hydrolysis with HCl provides 2-aminopropane-1,2,3-tricarboxylic acid as its HCl salt. Esterification of the resulting acid with methanol in the presence of thionyl chloride leads selectively to its symmetrical diester.
- Nizovtsev, Alexey V.,Bovin, Nicolai V.
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supporting information
p. 4428 - 4432
(2021/08/20)
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- Synthesis and in vitro carbonic anhydrases and acetylcholinesterase inhibitory activities of novel imidazolinone-based benzenesulfonamides
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New imidazolinone-based benzenesulfonamides 3a–e and 4a–e were synthesized in three steps?and their chemical structures were confirmed by 1H NMR (nuclear magnetic resonance), 13C NMR, and high-resolution mass spectrometry. The benzenesulfonamides used were sulfacetamide (3a, 4a), sulfaguanidine (3b, 4b), sulfanilamide (3c, 4c), sulfadiazine (3d, 4d), sulfamerazine (3e), and sulfathiazole (4e). The compounds were evaluated against carbonic anhydrase (CA) and acetylcholinesterase (AChE) enzymes to obtain possible drug candidate/s. The lead compounds of the series were 3a and 4a against human CA (hCA) I, whereas?3d and 4a were leads against hCA II in terms of Ki values. Series 4 includes more effective CAs inhibitors than series 3 (except 3d). Series 4 compounds having a nitro group (except 4d) were 3.3–4.8 times more selective inhibitors than their corresponding analogues 3a–d in series 3, in which hydrogen was located in place of the nitro group, by considering Ki values against hCA II. Compounds 3c and 4c, where the sulfanilamide moiety is available, were the leads in terms of AChE inhibition with the lowest Ki values. The use of secondary sulfonamides was a more effective modification on CA inhibition, whereas the primary sulfonamide was the effective substitution in terms of AChE inhibitory potency.
- Tugrak, Mehtap,Gul, Halise Inci,Demir, Yeliz,Levent, Serkan,Gulcin, Ilhami
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- Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents
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As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value of 4Bs was above 526, indicating the favorable safety profile. Interestingly, unlike nucleoside analogue 3TC, 4Bs could significantly inhibit 3.5 kb pgRNA expression. Molecular docking study revealed that 4Bs could fit well into the dimer-dimer interface of HBV core protein by hydrophobic, π–π and H-bond interactions. Considering the potent anti-HBV activity, low toxicity and diverse anti-HBV mechanism from that of nucleoside anti-HBV agent 3TC, compound 4Bs might be a promising lead to develop novel non-nucleoside anti-HBV therapeutic agents, and warranted further investigation.
- Gu, Xiaoke,Zhang, Yinpeng,Zou, Yueting,Li, Xin,Guan, Mingyu,Zhou, Qingqing,Qiu, Jingying
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- Cu(II)-promoted oxidative C-N bond cleavage of N-benzoylamino acids to primary aryl amides
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A novel protocol for CuCl2-promoted oxidative C-N bond cleavage of N-benzoyl amino acids was developed. It is the first example of using accessible amino acid as an ammonia synthetic equivalent for the synthesis of primary aryl amides via CuCl2-promoted oxidative C-N bond cleavage reaction. The present protocol shows excellent functional group tolerance and provides an alternative method for the synthetic of primary aryl amides in 84-96% yields.
- Zhou, Liandi,Liu, Wei,Zhao, Yongli,Chen, Junmin
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- Design, synthesis and anti-inflammatory/analgesic evaluation of novel di-substituted urea derivatives bearing diaryl-1,2,4-triazole with dual COX-2/sEH inhibitory activities
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Herein, two novel series of diaryl-1,2,4-triazole hybrid to amide conjugates (5a-e) or urea conjugates (10a-f) have been synthesized followed by in vitro evaluation against cyclooxygenase-2/soluble epoxide hydrolase (COX-2/sEH) enzymes using ELISA enzyme assays. In vivo analgesic and anti-inflammatory activities for the new compounds have been carried out using the reported animal protocols. The preliminary results revealed that compounds 10e and 10c were the most active compounds against both COX-2/sEH enzymes (COX-2 IC50 = 1.98 μM and 2.13 μM; sEH = 1.09 and 1.23 nM, respectively). Moreover, the in vivo screening assays confirmed their superiority compared to the other derivatives by exhibiting higher anti-inflammatory and analgesic activity (91.27 and 89.32% edema inhibition; 55.97–50.00% writhing inhibition, respectively) than celecoxib (88.30% edema inhibition; 13.43% writhing inhibition). Collectively, compounds 10e and 10c can be considered as promising dual COX-2/sEH inhibitors with expected less cardiovascular adverse effects affording good anti-inflammatory and analgesic leads for further optimization.
- Abdelazeem, Ahmed H.,El-Din, Asmaa G. Safi,Arab, Hany H.,El-Saadi, Mohammed T.,El-Moghazy, Samir M.,Amin, Noha H.
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- 4-Sulfamoylphenylalkylamides as Inhibitors of Carbonic Anhydrases Expressed in Vibrio cholerae
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A current issue of antimicrobial therapy is the resistance to treatment with worldwide consequences. Thus, the identification of innovative targets is an intriguing challenge in the drug and development process aimed at newer antimicrobial agents. The state-of-art of anticholera therapy might comprise the reduction of the expression of cholera toxin, which could be reached through the inhibition of carbonic anhydrases expressed in Vibrio cholerae (VchCAα, VchCAβ, and VchCAγ). Therefore, we focused our interest on the exploitation of sulfonamides as VchCA inhibitors. We planned to design and synthesize new benzenesulfonamides based on our knowledge of the VchCA catalytic site. The synthesized compounds were tested thus collecting useful SAR information. From our investigation, we identified new potent VchCA inhibitors, some of them displayed high affinity toward VchCAγ class, for which few inhibitors are currently reported in literature. The best interesting VchCAγ inhibitor (S)-N-(1-oxo-1-((4-sulfamoylbenzyl)amino)propan-2-yl)furan-2-carboxamide (40) resulted more active and selective inhibitor when compared with acetazolamide (AAZ) as well as previously reported VchCA inhibitors.
