| 1585245-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• CAS: 1585245-03-9
• 化学式: C₂HF₃O₂*C₁₉H₁₇N₃O₂S
• 分子量: 465.453
• InChiKey: BKWSEKGVONRJLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  121.52
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以61%的产率得到2-(1-naphthamido)-6-acetyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide
  参考文献：
  名称：

  Development of antimycobacterial tetrahydrothieno[2,3-c]pyridine-3-carboxamides and hexahydrocycloocta[b]thiophene-3-carboxamides: Molecular modification from known antimycobacterial lead

  摘要：

  Twenty derivatives of 2,6-disubstituted 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide and ten of 2-substituted 4,5,6,7,8,9-hexahydrocycloocta[b]thiophene-3-carboxamide were synthesized by molecular modification of a known antimycobacterial molecule. Compounds were evaluated in vitro against Mycobacterium tuberculosis (MTB), and cytotoxicity against RAW 264.7 cell line. Among the compounds, 2-(4-phenoxybenzamido)-4,5,6,7,8,9-hexahydrocycloocta[b]thiophene-3-carboxamide (12f) was found to be the most active compound against MTB with MIC of 3.70 mu M and was more potent than Ethambutol (MIC of 7.64 mu M), Ciprofloxacin (MIC of 9.41 mu M) and standard lead compound SID 92097880 (MIC of 9.15 mu M). Compound 12f also showed MTB MIC of 1.23 mu M in the presence of an efflux pump inhibitor verapamil, and showed no cytotoxicity at 50 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.028
• 作为产物：
  描述：

  N-叔丁氧羰基-4-哌啶酮 在 吗啉 、 1-羟基苯并三唑 、 sulfur 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  Development of antimycobacterial tetrahydrothieno[2,3-c]pyridine-3-carboxamides and hexahydrocycloocta[b]thiophene-3-carboxamides: Molecular modification from known antimycobacterial lead

  摘要：

  Twenty derivatives of 2,6-disubstituted 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide and ten of 2-substituted 4,5,6,7,8,9-hexahydrocycloocta[b]thiophene-3-carboxamide were synthesized by molecular modification of a known antimycobacterial molecule. Compounds were evaluated in vitro against Mycobacterium tuberculosis (MTB), and cytotoxicity against RAW 264.7 cell line. Among the compounds, 2-(4-phenoxybenzamido)-4,5,6,7,8,9-hexahydrocycloocta[b]thiophene-3-carboxamide (12f) was found to be the most active compound against MTB with MIC of 3.70 mu M and was more potent than Ethambutol (MIC of 7.64 mu M), Ciprofloxacin (MIC of 9.41 mu M) and standard lead compound SID 92097880 (MIC of 9.15 mu M). Compound 12f also showed MTB MIC of 1.23 mu M in the presence of an efflux pump inhibitor verapamil, and showed no cytotoxicity at 50 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.028