N-(2,2-Diethoxyethyl)-3-hydroxy-2-nitro-N-(prop-2-yn-1-yl)benzamide | 94295-90-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(2,2-Diethoxyethyl)-3-hydroxy-2-nitro-N-(prop-2-yn-1-yl)benzamide
• 英文别名: N-(2,2-diethoxyethyl)-3-hydroxy-2-nitro-N-prop-2-ynylbenzamide
• CAS: 94295-90-6
• 化学式: C₁₆H₂₀N₂O₆
• 分子量: 336.345
• InChiKey: JVWQBOHADDBQGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2,2-Diethoxyethyl)-3-hydroxy-2-nitro-N-(prop-2-yn-1-yl)benzamide 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 3-hydroxy-2-nitro-N-(2-oxoethyl)-N-prop-2-ynylbenzamide
  参考文献：
  名称：

  Bicyclic and tricyclic analogs of anthramycin

  摘要：

  As analogues of pyrrolo[2,1-c][1,4]benzodiazepine antitumor antibiotics, such as anthramycin and tomaymycin, several benzo[1,4]diazepine imines and carbinolamine ethers were prepared and tested in vivo against P388 leukemia. Two different synthetic approaches, namely, a reduction of an aromatic nitro group with a concomitant cyclization and a reduction of a lactam, were employed to generate an imine or a carbinolamine moiety. Bicyclic analogues 6a', 6f, and 6g were found to be active, indicating that the pyrroline ring of anthramycin is not an absolute necessity for the antitumor activity. Compound 6g, 3,4-dihydro-9-hydroxy-4-propargyl-5H-1,4-benzodiazepin-5-one, was at least as active as neothramycin although it was 5 times less potent. Among the tricyclic analogues, compounds 5, 7a, and 8b were active against P388 leukemia, and they generally appear to be more potent than bicyclic analogues.

  DOI：

  10.1021/jm00381a020
• 作为产物：
  描述：

  3-羟基-2-硝基苯甲酸 在 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-(2,2-Diethoxyethyl)-3-hydroxy-2-nitro-N-(prop-2-yn-1-yl)benzamide
  参考文献：
  名称：

  Bicyclic and tricyclic analogs of anthramycin

  摘要：

  As analogues of pyrrolo[2,1-c][1,4]benzodiazepine antitumor antibiotics, such as anthramycin and tomaymycin, several benzo[1,4]diazepine imines and carbinolamine ethers were prepared and tested in vivo against P388 leukemia. Two different synthetic approaches, namely, a reduction of an aromatic nitro group with a concomitant cyclization and a reduction of a lactam, were employed to generate an imine or a carbinolamine moiety. Bicyclic analogues 6a', 6f, and 6g were found to be active, indicating that the pyrroline ring of anthramycin is not an absolute necessity for the antitumor activity. Compound 6g, 3,4-dihydro-9-hydroxy-4-propargyl-5H-1,4-benzodiazepin-5-one, was at least as active as neothramycin although it was 5 times less potent. Among the tricyclic analogues, compounds 5, 7a, and 8b were active against P388 leukemia, and they generally appear to be more potent than bicyclic analogues.

  DOI：

  10.1021/jm00381a020

文献信息

• Bicyclic and tricyclic analogs of anthramycin
  作者：T. Kaneko、H. Wong、T. W. Doyle、W. C. Rose、W. T. Bradner

  DOI：10.1021/jm00381a020

  日期：1985.3

  As analogues of pyrrolo[2,1-c][1,4]benzodiazepine antitumor antibiotics, such as anthramycin and tomaymycin, several benzo[1,4]diazepine imines and carbinolamine ethers were prepared and tested in vivo against P388 leukemia. Two different synthetic approaches, namely, a reduction of an aromatic nitro group with a concomitant cyclization and a reduction of a lactam, were employed to generate an imine or a carbinolamine moiety. Bicyclic analogues 6a', 6f, and 6g were found to be active, indicating that the pyrroline ring of anthramycin is not an absolute necessity for the antitumor activity. Compound 6g, 3,4-dihydro-9-hydroxy-4-propargyl-5H-1,4-benzodiazepin-5-one, was at least as active as neothramycin although it was 5 times less potent. Among the tricyclic analogues, compounds 5, 7a, and 8b were active against P388 leukemia, and they generally appear to be more potent than bicyclic analogues.