succinimido 3-benzoyl-2-methylpropionate | 75380-99-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: succinimido 3-benzoyl-2-methylpropionate
• 英文别名: 3-benzoyl-2-methylpropionic acid, N-hydroxysuccinimide ester；2,5-Dioxo-1-pyrrolidinyl I+/--methyl-I(3)-oxobenzenebutanoate；(2,5-dioxopyrrolidin-1-yl) 2-methyl-4-oxo-4-phenylbutanoate
• CAS: 75380-99-3
• 化学式: C₁₅H₁₅NO₅
• 分子量: 289.288
• InChiKey: XPRZWSBCHQRGKH-UHFFFAOYSA-N

物化性质

• 沸点：
  442.2±47.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  succinimido 3-benzoyl-2-methylpropionate 、 L-脯氨酸 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以10%的产率得到(2S)-1-[(2R)-4-(4-bromophenyl)-2-methyl-4-oxobutanoyl]pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Antihypertensive agents: angiotensin converting enzyme inhibitors. 1-[3-(Acylthio)-3-aroylpropionyl]-L-prolines

  摘要：

  A series of 1-[3-(acylthio)-3-aroylpropionyl]-L-proline derivatives was synthesized. A number of these compounds are potent angiotensin converting enzyme (ACE) inhibitors that lowered blood pressure in aorta-coarcted renal hypertensive rats. The most active derivatives are 1-[3(R)-(acetylthio) -3-substituted-benzoyl)-2(S)-methyl-propionyl]-L-prolines with an in vivo activity equivalent to SQ 14,225 (captopril). Structure-activity relationships are discussed. Changes in the configuration of the alpha-methyl group and the S-acetyl group affect the ACE activity. Coupling of 3-(substituted-benzoyl)-2-methylpropionic acids to L-proline via enol lactones is described.

  DOI：

  10.1021/jm00357a013
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 2-甲基-4-氧-4-苯基丁酸 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以65%的产率得到succinimido 3-benzoyl-2-methylpropionate
  参考文献：
  名称：

  Antihypertensive agents: angiotensin converting enzyme inhibitors. 1-[3-(Acylthio)-3-aroylpropionyl]-L-prolines

  摘要：

  A series of 1-[3-(acylthio)-3-aroylpropionyl]-L-proline derivatives was synthesized. A number of these compounds are potent angiotensin converting enzyme (ACE) inhibitors that lowered blood pressure in aorta-coarcted renal hypertensive rats. The most active derivatives are 1-[3(R)-(acetylthio) -3-substituted-benzoyl)-2(S)-methyl-propionyl]-L-prolines with an in vivo activity equivalent to SQ 14,225 (captopril). Structure-activity relationships are discussed. Changes in the configuration of the alpha-methyl group and the S-acetyl group affect the ACE activity. Coupling of 3-(substituted-benzoyl)-2-methylpropionic acids to L-proline via enol lactones is described.

  DOI：

  10.1021/jm00357a013

文献信息

• Substituted N-(.omega.-aroylpropionyl) derivatives of .alpha.-amino
  申请人：American Cyanamid Company

  公开号：US04435329A1

  公开（公告）日：1984-03-06

  Novel compounds are described having the formula ##STR1## wherein Z is ##STR2## R.sub.1 is hydrogen or a C.sub.1 -C.sub.4 lower alkyl; R.sub.2 is hydrogen, a C.sub.1 -C.sub.4 lower alkyl, hydroxy-R.sub.8 -, lower alkyl-R.sub.8 -, mercapto-R.sub.8 -, cyclohexyl, cyclopentyl, phenyl, phenyl-R.sub.8 -, indolyl-R.sub.8 -, carboxy-R.sub.8 -, amino-R.sub.8 - or carbamoyl-R.sub.8 -, wherein R.sub.8 - is a divalent C.sub.1 -C.sub.6 straight chain parafinic moiety; R.sub.3 is hydrogen or C.sub.1 -C.sub.4 lower alkyl; R.sub.4 is hydrogen, lower alkanoyl, benzoyl or phenyl-substituted-lower alkanoyl; R.sub.5 is hydrogen or a C.sub.1 -C.sub.4 lower alkyl; R.sub.1, R.sub.2 and R.sub.5 excluding tertiary butyl; ARYL is 1-naphthyl, 2-naphthyl, 4-chloro-1-naphthyl, 4-methoxy-1-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, 4-biphenylyl, 5-indanyl, 4-indanyl, phenyl, or substituted phenyl moieties having the formula ##STR3## wherein R.sub.6 is fluoro, chloro, bromo, trifluoromethyl, cyano, phenoxy, halophenoxy, phenylthio, halophenylthio, a C.sub.1 -C.sub.4 lower alkyl or a C.sub.1 -C.sub.4 lower alkoxy, and R.sub.7 is chloro, fluoro, bromo, a C.sub.1 -C.sub.4 lower alkyl or a C.sub.1 -C.sub.4 lower alkoxy; and where m is an integer of zero, one or two; including individual optically active isomers; racemic mixtures thereof; non-toxic pharmacologically-acceptable salts of the foregoing; and mixtures of the foregoing. Processes of preparing such compounds are also described. Such compounds are useful in ameliorating hypertension in mammals.

  描述了具有以下公式的新化合物##STR1##其中Z为##STR2##R.sub.1为氢或C.sub.1-C.sub.4较低的烷基; R.sub.2为氢，C.sub.1-C.sub.4较低的烷基，羟基-R.sub.8-，较低的烷基-R.sub.8-，巯基-R.sub.8-，环己基，环戊基，苯基，苯基-R.sub.8-，吲哚基-R.sub.8-，羧基-R.sub.8-，氨基-R.sub.8-或氨基-R.sub.8-，其中R.sub.8-为双价的C.sub.1-C.sub.6直链烷烃基; R.sub.3为氢或C.sub.1-C.sub.4较低的烷基; R.sub.4为氢，较低的烷酰基，苯甲酰基或苯基取代的较低的烷酰基; R.sub.5为氢或C.sub.1-C.sub.4较低的烷基; R.sub.1，R.sub.2和R.sub.5不包括叔丁基; ARYL为1-萘基，2-萘基，4-氯-1-萘基，4-甲氧基-1-萘基，5,6,7,8-四氢-1-萘基，5,6,7,8-四氢-2-萘基，4-联苯基，5-吲哚基，4-吲哚基，苯基，或取代的苯基基团，具有以下公式##STR3##其中R.sub.6为氟，氯，溴，三氟甲基，氰基，苯氧基，卤苯氧基，苯硫基，卤苯硫基，C.sub.1-C.sub.4较低的烷基或C.sub.1-C.sub.4较低的烷氧基，而R.sub.7为氯，氟，溴，C.sub.1-C.sub.4较低的烷基或C.sub.1-C.sub.4较低的烷氧基; m为零，一或二的整数; 包括各个光学活性异构体; 其外消旋混合物; 上述化合物的无毒的药理学上可接受的盐; 和上述混合物。还描述了制备这种化合物的方法。这些化合物在改善哺乳动物的高血压方面是有用的。
• US4374249A
  申请人：——

  公开号：US4374249A

  公开（公告）日：1983-02-15