- Mancuso, Francesca,De Luca, Laura,Bucolo, Federica,Vrabel, Milan,Angeli, Andrea,Capasso, Clemente,Supuran, Claudiu T.,Gitto, Rosaria
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p. 3787 - 3794
(2021/10/20)
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- Synthesis, antimicrobial evaluation and docking studies of oxazolone-1,2,3-triazole-amide hybrids
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In an attempt to develop quality antimicrobial agents, a series of oxazolone-1,2,3-triazole-amide hybrids were obtained from oxazolone tethered with a terminal alkyne and in situ generated 2-azido-N-phenylacetamides. All the synthesized compounds were characterized by using various spectroscopic techniques. The developed hybrids were evaluated for their in vitro antimicrobial activity toward three Gram-positive bacteria S. aureus, B. subtilis and S. gorodonii and three Gram-negative bacteria—E. coli, S. enterica and P. aeruginosa—and two fungi, viz. C. albicans and A. niger. Oxazolone-amide-1,2,3-triazoles (8a–e, 9a–e, 10a–e) exhibited almost 15 times better efficacy than alkyne precursors, i.e., oxazolone-linked terminal alkynes (6a–c). Compound 10d exhibited very good antimicrobial activity toward all the tested microorganisms. Docking studies of compounds 10d and 6c were also carried out in the binding site of enzyme sterol-14-α-demethylase of C. albicans, which supported the in vitro experimental results.
- Kumar, Lokesh,Lal, Kashmiri,Kumar, Aman,Kumar, Ashwani
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p. 5079 - 5097
(2021/09/22)
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- Site-Specific Oxidation of (sp3)C-C(sp3)/H Bonds by NaNO2/HCl
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A site-specific oxidation of (sp3)C-C(sp3) and (sp3)C-H bonds in aryl alkanes by the use of NaNO2/HCl was explored. The method is chemical-oxidant-free, transition-metal-free, uses water as the solvent, and proceeds under mild conditions, making it valuable and attractive to synthetic organic chemistry.
- Zhao, Jianyou,Shen, Tong,Sun, Zhihui,Wang, Nengyong,Yang, Le,Wu, Jintao,You, Huichao,Liu, Zhong-Quan
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p. 4057 - 4061
(2021/05/26)
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- Base Induced Condensation of Malononitrile with Erlenmeyer Azlactones: An Unexpected Synthesis of Multi-Substituted Δ2-Pyrrolines and Their Cytotoxicity
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An efficient, metal free approach to synthesize multi-substituted Δ2-pyrroline derivatives by mild base catalyzed cyclocondensation of malononitrile with Erlenmeyer azlactones via 1,2 addition was developed. The modularity of this reaction was used to assemble a range of poly-substituted pyrrolines. Further, synthesized products were screened for cytotoxic properties on different cancer cell lines such as A549 (Human lung adenocarcinoma cells), HeLa (Human cervical adenocarcinoma cells), Jurkat (Human chronic myeloid leukemia cells) and K562 (Human leukemic T cell Lymphoblast cells). Among the synthesized library of compounds, 6f and 6q displayed potent cytotoxic activity.
- Anil, Seegehalli M.,Kiran, Kuppalli R.,Rajeev, Narasimhamurthy,Sadashiva, Maralinganadoddi P.,Shobith, Rangappa,Sudhanva, Muddenahalli S.,Swaroop, Toreshettahally R.,Vinayaka, Ajjampura C.
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- Synthesis and pharmacological effects of novel benzenesulfonamides carrying benzamide moiety as carbonic anhydrase and acetylcholinesterase inhibitors
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N-(1-(4-Methoxyphenyl)-3-oxo-3-((4-(N-(substituted)sulfamoyl)phenyl)amino)prop-1-en-1-yl)benzamides 3a - g were designed since sulfonamide and benzamide pharmacophores draw great attention in novel drug design due to their wide range of bioactivities including acetylcholinesterase (AChE) and human carbonic anhydrase I and II (hCA I and hCA II) inhibitory potencies. Structure elucidation of the compounds was carried out by 1H NMR, 13C NMR, and HRMS spectra. In vitro enzyme assays showed that the compounds had significant inhibitory potential against hCA I, hCA II, and AChE enzymes at nanomolar levels. Ki values were in the range of 4.07 ± 0.38 - 29.70 ± 3.18 nM for hCA I and 10.68 ± 0.98 - 37.16 ± 7.55 nM for hCA II while Ki values for AChE were in the range of 8.91 ± 1.65 - 34.02 ± 5.90 nM. The most potent inhibitors 3g (Ki = 4.07 ± 0.38 nM, hCA I), 3c (Ki = 10.68 ± 0.98 nM, hCA II), and 3f (Ki = 8.91 ± 1.65 nM, AChE) can be considered as lead compounds of this study with their promising bioactivity results. Secondary sulfonamides showed promising enzyme inhibitory effects on AChE while primary sulfonamide derivative was generally effective on hCA I and hCA II isoenzymes.
- Tu?rak, Mehtap,Gül, Halise Inci,Anil, Bar??,Gül?in, Ilhami
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p. 1601 - 1609
(2021/01/05)
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- Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates
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Earth-abundant nickel, coordinated with a suitable chiral bisphosphine ligand, was found to be an efficient catalyst for the asymmetric hydrogenation of 2-amidoacrylates, affording the chiral α-amino acid esters in quantitative yields and excellent enantioselectivity (up to 96 % ee). The active catalyst component was studied by NMR and HRMS, which helped us to realize high catalytic efficiency on a gram scale with a low catalyst loading (S/C=2000). The hydrogenated products could be simply converted into chiral α-amino acids, β-amino alcohols, and their bioactive derivatives. Furthermore, the catalytic mechanism was investigated using deuterium-labeling experiments and computational calculations.
- Chen, Jianzhong,Gridnev, Ilya D.,Hu, Yawen,Li, Bowen,Zhang, Wanbin,Zhang, Zhenfeng
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supporting information
p. 5371 - 5375
(2020/02/15)
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- A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids
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Abstract: –A simple trituration method for the synthesis of 2-substituted benzothiazoles derived from N-protected amino acids and 2-aminothiophenol using molecular iodine as a mild Lewis acid catalyst has been proposed. The reaction occurs in one step for 20–25 min in solve-free conditions and provides the target products in excellent yields.
- Arfan, M.,Fatima, T.,Mannan, A.,Tahira, A.
