3-[(4-氨基苯甲酰基)氨基]-1-(2-氯乙基)-1-亚硝基脲 | 147217-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-[(4-氨基苯甲酰基)氨基]-1-(2-氯乙基)-1-亚硝基脲
• 英文名称: 4-(2-aminobenzoyl)-1-(2-chloroethyl)-1-nitrosohydrazinecarboxamide
• 英文别名: Benzoic acid, 4-amino-, 2-(((2-chloroethyl)nitrosoamino)carbonyl)hydrazide；3-[(4-aminobenzoyl)amino]-1-(2-chloroethyl)-1-nitrosourea
• CAS: 147217-64-9
• 化学式: C₁₀H₁₂ClN₅O₃
• 分子量: 285.69
• InChiKey: SKYUQLKGOGQTRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N₁-(2-chloroethyl)-N₁-nitrosocarbamoyl azide 、 4-氨基苯甲酰肼 在 吡啶 作用下， 以78%的产率得到3-[(4-氨基苯甲酰基)氨基]-1-(2-氯乙基)-1-亚硝基脲
  参考文献：
  名称：

  4-Aroyl-1-nitrosohydrazinecarboxamides: synthesis, in vivo and in vitro antitumor activity

  摘要：

  4-Benzoyl-1-(2-chloroethyl)-1-nitrosohydrazinecarboxamide (I), 1-(2-chloroethyl)-1-nitroso-4-phenylacetylhydrazine-carboxamide (II), 1-(2-chloroethyl)-4-(2-hydroxybenzoyl)-1-nitrosohydrazinecarboxamide (III), 4-(4-aminobenzoyl)-1-(2-chloroethyl)-1-nitrosohydrazinecarboxamide (IV), 4-(4-chlorobenzoyl)-1-(2-chloroethyl)-1-nitrosohydrazinecarboxamide (V), all novel class nitrosoureas, were synthesized. All five compounds showed a dose-dependent activity against leukemias L1210, P388 and Ehrlich ascites tumor (EAT). Compound I was superior, yielding T/C% values of 400%, resulting in many cures, reaching 100% in EAT mice. The effect of the above substances on the incorporation of radioactive precursors into DNA, RNA and proteins of EAT cells was investigated. It was found that treatment of cells with 50 mug/ml of the compounds causes significant inhibition (approximately 70%) of the incorporation of H-3-thymidine into DNA. Finally, the effect of these compounds on sister chromatid exchange (SCE) values and on cell kinetics in cultured human lymphocytes was studied. Compound I was found to be the most effective in causing markedly increased SCE values and cell division delays.

  DOI：

  10.1016/0223-5234(92)90109-e

文献信息

• 4-Aroyl-1-nitrosohydrazinecarboxamides: synthesis, in vivo and in vitro antitumor activity
  作者：RG Gugova、A Papageorgiou、SI Taksirov、VV Topakbashian、E Margariti、L Boutis、D Mourelatos、J Dozi-Vassiliades、EV Golovinsky、GD Demirov

  DOI：10.1016/0223-5234(92)90109-e

  日期：1992.11

  4-Benzoyl-1-(2-chloroethyl)-1-nitrosohydrazinecarboxamide (I), 1-(2-chloroethyl)-1-nitroso-4-phenylacetylhydrazine-carboxamide (II), 1-(2-chloroethyl)-4-(2-hydroxybenzoyl)-1-nitrosohydrazinecarboxamide (III), 4-(4-aminobenzoyl)-1-(2-chloroethyl)-1-nitrosohydrazinecarboxamide (IV), 4-(4-chlorobenzoyl)-1-(2-chloroethyl)-1-nitrosohydrazinecarboxamide (V), all novel class nitrosoureas, were synthesized. All five compounds showed a dose-dependent activity against leukemias L1210, P388 and Ehrlich ascites tumor (EAT). Compound I was superior, yielding T/C% values of 400%, resulting in many cures, reaching 100% in EAT mice. The effect of the above substances on the incorporation of radioactive precursors into DNA, RNA and proteins of EAT cells was investigated. It was found that treatment of cells with 50 mug/ml of the compounds causes significant inhibition (approximately 70%) of the incorporation of H-3-thymidine into DNA. Finally, the effect of these compounds on sister chromatid exchange (SCE) values and on cell kinetics in cultured human lymphocytes was studied. Compound I was found to be the most effective in causing markedly increased SCE values and cell division delays.