5-chloro-2-(pyridin-3-yl)-1H-benzimidazole | 20100-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-chloro-2-(pyridin-3-yl)-1H-benzimidazole
• 英文别名: 6-chloro-2-pyridin-3-yl-1H-benzimidazole
• CAS: 20100-20-3
• 化学式: C₁₂H₈ClN₃
• mdl: MFCD01004486
• 分子量: 229.669
• InChiKey: CSCZCHYKBHZJPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(pyridin-3-yl)-1H-benzimidazole 在 sodium tetrahydroborate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 22.0h， 生成 5-chloro-2-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-benzimidazole
  参考文献：
  名称：

  2-（1-甲基-1,2,5,6-四氢吡啶-3-基）苯并咪唑的合成

  摘要：

  描述了一种合成具有药理活性的四氢吡啶基苯并咪唑的有用方法。2-吡啶-3-基苯并咪唑类3a-d是通过在用碘代苯二乙酸酯进行氧化环化后，将3-吡啶羧醛1与取代的1,2-苯二胺2a-d缩合而合成的。用碘甲烷和氢氧化钾使3a-d甲基化，随后形成甲基吡啶鎓盐4a-d和7a-d，然后还原，得到四氢吡啶基苯并咪唑5a-d和8a-d。

  DOI：

  10.1002/jhet.5570400104
• 作为产物：
  描述：

  3-吡啶甲醛 、 4-氯-1,2-苯二胺 在 sodium metabisulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.22h， 以70.9%的产率得到5-chloro-2-(pyridin-3-yl)-1H-benzimidazole
  参考文献：
  名称：

  2,5-二取代苯并咪唑的设计、微波辅助合成及体外抗菌和抗真菌活性

  摘要：

  设计、合成了 17 种新型 2,5-二取代苯并咪唑衍生物并评估了它们的抗菌活性。受试化合物B1-B4和C2-C6不仅表现出良好的抗真菌活性，而且具有良好的广谱抗菌活性。此外，抗菌和抗真菌活性的最低 MIC 分别为 2 μg/mL 和 4 μg/mL。这表明包括不同取代基及其位点的化合物的结构直接影响合成化合物的功效。

  DOI：

  10.1002/cbdv.201800510

文献信息

• QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS
  申请人：Smith Nicholas D.

  公开号：US20080139558A1

  公开（公告）日：2008-06-12

  The present invention relates to novel quinolones of Formula I that inhibit inducible NOS synthase together with methods of synthesizing and using the compounds including methods for inhibiting or modulating nitric oxide synthesis and/or lowering nitric oxide levels in a patient by administering the compounds for the treatment of disease.

  本发明涉及抑制诱导型NOS合酶的新奎诺酮化合物（化学式I），以及合成和使用这些化合物的方法，包括通过向患者施用这些化合物来治疗疾病的抑制或调节一氧化氮合成和/或降低一氧化氮水平的方法。
• Synthesis of Pyridinyl-benzo[d]imidazole/Pyridinyl-benzo[d]thiazole Derivatives and their Yeast Glucose Uptake Activity In Vitro
  作者：Momin Khan、Riaz Ahmad、Gauhar Rehman、Naeem Gul、Sana Shah、Uzma Salar、Shahnaz Perveen、Khalid Mohammed Khan

  DOI：10.2174/1570180815666181004102209

  日期：2019.9.11

  Diabetes is the primary cause of fatality and disability all over the world, in recent past, we have reported various classes of compounds as anti-glycating agents and we have also reported benzimidazole and benzothiazole derivatives as a potential class of anti-glycating agents. This encouraged us to evaluate the pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 for yeast glucose uptake activity.

  In the present study, an equimolar mixture of pyridine carboxaldehyde derivatives (1 mmol) and sodium metabisulphite (1 mmol) in DMF (10 mL) was stirred for 10 to 15 min, followed by addition of o-phenylene diamine/2-aminothiophenol (1 mmol) into it and refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was poured into crushed ice. Precipitates were formed which were collected by filtration to produce compounds 1-27 in good yields. Recrystallization from methanol yielded pure crystals.

  Our present study showed that all compounds showed a varying degree of yeast glucose uptake activity in the range IC50 = 36.43-272.20 µM, compared to standard metronidazole (IC50 = 41.86 ± 0.09 µM). Compounds 5 (IC50 = 38.14 ± 0.17 µM), 6 (IC50 = 40.23 ± 0.20 µM), and 7 (IC50 = 36.43 ± 0.02 µM) showed an excellent yeast glucose uptake activity better than the standard.

  Pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 were synthesized, structurally characterized, and evaluated for in vitro yeast glucose uptake activity. Compounds 5 (IC50 = 38.14 ± 0.17 µM), 6 (IC50 = 40.23 ± 0.20 µM), and 7 (IC50 = 36.43 ± 0.02 µM) demonstrated potent yeast glucose uptake activity as compared to standard metronidazole (IC50 = 41.86 ± 0.09 µM). This study identified a number of potential lead molecules which can be helpful in lowering the blood glucose level in hyperglycemia.

