咪唑并[2,1-b]苯并噻唑-2-羧酸 | 64951-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 咪唑并[2,1-b]苯并噻唑-2-羧酸
• 英文名称: imidazo<2,1-b>benzothiazole-2-carboxylic acid
• 英文别名: imidazo[2,1-b]benzothiazole-6-carboxylic acid；benzo[d]imidazo[2,1-b]thiazole-2-carboxylic acid；Imidazo-benzothiazol-2-carbonsaeure；Imidazo[2,1-b][1,3]benzothiazole-2-carboxylic acid
• CAS: 64951-09-3
• 化学式: C₁₀H₆N₂O₂S
• mdl: MFCD00203011
• 分子量: 218.236
• InChiKey: RPTIDKXUZBSTRL-UHFFFAOYSA-N

物化性质

• 熔点：
  266-268
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 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：
  82.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  咪唑并[2,1-b]苯并噻唑-2-羧酸 在 copper(ll) sulfate pentahydrate 、 1-羟基苯并三唑 、 sodium ascorbate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 13.0h， 生成 N-((1-(3-hydroxy-4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)benzo[d]imidazo[2,1-b]thiazole-2-carboxamide
  参考文献：
  名称：

  设计和合成1,2,3-三唑连接的苯并[d]咪唑并[2,1-b]噻唑共轭物作为微管蛋白聚合抑制剂。

  摘要：

  设计，合成和合成1,2,3-三唑并连接的苯并[d]咪唑并[2,1-b]噻唑共轭物（5a-v），并评估其对某些人类癌细胞系如DU-145（前列腺）的细胞毒性。 ，HeLa（子宫颈），MCF-7（乳腺癌）HepG2（肝脏）和A549（肺）。初步结果显示，其中的一些缀合物（如5f和5k）对人乳腺癌细胞（MCF-7）表现出显着的抗增殖作用，IC50值分别为0.60和0.78µM。细胞周期的流式细胞术分析表明，G2 / M期细胞的百分比增加，这通过细胞周期蛋白B1蛋白水平的升高进一步证实。免疫细胞化学分析显示，用5f和5k处理的细胞中完整的微管结构丧失，蛋白质印迹分析表明这些结合物在可溶性部分中积累了更多的微管蛋白。此外，结合物引起细胞的凋亡，这通过线粒体膜电位和膜联蛋白V-FITC测定证实。分子对接研究表明，这些结合物占据了微管蛋白的秋水仙碱结合位点。

  DOI：

  10.1016/j.bmc.2017.04.013
• 作为产物：
  描述：

  6-乙基-(9ci)-2-氨基苯并噻唑 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 咪唑并[2,1-b]苯并噻唑-2-羧酸
  参考文献：
  名称：

  (Imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones and related compounds as potential nonsedative anxiolytics

  摘要：

  Several series of heterocyclic carboxylic esters were found to be active in the benzodiazepine receptor binding assay, a typical example being ethyl 7-ethyl-5-methoxyimidazo[1,2-a]quinoline-2-carboxylate (4b) with an IC50 of 150 nM. The corresponding phenylmethanone 5d was more potent with an IC50 of 14 nM and was orally active in animal models thought to predict anxiolytic effects. The synthesis of a large number of compounds resulted in the optimization of this activity in a series of (imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones of which compounds 7e, 8b, 8h, 8j, and 8k were equipotent with chlordiazepoxide while exhibiting reduced anticonvulsant activity, little or no muscle relaxation, and negligible sedative effects.

  DOI：

  10.1021/jm00401a025

文献信息

• [EN] SUBSTITUTED N-PHENYL-BIPYRROLIDINE CARBOXAMIDES AND THERAPEUTIC USE THEREOF<br/>[FR] CARBOXAMIDES DE N-PHÉNYL-BIPYRROLIDINE SUBSTITUÉS ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：SANOFI AVENTIS

  公开号：WO2009052065A1

  公开（公告）日：2009-04-23

  The present invention discloses and claims a series of substituted N-phenyl-bipyrrolidine carboxamides of formula (I), Wherein R, R1, R2, R3 and R4 are as described herein. More specifically, the compounds of this invention are modulators of H3 receptors and are, therefore, useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of diseases modulated by H3 receptors including diseases associated with the central nervous system. Additionally, this invention also discloses methods of preparation of substituted N-phenyl-bipyrrolidine carboxamides and intermediates therefor.

