N-(2-氯乙基)-N-亚硝基氨基甲酰缬氨酰胺 | 81965-44-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-(2-氯乙基)-N-亚硝基氨基甲酰缬氨酰胺
• 中文别名: 丙酸,3-氨基-2-重氮基-3-羰基-,乙基酯
• 英文名称: N-(2-chloroethyl)-N-nitrosocarbamoyl prolinamide
• 英文别名: N-(2-Chloroethyl)-N-nitrosocarbamoylvalinamide；(2S)-1-N-(2-chloroethyl)-1-N-nitrosopyrrolidine-1,2-dicarboxamide
• CAS: 81965-44-8
• 化学式: C₈H₁₃ClN₄O₃
• 分子量: 248.669
• InChiKey: ZOBZYPPNZPDEHJ-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  96.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  环己胺 、 N-(2-氯乙基)-N-亚硝基氨基甲酰缬氨酰胺 以 水 为溶剂， 反应 0.75h， 以8%的产率得到(cyclohexylcarbamoyl)prolinamide
  参考文献：
  名称：

  N-（2-氯乙基）-N-亚硝基氨基甲酰基氨基酸酰胺的分解。

  摘要：

  在生理条件下研究了N-（2-氯乙基）-N-亚硝基氨基甲酰基（Q（NO）脯氨酰胺和缬氨酰胺）的化学分解，用气相色谱仪鉴定了挥发性产物，Q（NO）-Pro-NH2给出了两倍的Q（NO）-Val-NH2或BCNU产生的乙二醇和2-氯乙醇中只有五分之一，表明它们的分解途径不同，并且在存在环己胺的情况下还研究了氨基甲酰化活性，发现导致分子内氨基甲酰化，并形成乙内酰脲衍生物。

  DOI：

  10.1021/jm00403a003
• 作为产物：
  描述：

  2-[3-(2-Chloro-ethyl)-1-methyl-ureido]-acetamide 在 sodium nitrate 、 甲酸 作用下， 反应 0.33h， 生成 N-(2-氯乙基)-N-亚硝基氨基甲酰缬氨酰胺
  参考文献：
  名称：

  (2-Chloroethyl)nitrosourea congeners of amino acid amides

  摘要：

  Fourteen (2-chloroethyl)nitrosourea congeners of L-amino acid amides have been synthesized as potential antineoplastic agents. Almost all the congeners tested were found to be highly active against experimental leukemia L1210 in mice. The chemical decomposition rates of the congeners were measured in a buffered solution (pH 7.4) at 37 degrees C. Acute toxicities of some of the congeners were determined for mice. The congener of sarcosinamide shows the longest half-life (T0.5 = 329.7 min) and the lowest toxicity, LD50 = 392.0 mg/kg (ip) and 426.6 mg/kg (iv), in this series.

  DOI：

  10.1021/jm00349a012

文献信息

• Synthesis and antitumor activity of N-terminal proline-containing peptide-(chloroethyl)nitrosoureas
  作者：Helga Suli-Vargha、Andras Jeney、Karoly Lapis、Kalman Medzihradszky

  DOI：10.1021/jm00386a024

  日期：1987.3

  The N alpha-(2-chloroethyl)-N-nitrosocarbamoyl derivatives of H-Pro-Lys(X)-Pro-Val-NH2 (X: tert-butyloxycarbonyl, formyl, (2-chloroethyl)nitrosocarbamoyl) were synthesized. It was found that the bis-substitution of the urea N3 in these derivatives does not decrease the antitumor activity influenced mainly by the nature of the carrier molecule as a whole.

  合成了H-Pro-Lys（X）-Pro-Val-NH2的Nα-（2-氯乙基）-N-亚硝基氨基甲酰基衍生物（X：叔丁氧羰基，甲酰基，（2-氯乙基）亚硝基氨基甲酰基）。发现这些衍生物中的尿素N 3的双取代不会降低主要受载体分子整体性质影响的抗肿瘤活性。
• US4452814A
  申请人：——

  公开号：US4452814A

  公开（公告）日：1984-06-05
• (2-Chloroethyl)nitrosourea congeners of amino acid amides
  作者：Tetsuo Suami、k Tsuguhiro Kato、Hiroaki Takino、Takashi Hisamatsu

  DOI：10.1021/jm00349a012

  日期：1982.7

  Fourteen (2-chloroethyl)nitrosourea congeners of L-amino acid amides have been synthesized as potential antineoplastic agents. Almost all the congeners tested were found to be highly active against experimental leukemia L1210 in mice. The chemical decomposition rates of the congeners were measured in a buffered solution (pH 7.4) at 37 degrees C. Acute toxicities of some of the congeners were determined for mice. The congener of sarcosinamide shows the longest half-life (T0.5 = 329.7 min) and the lowest toxicity, LD50 = 392.0 mg/kg (ip) and 426.6 mg/kg (iv), in this series.
• Decomposition of N-(2-chloroethyl)-N-nitrosocarbamoyl amino acid amides
  作者：Helga Suli-Vargha、Jozsef Bodi、Miomir Meszaros、Kalman Medzihradszky

  DOI：10.1021/jm00403a003

  日期：1988.8

  The chemical decomposition of N-(2-chloroethyl)-N-nitrosocarbamoyl (Q(NO] prolinamide and valinamide were studied under physiological conditions. The volatile products were identified with GC. Q(NO)-Pro-NH2 gave twice the amount of ethylene glycol and only one-fifth of the 2-chloroethanol produced by Q(NO)-Val-NH2 or BCNU, pointing to different pathways of their decomposition. The carbamoylating activity

  在生理条件下研究了N-（2-氯乙基）-N-亚硝基氨基甲酰基（Q（NO）脯氨酰胺和缬氨酰胺）的化学分解，用气相色谱仪鉴定了挥发性产物，Q（NO）-Pro-NH2给出了两倍的Q（NO）-Val-NH2或BCNU产生的乙二醇和2-氯乙醇中只有五分之一，表明它们的分解途径不同，并且在存在环己胺的情况下还研究了氨基甲酰化活性，发现导致分子内氨基甲酰化，并形成乙内酰脲衍生物。