2-氯-3-甲基-3H-咪唑并[4,5-b]吡啶 | 30458-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 2-氯-3-甲基-3H-咪唑并[4,5-b]吡啶
• 英文名称: 2-chloro-3-methyl-3H-imidazo[4,5-b]pyridine
• 英文别名: 2-chloro-3-methyl-4-azabenzimidazole；2-chloro-3-methylimidazo[4,5-b]pyridine
• CAS: 30458-68-5
• 化学式: C₇H₆ClN₃
• 分子量: 167.598
• InChiKey: YPHGAEKALDRGJE-UHFFFAOYSA-N

物化性质

• 熔点：
  65-67 °C
• 沸点：
  321.3±34.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  2-氯-3-甲基-3H-咪唑并[4,5-b]吡啶 在 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 15.0h， 以75%的产率得到3-甲基-3H-咪唑并[4,5-b]吡啶-2-胺
  参考文献：
  名称：

  Probing the molecular and structural elements of ligands binding to the active site versus an allosteric pocket of the human farnesyl pyrophosphate synthase

  摘要：

  In order to explore the interactions of bisphosphonate ligands with the active site and an allosteric pocket of the human farnesyl pyrophosphate synthase (hFPPS), substituted indole and azabenzimidazole bisphosphonates were designed as chameleon ligands. NMR and crystallographic studies revealed that these compounds can occupy both subpockets of the active site cavity, as well as the allosteric pocket of hFPPS in the presence of the enzyme's Mg2+ ion cofactor. These results are consistent with the previously proposed hypothesis that the allosteric pocket of hFPPS, located near the active site, plays a feedback regulatory role for this enzyme. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.089
• 作为产物：
  描述：

  3-甲基-3H-咪唑并[4,5-b]吡啶 在 lithium diisopropyl amide 、 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 1.0h， 以49%的产率得到2-氯-3-甲基-3H-咪唑并[4,5-b]吡啶
  参考文献：
  名称：

  4-氮杂苯并咪唑衍生物的合成及配位化学

  摘要：

  介绍了一种制备 N1- (1a-6a) 和 N3-烷基化 (1b-6b) 4-氮杂苯并咪唑衍生物的简便方法。两种异构体均通过 4-氮杂苯并咪唑的烷基化获得。分离异构体，观察到优选形成 N1-烷基化衍生物 (1a-6a)。通过用甲基锂和碘处理，烷基化苯并咪唑中的 C2-质子可以交换为碘原子，产生 N-烷基化 2-碘-4-氮杂苯并咪唑 7a、b 和 8a。2,2'-双（4-氮杂苯并咪唑）衍生物 9a、b 和 10a 作为质子 - 卤素交换的副产物被分离出来。用甲基锂和 N-氯代琥珀酰亚胺作为氯源处理 N1-或 N3-甲基-4-氮杂苯并咪唑 1a、b 得到 2-氯-4-氮杂苯并咪唑 11a、b，而没有形成偶联产物，但2-氯-1-甲基-4-氮杂苯并咪唑11a的产率低（9%），而2-氯-3-甲基-4-氮杂苯并咪唑11b的产率合理（49%）。3-丁基-2-碘-4-氮杂苯并咪唑 7b 与 [IrCl2Cp*]2

  DOI：

  10.1002/hc.20711

文献信息

• FUSED HETEROCYCLIC COMPOUNDS
  申请人：TANIGUCHI Takahiko

  公开号：US20110319394A1

  公开（公告）日：2011-12-29

  The present invention provides a compound which has the effect of PDE inhibition, and which is useful as an agent for preventing or treating schizophrenia. The compound is represented by the formula (I): wherein the symbols are defined in the specification.

  本发明提供了一种具有磷酸二酯酶抑制作用的化合物，可用作预防或治疗精神分裂症的药剂。该化合物由以下式表示（I）： 其中符号在规范中定义。
• Molecular Design, Synthesis, and Hypoglycemic Activity of a Series of Thiazolidine-2,4-diones
  作者：Minoru Oguchi、Kunio Wada、Hidehito Honma、Asako Tanaka、Tomoko Kaneko、Sachiko Sakakibara、Jun Ohsumi、Nobufusa Serizawa、Toshihiko Fujiwara、Hiroyoshi Horikoshi、Takashi Fujita

