2-ethyl-N-(p-tolyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 2-ethyl-N-(p-tolyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine
• 英文别名: 2-ethyl-N-(p-tolyl)-5,6,7,8-tetrahydrobenzothiopheno[2,3-d]pyrimidin-4-amine；2-ethyl-N-(4-methylphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine
• 化学式: C₁₉H₂₁N₃S
• 分子量: 323.462
• InChiKey: CXVUZGUWPNWZFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-4,5,6,7-四氢苯并[b]噻吩-3-甲酰胺 在 对甲苯磺酸 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 9.75h， 生成 2-ethyl-N-(p-tolyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Anti-tubercular activities of 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3- d ]pyrimidin-4-amine analogues endowed with high activity toward non-replicative Mycobacterium tuberculosis

  摘要：

  Thirty three derivatives of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues were synthesized by molecular modification of a reported antimycobacterial molecule (GSK163574A). Compounds were evaluated in vitro against actively replicative and nutrient starved non-replicative Mycobacterium tuberculosis (MTB), enzymatic screening and cytotoxicity against RAW 264.7 cell line. Among the compounds, 2-ethyl-N-phenethy1-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d] pyrimidin-4-amine (5c) was found to be the most active compound against non-replicative MTB with 2.7 log reduction of bacteria at 10 mu g/mL and was more potent than isoniazid (1.2 log reduction) and rifampicin (2.0 log reduction) at same dose level. Compound 5c also showed activity against MTB alanine dehydrogenase enzyme with IC50 of 1.82 +/- 0.42 mu M and showed 25% cytotoxicity against RAW 264.7 cell line at 50 mu g/mL. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.09.012

文献信息

• Anti-tubercular activities of 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3- d ]pyrimidin-4-amine analogues endowed with high activity toward non-replicative Mycobacterium tuberculosis
  作者：Ganesh Samala、Parthiban Brindha Devi、Shalini Saxena、Saritha Gunda、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2016.09.012

  日期：2016.11

  Thirty three derivatives of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues were synthesized by molecular modification of a reported antimycobacterial molecule (GSK163574A). Compounds were evaluated in vitro against actively replicative and nutrient starved non-replicative Mycobacterium tuberculosis (MTB), enzymatic screening and cytotoxicity against RAW 264.7 cell line. Among the compounds, 2-ethyl-N-phenethy1-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d] pyrimidin-4-amine (5c) was found to be the most active compound against non-replicative MTB with 2.7 log reduction of bacteria at 10 mu g/mL and was more potent than isoniazid (1.2 log reduction) and rifampicin (2.0 log reduction) at same dose level. Compound 5c also showed activity against MTB alanine dehydrogenase enzyme with IC50 of 1.82 +/- 0.42 mu M and showed 25% cytotoxicity against RAW 264.7 cell line at 50 mu g/mL. (C) 2016 Elsevier Ltd. All rights reserved.