  本发明公开并声明了一系列式(I)的取代N-苯基-双吡咯烷羧酰胺，其中R、R1、R2、R3和R4如本文所述。更具体地说，本发明的化合物是H3受体调节剂，因此在制药方面特别有用，尤其是在治疗和/或预防通过H3受体调节的各种疾病，包括与中枢神经系统相关的疾病。此外，本发明还公开了取代N-苯基-双吡咯烷羧酰胺及其中间体的制备方法。
• Methods of screening for compounds which inhibit the activity of Cdc34 in a zinc-mediated manner and compounds obtained by this method
  申请人：Furet Pascal

  公开号：US20060211747A1

  公开（公告）日：2006-09-21

  The present invention relates to methods of searching/screening for compounds which inhibit the activity of the ubiquitin conjugating enzyme Cdc34 in a zinc-mediated manner, to compounds obtainable by such a method, to a method of treating mammalian subjects with such compounds, to pharmaceutical compositions containing such compounds, to the use of such compounds for the treatment of diseases which respond to an inhibition of the activity of Cdc34 such as proliferative diseases, especially tumor diseases, and to the use of such compounds for the preparation of such pharmaceutical compositions for the treatment of such diseases.

  本发明涉及一种通过锌介导方式抑制泛素结合酶Cdc34活性的化合物搜索/筛选方法，涉及通过这种方法获得的化合物，涉及使用这种化合物治疗哺乳动物受试者的方法，涉及含有这种化合物的药物组合物，涉及使用这种化合物治疗对Cdc34活性抑制有反应的疾病，如增殖性疾病，尤其是肿瘤疾病，以及使用这种化合物制备这种药物组合物以治疗这种疾病。
• Fully Automated Continuous Flow Synthesis of Highly Functionalized Imidazo[1,2-a] Heterocycles
  作者：Ananda Herath、Russell Dahl、Nicholas D. P. Cosford

  DOI：10.1021/ol902433a

  日期：2010.2.5

  first continuous flow synthesis of imidazo[1,2-a]pyridine-2-carboxylic acids directly from 2-aminopyridines and bromopyruvic acid has been developed, representing a significant advance over the corresponding in-flask method. The process was applied to the multistep synthesis of imidazo[1,2-a]pyridine-2-carboxamides, including a Mur ligase inhibitor, using a two microreactor, multistep continuous flow

  第一个直接从 2-氨基吡啶和溴丙酮酸连续流动合成咪唑并[1,2-a]吡啶-2-羧酸的方法已经开发出来，这代表了相对于相应烧瓶内方法的显着进步。该工艺适用于咪唑并[1,2-a]吡啶-2-甲酰胺（包括Mur连接酶抑制剂）的多步合成，使用两个微反应器、多步连续流动工艺，无需分离中间体。
• Pyrazoles as inhibitors of tumor necrosis factor
  申请人：Borcherding R. David

  公开号：US20060063796A1

  公开（公告）日：2006-03-23

  The present invention provides compounds of Formula (I) and ester prodrugs, pharmaceutically acceptable salts or solvates of such compounds; or ester prodrugs of such salts or solvates; pharmaceutical compositions comprising such compounds, their preparation, and their pharmaceutical use in the treatment of disease states capable of being modulated by the inhibition of p38 kinase and/or tumor necrosis factor (TNF).

  本发明提供了式（I）的化合物和酯前药、这些化合物的药学上可接受的盐或溶剂；或这些盐或溶剂的酯前药；包括这些化合物的制药组合物，其制备以及它们在治疗能够通过抑制p38激酶和/或肿瘤坏死因子（TNF）调节的疾病状态中的药物应用。
• SUBSTITUTED N-PHENYL-BIPYRROLIDINE CARBOXAMIDES AND THERAPEUTIC USE THEREOF
  申请人：CZECHTIZKY Werngard

  公开号：US20100173897A1

  公开（公告）日：2010-07-08

  The present invention discloses and claims a series of substituted N-phenyl-bipyrrolidine carboxamides of formula (I). Wherein R, R 1 , R 2 , R 3 and R 4 are as described herein. More specifically, the compounds of this invention are modulators of H3 receptors and are, therefore, useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of diseases modulated by H3 receptors including diseases associated with the central nervous system. Additionally, this invention also discloses methods of preparation of substituted N-phenyl-bipyrrolidine carboxamides and intermediates therefor.

  本发明揭示和声明了一系列取代的N-苯基双吡咯烷羧酰胺化合物，其化学式为(I)，其中R、R1、R2、R3和R4如本文所述。更具体地，本发明的化合物是H3受体调节剂，因此在治疗和/或预防包括与中枢神经系统相关的多种H3受体调节的疾病方面，特别是作为药物剂量是有用的。此外，本发明还揭示了取代的N-苯基双吡咯烷羧酰胺及其中间体的制备方法。