8-Thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene-14-carboxylic acid | 865798-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-Thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene-14-carboxylic acid
• CAS: 865798-99-8
• 化学式: C₁₇H₁₀O₂S
• 分子量: 278.331
• InChiKey: HZCQVZLCBPZZGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-Thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene-14-carboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 N-[3-(dimethylamino)propyl]-8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene-14-carboxamide
  参考文献：
  名称：

  Synthesis, antitumor and DNA photocleaving activities of novel naphthalene carboxamides: effects of different thio-heterocyclic rings and aminoalkyl side chains

  摘要：

  Two kinds of thio-heterocyclic fused naphthalene carboxamides, 3a-b, 4a-b, were designed, synthesized and quantitatively evaluated as efficient antitumor and DNA photocleaving agents. Compound 3a or 3b, having the thiophene ring, intercalated into DNA more strongly than compound 4a or 4b, having the thioxanthene ring. Compound 4a or 4b, photocleaved DNA more efficiently than 3a or 3b via superoxide anion. Compound 4a was the strongest inhibitor for P388 (murine leukemia cell), while 3a was the most cytotoxic one against A549 (human lung cancer cell). Each new compound showed stronger DNA photocleaving activity than corresponding naphthalimide. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.097
• 作为产物：
  描述：

  5-溴-萘-1-羧酸甲酯 在 盐酸 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 93.5h， 生成 8-Thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene-14-carboxylic acid
  参考文献：
  名称：

  Synthesis, antitumor and DNA photocleaving activities of novel naphthalene carboxamides: effects of different thio-heterocyclic rings and aminoalkyl side chains

  摘要：

  Two kinds of thio-heterocyclic fused naphthalene carboxamides, 3a-b, 4a-b, were designed, synthesized and quantitatively evaluated as efficient antitumor and DNA photocleaving agents. Compound 3a or 3b, having the thiophene ring, intercalated into DNA more strongly than compound 4a or 4b, having the thioxanthene ring. Compound 4a or 4b, photocleaved DNA more efficiently than 3a or 3b via superoxide anion. Compound 4a was the strongest inhibitor for P388 (murine leukemia cell), while 3a was the most cytotoxic one against A549 (human lung cancer cell). Each new compound showed stronger DNA photocleaving activity than corresponding naphthalimide. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.097