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p. 292 - 297
(2020/04/21)
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- 5-(4H)-oxazolones and their benzamides as potential bioactive small molecules
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The five membered heterocyclic oxazole group plays an important role in drug discovery. Oxazolones present a wide range of biological activities. In this article the synthesis of 4-substituted-2-phenyloxazol-5(4H)-ones from the appropriate substituted aldehydes via an Erlenmeyer-Plochl reaction is reported. Subsequently, the corresponding benzamides were produced via a nucleophilic attack of a secondary amine on the oxazolone ring applying microwave irradiation. The compounds are obtained in good yields up to 94percent and their structures were confirmed using IR, 1H-NMR, 13C-NMR and LC/MS data. The in vitro anti-lipid peroxidation activity and inhibitory activity against lipoxygenase and trypsin induced proteolysis of the novel derivatives were studied. Inhibition of carrageenin-induced paw edema (CPE) and nociception was also determined for compounds 4a and 4c. Oxazolones 2a and 2c strongly inhibit lipid peroxidation, followed by oxazolones 2b and 2d with an average inhibition of 86.5percent. The most potent lipoxygenase inhibitor was the bisbenzamide derivative 4c, with IC50 41 μM. The benzamides 3c, 4a-4e and 5c were strong inhibitors of proteolysis. The replacement of the thienyl moiety by a phenyl group does not favor the protection. Compound 4c inhibited nociception higher than 4a. The replacement of thienyl groups by phenyl ring led to reduced biological activity. Docking studies of the most potent LOX inhibitor highlight interactions through allosteric mechanism. All the potent derivatives present good oral bioavailability.
- Bermperoglou, Eleftherios,Hadjipavlou-Litina, Dimitra,Mavridis, Evangelos,Pontiki, Eleni
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- Discovery of N-(2-(Benzylamino)-2-oxoethyl)benzamide analogs as a novel scaffold of pancreatic β-cell protective agents against endoplasmic reticulum stress
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Endoplasmic reticulum (ER) stress-induced pancreatic β-cell dysfunction and death play important roles in the development of diabetes. The 1,2,3-triazole derivative 1 is one of only a few structures that have thus far been identified that protect β cells against ER stress. However, this compound has narrow activity range and limited aqueous solubility. To overcome these, we designed and synthesized a new scaffold in which the triazole pharmacophore was substituted with a glycine-like amino acid. Structure–activity relationship studies on this scaffold identified a N-(2-(Benzylamino)-2-oxoethyl)benzamide analog WO5m that possesses β-cell protective activity against ER stress with much improved potency (maximal activity at 100% with EC50 at 0.1?±?0.01?μm) and water solubility. Identification of this novel β-cell protective scaffold thus provides a new promising modality for the treatment of diabetes.
- Eeda, Venkateswararao,Herlea-Pana, Oana,Lim, Hui-Ying,Wang, Weidong
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p. 388 - 393
(2020/01/02)
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- Synthesis, assessment and corrosion protection investigations of some novel peptidomimetic cationic surfactants: Empirical and theoretical insights
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Three novel peptidomimetic cationic surfactants were synthesized in good yields. The chemical configurations of these surfactants were clarified using 1H, 13C NMR and FT-IR spectroscopy. The inhibition capacity and adsorption performance of these compounds on C-steel were studied by electrochemical techniques (Electrochemical impedance spectroscopy (EIS) and Potentiodynamic polarization (PDP) methods). The prepared compounds demonstrated outstanding protection power for the erosion of C-steel in 0.5 M HCl at 323 K. The PDP studies demonstrated that the novel surfactants behaved as mixed-type additives. The protection capacity rises with an increasing surfactant dose, with values ranging from 93.10 to 98.25percent at 100 ppm. The adsorption of additives on the electrode interface follows the Langmuir model and contains chemisorption modes. The Monte Carlo (MD) simulations and density functional theory (DFT) calculations support the experimental findings and provide insight into the understanding of the adsorption features and protection performance mechanisms of the examined surfactants.
- Abd El-Lateef, Hany M.,Abdrabo, Wessam S.,Elgendy, Bahaa,Soliman, Kamal A.,Tantawy, Ahmed H.
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- Reactivity of Tyrosyl–Proline toward Benzoylation in Aqueous 1,4-Dioxane
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Abstract: The kinetics of the reaction of L-tyrosyl-L-proline (Tyr–Pro) with di- andtrinitrophenyl benzoates in aqueous 1,4-dioxane (40 wt percent of water) were studiedin the temperature range 298–313 K. The reaction rate constant k298 was fou
- Khachatryan, D. S.,Kochetova, L. B.,Kustova, T. P.,Lokteva, I. I.
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p. 1034 - 1040
(2020/07/25)
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- GRANZYME B DIRECTED IMAGING AND THERAPY
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Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.
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Page/Page column 82; 98
(2019/09/04)
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- Concise Modular Synthesis of Thalassotalic Acids A-C
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The novel N-acyldehydrotyrosine analogues known as thalassotalic acids A-C were isolated from a marine bacterium by Deering et al. in 2016. These molecules were shown to have tyrosinase inhibition activity and thus are an attractive set of molecules for further study and optimization. To this end, a concise and modular synthesis has been devised and executed to produce thalassotalic acids A-C and two unnatural analogues. This synthesis has confirmed the identity and inhibitory data of thalassotalic acids A-C, more potent synthetic analogues (IC50 = 65 μM), and provides a route for further structure-activity relationship studies to optimize these molecules.
- Schulz, Joseph M.,Lanovoi, Hunter T.,Ames, Amanda M.,McKegg, Phillip C.,Patrone, James D.
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supporting information
p. 1045 - 1048
(2019/05/14)
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- Piperidine thiazole derivative containing bisamide structure as well as preparation method and application thereof
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The invention discloses a piperidine thiazole derivative containing a bisamide structure, and also discloses a preparation method of the piperidine thiazole derivative and application of the piperidine thiazole derivative as a sterilization agent and an insecticide. The invention provides the novel piperidine thiazole derivative containing the bisamide structure; the preparation method is simpleand convenient; the piperidine thiazole derivative can be used for preventing and treating cucumber gray mold, rice sheath blight diseases and potato late blight diseases, has good sterilization activity, can be used for preventing and treating insect pest of armyworm, black bean aphid, tetranychus telarius linne and the like, and lays the foundation for the invention and development of piperidinethiazole pesticides.
