N'-甲基-N'-甲基磺酰基甲烷磺酰肼 | 110295-69-7

• 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
• 中文名称: N'-甲基-N'-甲基磺酰基甲烷磺酰肼
• 英文名称: 1,2-bis(methylsulfonyl)-1-methylhydrazine
• 英文别名: N'-methyl-N'-methylsulfonylmethanesulfonohydrazide
• CAS: 110295-69-7
• 化学式: C₃H₁₀N₂O₄S₂
• 分子量: 202.255
• InChiKey: KYRBDGFWRYSMFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N'-甲基-N'-甲基磺酰基甲烷磺酰肼 、 2-溴乙基氯甲酸酯 在 三乙胺 作用下， 以 氯仿 、 丙酮 为溶剂， 生成 2-(2-bromoethoxy)carbonyl-1,2-bis(methylsulfonyl)-1-methylhydrazine
  参考文献：
  名称：

  N,n-bis(sulfonyl)hydrazines useful as antineoplastic agents

  摘要：

  本发明涉及一种化合物，其化学式如下：其中R.sup.1和R.sup.2选自具有1-6个碳原子的低烷基基团，取代或未取代的芳基团，以及具有1-6个碳原子的不饱和烷基基团；R.sup.3是取代或未取代的具有1-6个碳原子的低烷基基团；R.sup.4选自具有1-6个碳原子的取代或未取代的低烷基基团，取代或未取代的芳基团，以及具有1-6个碳原子的不饱和烷基基团。本发明还涉及包含上述化合物的药物组合物，以及使用该化合物治疗肿瘤细胞的方法。

  公开号：

  US06040338A1
• 作为产物：
  描述：

  methanesulfonic acid 1-methylhydrazide 、 甲基磺酰氯 在 吡啶 作用下， 以34%的产率得到N'-甲基-N'-甲基磺酰基甲烷磺酰肼
  参考文献：
  名称：

  1,2-Bis(sulfonyl)hydrazines. 3. Effects of structural modification on antineoplastic activity

  摘要：

  A series of 1,2-bis(sulfonyl)hydrazines was synthesized and evaluated for antineoplastic activity against the L1210 leukemia and the B16 melanoma. The most active agent to emerge from this study, 1,2-bis(methylsulfonyl)-1-methylhydrazine, produced a maximum % T/C for mice bearing the L1210 leukemia or the B16 melanoma of 340% and 278%, respectively. Two N-chloroethyl analogues, conceived as bifunctional alkylating agents, were also synthesized and evaluated for antineoplastic activity against the L1210 leukemia and the B16 melanoma. Although such a modification resulted in retention of antineoplastic activity against both tumor cell lines, it did not result in enhanced antineoplastic activity.

  DOI：

  10.1021/jm00394a040

文献信息

• Synthesis and evaluation of 1,2,2-tris(sulfonyl)hydrazines as antineoplastic and trypanocidal agents
  作者：Krishnamurthy Shyam、Philip G. Penketh、Alan A. Divo、Regina H. Loomis、Curtis L. Patton、Alan C. Sartorelli

  DOI：10.1021/jm00170a033

  日期：1990.8

  Several 1,2,2-tris(sulfonyl)hydrazines, conceived as prodrugs of 1,2-bis(sulfonyl)hydrazines, were synthesized and evaluated for antineoplastic and trypanocidal activities in mice. 1-Methyl-1,2,2-tris(methylsulfonyl)hydrazine emerged as an extremely efficacious antitrypanosomal agent, whereas 1-(2-chloroethyl)-1,2,2-tris(methylsulfonyl)hydrazine was inactive. In contrast, 1-(2-chloroethyl)-1,2,2-t

  合成了几种1,2,2-三（磺酰基）肼，被认为是1,2-双（磺酰基）肼的前药，并评估了它们在小鼠中的抗肿瘤和锥虫活性。1-甲基-1,2,2-三（甲基磺酰基）肼是一种非常有效的抗锥虫剂，而1-（2-氯乙基）-1,2,2-三（甲基磺酰基）肼则没有活性。相比之下，1-（2-氯乙基）-1,2,2-三（甲基磺酰基）肼显示出强大的抗肿瘤活性，产生了患有白血病L1210，白血病P388或肉瘤180的小鼠数个60天的“治愈”。三（磺酰基）衍生物不会产生异氰酸酯这一事实会加剧亚硝基脲如1,3-双（2-氯乙基）-1-亚硝基脲（BCNU）的宿主毒性，使其成为锥虫和锥虫的重要药物。癌症化疗。
• N,n-bis(sulfonyl)hydrazines useful as antineoplastic agents
  申请人：Yale University

  公开号：US06040338A1

  公开（公告）日：2000-03-21

  The present invention relates to a compound of the formula wherein R.sup.1 and R.sup.2 are selected from lower alkyl groups having 1-6 carbon atoms, substituted or unsubstituted aryl groups, and unsaturated alkyl groups having 1-6 carbon atoms; R.sup.3 is a substituted or unsubstituted lower alkyl group having 1-6 carbons; and R.sup.4 is selected from substituted or unsubstituted lower alkyl groups having 1-6 carbon atoms, substituted or unsubstituted aryl groups, and unsaturated alkyl groups having 1-6 carbon atoms. The present invention also relates to a pharmaceutical composition comprising the above compound, as well as a method of treating tumor cells with the compound.

  本发明涉及一种化合物，其化学式如下：其中R.sup.1和R.sup.2选自具有1-6个碳原子的低烷基基团，取代或未取代的芳基团，以及具有1-6个碳原子的不饱和烷基基团；R.sup.3是取代或未取代的具有1-6个碳原子的低烷基基团；R.sup.4选自具有1-6个碳原子的取代或未取代的低烷基基团，取代或未取代的芳基团，以及具有1-6个碳原子的不饱和烷基基团。本发明还涉及包含上述化合物的药物组合物，以及使用该化合物治疗肿瘤细胞的方法。
• 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.
• SHYAM, KRISHNAMURTHY;PENKETH, PHILIP G.;DIVO, ALAN A.;LOOMIS, REGINA H.;P+, J. MED. CHEM., 33,(1990) N, C. 2259-2264
  作者：SHYAM, KRISHNAMURTHY、PENKETH, PHILIP G.、DIVO, ALAN A.、LOOMIS, REGINA H.、P+

  DOI：——

  日期：——
• SHYAM, KRISHNAMURTHY;HRUBIEC, ROBERT T.;FURUBAYASHI, RYOSUKE;COSBY, LUCIL+, J. MED. CHEM., 30,(1987) N 11, 2157-2161
  作者：SHYAM, KRISHNAMURTHY、HRUBIEC, ROBERT T.、FURUBAYASHI, RYOSUKE、COSBY, LUCIL+

  DOI：——

  日期：——