[(1R,2S,10R,12R,13S)-12-cyano-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),6,15(20),17-tetraen-10-yl]methyl 3-methylbut-2-enoate | 1178895-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: [(1R,2S,10R,12R,13S)-12-cyano-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),6,15(20),17-tetraen-10-yl]methyl 3-methylbut-2-enoate
• CAS: 1178895-16-3
• 化学式: C₃₁H₃₃N₃O₈
• 分子量: 575.618
• InChiKey: LOXCSNDVAWDYML-SQDATOHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (isopropyl carbonic) 3-methylbut-2-enoic anhydride 、 jorunnamycin A 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80.6%的产率得到[(1R,2S,10R,12R,13S)-12-cyano-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),6,15(20),17-tetraen-10-yl]methyl 3-methylbut-2-enoate
  参考文献：
  名称：

  Chemistry of renieramycins. Part 8: Synthesis and cytotoxicity evaluation of renieramycin M–jorunnamycin A analogues

  摘要：

  Twenty-four ester analogues of renieramycin M (1m) were prepared from jorunnamycin A (3a), which was easily transformed from marine natural 1m in three steps. These analogues, along with 1m itself, cyanojorumycin (2b), and jorunnamycins A (3a) and C (3b), were evaluated in vitro for cytotoxicity by measuring IC50 values through the 3-(4,5-dimethyltriazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay using human HCT116 colon carcinoma and MDA-MB-435 breast carcinoma cell lines. Nitrogen-containing heterocyclic ester derivatives 9a-f showed similar in vitro cytotoxicity to 1m, whereas the other derivatives were slightly less cytotoxic than 1m. 2'-Pyridinecarboxylic acid ester derivative (9c) exhibited a threefold increase in cytotoxicity relative to 1m. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.009

文献信息

• Chemistry of renieramycins. Part 8: Synthesis and cytotoxicity evaluation of renieramycin M–jorunnamycin A analogues
  作者：Kornvika Charupant、Naomi Daikuhara、Emi Saito、Surattana Amnuoypol、Khanit Suwanborirux、Takashi Owa、Naoki Saito

  DOI：10.1016/j.bmc.2009.05.009

  日期：2009.7

  Twenty-four ester analogues of renieramycin M (1m) were prepared from jorunnamycin A (3a), which was easily transformed from marine natural 1m in three steps. These analogues, along with 1m itself, cyanojorumycin (2b), and jorunnamycins A (3a) and C (3b), were evaluated in vitro for cytotoxicity by measuring IC50 values through the 3-(4,5-dimethyltriazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay using human HCT116 colon carcinoma and MDA-MB-435 breast carcinoma cell lines. Nitrogen-containing heterocyclic ester derivatives 9a-f showed similar in vitro cytotoxicity to 1m, whereas the other derivatives were slightly less cytotoxic than 1m. 2'-Pyridinecarboxylic acid ester derivative (9c) exhibited a threefold increase in cytotoxicity relative to 1m. (C) 2009 Elsevier Ltd. All rights reserved.