- -
-
Paragraph 0020
(2019/02/03)
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- Synthesis, biological evaluation and in silico studies with 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides as novel selective carbonic anhydrase IX inhibitors endowed with anticancer activity
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In the presented work, we report the synthesis of a series of 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides 7a-f via the Erlenmeyer–Pl?chl reaction. All the prepared imidazolones 7a-f were evaluated as inhibitors of human (h) carbonic anhydrases (CA, EC 4.2.1.1) cytosolic isoforms hCA I and II, as well as transmembrane tumor-associated isoforms hCA IX and XII. All the tested hCA isoforms were inhibited by the prepared imidazolones 7a-f in variable degrees with the following KIs ranges: 673.2–8169 nM for hCA I, 61.2–592.1 nM for hCA II, 23–155.4 nM for hCA XI, and 21.8–179.6 nM for hCA XII. In particular, imidazolones 7a, 7e, and 7f exhibited good selectivity towards the tumor-associated isoforms (CAs IX and XII) over the off-target cytosolic (CAs I and II) with selectivity index (SI) in the range of 6.2–19.4 and 3.3–8, respectively. Moreover, imidazolones 7a-f were screened for their anticancer activity in one dose (10?5 M) assay against a panel of 60 cancer cell lines according to US-NCI protocol. Furthermore, 7a, 7e and 7f were evaluated for their anti-proliferative activity against colorectal cancer HCT-116 and breast cancer MCF-7 cell lines. Furthermore, 7e and 7f were screened for cell cycle disturbance and apoptosis induction in HCT-116 cells. Finally, a molecular docking study was carried out to rationalize the obtained results.
- Eldehna, Wagdy M.,Abdelrahman, Mohamed A.,Nocentini, Alessio,Bua, Silvia,Al-Rashood, Sara T.,Hassan, Ghada S.,Bonardi, Alessandro,Almehizia, Abdulrahman A.,Alkahtani, Hamad M.,Alharbi, Amal,Gratteri, Paola,Supuran, Claudiu T.
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- Synthesis of Novel Benzamide- piperazine-sulfonamide Hybrids as Potential Anticancer Agents
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The synthesis of a series of substituted hippuric acid (2-benzamidoacetic acid) derivatives containing arylsulfonylpiperazine nucleus (3a–j, 4a–j) is described. The compounds were synthesized by coupling hippuric/4-fluorohippuric acid with various arylsulfonylpiperazines using N-(3-dimethylaminopropyl)-N-ethylcarbodiimide (EDCI). The structures of all the new compounds were confirmed by IR, NMR and MS spectral data. All the synthesized compounds have been evaluated for their in vitro cytotoxicity towards five human cancer cell lines of different origins viz. HeLa (Cervical), A549 (Lung), A375 (Skin), MD-AMB-231(Breast) and T98G (brain) and their IC50 values were determined. Among the compounds tested, 3b, 3d, 3g, 4c and 4e displayed significant cytotoxic activity (IC50 = 24.2–38.2 μM). T98G was the most sensitive cell line towards the compounds studied followed by HeLa, A375, A549 and MD-AMB-231.
- Ramalingeswara Rao,Mohana Rao Katiki,Dileep Kommula,SaiShyam Narayanan,Ruby John Anto,Murty
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p. 393 - 402
(2019/12/12)
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- STRUCTURE AND SYNTHESIS OF HIGHLY FLUORINATED AMINO ACID DERIVATIVES
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Methods of synthesizing polyfluorinated amino acid derivatives are disclosed, along with polyfluorinated amino acid derivatives produced from said methods, as well as compositions containing same. The synthesis methods utilize an oxazolone and a perfluoroarene to produce the polyfluorinated amino acid derivatives.
- -
-
Paragraph 0164; 0165; 0166
(2018/09/19)
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- Formation of Non-Natural α,α-Disubstituted Amino Esters via Catalytic Michael Addition
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The enolate monoanion of amino esters is explored, and the first catalytic Michael addition of α-amino esters is demonstrated. These studies indicate that the acidity of the αC-H is the primary factor determining reactivity. Thus, polyfluorophenylglycine amino esters yield novel α-amino esters in the presence of a catalytic amount of a guanidine-derived base and Michael acceptors. Reactivity requires an acidic N-H, which is accomplished using common protecting groups such as N-Bz, N-Boc, and N-Cbz. Calculations and labeling experiments provide insight into the governing principles in which a key C-to-N proton transfer occurs, resulting in an expansion of the scope to include a number of natural amino esters. The study culminates with a late-stage functionalization of peptidic γ-secretase inhibitor, DAPT.
- Teegardin, Kip A.,Gotcher, Lacey,Weaver, Jimmie D.
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supporting information
p. 7239 - 7244
(2018/11/25)
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- Latent Bronsted Base Solvent-Assisted Amide Formation from Amines and Acid Chlorides
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Weakly basic amines, including even neutral amines such as nitroaniline and aminocarboxylic acids, react with acid chlorides very efficiently in N, N -dimethylacetamide (DMAC), without addition of a base, to give the corresponding amides in high yields. The role of DMAC and related solvents as latent Bronsted bases was studied in these amidation reactions. Less basic amines, such as aromatic amines, reacted with benzoyl chloride faster than more basic aliphatic amines.
- Otsuka, Rikuto,Maruhashi, Kazuo,Ohwada, Tomohiko
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supporting information
p. 2041 - 2057
(2018/05/04)
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- Design, synthesis and evaluation of novel phenyl propionamide derivatives as non-nucleoside hepatitis B virus inhibitors
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As an ongoing search for potent non-nucleoside anti-HBV agents with novel structures, we described a series of phenyl propionamide derivatives (3a-b, 4a-e, 7a-g, 8a-h and 9a-b) by pharmacophore fusion strategy in the present work. All the compounds exhibited an anti-HBV activity to some extent. Among them, compounds 8d and 9b displayed most potent anti-HBV activity with IC50 values on HBV DNA replication of 0.46 and 0.14 μM, respectively. And the selective index values of 8d and 9b were more than 217.39 and 153.14, suggesting that 8d and 9b exhibited favorable safety profiles. Interestingly, 8d and 9b possessed significantly antiviral activities against lamivudine and entecavir resistant HBV mutants with IC50 values of 0.77 and 0.32 μM. Notably, preliminary anti-HBV action mechanism studies showed that 8d could inhibit intracellular HBV pgRNA and RT activity of the HBV polymerase. Molecular docking studies suggested that compound 8d could fit into the dimer-dimer interface of HBV core protein by hydrophobic interaction. In addition, in silico prediction of physicochemical properties showed that 8d conformed well to the Lipinski's rule of five, suggesting its potential for use as a drug like molecule. Taken together, 8d possessed significantly anti-HBV activity, low toxicity, diverse anti-HBV mechanism and favorable physicochemical properties, and warranted further investigation as a promising non-nucleoside anti-HBV candidate.
