1-methyl-4-[(2S,3S)-3-phenyloxiran-2-yl]sulfonylpiperazine | 110380-91-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-methyl-4-[(2S,3S)-3-phenyloxiran-2-yl]sulfonylpiperazine
• CAS: 110380-91-1
• 化学式: C₁₃H₁₈N₂O₃S
• 分子量: 282.364
• InChiKey: XYZKHFFGMOQCLX-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  61.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl-4-[(2S,3S)-3-phenyloxiran-2-yl]sulfonylpiperazine 以 二甲基亚砜 为溶剂， 反应 264.0h， 生成 N-甲基哌嗪 、 2-(4-甲基-哌嗪-1-基)-1-苯基-乙酮
  参考文献：
  名称：

  New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides

  摘要：

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.

  DOI：

  10.1021/jm00395a010
• 作为产物：
  描述：

  苯甲醛 、 1-((chloromethyl)sulfonyl)-4-methylpiperazine 在 potassium hydride 作用下， 生成 1-methyl-4-[(2S,3S)-3-phenyloxiran-2-yl]sulfonylpiperazine
  参考文献：
  名称：

  New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides

  摘要：

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.

  DOI：

  10.1021/jm00395a010

文献信息

• Radembino, Nathalie; Loiseau, Philippe M.; Dessalles, Marie-Christine, Arzneimittel-Forschung/Drug Research, 1998, vol. 48, # 3, p. 294 - 299
  作者：Radembino, Nathalie、Loiseau, Philippe M.、Dessalles, Marie-Christine、Marchat, Laurence、Bories, Christian、Gayral, Philippe、Mahuzier, Georges

  DOI：——

  日期：——
• New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides
  作者：Marie Josephe Brienne、Daniel Varech、Martine Leclercq、Jean Jacques、Nathalie Radembino、Christine Dessalles、Georges Mahuzier、Chantal Gueyouche、Christian Bories

  DOI：10.1021/jm00395a010

  日期：1987.12

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.