1,2-二甲基-1H-苯并咪唑-6-羧酸 | 6595-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1,2-二甲基-1H-苯并咪唑-6-羧酸
• 中文别名: 1,2-二甲基-1H-苯并[D]咪唑-6-羧酸
• 英文名称: 1,2-dimethyl-1H-benzimidazole-6-carboxylic acid
• 英文别名: 2,3-dimethyl-3H-benzoimidazole-5-carboxylic acid；1.2-Dimethyl-benzimidazol-6-carbonsaeure；1,2-Dimethyl-1H-benzo[d]imidazole-6-carboxylic acid；2,3-dimethylbenzimidazole-5-carboxylic acid
• CAS: 6595-00-2
• 化学式: C₁₀H₁₀N₂O₂
• mdl: MFCD13562914
• 分子量: 190.202
• InChiKey: PAHCNWPMLGFQKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-氨基-5-硝基噻唑 、 1,2-二甲基-1H-苯并咪唑-6-羧酸 在 N,N'-羰基二咪唑 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以63.6%的产率得到1,2-dimethyl-N-(5-nitro-1,3-thiazol-2-yl)-1H-benzimidazole-6-carboxamide
  参考文献：
  名称：

  Synthesis and antiprotozoal activity of nitazoxanide–N-methylbenzimidazole hybrids

  摘要：

  A series of a novel hybrid compounds between nitazoxanide and N-methylbenzimidazole were synthesized starting from the corresponding N-methyl-2-nitroanilines. The new hybrid compounds (1-13) were evaluated in vitro against Giardia intestinalis, Entamoeba histolytica, Trichomonas vaginalis. NTZ, MTZ and ABZ were used as drug standards. Experimental evaluations revealed all of the new compounds (1-13) were active and showed strong activity against the three protozoa, particularly with E. histolytica where the IC50 values ranged between 3 and 69 nM.Overall, compounds 2, 5, 7, 8, 9, 11 and 12 stood out with values lower than 87 nM for all three protozoa, comparatively better than the reference drugs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.011
• 作为产物：
  描述：

  3-(甲基氨基)-4-硝基苯羧酸甲酯 在 盐酸 、 palladium on activated charcoal 、 水 、 氢气 、 potassium hydroxide 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 1,2-二甲基-1H-苯并咪唑-6-羧酸
  参考文献：
  名称：

  Synthesis and antiprotozoal activity of nitazoxanide–N-methylbenzimidazole hybrids

  摘要：

  A series of a novel hybrid compounds between nitazoxanide and N-methylbenzimidazole were synthesized starting from the corresponding N-methyl-2-nitroanilines. The new hybrid compounds (1-13) were evaluated in vitro against Giardia intestinalis, Entamoeba histolytica, Trichomonas vaginalis. NTZ, MTZ and ABZ were used as drug standards. Experimental evaluations revealed all of the new compounds (1-13) were active and showed strong activity against the three protozoa, particularly with E. histolytica where the IC50 values ranged between 3 and 69 nM.Overall, compounds 2, 5, 7, 8, 9, 11 and 12 stood out with values lower than 87 nM for all three protozoa, comparatively better than the reference drugs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.011

文献信息

• [EN] BENZOIMIDAZOLE DERIVATIVES AS PAD4 INHIBITORS<br/>[FR] DÉRIVÉS DE BENZOIMIDAZOLE EN TANT QU'INHIBITEURS DE PAD4
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2016185279A1

  公开（公告）日：2016-11-24

  Compounds of formula (I): wherein X, Y, R1 and R3-R11 are as herein defined, and salts thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosus, ulcerative colitis, cancer, cystic fibrosis, asthma, cutaneous lupus erythematosis, and psoriasis.

  式(I)的化合物：其中X、Y、R1和R3-R11如本文所定义，并其盐为PAD4抑制剂，可能在治疗各种疾病中有用，例如类风湿关节炎、血管炎、系统性红斑狼疮、溃疡性结肠炎、癌症、囊性纤维化、哮喘、皮肤红斑狼疮和牛皮癣。
• Discovery of a novel 2,3-dimethylimidazo[1,2-a]pyrazine-6-carboxamide M4 positive allosteric modulator (PAM) chemotype
  作者：Kayla J. Temple、Julie L. Engers、Madeline F. Long、Katherine J. Watson、Sichen Chang、Vincent B. Luscombe、Matthew T. Jenkins、Alice L. Rodriguez、Colleen M. Niswender、Thomas M. Bridges、P. Jeffrey Conn、Darren W. Engers、Craig W. Lindsley

  DOI：10.1016/j.bmcl.2019.126812

  日期：2020.2

  This Letter details our efforts to discover structurally unique M-4 PAMs containing 5,6-heteroaryl ring systems. In an attempt to improve the DMPK profiles of the 2,3-dimethyl-2H-indazole-5-carboxamide and 1-methyl-1H-benzo[d][1,2,3]triazole-6-carboxamide cores, we investigated a plethora of core replacements. This exercise identified a novel 2,3-dimethylimidazo[1,2-a]pyrazine-6-carboxamide core that provided improved M-4 PAM activity and CNS penetration.
• BENZOIMIDAZOLE DERIVATIVES AS PAD4 INHIBITORS
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：EP3298003A1

  公开（公告）日：2018-03-28