- Qiu, Jingying,Gong, Qineng,Gao, Jian,Chen, Wang,Zhang, Yinpeng,Gu, Xiaoke,Tang, Daoquan
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p. 424 - 434
(2018/01/01)
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- Synthesis, Spectroscopic Characterization and Polymerization Abilities of Blue and Green Light Emitting Oxazol-5-one Fluorophores
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New fluorescent thiophenyl group containing oxazol-5-one fluorophores of 3a (4-(3-thiophenylmethylene)-2-phenyloxazol-5-one), 3b (4-(3-thiophenylmethylene)-2-(4-tolyl)oxazol-5-one) and 3c (4-(3-thiophenylmethylene)-2-(4-nitrophenyl)oxazol-5-one) were synthesized and characterized. The newly synthesized oxazol-5-ones absorption and fluorescence characteristics were studied in some solvents of varying polarities. The heterocyclic chromophores were fluorescent, with two of them, 3a and 3b, emitting blue light, whilst the other one, 3c, emitting green light. The emission maxima of the derivatives varied between 415 and 572?nm according as the extent of conjugation and solvent polarity. As solvent polarity increased, 3c derivatives emission spectra displayed a large bathochromic shift, which revealed the considerable change of the dipole moment of the fluorescent structure because of an intramolecular charge transfer interaction. Furthermore, oxazolones polymerization ability via the thiophenyl group linked to the oxazol-5-one heterocycle showed that copolymerization of 3a was achieved, but homopolymerization was not observed.
- Urut, Gulsiye Ozturk,Aydin, Seher,Topkaya, Derya,Sahin, Elif,Alp, Serap
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p. 735 - 741
(2018/05/26)
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- Design, synthesis, and molecular docking of novel indole scaffold-based VEGFR-2 inhibitors as targeted anticancer agents
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A series of new indole derivatives 1–18 was synthesized and tested for their cytotoxic activity on a panel of 60 tumor cell lines. Additionally, molecular docking was carried out to study their binding pattern and binding affinity in the VEGFR-2 active site using sorafenib as a reference VEGFR-2 inhibitor. Based on the molecular docking results, compounds 5a, 5b, 6, 7, 14b, 18b, and 18c were selected to be evaluated for their VEGFR-2 inhibitory activity. Compound 18b exhibited a broad-spectrum antiproliferative activity on 47 cell lines, with GI % ranging from 31 to 82.5%. Moreover, compound 18b was the most potent VEGFR-2 inhibitor with an IC50 value of 0.07 μM, which is more potent than that of sorafenib (0.09 μM). A molecular docking study attributed the promising activity of this series to their hydrophobic interaction with the VEGFR-2 binding site hydrophobic side chains and their hydrogen bonding interaction with the key amino acids Glu885 and/or Asp1046.
- Roaiah, Hanaa M.,Ghannam, Iman A. Y.,Ali, Islam H.,El Kerdawy, Ahmed M.,Ali, Mamdouh M.,Abbas, Safinaz E-S.,El-Nakkady, Sally S.
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- Design, synthesis, anticonvulsant activity, and pharmacophore study of new 1,5-diaryl-1H-1,2,4-triazole-3-carboxamide derivatives
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1,5-Diaryl-1H-1,2,4-triazole-3-carboxamide derivatives were designed, synthesized, and evaluated for its anticonvulsant activity using maximal electroshock (MES) and chemoshock (scPTZ and Strychnine) animal screen methods. Neurotoxicity was also assessed. In MES model, compound 4f showed 100% of phenytoin activity after both 0.5 and 4 h. In scPTZ model, compound 4e showed 100% of sodium valproate activity. In Strychnine model, compound 4e showed 120% more delay of onset of convulsion and 124% more delay of time of death relative to sodium valproate. Most of the target compounds showed mild neurotoxicity especially compound 4f which showed excellent activity against electroshock. Pharmacophoric study reveals that the synthesized compounds showed good fitting on the pharmacophoric query with good RMSDX results.
- Abuelhassan, Abdelfattah H.,Badran, Mostafa M.,Hassan, Heba A.,Abdelhamed, Dalia,Elnabtity, Sameh,Aly, Omar M.
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p. 928 - 938
(2017/11/27)
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- Inhibition studies on a panel of human carbonic anhydrases with N1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails
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Being the primary sulfonamide among the most efficient zinc binding group (ZBG) to design inhibitors for the metallo-enzymes carbonic anhydrases (CA, EC 4.2.1.1), herein, we propose an investigation on four physiologically important human (h) CAs (hCA I, II, IV, and IX) with N1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails. The effect of the functionalisation of the sulfonamide group with five different substitution patterns, namely acetyl, pyridine, thiazole, pyrimidine, and carbamimidoyl, was evaluated in relation to the inhibition profile of the corresponding primary sulfonamide analogues. With most of these latter being nanomolar inhibitors of all four considered isoforms, a totally counterproductive effect on the inhibition potency can be ascribed to N1-functionalisations of the ZBG primary sulfonamide structure with pyridine, thiazole, and pyrimidine moieties. On the other hand, incorporation of less hindered groups, such as sulfonylacetamides and sulfonylguanidines, maintained a certain degree of activity dependent on the tailing moiety, with KIs spanning in the low micromolar range.
- Awadallah, Fadi M.,Bua, Silvia,Mahmoud, Walaa R.,Nada, Hossam H.,Nocentini, Alessio,Supuran, Claudiu T.
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p. 629 - 638
(2018/03/26)
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- A potential greener protocol for peptide coupling reactions using recyclable/reusable ionic liquid [ C 4-DABCO ] [ N(CN) 2 ]
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Abstract : Development of greener methodologies in synthetic organic chemistry has brought awareness in recent decades due to the ecological performance of green solvent media and catalytic systems. Here, we carried out the peptide bond formation reaction in one of the environmentally secure solvents, ‘ionic liquids’ in the presence of coupling reagent and in the absence of external base at room temperature, affording dipeptides in good to excellent yields. GRAPHICAL ABSTRACT: SYNOPSIS We carried out the peptide bond formation reaction in ionic liquids in the presence of a coupling reagent at room temperature, in the absence of an external base, affording dipeptides in good to excellent yields.
