1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-methoxyacetylhydrazine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-methoxyacetylhydrazine
• 英文别名: 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)-2-(methoxyacetyl)hydrazine；N'-(2-chloroethyl)-2-methoxy-N,N'-bis(methylsulfonyl)acetohydrazide
• 化学式: C₇H₁₅ClN₂O₆S₂
• 分子量: 322.791
• InChiKey: WHCOTDAPWIVUCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲氧基乙酰氯 、 1,2-双(甲基磺酰基)-1-(2-氯乙基)肼 在 三乙胺 作用下， 以 丙酮 为溶剂， 以77.7%的产率得到1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-methoxyacetylhydrazine
  参考文献：
  名称：

  Synthesis and evaluation of 1-acyl-1,2-bis(methylsulfonyl)-2-(2-chloroethyl)hydrazines as antineoplastic agents

  摘要：

  A series of 1-acyl-1,2-bis(methylsulfonyl)-2-(2-chloroethyl)hydrazines, conceived as more potent analogs of 1-(2-chloroethyl)-1,2,2-tris(methylsulfonyl)hydrazine, were synthesized and evaluated for antineoplastic activity against the L1210 leukemia in mice. Of these, 1-acetyl-1,2-bis-(methylsulfonyl)-2-(2-chloroethyl)hydrazine produced ''cures'' of mice bearing the L1210 leukemia at dosage levels that were considerably less than those at which the tris(sulfonyl) analog produced its antineoplastic effects. This compound was also found to have pronounced activity against the P388 leukemia and against several solid tumors, including the B16F10 melanoma, the M5076 reticulum cell sarcoma, and the M109 lung carcinoma. Furthermore, the acyl derivatives were in general considerably more resistant to hydrolysis in aqueous media and more prone to protease- and thiol-mediated activation than the tris(sulfonyl) analog. The former property is important to formulation, while the latter properties may result in some degree of drug targeting and enhancement of the therapeutic indices of these agents.

  DOI：

  10.1021/jm00075a002

文献信息

• 1-Alkyl-2-acyl-1,2-disulfonylhydrazines with antineoplastic activity
  申请人：YALE UNIVERSITY

  公开号：EP0541322B1

  公开（公告）日：1996-09-11
• US5256820A
  申请人：——

  公开号：US5256820A

  公开（公告）日：1993-10-26
• Synthesis and evaluation of 1-acyl-1,2-bis(methylsulfonyl)-2-(2-chloroethyl)hydrazines as antineoplastic agents
  作者：Krishnamurthy Shyam、Philip G. Penketh、Alan A. Divo、Regina H. Loomis、William C. Rose、Alan C. Sartorelli

  DOI：10.1021/jm00075a002

  日期：1993.11

  A series of 1-acyl-1,2-bis(methylsulfonyl)-2-(2-chloroethyl)hydrazines, conceived as more potent analogs of 1-(2-chloroethyl)-1,2,2-tris(methylsulfonyl)hydrazine, were synthesized and evaluated for antineoplastic activity against the L1210 leukemia in mice. Of these, 1-acetyl-1,2-bis-(methylsulfonyl)-2-(2-chloroethyl)hydrazine produced ''cures'' of mice bearing the L1210 leukemia at dosage levels that were considerably less than those at which the tris(sulfonyl) analog produced its antineoplastic effects. This compound was also found to have pronounced activity against the P388 leukemia and against several solid tumors, including the B16F10 melanoma, the M5076 reticulum cell sarcoma, and the M109 lung carcinoma. Furthermore, the acyl derivatives were in general considerably more resistant to hydrolysis in aqueous media and more prone to protease- and thiol-mediated activation than the tris(sulfonyl) analog. The former property is important to formulation, while the latter properties may result in some degree of drug targeting and enhancement of the therapeutic indices of these agents.