6-(methoxy)geiparvarin | 136823-58-0

• 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: 6-(methoxy)geiparvarin
• 英文别名: 7-[(E)-3-(5,5-dimethyl-4-oxofuran-2-yl)but-2-enoxy]-6-methoxychromen-2-one
• CAS: 136823-58-0
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: BIJYEYOCTGXNJX-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  东莨菪内酯 在 molybdenum hexacarbonyl 、 水 、 potassium carbonate 、 溶剂黄146 、 lithium bromide 作用下， 以 四氢呋喃 、 丙酮 、 乙腈 为溶剂， 反应 26.0h， 生成 6-(methoxy)geiparvarin
  参考文献：
  名称：

  Geiparvarin analogs. 2. Synthesis and cytostatic activity of 5-(4-arylbutadienyl)-3(2H)-furanones and of N-substituted 3-(4-oxo-2-furanyl)-2-buten-2-yl carbamates

  摘要：

  In an attempt to determine some of the structural features of geiparvarin (1) that account for its cytostatic activity in vitro, a series of geiparvarin analogues (10a-i, 1, 12, and 14-16) which contain novel modifications in the region of the olefinic double bond and of the coumarin moiety have been designed and synthesized. Among the derivatives containing a carbamate moiety, only the analogues containing a carbamate group linked to an alkyl moiety 10b-i were endowed with potent cytostatic activity, whereas the corresponding benzene derivative 10a was devoid of any antiproliferative activity. 6-Methoxygeiparvarin 101 proved equally effective as geiparvin (1), while compounds containing an additional double bond at the side chain (12 and 14-16) were invariably 5-100-fold less effective than geiparvarin. Diene derivative 15, bearing a coumarin moiety, was essentially inactive against murine (L1210, FM3A) tumor cells but exhibited good activity against human (Molt/4F, MT-4) tumor cells.

  DOI：

  10.1021/jm00115a004

文献信息

• Geiparvarin analogs. 2. Synthesis and cytostatic activity of 5-(4-arylbutadienyl)-3(2H)-furanones and of N-substituted 3-(4-oxo-2-furanyl)-2-buten-2-yl carbamates
  作者：Daniele Simoni、Stefano Manfredini、Mojgan Aghazadeh Tabrizi、Rita Bazzanini、Pier G. Baraldi、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00115a004

  日期：1991.11

  In an attempt to determine some of the structural features of geiparvarin (1) that account for its cytostatic activity in vitro, a series of geiparvarin analogues (10a-i, 1, 12, and 14-16) which contain novel modifications in the region of the olefinic double bond and of the coumarin moiety have been designed and synthesized. Among the derivatives containing a carbamate moiety, only the analogues containing a carbamate group linked to an alkyl moiety 10b-i were endowed with potent cytostatic activity, whereas the corresponding benzene derivative 10a was devoid of any antiproliferative activity. 6-Methoxygeiparvarin 101 proved equally effective as geiparvin (1), while compounds containing an additional double bond at the side chain (12 and 14-16) were invariably 5-100-fold less effective than geiparvarin. Diene derivative 15, bearing a coumarin moiety, was essentially inactive against murine (L1210, FM3A) tumor cells but exhibited good activity against human (Molt/4F, MT-4) tumor cells.