- Konwar, Manashjyoti,Khupse, Nageshwar D,Saikia, Prakash J,Sarma, Diganta
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- Synthesis and cytotoxicity of novel dispiro derivatives of 5-arylidenoxazolones, potential inhibitors of p53—MDM2 protein-protein interaction
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Regioselective synthesis of new dispiro indolinones combining both an indolinone and an oxazolone fragment in their structure comprised the 1,3-dipolar cycloaddition of azomethine ylides, generated in situ from isatin and sarcosine, at 2-aryl-5-arylmethylidene-substituted 1,3-oxazol-5(4H)-ones. When ortho and para halogen atoms were present in the aromatic substituents of the starting oxazolones, complex mixtures containing large amounts of oxazoline ring opening products and their dispiro derivatives were formed. The cytotoxicity of compounds was tested by MTT on LNCaP, PC3, HCT116, MCF7, A549, HEK, and VA13 cell lines. The compound possessing the best cytotoxicity revealed the IC50 = 1.08±0.96 μM towards the p53- expressing LNCaP cells and lower activity (IC50 = 3.21±1.45 μM) towards the non-expressing p53 protein PC3 cells, however, it has proved inactive towards the HCT cells, both expressing (HCТ+/+) and non-expressing (HCT–/–) p53.
- Beloglazkina,Skvortsov,Tafeenko,Majouga,Zyk,Beloglazkina
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p. 562 - 569
(2018/07/06)
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- Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media
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The kinetics of the reaction of a series of α-amino acids with 4-nitrophenyl acetate, 4-nitrophenyl benzoate, and 2,4,6-trinitrophenyl benzoate in aqueous 1,4-dioxane medium has been studied. Kinetics of the reactions involving 4-nitrophenyl acetate and 2,4,6-trinitrophenyl benzoate has complied with the Br?nsted dependence and revealed linear correlation between rate constant logarithm and the energy difference of the frontier orbitals of α-amino acids anions.
- Kochetova,Kustova,Kuritsyn
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- Supported ruthenium hydride catalysts for direct conversion of alcohols to carboxylic acids using styrene oxide as oxidant
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In the present work, the ability of two ruthenium hydride catalysts supported on multiwall carbon nanotubes, [Ru–H@EDT–MWCNT], and gold nanoparticles cored triazine dendrimer, [Ru–H@AuNPs–TD], in the direct conversion of alcohols to carboxylic acids via transfer hydrogenation using styrene oxide as oxidant is reported. Different alcohols were successfully converted to their corresponding carboxylic acids. The results showed that these two heterogeneous catalysts are more efficient than the homogeneous counterpart. In addition, the catalysts were reused several times.
- Ghafouri, Moloud,Moghadam, Majid,Mehrani, Kheirollah,Daneshvar, Anahita
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- A Flexible Polyphosphate-Driven Regeneration System for Coenzyme A Dependent Catalysis
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Coenzyme A (CoA) is a common cofactor in biochemical reactions, and CoA-dependent enzymes catalyze essential steps in anabolism and catabolism. This complex molecule also plays an important role in the synthesis of many high-value products, such as synthetic antibiotics, vitamins, pheromones, and biopolymers. Nevertheless, the synthetic potential for biocatalytic processes cannot be fully exploited owing to the lack of an efficient regeneration system. Here, we report an acyl-CoA regeneration system with integrated adenosine triphosphate (ATP) regeneration that is based on inexpensive polyphosphate as the single energy source. In the four-enzyme cascade, two cofactors, acyl-CoA and ATP, are each regenerated up to 2000 times. The applicability for different acyl donors and acceptors is shown by HPLC analysis. Owing to its flexibility toward virtually all relevant substrates, the system has the potential to make CoA-dependent reactions more accessible for chemical synthesis in vitro.
- Mordhorst, Silja,Maurer, Alice,Popadi?, Désirée,Brech, Johanna,Andexer, Jennifer N.
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p. 4164 - 4168
(2017/10/23)
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- Synthesis of N-Lauroyl Sarcosine by Amidocarbonylation: Comparing Homogeneous and Heterogeneous Palladium Catalysts
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An improved system for the synthesis of N-acyl amino acids via Pd-catalyzed amidocarbonylation is reported. Utilizing inexpensive Pd black gives the industrially important surfactant N-lauroyl sarcosine in excellent yields (95%) on a multi-gram scale. Advantages of the new system include reusability, decreased process temperature, and, importantly, drastically decreased co-catalyst loading.
- Hancker, S?ren,Kreft, Stefanie,Neumann, Helfried,Beller, Matthias
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supporting information
p. 2045 - 2051
(2017/12/26)
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- Preparation method of 5-aminolevulinic acid hydrochloride
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The invention relates to a preparation method of 5-aminolevulinic acid hydrochloride, belonging to the technical field of drug intermediate synthesis. In order to solve the problems of long route and great pollution at present, the invention provides the preparation method of the 5-aminolevulinic acid hydrochloride. The preparation method is characterized in that the method comprise the following steps of under the existence of organic alkali and DMAP, enabling benzoyl glycine to react with butanedioic anhydride by using Dakin-West to obtain benzoyl aminolevulinic acid; under the existence of hydrochloric acid, enabling the benzoyl aminolevulinic acid to be subjected to hydrolysis reaction to obtain the 5-aminolevulinic acid hydrochloride. The synthetic method has the advantages that the reaction route is short, the raw materials are convenient to obtain, the cost is low, the reaction operation is simple and convenient and the pollution is less, and the method has the effects of high product yield and high purity.
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Paragraph 0028; 0032; 0033
(2018/01/14)
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- Microwave-assisted facile synthesis, anticancer evaluation and docking study of N-((5-(substituted methylene amino)-1,3,4-thiadiazol-2-yl)methyl) benzamide derivatives
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In the present work, 12 novel Schiff’s bases containing a thiadiazole scaffold and benzamide groups coupled through appropriate pharmacophore were synthesized. These moieties are associated with important biological properties. A facile, solvent-free synthesis of a series of novel 7(a–l) N-((5-(substituted methylene amino)-1,3,4-thiadiazol-2-yl)methyl) benzamide was carried out under microwave irradiation. Structures of the synthesized compounds were confirmed by IR, NMR, mass spectral study and elemental analysis. All the synthesized hybrids were evaluated for their in vitro anticancer activity against a panel of four human cancer cell lines, viz. SK-MEL-2 (melanoma), HL-60 (leukemia), HeLa (cervical cancer), MCF-7 (breast cancer) and normal breast epithelial cell (MCF-10A) using 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay method. Most of the synthesized compounds exhibited promising anticancer activity, showed comparable GI50 values comparable to that of the standard drug Adriamycin. The compounds 7k, 7l, 7b, and 7a were found to be the most promising anticancer agents in this study. A molecular docking study was performed to predict the probable mechanism of action and computational study of the synthesized compounds 7(a–l) was performed to predict absorption, distribution, metabolism, excretion and toxicity (ADMET) properties, by using QikProp v3.5 (Schr dinger LLC). The results showed the good oral drug-like behavior of the synthesized compounds 7(a–l).
