4-Amino-12,26-dioxa-5-thia-3-azahexacyclo[25.2.2.17,11.121,25.02,6.013,18]tritriaconta-1(29),2(6),3,7(33),8,10,13(18),14,16,21(32),22,24,27,30-tetradecaene-16,24-diol | 1186601-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Amino-12,26-dioxa-5-thia-3-azahexacyclo[25.2.2.17,11.121,25.02,6.013,18]tritriaconta-1(29),2(6),3,7(33),8,10,13(18),14,16,21(32),22,24,27,30-tetradecaene-16,24-diol
• CAS: 1186601-55-7
• 化学式: C₂₉H₂₂N₂O₄S
• 分子量: 494.571
• InChiKey: RFLZUDFYNRUVRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  36
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-Amino-thiazole dihydroptychantol A dimethyl ether 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以76%的产率得到4-Amino-12,26-dioxa-5-thia-3-azahexacyclo[25.2.2.17,11.121,25.02,6.013,18]tritriaconta-1(29),2(6),3,7(33),8,10,13(18),14,16,21(32),22,24,27,30-tetradecaene-16,24-diol
  参考文献：
  名称：

  Synthesis and multidrug resistance reversal activity of dihydroptychantol A and its novel derivatives

  摘要：

  The macrocyclic bisbibenzyl dihydroptychantol A (DHA), previously isolated from Asterella angusta, was synthesized and showed significant multidrug resistance (MDR) reverting activity in chemoresistant cancer cells. In an attempt to discover more potent MDR reversal agents for efficient cancer chemotherapy, DHA derivatives with thiazole rings (19-22) were synthesized, and their cytotoxicities and MDR reversal activities were evaluated in adriamycin-resistant K562/A02, vincristine-resistant KB/VCR and in their parental cells by MTT assays. In response to treatment with each compound, the K562 cell line was the most sensitive, and the vincristine-resistant KB/VCR cell line was the most resistant. Marked decreases in K562 and K562/A02 cell viability were detectable after treatment with the synthesized derivatives of DHA, while less inhibitory effects on cell growth were observed in chemical- resistant KB/VCR and KB cells. Moreover, among the tested compounds, the intermediate 17 and the analogues 19, 20, and 21 showed potent MDR reversal activities and increased vincristine cytotoxicity in KB/VCR cells, with the reversal fold ranges from 10.54 to 13.81 (10 mu M), which is 3.2-4.3-fold stronger than the natural product DHA. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.077

文献信息

• Synthesis and multidrug resistance reversal activity of dihydroptychantol A and its novel derivatives
  作者：Bin Sun、Hui-qing Yuan、Guang-min Xi、Yu-dao Ma、Hong-xiang Lou

  DOI：10.1016/j.bmc.2009.05.077

  日期：2009.7

  The macrocyclic bisbibenzyl dihydroptychantol A (DHA), previously isolated from Asterella angusta, was synthesized and showed significant multidrug resistance (MDR) reverting activity in chemoresistant cancer cells. In an attempt to discover more potent MDR reversal agents for efficient cancer chemotherapy, DHA derivatives with thiazole rings (19-22) were synthesized, and their cytotoxicities and MDR reversal activities were evaluated in adriamycin-resistant K562/A02, vincristine-resistant KB/VCR and in their parental cells by MTT assays. In response to treatment with each compound, the K562 cell line was the most sensitive, and the vincristine-resistant KB/VCR cell line was the most resistant. Marked decreases in K562 and K562/A02 cell viability were detectable after treatment with the synthesized derivatives of DHA, while less inhibitory effects on cell growth were observed in chemical- resistant KB/VCR and KB cells. Moreover, among the tested compounds, the intermediate 17 and the analogues 19, 20, and 21 showed potent MDR reversal activities and increased vincristine cytotoxicity in KB/VCR cells, with the reversal fold ranges from 10.54 to 13.81 (10 mu M), which is 3.2-4.3-fold stronger than the natural product DHA. (C) 2009 Elsevier Ltd. All rights reserved.