(3S)-2-oxo-4-phenyl-3-[[[3-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester | 322729-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: (3S)-2-oxo-4-phenyl-3-[[[3-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester
• CAS: 322729-68-0
• 化学式: C₂₄H₂₁N₃O₄
• 分子量: 415.448
• InChiKey: IHCVNBIUEVTMQR-ZPKNHPDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  97.19
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S)-2-oxo-4-phenyl-3-[[[3-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester 在 水 作用下， 以 氘代乙腈 为溶剂， 生成 (3S)-2-oxo-4-phenyl-3-[[[3-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester 、 (S)-2,2-Dihydroxy-4-phenyl-3-(3-phenylazo-benzoylamino)-butyric acid methyl ester 、 (S)-2,2-Dihydroxy-4-phenyl-3-(3-phenylazo-benzoylamino)-butyric acid methyl ester
  参考文献：
  名称：

  Azobenzene-Containing, Peptidyl α-Ketoesters as Photobiological Switches of α-Chymotrypsin

  摘要：

  Three photoswitchable, peptidomimetic inhibitors of oc-chymotrypsin have been synthesised. The compounds comprise an azobenzene, an alpha -ketoester and L-phenylalanine. The compounds were photoisomerised to give enriched states of the (E) and (Z) isomers and these states were assayed against alpha -chymotrypsin. The inhibitors were shown to be moderately active with switching ability of between two- and three-fold between the two isomer-enriched states. The behaviour of the inhibitors in solution was examined; specifically, their hydration and configurational stability. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00883-8
• 作为产物：
  描述：

  (2R,3S)-3-[(benzyloxycarbonyl)amino]-2-hydroxy-4-phenylbutanoic acid methyl ester 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 氢溴酸 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 potassium bromide 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.83h， 生成 (3S)-2-oxo-4-phenyl-3-[[[3-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester
  参考文献：
  名称：

  Azobenzene-Containing, Peptidyl α-Ketoesters as Photobiological Switches of α-Chymotrypsin

  摘要：

  Three photoswitchable, peptidomimetic inhibitors of oc-chymotrypsin have been synthesised. The compounds comprise an azobenzene, an alpha -ketoester and L-phenylalanine. The compounds were photoisomerised to give enriched states of the (E) and (Z) isomers and these states were assayed against alpha -chymotrypsin. The inhibitors were shown to be moderately active with switching ability of between two- and three-fold between the two isomer-enriched states. The behaviour of the inhibitors in solution was examined; specifically, their hydration and configurational stability. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00883-8