- Tiwari, Shailee V.,Siddiqui, Sumaiya,Seijas, Julio A.,Vazquez-Tato, M. Pilar,Sarkate, Aniket P.,Lokwani, Deepak K.,Nikalje, Anna Pratima G.
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- Polyfluoroarylation of oxazolones: Access to non-natural fluorinated amino acids
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Herein, conditions are provided for the formation and use of the oxazolone enolate for the nucleophilic substitution of highly fluorinated (hetero)arenes, which after unmasking yield highly fluorinated non-natural amino acids and derivatives. In addition, the properties and chemical behavior of this new class of amino acids are explored. The utility is demonstrated in the one pot synthesis of medicinally relevant 2-aminohydantoins.
- Teegardin, Kip A.,Weaver, Jimmie D.
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supporting information
p. 4771 - 4774
(2017/07/06)
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- Acrylamide compound and preparation method and medical application thereof
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The invention discloses an acrylamide compound and a preparation method and medical application thereof, and relates to a compound shown in formula I and an isomer or a pharmaceutically acceptable salt thereof. The acrylamide compound and the isomer or the pharmaceutically acceptable salt thereof can be applied to prepare HBV (hepatitis B virus)-resistant medicines. The formula is shown in the specification.
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Paragraph 0081
(2017/09/01)
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- Palladium-Catalyzed Ortho-Alkoxylation of N-Benzoyl α-Amino Acid Derivatives at Room Temperature
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An efficient palladium-catalyzed ortho-alkoxylation of N-benzoyl α-amino acid derivatives at room temperature has been explored. This novel transformation, using amino acids as directing groups, Pd(OAc)2 as catalyst, alcohols as the alkoxylation reagents, and PhI(OAc)2 as the oxidant, showed wide generality, good functional tolerance, and high monoselectivity and regioselectivity.
- Li, Shuangjie,Zhu, Wei,Gao, Feng,Li, Chunpu,Wang, Jiang,Liu, Hong
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p. 126 - 134
(2017/04/26)
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- Synthesis of Hydrazones from Amino Acids and their Antimicrobial and Cytotoxic Activities
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Hydrazones 6a–6n were synthesized from different amino acids with various aldehydes under reflux in methanol/ethanol. The structures of synthesized compounds were ascertained by elemental analysis and spectroscopic techniques. A comparative study of the antimicrobial activity and cytotoxicity was carried out of the N-protected amino acids, their esters, hydrazides, and the respective hydrazones, providing good results in cytotoxicity studies.
- Abid, Obaid-Ur-Rahman,Khatoon, Ghamama,Arfan, Muhammad,Sajid, Imran,Langer, Peter,Rehman, Wajid,Rahim, Fazal,Yasir, Muhammad,Waqar, Muhammad,Haleem, Kashif Syed
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p. 1079 - 1087
(2017/09/26)
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- Synthesis and characterization of new green and orange region emitting anthracene based oxazol-5-one dyes
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New anthracene oxazol-5-one dyes featuring an extended π-conjugated electron system have been successfully prepared by Erlenmeyer synthesis, structurally characterized and their spectroscopic properties were investigated by UV–vis absorption spectroscopy and fluorescence spectroscopy. The oxazol-5-ones were attached to the 9-position of the anthracene to obtain the desired structures. The dyes are having extended conjugation throughout their structure with oxazol-5-one ring as the chromophore. The spectral properties of the oxazol-5-one ring were monitored with respect to the substituents at the phenyl ring. All of the dyes synthesized show good solubility in common organic solvents. Also in order to establish whether there was any solvent affects the absorption and emission spectra of the compounds were measured in the solvents of acetonitrile, tetrahydrofuran and chloroform which have different polarity. Moreover, their absorption and emission properties were investigated in plasticized PVC film matrix. In comparison to the solution phase, the dyes displayed enhanced fluorescence emission quantum yield values when embedded in poly(vinyl chloride) polymer film. The anthracene based oxazol-5-ones were found to emit in the green portion of the spectrum for 2a and 2b, and in the orange portion of the spectrum for 2c. By attachment of nitro substituent at the para position of the phenyl ring bound to oxazol-5-one core, the fluorescence maxima could be effectively modulated from the green region of the spectra to the orange region. 4-(9-anthralydene)-2-(4-nitrophenyl)oxazol-5-one (2c) exhibits large Stokes shift up to 146 nm presumably due to intramolecular charge transfer.
- Ozturk Urut, Gulsiye,Alp, Serap,Topkaya, Derya
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p. 103 - 109
(2017/06/06)
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- Synthesis and insecticidal evaluation of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives
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A series of novel tetrahydroimidazo[1,2-a]pyridine-5(1H)-one derivatives containing a electronegative pharmacophore (=CNO2) were synthesized via practical aza-ene reaction and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. Preliminary bioassays showed that some of the target compounds exhibited good insecticidal activity against brown planthopper (Nilaparvata lugens) and cowpea aphids (Aphis craccivora) at 500 mg L-1. Among them, compound 11h was active against brown planthopper at 100 mg L-1. The insecticidal activities varied significantly depending on the types and patterns of the substituents, which provided guidance for further investigation on structure modifications.
- Liu, Xuan-Qi,Liu, Ya-Qin,Shao, Xu-Sheng,Xu, Zhi-Ping,Xu, Xiao-Yong,Li, Zhong
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- Synthesis of 4-(thiazol-2-ylamino)-benzenesulfonamides with carbonic anhydrase I, II and IX inhibitory activity and cytotoxic effects against breast cancer cell lines
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A series of 4-(thiazol-2-ylamino)-benzenesulfonamides was synthesized and screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibitory and cytotoxic activity on human breast cancer cell line MCF-7. Human (h) CA isoforms I, II and IX were included in the study. The new sulfonamides showed excellent inhibition of all three isoforms, with KIs in the range of 0.84-702 nM against hCA I, of 0.41-288 nM against hCA II and of 5.6-29.2 against the tumor-associated hCA IX, a validated anti-tumor target, with a sulfonamide (SLC-0111) in Phase I clinical trials for the treatment of hypoxic, metastatic solid tumors overexpressing CA IX. The new compounds showed micromolar inhibition of growth efficacy against breast cancer MCF-7 cell lines.
- Abdel Gawad, Nagwa M.,Amin, Noha H.,Elsaadi, Mohammed T.,Mohamed, Fatma M.M.,Angeli, Andrea,De Luca, Viviana,Capasso, Clemente,Supuran, Claudiu T.
