(S)-2-<(tert-butylsulfonyl)methyl>-3-phenylpropionic acid succinimido ester | 135902-06-6

• 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: (S)-2-<(tert-butylsulfonyl)methyl>-3-phenylpropionic acid succinimido ester
• 英文别名: 2-benzyl-3-tert-(butylsulfonyl)propionic acid hydroxysuccinimide ester；(2,5-dioxopyrrolidin-1-yl) (2S)-2-benzyl-3-tert-butylsulfonylpropanoate
• CAS: 135902-06-6
• 化学式: C₁₈H₂₃NO₆S
• 分子量: 381.45
• InChiKey: GBEWBAZKFPGKJT-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-<(tert-butylsulfonyl)methyl>-3-phenylpropionic acid succinimido ester 在 N-乙基哌啶 、 三甲基乙酰氯 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 44.17h， 生成 <2-benzyl-3-(tert-butylsulfonyl)propionyl>-Nim-(2,4-dinitrophenyl)histidyl <(2S,3R,4R,5R,6R)-1-cyclohexyl-3,4:6,7-di-O-isopropylidene-3,4,5,6,7-pentahydroxyhept-2-yl>amide
  参考文献：
  名称：

  Renin inhibitory pentols showing improved enteral bioavailability

  摘要：

  Incorporation of a C-terminal pentahydroxy functionality led to potent, low molecular weight hydrophilic renin inhibitors lacking the P1' side chain. As these compounds are easy to synthesize and have sufficient water solubility, they were chosen for further study. Compound 33 was transported across rabbit intestinal brush border membrane vesicles and yielded a hypotensive effect in sodium-depleted rhesus monkeys which lasted for 90 min when dosed at 2 mg/kg id.

  DOI：

  10.1021/jm00081a019
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 (S)-α-[[(1,1-dimethylethyl)-sulfonyl]methyl]benzenepropanoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以76%的产率得到(S)-2-<(tert-butylsulfonyl)methyl>-3-phenylpropionic acid succinimido ester
  参考文献：
  名称：

  Inhibitors of human renin with C-termini derived from amides and esters of .alpha.-mercaptoalkanoic acids

  摘要：

  New transition-state analogues bearing C-termini derived from alpha-mercaptoalkanoic acids, esters, and amides were prepared and evaluated as inhibitors of human renin. Addition of alpha-mercaptoalkanoate esters to a chiral Boc-amino epoxide intermediate led ultimately to the target [(2R,3S)-3-(BocPheHis-amino)-4-cyclohexyl-2-hydroxy-1-butyl]thio derivatives. The corresponding sulfoxide and sulfone analogues were also investigated. Some of these derivatives, including one with a stable BocPhe replacement, were relatively potent inhibitors of human plasma renin, having IC50 values below 10 nM. When selected compounds were administered intravenously to sodium-deficient rhesus monkeys (Macaca mulatta) at 0.06-1 mg/kg, they reduced plasma renin activity by 87-94%. However, the accompanying drop in blood pressure was of short duration.

  DOI：

  10.1021/jm00093a009

文献信息

• Renin-hemmende Aminooligohydroxy-Derivate
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0410278B1

  公开（公告）日：1994-01-19
• US5114925A
  申请人：——

  公开号：US5114925A

  公开（公告）日：1992-05-19
• Renin inhibitory pentols showing improved enteral bioavailability
  作者：Heinz Werner Kleemann、Holger Heitsch、Rainer Henning、Werner Kramer、Walter Kocher、Ulrich Lerch、Wolfgang Linz、Wolf Ulrich Nickel、Dieter Ruppert

  DOI：10.1021/jm00081a019

  日期：1992.2

  Incorporation of a C-terminal pentahydroxy functionality led to potent, low molecular weight hydrophilic renin inhibitors lacking the P1' side chain. As these compounds are easy to synthesize and have sufficient water solubility, they were chosen for further study. Compound 33 was transported across rabbit intestinal brush border membrane vesicles and yielded a hypotensive effect in sodium-depleted rhesus monkeys which lasted for 90 min when dosed at 2 mg/kg id.
• Inhibitors of human renin with C-termini derived from amides and esters of .alpha.-mercaptoalkanoic acids
  作者：Wallace T. Ashton、Christine L. Cantone、Richard L. Tolman、William J. Greenlee、Robert J. Lynch、Terry W. Schorn、John F. Strouse、Peter K. S. Siegl

  DOI：10.1021/jm00093a009

  日期：1992.7

  New transition-state analogues bearing C-termini derived from alpha-mercaptoalkanoic acids, esters, and amides were prepared and evaluated as inhibitors of human renin. Addition of alpha-mercaptoalkanoate esters to a chiral Boc-amino epoxide intermediate led ultimately to the target [(2R,3S)-3-(BocPheHis-amino)-4-cyclohexyl-2-hydroxy-1-butyl]thio derivatives. The corresponding sulfoxide and sulfone analogues were also investigated. Some of these derivatives, including one with a stable BocPhe replacement, were relatively potent inhibitors of human plasma renin, having IC50 values below 10 nM. When selected compounds were administered intravenously to sodium-deficient rhesus monkeys (Macaca mulatta) at 0.06-1 mg/kg, they reduced plasma renin activity by 87-94%. However, the accompanying drop in blood pressure was of short duration.