(S)-(+)-4-benzyl-1,2,5-thiadiazolidin-3-one | 139164-33-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-(+)-4-benzyl-1,2,5-thiadiazolidin-3-one
• 英文别名: 1,2,5-Thiadiazolidin-3-one, 4-(phenylmethyl)-, 1,1-dioxide, (4S)-；(4S)-4-benzyl-1,1-dioxo-1,2,5-thiadiazolidin-3-one
• CAS: 139164-33-3
• 化学式: C₉H₁₀N₂O₃S
• 分子量: 226.256
• InChiKey: MGUCQKMVEFZINK-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-4-benzyl-1,2,5-thiadiazolidin-3-one 在 sodium hydride 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Potent and Specific Inhibition of Human Leukocyte Elastase, Cathepsin G and Proteinase 3 by Sulfone Derivatives Employing the 1,2,5-Thiadiazolidin-3-one 1,1 Dioxide Scaffold

  摘要：

  This paper describes the results of structure-activity relationship studies in a series of heterocyclic mechanism-based inhibitors based on the 1,2,5-thiadiazolidin-3-one 1,1 dioxide scaffold I and capable of interacting with the S-n and S-n' subsites of a serine proteinase. Sulfone derivatives of I were found to be highly effective, time-dependent inhibitors of human leukocyte elastase (HLE), cathepsin G (Cat G) and proteinase 3 (PR 3). The judicious selection of an R-1 group (accommodated at the primary specificity site S-1) that is based on the known substrate specificity of a target serine proteinase, was found to yield highly selective inhibitors. The presence of a benzyl group (R-2 = benzyl) at the S-2 subsite was found to lead to a pronounced enhancement in inhibitory potency. Furthermore, the effective use of computer graphics and modeling has led to the design of potent, water-soluble inhibitors. The results of these studies demonstrate that the 1,2,5-thiadiazolidin-3-one 1,1, dioxide platform provides an effective means for appending recognition elements in a well-defined vector relationship, and in fashioning highly-selective and potent inhibitors of serine proteinases. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00006-6
• 作为产物：
  描述：

  <(S)(+)> methyl -phenylalaninate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以78%的产率得到(S)-(+)-4-benzyl-1,2,5-thiadiazolidin-3-one
  参考文献：
  名称：

  含有手性磺胺乙内酰脲作为糖苷配基的假核苷的合成（II）

  摘要：

  从N-氨磺酰基氨基酸甲基酯开始，通过碱环化合成了一系列手性磺基缩乙胆苷。这些伪嘧啶杂环的区域选择性糖基化是在N-磺酰基氨基甲酸酯位置上的苄基保护基进行的。最佳的糖基化结果是通过对磺胺丁丹酮进行初步的甲硅烷基化，以及它们与四酰基核呋喃糖的缩合反应而获得的，从而产生呈β-异头构型的假核苷。

  DOI：

  10.1016/0040-4020(95)00932-9

文献信息

• Synthese et cyclisation de carboxylsulfamides derives d'aminoacides
  作者：Nourreddine Aouf、Georges Dewynter、Jean-Louis Montero

  DOI：10.1016/0040-4039(91)80216-s

  日期：1991.11

  3-Oxo-4-substituted-1,2,5-thiadiazolidine 1,1,-dioxides are synthesized from the carboxylsulfamides of aminoacids.

  由氨基酸的羧基磺酰胺合成3-氧-4-取代的1,2,5-噻二唑烷1,1，-二氧化物。
• Unusual reactivity of sulfahydantoins in the Mitsunobu reaction
  作者：Georges Dewynter、Sophie Ubaldi、Normand Voyer、Loic Toupet

  DOI：10.1016/s0040-4039(98)01630-x

  日期：1998.10

  The use of sulfahydantoins in the Mitsunobu reaction with hydroxyacids lead to O-substituted compounds rather than the expected N-alkylated structures. Crystallographic analysis by X-ray diffraction confirmed the structure of unusual compounds and a mechanism for their formation is proposed. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Groutas William C., Kuang Rongze, Venkataraman Radhika, Biochem. and Biophys. Res. Commun, 198 (1994) N 1, S 341-349
  作者：Groutas William C., Kuang Rongze, Venkataraman Radhika

  DOI：——

  日期：——
• EP0739338A4
  申请人：——

  公开号：EP0739338A4

  公开（公告）日：1997-03-26
• NOVEL SERINE PROTEASE INHIBITORS: DERIVATIVES OF ISOTHIAZOLIDIN-3-ONE-1,1 DIOXIDE AND 3-OXO-1,2,5-THIADIAZOLIDINE-1,1-DIOXIDE
  申请人：THE WICHITA STATE UNIVERSITY

  公开号：EP0739338A1

  公开（公告）日：1996-10-30