(3aS,10bS,11S,12bS)-9,11-Dibromo-3a-ethyl-2,3,3a,4,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester | 436808-78-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 冬青素型生物碱
• 英文名称: (3aS,10bS,11S,12bS)-9,11-Dibromo-3a-ethyl-2,3,3a,4,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester
• 英文别名: methyl (1S,12S,18S,19S)-4,18-dibromo-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,9-tetraene-10-carboxylate
• CAS: 436808-78-5
• 化学式: C₂₁H₂₄Br₂N₂O₂
• 分子量: 496.242
• InChiKey: XHHDSMUMRUEZCJ-MBPVOVBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,10bS,11S,12bS)-9,11-Dibromo-3a-ethyl-2,3,3a,4,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester 在 次氯酸叔丁酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以88%的产率得到(3aS,5R,10bS,11S,12bS)-9,11-Dibromo-5-chloro-3a-ethyl-2,3,3a,4,5,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Cytotoxicity of 6,16-Disubstituted analogues of (−)-Vincadifformine

  摘要：

  Eight analogues of (-)-16-chloro-1-dehydro-6S-bromovincadifformine 1 were synthesized and evaluated for cytotoxicity in L1210 cell culture. None of the new compounds was more active than 1 but the modulation at C6, C16 and on the aromatic ring at C10 informs about structure-activity relationships within this series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00757-0
• 作为产物：
  描述：

  (-)-6S-bromovincadifformine 在 N-溴代丁二酰亚胺(NBS) 、 三氟乙酸 作用下， 反应 2.0h， 以80%的产率得到(3aS,10bS,11S,12bS)-9,11-Dibromo-3a-ethyl-2,3,3a,4,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Cytotoxicity of 6,16-Disubstituted analogues of (−)-Vincadifformine

  摘要：

  Eight analogues of (-)-16-chloro-1-dehydro-6S-bromovincadifformine 1 were synthesized and evaluated for cytotoxicity in L1210 cell culture. None of the new compounds was more active than 1 but the modulation at C6, C16 and on the aromatic ring at C10 informs about structure-activity relationships within this series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00757-0

文献信息

• Cytotoxicity of 6,16-Disubstituted analogues of (−)-Vincadifformine
  作者：Guy Lewin、Reynald Hocquemiller、Corinne Schaeffer、Pierre-Hervé Lambert、Stéphane Léonce、Alain Pierré

  DOI：10.1016/s0960-894x(01)00757-0

  日期：2002.2

  Eight analogues of (-)-16-chloro-1-dehydro-6S-bromovincadifformine 1 were synthesized and evaluated for cytotoxicity in L1210 cell culture. None of the new compounds was more active than 1 but the modulation at C6, C16 and on the aromatic ring at C10 informs about structure-activity relationships within this series. (C) 2002 Elsevier Science Ltd. All rights reserved.