(R)-4-Phenyl-2-trifluoromethanesulfonyloxy-butyric acid benzyl ester | 138333-10-5

• 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: (R)-4-Phenyl-2-trifluoromethanesulfonyloxy-butyric acid benzyl ester
• 英文别名: (R)-Benzyl 4-Phenyl-2-(((trifluoromethyl)sulfonyl)oxy)butanoate；benzyl (2R)-4-phenyl-2-(trifluoromethylsulfonyloxy)butanoate
• CAS: 138333-10-5
• 化学式: C₁₈H₁₇F₃O₅S
• 分子量: 402.391
• InChiKey: PRFDZYLJSQYZTJ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-4-Phenyl-2-trifluoromethanesulfonyloxy-butyric acid benzyl ester 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 Methyl 2(R)-(1(S)-carboxy-3-phenylpropylamino)-4-(p-toluenesulfonylamino)butyrate
  参考文献：
  名称：

  Potent matrix metalloproteinase inhibitors: Amino-carboxylate compounds containing modifications of the P1 residue

  摘要：

  A series of amino-carboxylate inhibitors of matrix metalloproteinases containing different p1 modifications have been synthesized. It was discovered that a toluenesulfonamide-type substituent at the P1 position considerably enhances the binding affinity of inhibitors for stromelysin. Replacements of the P2'-P3' residues with nonpeptide components result in loss of inhibitory activity.

  DOI：

  10.1016/0960-894x(96)00028-5
• 作为产物：
  描述：

  (R)-2-羟基-4-苯基丁酸 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (R)-4-Phenyl-2-trifluoromethanesulfonyloxy-butyric acid benzyl ester
  参考文献：
  名称：

  Potent matrix metalloproteinase inhibitors: Amino-carboxylate compounds containing modifications of the P1 residue

  摘要：

  A series of amino-carboxylate inhibitors of matrix metalloproteinases containing different p1 modifications have been synthesized. It was discovered that a toluenesulfonamide-type substituent at the P1 position considerably enhances the binding affinity of inhibitors for stromelysin. Replacements of the P2'-P3' residues with nonpeptide components result in loss of inhibitory activity.

  DOI：

  10.1016/0960-894x(96)00028-5

文献信息

• CARBOXYALKYL DIPEPTIDE INHIBITORS OF ENDOPEPTIDASES
  申请人：SCHERING CORPORATION

  公开号：EP0495822A1

  公开（公告）日：1992-07-29
• US5043346A
  申请人：——

  公开号：US5043346A

  公开（公告）日：1991-08-27
• [EN] CARBOXYALKYL DIPEPTIDE INHIBITORS OF ENDOPEPTIDASES
  申请人：SCHERING CORPORATION

  公开号：WO1991005796A1

  公开（公告）日：1991-05-02

  (EN) Carboxyalkyl dipeptide inhibitors of endopeptidases of formula (I) or pharmaceutically acceptable salt thereof, wherein R1 is H, alkyl, arylalkyl or aryl; R2 is H, alkyl, alkenyl or alkynyl, wherein the alkyl portion is substituted with 0-3 substituents independently selected from the group consisting of hydroxy, alkoxy, alkoxyalkoxy, alkylthio, aryl, alkoxyalkylthio, arylalkoxy and arylalkylthio; R3 and R4 are independently alkyl or arylalkyl; or R3 and R4 together with the carbon to which they are attached form an optionally substituted 5-, 6- or 7-membered ring wherein said ring comprises 0 to 1 heteroatoms selected from the group consisting of sulfur and oxygen; R5 is H, alkyl, alkoxyalkyl, alkylthioalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, arylalkoxyalkyl or arylalkylthioalkyl; R6 is hydroxy, alkoxy, or R5; R7 is hydroxy, alkoxy, aryloxy, arylalkoxy, amino, alkylamino or dialkylamino; m is 0 or 1; and n is 0, 1, 2, or 3, use of the compounds, alone or in combination with an ACE inhibitor or an ANF, in the treatment of cardiovascular disorders such as hypertension, congestive heart failure, edema and renal insufficiency, use of the compounds in the treatment of pain conditions, and pharmaceutical compositions containing said compounds are disclosed.(FR) Inhibiteurs dipeptidiques carboxyalkyles d'endopeptidases de la formule (I), où leur sel pharmaceutiquement acceptable, dans laquelle R1 représente H, alkyle, arylalkyle, ou aryle; R2 représente H, alkyle, alcényle ou alkynyle, dans lequel la partie alkyle est remplacée par 0 à 3 substituants choisis indépendant dans le groupe composé de hydroxy, alkoxy, alkoxyalkoxy, alkylthio, aryle, alkoxyalkylthio, arylalkoxy et arylalkylthio; R3 et R4 représentent indépendamment alkyle ou arylalkyle; ou R3 et R4 ainsi que l'atome de carbone auquel ils sont fixés, forment un anneau à 5, 6 ou 7 éléments à substitution facultative, dans lesquels ledit anneau comprend 0 à 1 hétéroatome choisi dans le groupe composé de soufre et d'oxygène; R5 représente H, alkyle, alkoxyalkyle, alkylthioalkyle, aryle, arylalkyle, hétéroaryle, hétérarylalkyle, arylakoxyalkyle ou arylakylthioakyle; R6 représente hydroxy, alkoxy, ou R5; R7 représente hydroxy, alkoxy, aryloxy, arylalkoxy, amino, alkylamino ou dialkylamino; m représente 0 ou 1; et n représente 0, 1, 2 ou 3, l'emploi des composés, seuls ou de manière combinée à un inhibiteur d'ACE ou un ANF, dans le traitement de troubles cardiovasculaires tels que l'hypertension, l'insuffisance cardiaque, l'÷dème, et l'insuffisance rénale, l'emploi des composés dans le traitement d'états algiques, et compositions pharmaceutiques contenant lesdits composés.
• Potent matrix metalloproteinase inhibitors: Amino-carboxylate compounds containing modifications of the P1 residue
  作者：Chu-Biao Xue、Xiaohua He、John Roderick、William F. DeGrado、Carl Decicco、Robert A. Copeland

  DOI：10.1016/0960-894x(96)00028-5

  日期：1996.2

  A series of amino-carboxylate inhibitors of matrix metalloproteinases containing different p1 modifications have been synthesized. It was discovered that a toluenesulfonamide-type substituent at the P1 position considerably enhances the binding affinity of inhibitors for stromelysin. Replacements of the P2'-P3' residues with nonpeptide components result in loss of inhibitory activity.