4-methyl-2-phenyl-1,3-thiazole-5-carbothioic S-acid | 1069135-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-2-phenyl-1,3-thiazole-5-carbothioic S-acid
• CAS: 1069135-25-6
• 化学式: C₁₁H₉NOS₂
• 分子量: 235.331
• InChiKey: RHCQCPWUHFHVRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-2-phenyl-1,3-thiazole-5-carbothioic S-acid 、 4-乙酰氨基苯磺酰叠氮 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.02h， 生成 N-{4-[(4-methyl-2-phenyl-thiazole-5-carbonyl)-sulfamoyl]-phenyl}-acetamide
  参考文献：
  名称：

  Sulfo-click reaction via in situ generated thioacids and its application in kinetic target-guided synthesis

  摘要：

  在此，我们描述了一种实用的硫-点击反应单锅变体，其中带有9-芴基甲基保护的硫酯迅速去保护，并与磺酰叠氮物进一步反应，生成N-酰基磺酰胺。

  DOI：

  10.1039/c1cc14724b
• 作为产物：
  描述：

  4-甲基-2-苯基-1,3-噻唑-5-碳酰氯 在 sodium hydrogensulfide 作用下， 以 水 为溶剂， 反应 3.0h， 以67%的产率得到4-methyl-2-phenyl-1,3-thiazole-5-carbothioic S-acid
  参考文献：
  名称：

  Bcl-X_L-Templated Assembly of Its Own Protein−Protein Interaction Modulator from Fragments Decorated with Thio Acids and Sulfonyl Azides

  摘要：

  Protein-protein interactions have key importance in various biological processes and modulation of particular protein-protein interactions has been shown to have therapeutic effects. However, disrupting or modulating protein-protein interactions with low-molecular-weight compounds is extremely difficult due to the lack of deep binding pockets on protein surfaces. Herein we describe the development of an unprecedented lead synthesis and discovery method that generated only biologically active compounds from a library of reactive fragments. Using the protein Bcl-X-L, a central regulator of programmed cell death, we demonstrated that an amidation reaction between thio acids and sulfonyl azides is applicable for Bcl-X-L-templated assembly of inhibitory compounds. We have demonstrated for the first time that kinetic target guided synthesis can be applied not only on enzymatic targets but also for the discovery of small molecules modulating protein-protein interactions.

  DOI：

  10.1021/ja802683u

文献信息

• [EN] ACYLSULFONAMIDES AND PROCESSES FOR PRODUCING THE SAME<br/>[FR] ACYLSULFONAMIDES ET PROCÉDÉS POUR PRODUIRE CEUX-CI
  申请人：UNIV SOUTH FLORIDA

  公开号：WO2012021486A3

  公开（公告）日：2012-05-31
• Acylsulfonamides and Processes for Producing the Same
  申请人：Manetsch Roman

  公开号：US20110130568A1

  公开（公告）日：2011-06-02

  The present disclosure relates to acylsulfonamides and processes for their preparation. The processes involve a target-guided synthesis approach, whereby a thioacid and a sulfonyl azide are reacted in the presence of a biological target protein, a Bcl-2 family protein, to form the acylsulfonamide.
• ACYLSULFONAMIDES AND PROCESSES FOR PRODUCING THE SAME
  申请人：Manetsch Roman

  公开号：US20130203709A1

  公开（公告）日：2013-08-08

  The present disclosure relates to acylsulfonamides and processes for their preparation. The processes involve a target-guided synthesis approach, whereby a thioacid and a sulfonyl azide are reacted in the presence of a biological target protein, a Bcl-2 family protein, to form the acylsulfonamide.
• US8524947B2
  申请人：——

  公开号：US8524947B2

  公开（公告）日：2013-09-03
• [EN] ACYLSULFONAMIDES AND PROCESSES FOR PRODUCING THE SAME<br/>[FR] ACYLSULFONAMIDES ET PROCÉDÉS DE PRODUCTION DE CES DERNIERS
  申请人：UNIV SOUTH FLORIDA

  公开号：WO2009105751A1

  公开（公告）日：2009-08-27

  The present disclosure relates to acylsulfonamides and processes for their preparation. The processes involve a target-guided synthesis approach, whereby a thioacid and a sulfonyl azide are reacted in the presence of a biological target protein, a Bcl-2 family protein, to form the acylsulfonamide.