2,6-二甲基-1H-吲哚-3-羧酸 | 1227267-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2,6-二甲基-1H-吲哚-3-羧酸
• 英文名称: 2,6-dimethyl-1H-indole-3-carboxylic acid
• CAS: 1227267-27-7
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: RINOZWROKFEBLM-UHFFFAOYSA-N

物化性质

• 沸点：
  407.7±40.0 °C(Predicted)
• 密度：
  1.287

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-二甲基-1H-吲哚-3-羧酸 、 苄胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以75%的产率得到N-benzyl-2,6-dimethyl-1H-indole-3-carboxamide
  参考文献：
  名称：

  Scaffold-switching: An exploration of 5,6-fused bicyclic heteroaromatics systems to afford antituberculosis activity akin to the imidazo[1,2-a]pyridine-3-carboxylates

  摘要：

  A set of 5,6-fused bicyclic heteroaromatic scaffolds were investigated for their in vitro anti-tubercular activity versus replicating and non-replicating strains of Mycobacterium tuberculosis (Mtb) in an attempt to find an alternative scaffold to the imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidines that were previously shown to have potent activity against replicating and drug resistant Mtb. The five new bicyclic heteroaromatic scaffolds explored in this study include a 2,6-dimethylimidazo[1,2-b]pyridazine-3-carboxamide (7), a 2,6-dimethyl-1H-indole-3-carboxamide (8), a 6-methyl-1H-indazole-3-carboxamide (9), a 7-methyl-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide (10), and a 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxamide (11). Additionally, imidazo[1,2-a]pyridines isomers (2 and 12) and a homologous imidazo[1,2-a]pyrimidine isomer (6) were prepared and compared. Compounds 2 and 6 were found to be the most potent against H(37)Rv Mtb (MIC's of 0.1 mu M and 1.3 mu M) and were inactive (MIC >128 mu M) against Staphylococcus aureus, Escherichia coli and Candida albicans. Against other non-tubercular mycobacteria strains, compounds 2 and 6 had activity against Mycobacterium avium (16 and 122 mu M, respectively), Mycobacterium kansasii (4 and 19 mu M, respectively), Mycobacterium bovis BCG (1 and 8 mu M, respectively) while all the other scaffolds were inactive (>128 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.062

文献信息

• Scaffold-switching: An exploration of 5,6-fused bicyclic heteroaromatics systems to afford antituberculosis activity akin to the imidazo[1,2-a]pyridine-3-carboxylates
  作者：Garrett C. Moraski、Allen G. Oliver、Lowell D. Markley、Sanghyun Cho、Scott G. Franzblau、Marvin J. Miller

  DOI：10.1016/j.bmcl.2014.05.062

  日期：2014.8

  A set of 5,6-fused bicyclic heteroaromatic scaffolds were investigated for their in vitro anti-tubercular activity versus replicating and non-replicating strains of Mycobacterium tuberculosis (Mtb) in an attempt to find an alternative scaffold to the imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidines that were previously shown to have potent activity against replicating and drug resistant Mtb. The five new bicyclic heteroaromatic scaffolds explored in this study include a 2,6-dimethylimidazo[1,2-b]pyridazine-3-carboxamide (7), a 2,6-dimethyl-1H-indole-3-carboxamide (8), a 6-methyl-1H-indazole-3-carboxamide (9), a 7-methyl-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide (10), and a 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxamide (11). Additionally, imidazo[1,2-a]pyridines isomers (2 and 12) and a homologous imidazo[1,2-a]pyrimidine isomer (6) were prepared and compared. Compounds 2 and 6 were found to be the most potent against H(37)Rv Mtb (MIC's of 0.1 mu M and 1.3 mu M) and were inactive (MIC >128 mu M) against Staphylococcus aureus, Escherichia coli and Candida albicans. Against other non-tubercular mycobacteria strains, compounds 2 and 6 had activity against Mycobacterium avium (16 and 122 mu M, respectively), Mycobacterium kansasii (4 and 19 mu M, respectively), Mycobacterium bovis BCG (1 and 8 mu M, respectively) while all the other scaffolds were inactive (>128 mu M). (C) 2014 Elsevier Ltd. All rights reserved.