(19S)-19-ethyl-19-hydroxy-7-phenylmethoxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione | 1398723-60-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 英文名称: (19S)-19-ethyl-19-hydroxy-7-phenylmethoxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• CAS: 1398723-60-8
• 化学式: C₂₇H₂₂N₂O₅
• 分子量: 454.482
• InChiKey: SBLPQSBMTUQVFJ-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (19S)-19-ethyl-19-hydroxy-7-phenylmethoxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione 在 钾硼氢 、 二乙胺基三氟化硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.17h， 生成 10-benzyloxy-(20S, 21S)-fluorcamptothecin
  参考文献：
  名称：

  Synthesis and biological activities of fluorinated 10-hydroxycamptothecin and SN38

  摘要：

  It is an important strategy for fluorine substitution in drug design because of its small size and high electronegativity. Fluorinated 10-hydroxycamptothecin and SN 38 were prepared and screened for antiproliferative activities. Among them, fluorinated compound MF-6 showed higher antiproliferative activities against A549, HCT116 and MDA-MB-435 cancer cells than unfluorinated compound. The result of Topoisomerase I activity also confirmed that the C-21 carbonyl group of camptothecin structure is unnecessary to antitumor activity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.10.016
• 作为产物：
  描述：

  10-羟基喜树碱 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80 %的产率得到(19S)-19-ethyl-19-hydroxy-7-phenylmethoxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
  参考文献：
  名称：

  10-alkoxy-5-spiro CPT的设计、合成及体外初步生物学评价

  摘要：

  以简便的方法合成了一系列10-烷氧基-5-螺环喜树碱衍生物。一方面，这些化合物的溶解度明显改变；另一方面，这些5-螺环喜树碱衍生物中的大多数对MGC803细胞系表现出更好的抑制活性。

  DOI：

  10.1016/j.tet.2023.133325

文献信息

• EP1254141A4
  申请人：——

  公开号：EP1254141A4

  公开（公告）日：2003-05-02
• CAMPTOTHECIN -BETA-ALANINE ESTERS WITH TOPOISOMERASE I INIBHITION
  申请人：Research Triangle Institute

  公开号：EP1254141B1

  公开（公告）日：2005-08-17
• [EN] CAMPTOTHECIN beta -ALANINE ESTERS WITH TOPOISOMERASE I INIBHITION<br/>[FR] ESTERS beta -ALANINE DE CAMPTOTHECINE AVEC INHIBITION DE LATOPOISOMERASE I
  申请人：WALL MONROE E

  公开号：WO2001049691A1

  公开（公告）日：2001-07-12

  β-Alanine esters of camptothecin compounds which are effective anti-tumor compounds are disclosed. These compounds inhibit the enzyme topoisomerase I and may alkylate DNA of the associated topoisomerase I-DNA cleavable complex.
• Synthesis and biological activities of fluorinated 10-hydroxycamptothecin and SN38
  作者：Yuelin Wu、Lingjian Zhu、Chunquan Sheng、Jianzhong Yao、Zhenyuan Miao、Wannian Zhang、Yunyang Wei、Ruofu Shi

  DOI：10.1016/j.jfluchem.2013.10.016

  日期：2014.1

  It is an important strategy for fluorine substitution in drug design because of its small size and high electronegativity. Fluorinated 10-hydroxycamptothecin and SN 38 were prepared and screened for antiproliferative activities. Among them, fluorinated compound MF-6 showed higher antiproliferative activities against A549, HCT116 and MDA-MB-435 cancer cells than unfluorinated compound. The result of Topoisomerase I activity also confirmed that the C-21 carbonyl group of camptothecin structure is unnecessary to antitumor activity. (C) 2013 Elsevier B.V. All rights reserved.
• Design, synthesis of 10-alkoxy-5-spiro CPT and preliminary biological evaluation in vitro
  作者：Xi Ke、Xianheng Wang、Yuan Liu、Yuhe Wang、Changkuo Zhao

  DOI：10.1016/j.tet.2023.133325

  日期：2023.4

  A series of 10-alkoxy-5-spirocycle campthothecin derivatives were synthesized in a convenient method. On the one hand, the solubility of these compounds was obviously modified; on the other hand, most of these 5-spirocycle campthothecin derivatives showed a better inhibition activity against MGC803 cell line.

  以简便的方法合成了一系列10-烷氧基-5-螺环喜树碱衍生物。一方面，这些化合物的溶解度明显改变；另一方面，这些5-螺环喜树碱衍生物中的大多数对MGC803细胞系表现出更好的抑制活性。