(E)-8-(3-bromobenzylidene)-4-(3-bromophenyl)-6-methyl-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione | 1310325-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: (E)-8-(3-bromobenzylidene)-4-(3-bromophenyl)-6-methyl-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione
• 英文别名: (8E)-4-(3-bromophenyl)-8-[(3-bromophenyl)methylene]-6-methyl-3,4,5,7-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2-thione；(8E)-4-(3-bromophenyl)-8-[(3-bromophenyl)methylidene]-6-methyl-3,4,5,7-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2-thione
• CAS: 1310325-74-6
• 化学式: C₂₁H₁₉Br₂N₃S
• 分子量: 505.276
• InChiKey: SCXAFDGHPIMNIR-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 间溴苯甲醛 、 硫脲 在 sodium ethanolate 作用下， 以96%的产率得到(E)-8-(3-bromobenzylidene)-4-(3-bromophenyl)-6-methyl-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione
  参考文献：
  名称：

  A green expedient synthesis of pyridopyrimidine-2-thiones and their antitubercular activity

  摘要：

  The pseudo four-component domino reactions of N-substituted-4-piperidones, substituted aromatic aldehydes and thiourea in the presence of solid sodium ethoxide under solvent-free conditions afforded pyridopyrimidine-2-thiones in almost quantitative yields by simply grinding for 1-2 min. at ambient temperature. The synthesized compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv. Among them, (E)-6-benzyl-8-(2,4-dichlorobenzylidene)-4-(2,4-dichlorophenyl)-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione (MIC 2.8 mu M) displays the maximum activity, being 2.7 and 1.7 times more active than the first line antitubercular drugs ethambutol and ciprofloxacin, respectively, and less active than rifampicin and isoniazid, by 28 and 7 times, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.045

文献信息

• A green expedient synthesis of pyridopyrimidine-2-thiones and their antitubercular activity
  作者：Stephen Michael Rajesh、Raju Suresh Kumar、Lawzer Arun Libertsen、Subbu Perumal、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2011.03.045

  日期：2011.5

  The pseudo four-component domino reactions of N-substituted-4-piperidones, substituted aromatic aldehydes and thiourea in the presence of solid sodium ethoxide under solvent-free conditions afforded pyridopyrimidine-2-thiones in almost quantitative yields by simply grinding for 1-2 min. at ambient temperature. The synthesized compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv. Among them, (E)-6-benzyl-8-(2,4-dichlorobenzylidene)-4-(2,4-dichlorophenyl)-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione (MIC 2.8 mu M) displays the maximum activity, being 2.7 and 1.7 times more active than the first line antitubercular drugs ethambutol and ciprofloxacin, respectively, and less active than rifampicin and isoniazid, by 28 and 7 times, respectively. (C) 2011 Elsevier Ltd. All rights reserved.