9-methoxy-2,2-dimethyl-1a,9b-dihydro-2H-1,3,5-trioxacyclopropa[a]anthracen-6-one | 1189776-08-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 9-methoxy-2,2-dimethyl-1a,9b-dihydro-2H-1,3,5-trioxacyclopropa[a]anthracen-6-one
• 英文别名: 9-Methoxy-14,14-dimethyl-4,12,15-trioxatetracyclo[8.5.0.03,8.011,13]pentadeca-1(10),2,6,8-tetraen-5-one
• CAS: 1189776-08-6
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: ZZWSHZQQJIEZLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  黄木亭 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 以87.1%的产率得到9-methoxy-2,2-dimethyl-1a,9b-dihydro-2H-1,3,5-trioxacyclopropa[a]anthracen-6-one
  参考文献：
  名称：

  Anti-HBV and cytotoxic activities of pyranocoumarin derivatives

  摘要：

  Four natural pyranocoumarins clausenidin (1), nordentatin (2), clausarin (3), and xanthoxyletin (4) were isolated from the medicinal plant Clausena excavata. Recently, we found that 1 and 2 suppressed hepatitis B virus surface antigen in HepA2 cells, and in addition, 1-3 showed cytotoxic activity against four human cancer cell lines (A549, MCF7, KB, and KB-VIN). To explore the SAR of 1-4, 17 pyranocoumarin analogues (5-21) were designed and synthesized. Among these analogues, 5 and 10 were the most potent against hepatitis B virus with EC50 values of 1.14 and 1.34 mu M, respectively. The most interesting result in the cytotoxicity assay was the significant activity of 1, 5, and 6 against the multi-drug resistant cell line, KB-VIN, without activity against the KB cell line. These data suggest that these three compounds could be useful hits for developing MDR-inverse drugs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.007

文献信息

• Anti-HBV and cytotoxic activities of pyranocoumarin derivatives
  作者：Chung-Ren Su、Sheau Farn Yeh、Chih Miem Liu、Amooru G. Damu、Tsung-Hsiao Kuo、Po-Cheng Chiang、Kenneth F. Bastow、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmc.2008.12.007

  日期：2009.8

  Four natural pyranocoumarins clausenidin (1), nordentatin (2), clausarin (3), and xanthoxyletin (4) were isolated from the medicinal plant Clausena excavata. Recently, we found that 1 and 2 suppressed hepatitis B virus surface antigen in HepA2 cells, and in addition, 1-3 showed cytotoxic activity against four human cancer cell lines (A549, MCF7, KB, and KB-VIN). To explore the SAR of 1-4, 17 pyranocoumarin analogues (5-21) were designed and synthesized. Among these analogues, 5 and 10 were the most potent against hepatitis B virus with EC50 values of 1.14 and 1.34 mu M, respectively. The most interesting result in the cytotoxicity assay was the significant activity of 1, 5, and 6 against the multi-drug resistant cell line, KB-VIN, without activity against the KB cell line. These data suggest that these three compounds could be useful hits for developing MDR-inverse drugs. (C) 2009 Elsevier Ltd. All rights reserved.