4-(phenylsulfonyl)-3-(thiophen-2-yl)isoxazol-5-amine | 1609152-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(phenylsulfonyl)-3-(thiophen-2-yl)isoxazol-5-amine
• 英文别名: 4-(Benzenesulfonyl)-3-thiophen-2-yl-1,2-oxazol-5-amine；4-(benzenesulfonyl)-3-thiophen-2-yl-1,2-oxazol-5-amine
• CAS: 1609152-28-4
• 化学式: C₁₃H₁₀N₂O₃S₂
• 分子量: 306.366
• InChiKey: RIGFLKNMBFOKQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(phenylsulfonyl)-3-(thiophen-2-yl)isoxazol-5-amine 、 4-硝基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到N-(4-(phenylsulfonyl)-3-(thiophen-2-yl)isoxazol-5-yl)-4-nitrobenzamide
  参考文献：
  名称：

  A green synthesis of new 3-aryl-4-phenylsulfonyl-5-aminoisoxazoles

  摘要：

  The present work describes a new protocol for the synthesis of 5-aminoisoxazoles using alpha-chlorooximes and 2-phenylsulfonyl acetonitrile via green chemistry routes. The titled 5-aminoisoxazoles 3 were further reacted with 4-nitrobenzoyl chloride to obtain 5-amidoisoxazoles with moderate yields. These heterocyclic compounds were tested in vitro MTT study to investigate inhibitive abilities to some cancer cell lines (C3a, L929, T98g and Mcf-7) and compounds 3a, 3c, 3e and 3h showed noticeable cytotoxic property against four cancer cell lines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.106
• 作为产物：
  描述：

  N-hydroxythiophene-2-carbimidoyl chloride 、 苯磺酰乙腈 在 三乙胺 作用下， 以 neat (no solvent) 为溶剂， 反应 0.08h， 以50%的产率得到4-(phenylsulfonyl)-3-(thiophen-2-yl)isoxazol-5-amine
  参考文献：
  名称：

  A green synthesis of new 3-aryl-4-phenylsulfonyl-5-aminoisoxazoles

  摘要：

  The present work describes a new protocol for the synthesis of 5-aminoisoxazoles using alpha-chlorooximes and 2-phenylsulfonyl acetonitrile via green chemistry routes. The titled 5-aminoisoxazoles 3 were further reacted with 4-nitrobenzoyl chloride to obtain 5-amidoisoxazoles with moderate yields. These heterocyclic compounds were tested in vitro MTT study to investigate inhibitive abilities to some cancer cell lines (C3a, L929, T98g and Mcf-7) and compounds 3a, 3c, 3e and 3h showed noticeable cytotoxic property against four cancer cell lines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.106

文献信息

• A green synthesis of new 3-aryl-4-phenylsulfonyl-5-aminoisoxazoles
  作者：Cevher Altuğ、Muhammet Büyükbayram、Özge Kavas、Muhsine Zeynep Yavuz

  DOI：10.1016/j.tet.2014.03.106

  日期：2014.6

  The present work describes a new protocol for the synthesis of 5-aminoisoxazoles using alpha-chlorooximes and 2-phenylsulfonyl acetonitrile via green chemistry routes. The titled 5-aminoisoxazoles 3 were further reacted with 4-nitrobenzoyl chloride to obtain 5-amidoisoxazoles with moderate yields. These heterocyclic compounds were tested in vitro MTT study to investigate inhibitive abilities to some cancer cell lines (C3a, L929, T98g and Mcf-7) and compounds 3a, 3c, 3e and 3h showed noticeable cytotoxic property against four cancer cell lines. (C) 2014 Elsevier Ltd. All rights reserved.