2-benzyl-3-(tert-butylsulfinyl)propionic acid | 114469-26-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-benzyl-3-(tert-butylsulfinyl)propionic acid
• 英文别名: 2-benzyl-3-tert.-butylsulphinyl-propionic acid；2-benzyl-3-tert-butylsulfinylpropanoic acid
• CAS: 114469-26-0
• 化学式: C₁₄H₂₀O₃S
• 分子量: 268.377
• InChiKey: JJILJYOPEMMTSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4S,5S)-5-[(S)-2-Amino-3-(1H-imidazol-4-yl)-propionylamino]-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid butylamide 、 2-benzyl-3-(tert-butylsulfinyl)propionic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4S,5S)-5-[[(2S)-2-[(2-benzyl-3-tert-butylsulfinylpropanoyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-N-butyl-6-cyclohexyl-4-hydroxy-2-propan-2-ylhexanamide
  参考文献：
  名称：

  Synthesis and biological activity of some transition-state inhibitors of human renin

  摘要：

  A series of renin inhibitors containing the dipeptide transition state mimics (2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-7-methyloctanoic acid (Leu (OH)/Val) and (2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-cyclohexylhexanoic acid (CHa /(OH)/Val) was prepared. A structure-activity study with Boc-Phe-His-Leu (OH)/Val-Ile-His-NH2 (8a) as starting material led to N-[(2S)-2-[(tert-butylsulfonyl)methyl]-3-phenylpropionyl]-His-Cha (OH)/ Val- NHC4H9-n (8i) which has the length of a tetrapeptide and contains only one natural amino acid. Compound 8i had an IC50 of 2 x 10(-9) M against human renin and showed high enzyme specificity; IC50 values against the related aspartic proteinases pepsin and cathepsin D were (8 x 10(-6) and 3 x 10(-6) M, respectively). In salt-depleted marmosets, 8i inhibited plasma renin activity PRA and lowered blood pressure for up to 2 h after oral administration of a dose of 10 mg/kg.

  DOI：

  10.1021/jm00117a027
• 作为产物：
  描述：

  乙基2-苄基丙烯酸酯 在 sodium hydroxide 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 77.0h， 生成 2-benzyl-3-(tert-butylsulfinyl)propionic acid
  参考文献：
  名称：

  Synthesis and biological activity of some transition-state inhibitors of human renin

  摘要：

  A series of renin inhibitors containing the dipeptide transition state mimics (2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-7-methyloctanoic acid (Leu (OH)/Val) and (2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-cyclohexylhexanoic acid (CHa /(OH)/Val) was prepared. A structure-activity study with Boc-Phe-His-Leu (OH)/Val-Ile-His-NH2 (8a) as starting material led to N-[(2S)-2-[(tert-butylsulfonyl)methyl]-3-phenylpropionyl]-His-Cha (OH)/ Val- NHC4H9-n (8i) which has the length of a tetrapeptide and contains only one natural amino acid. Compound 8i had an IC50 of 2 x 10(-9) M against human renin and showed high enzyme specificity; IC50 values against the related aspartic proteinases pepsin and cathepsin D were (8 x 10(-6) and 3 x 10(-6) M, respectively). In salt-depleted marmosets, 8i inhibited plasma renin activity PRA and lowered blood pressure for up to 2 h after oral administration of a dose of 10 mg/kg.

  DOI：

  10.1021/jm00117a027

文献信息

• Antihypertensive 5-amino-4-hydroxyvaleryl derivatives substituted by
  申请人：Ciba-Geigy Corporation

  公开号：US04758584A1

  公开（公告）日：1988-07-19

  Compounds of the formula ##STR1## in which R.sub.1 represents acyl substituted by a thio, sulphinyl or sulphonyl group, A represents an optionally N-alkylated .alpha.-amino acid residue that is bonded N-terminally to R.sub.1 and C-terminally to the group --NR.sub.2 --, R.sub.2 represents hydrogen or lower alkyl, R.sub.3 represents hydrogen, lower alkyl, optionally etherified or esterified hydroxy-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, tricycloalkyl-lower alkyl, aryl or aryl-lower alkyl, R.sub.4 represents hydroxy or etherified or esterified hydroxy, R.sub.5 represents lower alkyl, optionally etherified or esterified hydroxy-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl, bicycloalkyl-lower alkyl, tricycloalkyl, tricycloalkyl-lower alkyl, aryl, aryl-lower alkyl, optionally substituted carbamoyl, optionally substituted amino, optionally substituted hydroxy, optionally substituted mercapto, sulphinyl or sulphonyl, and R.sub.6 represents substituted amino, and salts of such compounds having salt-forming groups, inhibit the blood pressure-increasing action of the enzyme renin and can be used as anti-hypertensives.

