N-[(7S)-1,2,3-三甲氧基-9-氧代-10-(苯基甲硫基)-6,7-二氢-5H-苯并[d]庚搭烯-7-基]乙酰胺 | 76129-12-9

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 中文名称: N-[(7S)-1,2,3-三甲氧基-9-氧代-10-(苯基甲硫基)-6,7-二氢-5H-苯并[d]庚搭烯-7-基]乙酰胺
• 英文名称: benzylthiocolchicine
• 英文别名: 10-benzylthiocolchicine；N-((S)-10-benzylsulfanyl-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide；(S)-7-Acetylamino-10-benzylmercapto-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-on；N-((S)-10-Benzylmercapto-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamid；N-[(7S)-10-benzylsulfanyl-1,2,3-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• CAS: 76129-12-9
• 化学式: C₂₈H₂₉NO₅S
• 分子量: 491.608
• InChiKey: GBYSTLGOMHZCPZ-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(7S)-1,2,3-三甲氧基-9-氧代-10-(苯基甲硫基)-6,7-二氢-5H-苯并[d]庚搭烯-7-基]乙酰胺 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 5.75h， 以82%的产率得到N-<5,6,7,9-tetrahydro-1,2,3-trimethoxy-9-oxo-10-<(phenylmethyl)sulfonyl>benzoheptalen-7-yl>-(S)-acetamide
  参考文献：
  名称：

  Quantitative structure-activity relationships of colchicines against P388 leukemia in mice

  摘要：

  A quantitative structure-activity relationship (QSAR) was derived for colchicine and 14 analogues acting against P388 lymphocytic leukemia in mice. Twelve additional compounds were synthesized to reinforce and confirm the correlation. The final correlation indicates that there is a parabolic dependence of antitumor potency on the partition coefficient with log P0=1.17. When an amino nitrogen is present on the B ring, increased potency is favored by acylation of the nitrogen. The most potent compound of the series was the 7-fluoroacetamide analogue. Strong electron-withdrawing groups substituted at the 10 position of the tropolone ring destroy activity. Electron-releasing groups at position 10 improve potency slightly but have a limited effect.

  DOI：

  10.1021/jm00135a004
• 作为产物：
  描述：

  秋水仙碱 、 苄硫醇 在 对甲苯磺酸 作用下， 生成 N-[(7S)-1,2,3-三甲氧基-9-氧代-10-(苯基甲硫基)-6,7-二氢-5H-苯并[d]庚搭烯-7-基]乙酰胺
  参考文献：
  名称：

  Velluz; Muller, Bulletin de la Societe Chimique de France, 1954, p. 194,195

  摘要：

  DOI：

文献信息

• Quantitative structure-activity relationships of colchicines against P388 leukemia in mice
  作者：Frank R. Quinn、John A. Beisler

  DOI：10.1021/jm00135a004

  日期：1981.3

  A quantitative structure-activity relationship (QSAR) was derived for colchicine and 14 analogues acting against P388 lymphocytic leukemia in mice. Twelve additional compounds were synthesized to reinforce and confirm the correlation. The final correlation indicates that there is a parabolic dependence of antitumor potency on the partition coefficient with log P0=1.17. When an amino nitrogen is present on the B ring, increased potency is favored by acylation of the nitrogen. The most potent compound of the series was the 7-fluoroacetamide analogue. Strong electron-withdrawing groups substituted at the 10 position of the tropolone ring destroy activity. Electron-releasing groups at position 10 improve potency slightly but have a limited effect.
• Velluz; Muller, Bulletin de la Societe Chimique de France, 1954, p. 194,195
  作者：Velluz、Muller

  DOI：——

  日期：——