4-chloro-2-(4-pyridyl)-5,6,7,8,9,10-hexahydrocycloocta[4,5]thieno[2,3-d]pyrimidine | 1442463-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-chloro-2-(4-pyridyl)-5,6,7,8,9,10-hexahydrocycloocta[4,5]thieno[2,3-d]pyrimidine
• 英文别名: 3-Chloro-5-pyridin-4-yl-8-thia-4,6-diazatricyclo[7.6.0.02,7]pentadeca-1(9),2(7),3,5-tetraene；3-chloro-5-pyridin-4-yl-8-thia-4,6-diazatricyclo[7.6.0.02,7]pentadeca-1(9),2(7),3,5-tetraene
• CAS: 1442463-86-6
• 化学式: C₁₇H₁₆ClN₃S
• 分子量: 329.853
• InChiKey: ZXRXHIJWIKJKGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-2-(4-pyridyl)-5,6,7,8,9,10-hexahydrocycloocta[4,5]thieno[2,3-d]pyrimidine 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以80%的产率得到4-hydrazinyl-2-(4-pyridyl)-5,6,7,8,9,10-hexahydrocycloocta[4,5]thieno[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis and anticancer activity of novel 2-pyridyl hexahyrocyclooctathieno[2,3-d]pyrimidine derivatives

  摘要：

  A series of new 2-pyridyl hexahydrocycloocta [4,5]thieno[2,3-d]pyrimidines with different substituents as C-4 position was synthesized. The anticancer activity of the newly synthesized compounds was tested in vitro using a two-stage process utilizing 60 different human tumor cell lines representing leukemia, melanoma and cancers of lung, colon, central nervous system, ovary, kidney, prostate as well as breast. Compounds 4a, 6a, 7a, 7d and 7g showed potent anticancer activity at low concentrations against most of the used human tumor cell lines comparable with doxorubicin as standard potent anticancer drug (average log(10) GI(50) over all cell lines = -6.85). Also, compound 4b was selective against SNB-75 (CNS cancer) log(10) GI(50) = -5.57. Interestingly, compound 7e exhibited promising selectivity against 13 tumor cell lines showing growth inhibition percentages between 54.05 and 89.23. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.011
• 作为产物：
  描述：

  2-氨基-4,5,6,7,8,9-六氢辛基[b]噻吩-3-羧酰胺 在 盐酸 、 三氯氧磷 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 4-chloro-2-(4-pyridyl)-5,6,7,8,9,10-hexahydrocycloocta[4,5]thieno[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis and anticancer activity of novel 2-pyridyl hexahyrocyclooctathieno[2,3-d]pyrimidine derivatives

  摘要：

  A series of new 2-pyridyl hexahydrocycloocta [4,5]thieno[2,3-d]pyrimidines with different substituents as C-4 position was synthesized. The anticancer activity of the newly synthesized compounds was tested in vitro using a two-stage process utilizing 60 different human tumor cell lines representing leukemia, melanoma and cancers of lung, colon, central nervous system, ovary, kidney, prostate as well as breast. Compounds 4a, 6a, 7a, 7d and 7g showed potent anticancer activity at low concentrations against most of the used human tumor cell lines comparable with doxorubicin as standard potent anticancer drug (average log(10) GI(50) over all cell lines = -6.85). Also, compound 4b was selective against SNB-75 (CNS cancer) log(10) GI(50) = -5.57. Interestingly, compound 7e exhibited promising selectivity against 13 tumor cell lines showing growth inhibition percentages between 54.05 and 89.23. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.011