(E)-6-methyl-4-(thiophen-2-yl)-8-(thiophen-2-ylmethylene)-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione

• 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)-6-methyl-4-(thiophen-2-yl)-8-(thiophen-2-ylmethylene)-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione
• 英文别名: (8E)-6-methyl-4-(2-thienyl)-8-(2-thienylmethylene)-3,4,5,7-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2-thione；(8E)-6-methyl-4-thiophen-2-yl-8-(thiophen-2-ylmethylidene)-3,4,5,7-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2-thione
• 化学式: C₁₇H₁₇N₃S₃
• 分子量: 359.54
• InChiKey: YNDASWLZIZPTTP-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 sodium hydroxide 、 sodium butanolate 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 10.17h， 生成 (E)-6-methyl-4-(thiophen-2-yl)-8-(thiophen-2-ylmethylene)-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine-2(1H)-thione
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Certain α,β-Unsaturated Ketones and Their Corresponding Fused Pyridines as Antiviral and Cytotoxic Agents

  摘要：

  A new series of 3,5-bis(arylidene)-4-piperidones, as chalcone analogues carrying variety of aryl and heteroaryl groups, pyrazolo[4,3-c]pyridines, pyrido[4,3-d]pyrimidines, and pyrido[3,2-c]-pyridines, carrying an arylidene moiety, and a series of pyrano[3,2-c]pyridines, as flavone and coumarin isosteres, were synthesized and screened for their in vitro antiviral and antitumor activities at the National Cancer Institute (NCI). Compounds 9 and 18 proved to be active against herpes simplex virus-1 (HSV-1), while compound 13 showed moderate activity against human immunodeficiency virus-1 (HIV-1). Compounds 14, 26, 28, 33, and 35 exhibited a broad spectrum antitumor activity. In addition, compounds 26, 33, and 35 proved to be of moderate selectivity toward leukemia cell lines. The pyrano[3,2-c]pyridines heterocyclic system proved to be the most active antitumors among the investigated heterocycles.

  DOI：

  10.1021/jm000038m

文献信息

• Synthesis and Biological Evaluation of Certain α,β-Unsaturated Ketones and Their Corresponding Fused Pyridines as Antiviral and Cytotoxic Agents
  作者：Hussein I. El-Subbagh、Suhair M. Abu-Zaid、Mona A. Mahran、Farid A. Badria、Abdulrahman M. Al-Obaid

  DOI：10.1021/jm000038m

  日期：2000.7.1

  A new series of 3,5-bis(arylidene)-4-piperidones, as chalcone analogues carrying variety of aryl and heteroaryl groups, pyrazolo[4,3-c]pyridines, pyrido[4,3-d]pyrimidines, and pyrido[3,2-c]-pyridines, carrying an arylidene moiety, and a series of pyrano[3,2-c]pyridines, as flavone and coumarin isosteres, were synthesized and screened for their in vitro antiviral and antitumor activities at the National Cancer Institute (NCI). Compounds 9 and 18 proved to be active against herpes simplex virus-1 (HSV-1), while compound 13 showed moderate activity against human immunodeficiency virus-1 (HIV-1). Compounds 14, 26, 28, 33, and 35 exhibited a broad spectrum antitumor activity. In addition, compounds 26, 33, and 35 proved to be of moderate selectivity toward leukemia cell lines. The pyrano[3,2-c]pyridines heterocyclic system proved to be the most active antitumors among the investigated heterocycles.