2'-(4-formyl)benzoyl cephalomannine | 385442-68-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2'-(4-formyl)benzoyl cephalomannine
• CAS: 385442-68-2
• 化学式: C₅₃H₅₇NO₁₆
• 分子量: 964.033
• InChiKey: IYCXSGWQMNJYME-RKALEAFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  70.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  244.43
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (5R,5aR,8aS,9S)-9-amino-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one 、 2'-(4-formyl)benzoyl cephalomannine 以 苯 为溶剂， 反应 24.0h， 以89%的产率得到
  参考文献：
  名称：

  Antitumor agents 210. synthesis and evaluation of taxoid–epipodophyllotoxin conjugates as novel cytotoxic agents

  摘要：

  Five compounds composed of a taxoid (paclitaxel or cephalomannine) and a 4'-O-demethyl epipodophyllotoxin derivative joined by an imine linkage were prepared and evaluated as cytotoxic agents and inhibitors of mammalian DNA topoisomerase II. Compounds 12 and 14-16 exhibited comparable or better activity than the unconjugated epipodophyllotoxin derivatives in most tumor cell lines, and 12, 15, and 16 also showed enhanced activity against paclitaxel-resistant cells. Compound 13, which contains an epipodophyllotoxin moiety at both the taxoid 2' and 7 positions, did not stimulate protein-DNA breaks, but was 2-fold more potent than 12 and 15 and comparable to GL-331 in the topo II inhibitory assay. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00206-1
• 作为产物：
  描述：

  对醛基苯甲酸 、 三尖杉宁碱 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 24.0h， 以95%的产率得到2'-(4-formyl)benzoyl cephalomannine
  参考文献：
  名称：

  Antitumor agents 210. synthesis and evaluation of taxoid–epipodophyllotoxin conjugates as novel cytotoxic agents

  摘要：

  Five compounds composed of a taxoid (paclitaxel or cephalomannine) and a 4'-O-demethyl epipodophyllotoxin derivative joined by an imine linkage were prepared and evaluated as cytotoxic agents and inhibitors of mammalian DNA topoisomerase II. Compounds 12 and 14-16 exhibited comparable or better activity than the unconjugated epipodophyllotoxin derivatives in most tumor cell lines, and 12, 15, and 16 also showed enhanced activity against paclitaxel-resistant cells. Compound 13, which contains an epipodophyllotoxin moiety at both the taxoid 2' and 7 positions, did not stimulate protein-DNA breaks, but was 2-fold more potent than 12 and 15 and comparable to GL-331 in the topo II inhibitory assay. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00206-1