  背景：糖尿病是全球致死和致残的主要原因，最近，我们已报告各种类别的化合物作为抗糖基化剂，并且我们还报告苯并咪唑和苯并噻唑衍生物作为一种潜在的抗糖基化剂类。这激励我们评估吡啶基苯并咪唑/吡啶基苯并噻唑衍生物1-27对酵母葡萄糖摄取活性的作用。 方法：在本研究中，将吡啶羧醛衍生物（1 mmol）和亚硫酸钠（1 mmol）在DMF（10 mL）中等摩尔混合物搅拌10至15分钟，然后加入邻苯二胺/2-氨基硫酚（1 mmol）并回流3小时。通过薄层色谱监测反应进展。反应完成后，将反应混合物倒入碎冰中。形成沉淀，通过过滤收集，产生产率良好的化合物1-27。用甲醇再结晶得到纯晶体。 结果：我们的研究表明，所有化合物在酵母葡萄糖摄取活性范围内显示出不同程度的活性，IC50 = 36.43-272.20 µM，与标准甲硝唑（IC50 = 41.86 ± 0.09 µM）相比。化合物5（IC50 = 38.14 ± 0.17 µM）、6（IC50 = 40.23 ± 0.20 µM）和7（IC50 = 36.43 ± 0.02 µM）显示出优异的酵母葡萄糖摄取活性，优于标准物质。 结论：合成了吡啶基苯并咪唑/吡啶基苯并噻唑衍生物1-27，进行了结构表征，并评估了体外酵母葡萄糖摄取活性。化合物5（IC50 = 38.14 ± 0.17 µM）、6（IC50 = 40.23 ± 0.20 µM）和7（IC50 = 36.43 ± 0.02 µM）表现出强大的酵母葡萄糖摄取活性，与标准甲硝唑（IC50 = 41.86 ± 0.09 µM）相比。该研究确定了一系列潜在的先导分子，有助于降低高血糖水平。
• Synthesis of benzoxazoles, benzothiazoles and benzimidazoles and evaluation of their antifungal, insecticidal and herbicidal activities.
  作者：TAKUZO HISANO、MASATAKA ICHIKAWA、KONOSUKE TSUMOTO、MASANOBU TASAKI

  DOI：10.1248/cpb.30.2996

  日期：——

  Benzoxazoles, benzothiazoles and benzimidazoles having substituents on the azole and benzene nuclei were synthesized evaluated for antifungal, insecticidal and herbicidal activities. It was found that benzimidazoles tended to exhibit antifungal activity while benzothiazoles tended to show herbicidal activity. Chloro, trifluoromethyl, methoxy and ethoxy groups at the 5 position were potent substituents, and the 2-pyridyl group at the 2 position is a common structural unit. Among several active derivatives, 7-chloro-2-(2-pyridyl) benzimidazole and 2-(2-pyridyl)-5-trifluoromethylbenzothiazole exhibited significant activity against Panonycus citri.

  合成了在偶氮和苯环上具有取代基的苯并噁唑、苯并噻唑和苯并咪唑，并评估其抗真菌、杀虫和除草活性。研究发现，苯并咪唑倾向于表现出抗真菌活性，而苯并噻唑则倾向于显示除草活性。在5位位置上的氯、三氟甲基、甲氧基和乙氧基基团是有效的取代基，而在2位位置的吡啶基是一个常见的结构单元。在几种具有活性的衍生物中，7-氯-2-(2-吡啶基)苯并咪唑和2-(2-吡啶基)-5-三氟甲基苯并噻唑对柑橘红蜘蛛表现出显著活性。
• Synthesis and in vitro α-chymotrypsin inhibitory activity of 6-chlorobenzimidazole derivatives
  作者：Hina Siddiqui、Rabia Farooq、Bishnu P. Marasini、Rizwana Malik、Naima Syed、Syed Tarique Moin、Atta-ur-Rahman、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2016.05.018

  日期：2016.8

  Compounds 2–8, 15, 17, and 18 showed significant inhibitory activities. All the inhibitors were found to be competitive inhibitors, except compound 17, which was a mixed type inhibitor. The substituents (R) in para and ortho positions of phenyl ring B, apparently played a key role in the inhibitory potential of the series. Compounds 1–20 were also studied for their cytotoxicity profile by using 3T3 mouse

  苯并咪唑衍生物的文库1 - 20合成，并研究了它们的α胰凝乳蛋白酶（α-CT）的体外抑制活性。进行动力学和分子对接研究以鉴定抑制类型。 与标准的胰凝乳蛋白酶抑制素（IC 50  = 5.7±0.13μM）相比，发现化合物1是α-胰凝乳蛋白酶的良好抑制剂（IC 50  = 14.8±0.1μM，K i = 16.4μM）。化合物2 - 8，15，17，和18显示出显著抑制活性。发现除化合物外，所有抑制剂均为竞争性抑制剂。图17是混合型抑制剂。苯环B对位和邻位的取代基（R）显然在该系列的抑制潜力中起关键作用。化合物1 - 20也通过使用3T3小鼠成纤维细胞研究了它们的细胞毒性曲线和化合物3，5，6，8，12 - 14，16，17，19，和20被发现具有细胞毒性。与标准化合物chymostatin相比，对该系列中最活跃的成员进行了分子对接，以鉴定最可能的结合方式。本文报道的化合物可作为进一步研究
• IMIDAZOLE DERIVATIVES HAVING ARYL PIPERIDINE SUBSTITUENT, METHOD FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
  申请人：Suh Jee Hee

  公开号：US20100145054A1

  公开（公告）日：2010-06-10

  The present invention is directed to a novel imidazole derivative having an aryl piperidine substituent of formula (I) and a method for preparation thereof, and a pharmaceutical composition containing said imidazole derivative as an active ingredient for preventing or treating a MCH (melanine-concentrating hormone)-related disease.

  本发明涉及一种具有式(I)的芳基哌啶取代基的新型咪唑衍生物及其制备方法，以及含有该咪唑衍生物作为活性成分的药物组合物，用于预防或治疗与MCH（黑色素浓集激素）相关的疾病。