1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity
摘要:
Versatile 1,2,3-triazole pharmacophore-based benzofused heterocycles containing halogen-substituted aromatic (9-17 and 25-28), 7-substituted coumarin (18-23 and 29-30) or penciclovir-like subunit (31a,b-38a) were designed and synthesized to evaluate their antibacterial activities against selected Gram-positive and Gram-negative bacteria. Hybridization approach using environmentally friendly Cu (I)-catalyzed click reaction under microwave irradiation was adopted in the synthesis of regioselective 1,4-disubstituted 1,2,3-triazole tethered heterocycles (9-23 and 25-30), while post-N-alkylation of NH-1,2,3-triazoles afforded both 2,4-(31a-38a) and 1,4-disubstituted (31b-33b, 35b-37b) 1,2,3-triazole regioisomers. The compounds 18-23 and 25-30 revealed fluorescence in the violet region of the visible spectrum with a strong influence of phenyl spacer in 25-30 on both wavelength and emission intensity. Fusion of selected subunits led to new hybrid architecture, benzothiazole-1,2,3-triazole-coumarin 29 that demonstrated extremely narrow spectrum activity towards fastidious Gram-negative bacteria Moraxella catarrhalis. Selected hybrid showed the potency against Moraxella catarrhalis (MIC <= 0.25 mu g/mL) comparable to that of reference antibiotic azithromycin, which suggested that further investigations are necessary to optimize this potential hit compound as a new anti-Moraxella catarrhalis agent. (C) 2015 Elsevier Ltd. All rights reserved.
Synthesis, antimicrobial and α-glucosidase inhibition of new benzimidazole-1,2,3-triazole-indoline derivatives: a combined experimental and computational venture
Controlling Selectivity for Cycloadditions of Nitrones and Alkenes Tethered by Benzimidazoles: Combining Experiment and Theory
作者:Liping Meng、Selina C. Wang、James C. Fettinger、Mark J. Kurth、Dean J. Tantillo
DOI:10.1002/ejoc.200801211
日期:2009.4
Herein we describe a combined experimental/theoretical study on the effects of substituents on regio- and stereoselectivity in intramolecular 1,3-dipolar cycloadditions of nitrones and alkenestethered by benzimidazoles. By employing a large substituent at position R2 or R3, complete selectivity was achieved for either the fused or bridged cycloadduct, respectively. In addition, these cycloadducts
[EN] TRICYCLIC PYRAZOLE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES A BASE DE TYRAZOLES TRICYCLIQUES
申请人:ABBOTT LAB
公开号:WO2005095387A1
公开(公告)日:2005-10-13
Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.
and simple procedure for the hydroamination of N‐allenylazoles with secondary amines. The reaction proceeds under mild conditions by copper(I) catalysis yielding the corresponding original linear E allylic amines with total regio‐ and stereoselectivity. Density Functional Theory (DFT) calculations offer a mechanistic explanation of the significantly higher reactivity of N‐allenyl‐(1,2)‐azoles compared
d-Glucose has been identified as an efficient C1 synthon in the synthesis of benzimidazoles from o-phenylenediamines via an oxidative cyclization strategy. Isotopic studies with 13C6-d-glucose and D2O unambiguously confirmed the source of methine. The notable features of this method include the following: broad functional group tolerance, a biorenewable methine source, excellent reaction yields, a
d-葡萄糖已被确定为通过氧化环化策略由邻苯二胺合成苯并咪唑的有效C1合成子。用13 C 6 - d-葡萄糖和D 2 O进行的同位素研究明确证实了次甲基的来源。该方法的显着特征包括:宽泛的官能团耐受性,可生物再生的次甲基来源,优异的反应收率,较短的反应时间,水作为环境友好的溶剂以及以克为单位的维生素B 12组分的合成。
‘Click Synthesis’ of 1H-1,2,3-Triazolyl-Based Oxiconazole (=(1Z)-1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone O-[(2,4-Dichlorophenyl)methyl]oxime) Analogs
four steps (Scheme 1). Oximation of phenacyl chloride (1) followed by azidation of 2‐chloro‐1‐phenylethanone oxime (2) provided azido ketoxime 3. The CuI‐catalyzed Huisgen cycloaddition of 3 with terminal alkynes gave the 4‐substituted (at the triazole) 2‐(1H‐1,2,3‐triazol‐1‐yl)‐1‐phenylethanone oximes 4a–4i. The O‐alkylation of 4a–4i with various alkyl halides resulted in the formation of the target molecules
在四个步骤中,通过Huisgen环加成反应,完成了一些具有1 H 1,2,3-三唑基残基的氧康唑类似物5a - 5v的“点击合成” (流程1)。苯甲酰氯的氧化(1),然后2-氯-1-苯基乙酮肟的叠氮化(2)提供了叠氮基酮肟3。CuI催化的3与末端炔烃的Huisgen环加成反应得到4-取代的(在三唑上)2-(1 H -1,2,3-三唑-1-基)-1-苯基乙酮肟4a - 4i。4a的O-烷基化– 4i与各种卤代烷一起以高收率形成了目标分子5a – 5v。