[1,3]Dioxolo[6,7]naphth[1,2-c]isoxazole-4-carboxylic acid, 3,3a,4,5-tetrahydro-5-(5-methoxy-3,4-dioxo-1,5-cyclohexadien-1-yl)-, methyl ester, (4R,5R)- | 646520-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [1,3]Dioxolo[6,7]naphth[1,2-c]isoxazole-4-carboxylic acid, 3,3a,4,5-tetrahydro-5-(5-methoxy-3,4-dioxo-1,5-cyclohexadien-1-yl)-, methyl ester, (4R,5R)-
• 英文别名: methyl (3aS,4R,5R)-5-(5-methoxy-3,4-dioxocyclohexa-1,5-dien-1-yl)-3,3a,4,5-tetrahydro-[1,3]benzodioxolo[6,5-g][2,1]benzoxazole-4-carboxylate
• CAS: 646520-01-6
• 化学式: C₂₁H₁₇NO₈
• 分子量: 411.368
• InChiKey: IYOYYRUKIMIAOQ-RZAIGCCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4,5-二氯邻苯二胺 、 [1,3]Dioxolo[6,7]naphth[1,2-c]isoxazole-4-carboxylic acid, 3,3a,4,5-tetrahydro-5-(5-methoxy-3,4-dioxo-1,5-cyclohexadien-1-yl)-, methyl ester, (4R,5R)- 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以81%的产率得到methyl (3aS,4R,5R)-5-(7,8-dichloro-4-methoxyphenazin-2-yl)-3,3a,4,5-tetrahydro-[1,3]benzodioxolo[6,5-g][2,1]benzoxazole-4-carboxylate
  参考文献：
  名称：

  Synthesis, cytotoxicity and antiviral activity of podophyllotoxin analogues modified in the E-ring

  摘要：

  Several podophyllotoxin derivatives modified in the E-ring were prepared and evaluated for their cytotoxicity on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28) and for their antiherpetic activity against Herpes simplex virus type II. The trimethoxyphenyl moiety was oxidized to ortho-quinone and further condensed with diamines and enamines to form different heterocycles. Most of the compounds maintained their cytotoxicity at the muM level and some of them showed antiherpetic activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.05.001
• 作为产物：
  描述：

  methyl (3aS,4R,5R)-5-(3,4,5-trimethoxyphenyl)-3,3a,4,5-tetrahydro-[1,3]benzodioxolo[6,5-g][2,1]benzoxazole-4-carboxylate 在 硝酸 、 丙酸 作用下， 反应 0.07h， 以94%的产率得到[1,3]Dioxolo[6,7]naphth[1,2-c]isoxazole-4-carboxylic acid, 3,3a,4,5-tetrahydro-5-(5-methoxy-3,4-dioxo-1,5-cyclohexadien-1-yl)-, methyl ester, (4R,5R)-
  参考文献：
  名称：

  Synthesis, cytotoxicity and antiviral activity of podophyllotoxin analogues modified in the E-ring

  摘要：

  Several podophyllotoxin derivatives modified in the E-ring were prepared and evaluated for their cytotoxicity on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28) and for their antiherpetic activity against Herpes simplex virus type II. The trimethoxyphenyl moiety was oxidized to ortho-quinone and further condensed with diamines and enamines to form different heterocycles. Most of the compounds maintained their cytotoxicity at the muM level and some of them showed antiherpetic activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.05.001

文献信息

• Synthesis, cytotoxicity and antiviral activity of podophyllotoxin analogues modified in the E-ring
  作者：M Castro

  DOI：10.1016/j.ejmech.2003.05.001

  日期：2003.10

  Several podophyllotoxin derivatives modified in the E-ring were prepared and evaluated for their cytotoxicity on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28) and for their antiherpetic activity against Herpes simplex virus type II. The trimethoxyphenyl moiety was oxidized to ortho-quinone and further condensed with diamines and enamines to form different heterocycles. Most of the compounds maintained their cytotoxicity at the muM level and some of them showed antiherpetic activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.