6-methoxy-7-<<(E)-3-<3-(1-hydroxy-1-methylethyl)isoxazol-5-yl>-2-butenyl>oxy>-2H-1-benzopyran-2-one | 136823-46-6

• 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: 6-methoxy-7-<<(E)-3-<3-(1-hydroxy-1-methylethyl)isoxazol-5-yl>-2-butenyl>oxy>-2H-1-benzopyran-2-one
• 英文别名: 7-[(E)-3-[3-(2-hydroxypropan-2-yl)-1,2-oxazol-5-yl]but-2-enoxy]-6-methoxychromen-2-one
• CAS: 136823-46-6
• 化学式: C₂₀H₂₁NO₆
• 分子量: 371.39
• InChiKey: KXGHBYYZGQPNEM-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  94.93
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-methoxy-7-<<(E)-3-<3-(1-hydroxy-1-methylethyl)isoxazol-5-yl>-2-butenyl>oxy>-2H-1-benzopyran-2-one 在 molybdenum hexacarbonyl 、 水 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以67%的产率得到6-methoxy-7-<<(E,E)-6-amino-7-hydroxy-3,7-dimethyl-4oxo-2,5-octadienyl>oxy>-2H-1-benzopyran-2-one
  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
• 作为产物：
  描述：

  5-<(E)-3-hydroxy-1-methyl-1-propenyl>-α,α-dimethyl-isoxazolemethanol 在 potassium carbonate 、 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 生成 6-methoxy-7-<<(E)-3-<3-(1-hydroxy-1-methylethyl)isoxazol-5-yl>-2-butenyl>oxy>-2H-1-benzopyran-2-one
  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