- Synthesis and Antimicrobial Evaluation of Novel Chiral 2-Amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridine Derivatives
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New N-substituted-2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridine derivatives were synthesized employing a convenient one-pot three-component method and their structures were characterized by 1H-NMR and single crystal X-ray diffraction analysis. All the synthesized compounds were in vitro screened for antimicrobial activity against Gram-positive (Sarcina lutea) and Gram-negative bacteria (Escherichia coli). In this work, we introduced a chiral residue on the tetrahydropyridine nitrogen, the hitherto the less investigated position on this pharmacophore in order to explore the effect. The antibacterial results showed that the synthesized compounds were active only against Gram-positive bacteria and the (R)-enantiomers displayed a greater antimicrobial potency than their (S)-counterparts. The structure–activity relationship here investigated may provide some interesting clues for future development of tetrahydrothienopyridine derivatives with higher antimicrobial activity.
- Rossetti, Arianna,Bono, Nina,Candiani, Gabriele,Meneghetti, Fiorella,Roda, Gabriella,Sacchetti, Alessandro
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- Novel 2H-pyrazolo[4,3-c]hexahydropyridine derivatives: Synthesis, crystal structure, fluorescence properties and cytotoxicity evaluation against human breast cancer cells
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A series of novel 2H-pyrazolo[4,3-c]hexahydropyridine derivatives (II) have been designed and synthesized. The target compounds have been identified by elemental analysis and spectral (1H NMR, IR, and MS) data and the absolute configuration of compound (II 1 ) was confirmed by single crystal X-ray diffraction. The cytotoxicity of the target compounds have been evaluated in vitro against two human breast cancer cell lines MCF-7 and MDA-MB-231 by MTT assay. Most compounds exhibited good inhibition, and compounds II 21 (IC50 = 4.7 μM for MCF-7 and IC50 = 9.3 μM for MDA-MB-231), II 33 (IC50 = 2.4 μM for MCF-7 and IC50 = 4.2 μM for MDA-MB-231) and II 40 (IC50 = 3.3 μM for MCF-7 and IC50 =8.6 μM for MDA-MB-231) displayed better inhibitory activity than 5-fluorouracil (IC 50 = 4.8 μM for MCF-7 and IC50 = 9.6 μM for MDA-MB-231, respectively). Flow cytometric analysis and DNA fragmentation suggest that II 33 is cytotoxic and able to induce the apoptosis of MCF-7 cells. The fluorescence properties of compounds II 1, II 6, II 11, II 16, II 23, II 28, and II 35 were also studied and compound II 28 afforded the highest photoluminescence quantum yield (38%).
- Pang, Chuncheng,Sun, Chuanwen,Wang, Jing,Xiao, Di,Ding, Li,Bu, Hongfei
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p. 702 - 715
(2013/07/19)
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- Novel symmetrical trans-bis-Schiff bases of N-substituted-4- piperidones: Synthesis, characterization, and preliminary antileukemia activity mensurations
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A series of novel symmetrical trans-bis-Schiff bases (11a, 11b, 11c, 11d, 11e, 11f, 11g, 11h, 11i, 11j, 11k, 11l, 11m) were designed and prepared as novel anticancer analogues, with the trans-configuration confirmed by X-ray diffraction. Preliminary inhibitory effects of these compounds on CML K562 cell growth were investigated, and the potential analogue 11e showed an excellent anti-leukemia activity (IC50=6.35 μg/mL), which is higher than that of the clinical drug 5-fluorouracil (IC50=8.48 μg/mL). Complete assignments had been achieved for the title compounds by spectroscopic techniques, and their structure-activity relationships have been studied.
- Sun, Chuan-Wen,Wang, Hai-Feng,Zhu, Jun,Yang, Ding-Rong,Xing, Jiahua,Jin, Jia
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p. 1374 - 1380
(2014/01/06)
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- Synthesis and biological effects of novel 2-amino-3-naphthoylthiophenes as allosteric enhancers of the A1, adenosine receptor
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The current study describes the synthesis and biological evaluation of a novel series of 2-amino-3-naphthoylthiophenes, with variable modifications at the 4- and 5-position of the thiophene as well as the naphthoyl ring. Allosteric enhancer activity was m
- Baraldi, Pier Giovanni,Romagnoli, Romeo,Pavani, Maria Giovanna,Del Carmen Nu?ez, Maria,Tabrizi, Mojgan Aghazadeh,Shryock, John C.,Leung, Edward,Moorman, Allan R.,Uluoglu, Canan,Iannotta, Valeria,Merighi, Stefania,Borea, Pier Andrea
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p. 794 - 809
(2007/10/03)
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- Green chemistry approach to the synthesis of N-substituted piperidones
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An efficient green chemistry approach to the synthesis of N-substituted piperidones and piperidines was developed and applied to the synthesis of 1-(2-pyridinylmethyl)-piperidin-4-one, 1, a key starting material for the synthesis of LY317615, an antiangio
- Faul, Margaret M.,Kobierski, Michael E.,Kopach, Michael E.
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p. 5739 - 5741
(2007/10/03)
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- Phthalimidopiperidines and anti-convulsant compositions thereof
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Phthalimidopiperidines of the formula STR1 are described where R1 is hydrogen, lower alkyl, cycloalkyl of 5 to 7 carbon atoms, phenyl(lower)alkyl, pyridyl(lower)alkyl, furyl(lower)alkyl or thienyl(lower)alkyl and R2 and R3 are hydrogen or various substituents. The compounds are useful pharmaceutically, particularly as anti-convulsants, and also in some cases as anti-arrhythmic agents and anti-inflammatory agents, and in some cases useful as intermediates for the preparation of 4-aminoquinoline derivatives having anti-malarial activity.
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