{(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester | 686781-16-8

• 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)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester
• CAS: 686781-16-8
• 化学式: C₂₄H₃₈N₄O₅S
• 分子量: 494.656
• InChiKey: ZRTWKFAHJUASMO-FKBYEOEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  108.05
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-苯乙基异氰酸酯 、 {(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以98%的产率得到benzyl N-[(2S)-3-methyl-1-[(2S)-2-[[(3S)-3-(2-methylpropyl)-1,1-dioxo-5-(2-phenylethylcarbamoyl)-1,2,5-thiadiazolidin-2-yl]methyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Design, synthesis, and in vitro evaluation of inhibitors of human leukocyte elastase based on a functionalized cyclic sulfamide scaffold

  摘要：

  The design of novel functionalized templates capable of binding to the active site of serine proteases could potentially lead to the development of potent and highly selective non-covalent inhibitors of these enzymes. Using the elastase-turkey ovomucoid inhibitor complex and insights gained from earlier work based on the 1,2,5-thiadiazolidin-3-one 1,1 dioxide scaffold (I), a surrogate cyclosulfamide scaffold (II) was used for the first time in the design of reversible inhibitors of human leukocyte elastase. Compounds 7 and 8 were found to be micromolar reversible inhibitors of the enzyme. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.059
• 作为产物：
  描述：

  Cbz-L-Val-L-propinal 在 锂硼氢 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 37.5h， 生成 {(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  Design, synthesis, and in vitro evaluation of inhibitors of human leukocyte elastase based on a functionalized cyclic sulfamide scaffold

  摘要：

  The design of novel functionalized templates capable of binding to the active site of serine proteases could potentially lead to the development of potent and highly selective non-covalent inhibitors of these enzymes. Using the elastase-turkey ovomucoid inhibitor complex and insights gained from earlier work based on the 1,2,5-thiadiazolidin-3-one 1,1 dioxide scaffold (I), a surrogate cyclosulfamide scaffold (II) was used for the first time in the design of reversible inhibitors of human leukocyte elastase. Compounds 7 and 8 were found to be micromolar reversible inhibitors of the enzyme. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.059