  公式为##STR1##的化合物，其中R.sub.1代表由硫、亚硫氧或磺酰基取代的酰基，A代表一个可选择地N-烷基化的α-氨基酸残基，该残基在N-端与R.sub.1和C-端与基团--NR.sub.2--键合，R.sub.2代表氢或较低的烷基，R.sub.3代表氢、较低的烷基、可选择地醚化或酯化的羟基较低烷基、环烷基、环烷基较低烷基、双环烷基较低烷基、三环烷基较低烷基、芳基或芳基较低烷基，R.sub.4代表羟基或醚化或酯化的羟基，R.sub.5代表较低的烷基、可选择地醚化或酯化的羟基较低烷基、环烷基、环烷基较低烷基、双环烷基、双环烷基较低烷基、三环烷基、三环烷基较低烷基、芳基、芳基较低烷基、可选择地取代的氨基甲酰、可选择地取代的氨基、可选择地取代的羟基、可选择地取代的巯基、亚硫
• Durch schwefelhaltigen Gruppen substituierte 5-Amino-4-hydroxyvalerylderivate
  申请人：CIBA-GEIGY AG

  公开号：EP0236734A2

  公开（公告）日：1987-09-16

  Verbindungen der Formel worin R, durch eine Thio-, Sulfinyl- oder Sulfonylgruppe substituiertes Acyl, A einen gegebenenfalls N-alkylierten α-Aminosäurerest, der N-terminal mit R1 und C-terminal mit der Gruppe -NR2- verbunden ist, R2 Wasserstoff oder Niederalkyl, R3 Wasserstoff, Niederalkyl, gegebenenfalls veräthertes oder verestertes Hydroxyniederalkyl, Cycloalkyl, Cycloalkylniederalkyl, Bicycloalkylniederalkyl, Tricycloalkylniederalkyl, Aryl oder Arylniederalkyl, R4 Hydroxy, veräthertes oder verestertes Hydroxy, R6 Niederalkyl, gegebenenfalls veräthertes oder verestertes Hydroxyniederarkyl, Cycloalkyl, Cycloalkylniederalkyl, Bicycloalkyl, Bicycloalkylniederalkyl, Tricycloalkyl, Tricycloalkylniederalkyl, Aryl, Arylniederalkyl, gegebenenfalls substituiertes Carbamoyl, gegebenenfalls substituiertes Amino, gegebenenfalls substituiertes Hydroxy oder gegebenenfalls substituiertes Mercapto, Sulfinyl oder Sulfonyl und R6 substituiertes Amino darstellen, und Salze von solchen Verbindungen mit salzbildenden Gruppen hemmen die blutdrucksteigernde Wirkung des Enzyms Renin und können als Antihypertensiva verwendet werden.

  式中的化合物 其中 R 是被硫代、亚砜基或磺酰基取代的酰基，A 是任选 N-烷基化的 α-氨基酸残基，其 N 端与 R1 连接，C 端与基团 -NR2- 连接，R2 是氢或低级烷基，R3 是氢，低级烷基环烷基、环烷基低级烷基、双环烷基低级烷基、三环烷基低级烷基、芳基或芳基低级烷基、R4 羟基、醚化或酯化羟基、R6 低级烷基、任选醚化或酯化羟基低级烷基、环烷基、环烷基低级烷基、双环烷基、双环烷基低级烷基、三环烷基、三环烷基低级烷基、芳基、芳基低级烷基、任选取代的氨基甲酰基、任选取代的氨基、任选取代的羟基或任选取代的巯基、亚磺酰基或磺酰基和 R6 取代的氨基，以及这类化合物的盐形成基团的盐能抑制肾素酶的降压作用，可用作降压药。
• BUHLMAYER, PETER;CASELLI, ANTHONY;FUHRER, WALTER;GOSCHKE, RICHARD;RASETTI+, J. MED. CHEM., 31,(1988) N 9, C. 1839-1846
  作者：BUHLMAYER, PETER、CASELLI, ANTHONY、FUHRER, WALTER、GOSCHKE, RICHARD、RASETTI+

  DOI：——

  日期：——
• US4758584A
  申请人：——

  公开号：US4758584A

  公开（公告）日：1988-07-19
• US4889869A
  申请人：——

  公开号：US4889869A

  公开（公告）日：1989-12-26