  DOI：10.1021/jm990522t

  日期：2000.8.1

  A series of imidazopyridine thiazolidine-2,4-diones were designed and synthesized from their corresponding pyridines. These compounds represent conformationally restricted analogues of the novel hypoglycemic compound rosiglitazone (5). The series was evaluated for its effect on insulin-induced 3T3-L1 adipocyte differentiation in vitro and its hypoglycemic activity in the genetically diabetic KK mouse

  从其相应的吡啶设计并合成了一系列咪唑并吡啶噻唑烷-2,4-二酮。这些化合物代表新型降血糖化合物罗格列酮（5）的构象受限类似物。评估该系列在体外对胰岛素诱导的3T3-L1脂肪细胞分化的影响以及在体内遗传性糖尿病KK小鼠中的降血糖活性。讨论了构效关系。基于体内效力，5- [4-（5-甲氧基-3-甲基-3H-咪唑并[4，5-b]吡啶-2-基甲氧基）苄基]噻唑烷-2,4-二酮（19a ）被选为在临床环境中进一步研究的候选人。
• Regioselective synthesis of C-2 substituted imidazo[4,5-b]pyridines utilizing palladium catalysed C–N bond forming reactions with enolizable heterocycles
  作者：K.K. Abdul Khader、Ayyiliath M. Sajith、M. Syed Ali Padusha、H.P. Nagaswarupa、A. Muralidharan

  DOI：10.1016/j.tetlet.2014.01.114

  日期：2014.3

  In this Letter we report a rapid and facile access to C2-substituted imidazo[4,5-b]pyridine analogues utilizing palladium mediated Buchwald–Hartwig cross-coupling reactions. The use of enolizable heterocycles as cross-coupling partners resulted in a wide range of imidazo[4,5-b]pyridine analogues which are prone to have medicinal relevance. Xantphos and Pd(OAc)2 were found to be more effective for the

  在这封信中，我们报告了利用钯介导的布赫瓦尔德-哈特维格交叉偶联反应快速而轻松地获得C2取代的咪唑并[4,5- b ]吡啶类似物的方法。使用可烯醇化的杂环作为交叉偶联伴侣会导致产生广泛的具有医学相关性的咪唑并[4,5- b ]吡啶类似物。发现Xantphos和Pd（OAc）2对于2-卤代咪唑并[4,5- b ]吡啶与吡啶酮亲核试剂的偶联更有效。还报道了区域选择性的合成2-取代的3 H-咪唑并[4，5- b ]吡啶和1 H-咪唑并[4，5- b ]吡啶的方法。
• Palladium(0)-catalyzed phenylation of imidazo[4,5-<i>b</i>]pyridines
  作者：Spiros Grivas、Stefan Lindström

  DOI：10.1002/jhet.5570320214

  日期：1995.3

  The tetrakis(triphenylphosphine)palladium(O)-catalyzed coupling of benzeneboronic acid with 2-chloro, 6-bromo and 6-bromo-2-chloro derivatives of 1- and 3-methylimidazo[4,5-b]pyridines to novel 2-phenyl-, 6-phenyl- and 2,6-diphenylimidazo[4,5-b]pyridines is described. The phenylation of imidazo[4,5-b]-pyridines containing labile hydrogens was not successful.

  四（三苯基膦）钯（O）催化的苯硼酸与1-和3-甲基咪唑并[4,5- b ]吡啶的2-氯，6-溴和6-溴-2-氯衍生物偶联至新型2描述了-苯基-，6-苯基-和2，6-二苯基咪唑并[4，5- b ]吡啶。含不稳定氢的咪唑并[4,5- b ]-吡啶的苯基化作用不成功。
• Substituted piperazine derivatives, the preparation thereofand their use as medicaments
  申请人：——

  公开号：US20030166637A1

  公开（公告）日：2003-09-04

  The present invention relates to substituted piperazine derivatives of general formula 1 , (I wherein R a , R b , R c , R f , R g , X, m and n are defined as in claim 1, the isomers and salts thereof, particularly the physiologically acceptable salts thereof, which are valuable inhibitors of the microsomal triglyceride-transfer protein (MTP), medicaments containing these compounds and their use, as well as the preparation thereof.

  本发明涉及一般式1的取代哌嗪衍生物，其中Ra、Rb、Rc、Rf、Rg、X、m和n如权利要求1所定义，其异构体和盐，尤其是生理上可接受的盐，这些化合物是微粒体甘油三酯转移蛋白（MTP）的有价值的抑制剂，药物含有这些化合物及其用途，以及其制备方法。