2,10-dihydroxy-6-[3-(hydroxybenzyl)amino]-13-(β-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione | 213039-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,10-dihydroxy-6-[3-(hydroxybenzyl)amino]-13-(β-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
• 英文别名: 6,20-dihydroxy-13-[(3-hydroxyphenyl)methylamino]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione
• CAS: 213039-71-5
• 化学式: C₃₃H₂₈N₄O₁₀
• 分子量: 640.606
• InChiKey: JCAAEISKJJZFLG-CBUVUTGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  47
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  221
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3-hydroxybenzylhydrazine dihydrochloride 、 2,10-dihydroxy-12-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-12,13-dihydrofuro[3,4-c]indolo[2,3-a]carbazole-5,7-dione 在 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以37%的产率得到2,10-dihydroxy-6-[3-(hydroxybenzyl)amino]-13-(β-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
  参考文献：
  名称：

  Synthesis and Biological Activities of Topoisomerase I Inhibitors, 6-Arylmethylamino Analogues of Edotecarin

  摘要：

  The replacement of 1,3-dihydroxy-2-propylamino moiety at the N6-position of edotecarin (1) by arylmethylamino groups yielded a number of more potent topoisomerase I inhibitors with better cytotoxic (CTX) activities in vitro than edotecarin. Among them, the three most potent pyridylmethyl analogues, compounds 22g, 22m, and 23c, showed better antitumor activities against MKN-45 human stomach cancer or MX-1 human breast cancer xenografted mice than those of edotecarin. Furthermore, compounds 22m and 23c exhibited complete response against MX-1 cells implanted in mice.

  DOI：

  10.1021/jm801641t

文献信息

• Synthesis and Biological Activities of Topoisomerase I Inhibitors, 6-Arylmethylamino Analogues of Edotecarin
  作者：Satoshi Sunami、Teruyuki Nishimura、Ikuko Nishimura、Satoru Ito、Hiroharu Arakawa、Mitsuru Ohkubo

  DOI：10.1021/jm801641t

  日期：2009.5.28

  The replacement of 1,3-dihydroxy-2-propylamino moiety at the N6-position of edotecarin (1) by arylmethylamino groups yielded a number of more potent topoisomerase I inhibitors with better cytotoxic (CTX) activities in vitro than edotecarin. Among them, the three most potent pyridylmethyl analogues, compounds 22g, 22m, and 23c, showed better antitumor activities against MKN-45 human stomach cancer or MX-1 human breast cancer xenografted mice than those of edotecarin. Furthermore, compounds 22m and 23c exhibited complete response against MX-1 cells implanted in mice.