N-(1-(tert-butyl)-6-methoxy-2-methyl-1H-benzo[d]imidazol-5-yl)-5-nitrofuran-2-carboxamide | 1465826-05-4

• 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: N-(1-(tert-butyl)-6-methoxy-2-methyl-1H-benzo[d]imidazol-5-yl)-5-nitrofuran-2-carboxamide
• 英文别名: N-(1-tert-butyl-6-methoxy-2-methyl-benzimidazol-5-yl)-5-nitro-furan-2-carboxamide；N-(1-tert-butyl-6-methoxy-2-methylbenzimidazol-5-yl)-5-nitrofuran-2-carboxamide
• CAS: 1465826-05-4
• 化学式: C₁₈H₂₀N₄O₅
• 分子量: 372.381
• InChiKey: DHHNCRJIGRBRGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-fluoro-5-methoxy-2,4-dinitrobenzene 在 palladium 10% on activated carbon 、 甲酸铵 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 生成 N-(1-(tert-butyl)-6-methoxy-2-methyl-1H-benzo[d]imidazol-5-yl)-5-nitrofuran-2-carboxamide
  参考文献：
  名称：

  Benzimidazole-based compounds kill Mycobacterium tuberculosis

  摘要：

  Tuberculosis remains one of the deadliest infectious diseases, killing 1.4 million people annually and showing a rapid increase in cases resistant to multiple drugs. New antibiotics against tuberculosis are urgently needed. Here we describe the design, synthesis and structure activity relationships of a series of benzimidazole-based compounds with activity against Mycobacterium tuberculosis (Mtb) in a replicating state, a physiologically-induced non-replicating state, or both. Compounds 49, 67, 68, 69, 70, and 72, which shared a 5-nitrofuranyl moiety, exhibited high potency and acceptable selectivity indices (SI). As illustrated by compound 70 (MIC90 < 0.049 mu g/mL, SI > 512), the 5-nitrofuranyl group was compatible with minimal cytotoxicity and good intra-macrophage killing, although it lacked non-replicating activity when assessed by CFU assays. Compound 70 had low mutagenic potential by SOS Chromotest assay, making this class of compounds good candidates for further evaluation and target identification. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.039

文献信息

• Benzimidazole-based compounds kill Mycobacterium tuberculosis
  作者：Yaling Gong、Selin Somersan Karakaya、Xiaoyong Guo、Purong Zheng、Ben Gold、Yao Ma、David Little、Julia Roberts、Thulasi Warrier、Xiuju Jiang、Maneesh Pingle、Carl F. Nathan、Gang Liu

  DOI：10.1016/j.ejmech.2014.01.039

  日期：2014.3

  Tuberculosis remains one of the deadliest infectious diseases, killing 1.4 million people annually and showing a rapid increase in cases resistant to multiple drugs. New antibiotics against tuberculosis are urgently needed. Here we describe the design, synthesis and structure activity relationships of a series of benzimidazole-based compounds with activity against Mycobacterium tuberculosis (Mtb) in a replicating state, a physiologically-induced non-replicating state, or both. Compounds 49, 67, 68, 69, 70, and 72, which shared a 5-nitrofuranyl moiety, exhibited high potency and acceptable selectivity indices (SI). As illustrated by compound 70 (MIC90 < 0.049 mu g/mL, SI > 512), the 5-nitrofuranyl group was compatible with minimal cytotoxicity and good intra-macrophage killing, although it lacked non-replicating activity when assessed by CFU assays. Compound 70 had low mutagenic potential by SOS Chromotest assay, making this class of compounds good candidates for further evaluation and target identification. (C) 2014 Elsevier Masson SAS. All rights reserved.