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p. 3043 - 3051
(2016/06/13)
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- Synthesis and biological testing of (5Z)-2-aryl-5-arylmethylidene-3,5-dihydro-4H-imidazol-4-ones as antimitotic agents
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Compounds interacting with cell protein tubulin and microtubules represent an important type of antimitotic agents. A series of tubulin-targeted 2-aryl-4-benzoyl-imidazoles were reported to possess high cytotoxicity, and so, we prepared a series of structural isomers of these to be evaluated as antimitotic agents. The synthesis of the novel (Z)-2-aryl-5-arylmethylidene-3,5-dihydro-4H-imidazol-4-ones involved coupling of substituted hippuric acids with aromatic aldehydes. Subsequent conversion of the resulting oxazolones to the corresponding imidazolones was carried out under microwave irradiation in the presence of urea and ammonium acetate. The cytotoxicity of the majority of the compounds to human epithelial carcinoma cancer cell line A549 was in the sub-micromolar range and was found to be more sensitive to the substituents on the 5-arylmethylidene fragment than on the 2-aryl ring in general. The cytotoxicities of the synthesized compounds were lower than those of the previously reported isomeric 2-aryl-4-benzoyl-imidazoles, and the basic structure–activity relationships in the isomeric pairs were different. Synthesized (5Z)-5-[(4-bromophenyl)methylidene]-2-(4-methylphenyl)-3,5-dihydro-4H-imidazol-4-one, which had the highest cytotoxicity (IC50?~?440?nM) in the series of novel compounds, had a definite cytostatic effect on the A549 cells, but its antiproliferative properties were not linked to action on the microtubules. This would be an interesting lead compound for additional investigation into the mechanism of cytostatic action, and further structural optimization.
- Beloglazkina, Anastasia A.,Wobith, Birgit,Barskaia, Elena S.,Zefirov, Nikolay A.,Majouga, Alexander G.,Beloglazkina, Elena K.,Zyk, Nikolay V.,Kuznetsov, Sergei A.,Zefirova, Olga N.
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p. 1239 - 1249
(2016/07/06)
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- A Facile and Efficient Synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones and Their Antimicrobial Evaluation against Selected Human and Phytopathogens
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A simple and convenient method has been developed for the synthesis of a series of 2-(4-substituted phenyl)-4-(substituted arylidene)-1,3-oxazol-5-ones (5a–j) via reactions of hippuric acid with differently substituted aromatic aldehydes (4a–j) in sodium acetate, potassium acetate, calcium acetate, and ammonium acetate, respectively, which were tested for their efficiency as catalysts in both conventional and microwave-assisted synthetic methods in presence of 4 ? zeolites. The title compounds were evaluated for their antimicrobial properties against selected human pathogens (bacterial and fungal) and phytopathogens (fungal) and were compared with standard drugs. The results of the study are reported.
- Voosala, Christopher,Kilaru, Padma Suhasini,Dasari, Uday Kumar
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p. 909 - 916
(2016/11/23)
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- Cu(II)-promoted oxidative C-N bond cleavage of N-benzoylamino acids to primary aryl amides
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A novel protocol for CuCl2-promoted oxidative C-N bond cleavage of N-benzoyl amino acids was developed. It is the first example of using accessible amino acid as an ammonia synthetic equivalent for the synthesis of primary aryl amides via CuCl2-promoted oxidative C-N bond cleavage reaction. The present protocol shows excellent functional group tolerance and provides an alternative method for the synthetic of primary aryl amides in 84-96percent yields.
- Chen, Junmin,Liu, Wei,Zhao, Yongli,Zhou, Liandi
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- One-pot oxidative cleavage of olefins to synthesize carboxylic acids by a telescoped ozonolysis-oxidation process
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A mild one-pot ozonolysis-oxidation process of alkenes to synthesize carboxylic acids is described. Conducting the ozonolysis in an aqueous organic solvent eliminates secondary ozonide formation and the intermediates generated are readily converted into a carboxylic acid by adding sodium chlorite. Following a reductive quench, the desired acids are isolated in high purity and high yield by simple extraction.
- Cochran, Brian M.
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supporting information
p. 245 - 248
(2016/01/20)
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- Associative chemosensing by fluorescent macrocycle-dye complexes-a versatile enzyme assay platform beyond indicator displacement
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A label-free in situ method to monitor reactions in real time by using fluorescent supramolecular chemosensors based on cucurbit[8]uril is presented. It allows sensing of enzymatic activity, inhibitor and activator screening, and analyte detection with unprecedented versatility and high sensitivity.
- Biedermann, Frank,Hathazi, Denisa,Nau, Werner M.
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supporting information
p. 4977 - 4980
(2015/03/30)
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- Isotope-labeled differential profiling of metabolites using N-benzoyloxysuccinimide derivatization coupled to liquid chromatography/high-resolution tandem mass spectrometry
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Rationale An isotopic labeling strategy based on derivatizing amine-containing metabolites has been developed using light (12C6) and heavy (13C6) N-benzoyloxysuccinimide reagents for semi-targeted metabolomic applications. Methods Differentially labeled samples were combined and analyzed simultaneously by liquid chromatography/high-resolution tandem mass spectrometry (LC/HR-MS/MS) to compare relative amounts of amine-containing metabolites. The selectivity of the reaction was determined with model metabolites and was shown to also be applicable to thiol and phenol moieties. The potential for relative quantitation was evaluated in cell extracts and the method was then applied to quantify metabolic perturbations occurring in human cultured cells under normal vs. oxidative stress conditions. Results A total of 279 derivatized features were detected in HL60 cell extracts, 77 of which yielded significant concentration changes upon oxidative stress treatment. Based on accurate mass measurements and MS/MS spectral matching with reference standard solutions, 10 metabolites were clearly identified. Derivatized compounds were found to have diagnostic fragment ions from the reagent itself, as well as structurally informative ions useful for metabolite identification. Conclusions This simple derivatization reaction can be applied to the relative quantitation of amine-, thiol- and phenol-containing compounds, with improved sensitivity and chromatographic peak shapes due to the increased hydrophobicity of polar metabolites not readily amenable to reversed-phase LC/MS analysis.
- Wagner, Michel,Ohlund, Leanne B.,Shiao, Tze Chieh,Vézina, Amélie,Annabi, Borhane,Roy, René,Sleno, Lekha
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p. 1632 - 1640
(2015/11/16)
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