4-Hydroxycolchicine | 1267986-29-7

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 4-Hydroxycolchicine
• 英文别名: N-[(7S)-4-hydroxy-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• CAS: 1267986-29-7
• 化学式: C₂₂H₂₅NO₇
• 分子量: 415.443
• InChiKey: NCOSWHAFUOTDGQ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  秋水仙碱 在 magnesium bis(monoperoxyphthalate)hexahydrate 、 四氯化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4-Hydroxycolchicine
  参考文献：
  名称：

  Design, Synthesis, and Antitumor Activity of 4-Halocolchicines and Their Pro-drugs Activated by Cathepsin B

  摘要：

  Novel colchicine derivatives possessing various substituents at the C4 position were prepared. Among them, 4-halo derivatives 3-6 were found to exhibit higher activity against cancer cell lines (A549, HT29, HCT116) as well as on mice transplanted with the HCT116 human colorectal carcinoma cell line than colchicine (1). Further, utilizing the 4-substituted colchicines, we prepared pro-drugs having a dipeptide side chain and demonstrated that these pro-drugs were activated by cathepsin B, an enzyme overexpressed in tumor cells, and exhibited selective toxicity to the tumor cells.

  DOI：

  10.1021/ml100287y

文献信息

• JP5829520
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, Synthesis, and Antitumor Activity of 4-Halocolchicines and Their Pro-drugs Activated by Cathepsin B
  作者：Naoko Yasobu、Mariko Kitajima、Noriyuki Kogure、Yoshiyuki Shishido、Takeshi Matsuzaki、Masato Nagaoka、Hiromitsu Takayama

  DOI：10.1021/ml100287y

  日期：2011.5.12

  Novel colchicine derivatives possessing various substituents at the C4 position were prepared. Among them, 4-halo derivatives 3-6 were found to exhibit higher activity against cancer cell lines (A549, HT29, HCT116) as well as on mice transplanted with the HCT116 human colorectal carcinoma cell line than colchicine (1). Further, utilizing the 4-substituted colchicines, we prepared pro-drugs having a dipeptide side chain and demonstrated that these pro-drugs were activated by cathepsin B, an enzyme overexpressed in tumor cells, and exhibited selective toxicity to the tumor cells.