(S,S)-2,4-dibenzylglutaric acid | 105182-19-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S,S)-2,4-dibenzylglutaric acid
• 英文别名: (2S,4S)-2,4-dibenzylpentanedioic acid
• CAS: 105182-19-2
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: MOARNHYQPSZZJV-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,S)-2,4-dibenzylglutaric acid 在 吡啶 、 乙酸酐 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 N-<(S,S)-2,4-dibenzyl-4-carboxybutyryl>-(S)-leucine
  参考文献：
  名称：

  Enkephalinase inhibitors. 1. 2,4-Dibenzylglutaric acid derivatives

  摘要：

  The synthesis of two new series of dicarboxylic acid dipeptides and two sulfhydryl-containing inhibitors are described. The in vitro enkephalinase inhibition data and some in vivo analgesic data are presented for these compounds. For the dibenzylglutaric acid series structure-activity relationships and in vivo analgesic activity are discussed. The reverse amides, i.e., 4-amino-2,4-dibenzylbutyric acid derivatives, are also discussed. Two sulfhydryl-containing inhibitors showed good in vivo potency in the mouse jump-latency hot-plate test after peripheral administration at moderate low doses.

  DOI：

  10.1021/jm00132a005
• 作为产物：
  描述：

  (S,S)-2,4-dibenzylglutaric anhydride 在 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 (S,S)-2,4-dibenzylglutaric acid
  参考文献：
  名称：

  Enkephalinase inhibitors. 1. 2,4-Dibenzylglutaric acid derivatives

  摘要：

  The synthesis of two new series of dicarboxylic acid dipeptides and two sulfhydryl-containing inhibitors are described. The in vitro enkephalinase inhibition data and some in vivo analgesic data are presented for these compounds. For the dibenzylglutaric acid series structure-activity relationships and in vivo analgesic activity are discussed. The reverse amides, i.e., 4-amino-2,4-dibenzylbutyric acid derivatives, are also discussed. Two sulfhydryl-containing inhibitors showed good in vivo potency in the mouse jump-latency hot-plate test after peripheral administration at moderate low doses.

  DOI：

  10.1021/jm00132a005

文献信息

• Certain N-substituted butyramide derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US05021430A1

  公开（公告）日：1991-06-04

  Disclosed are compound of the formula ##STR1## wherein X and Y independently represent hydroxymethyl; cyano; carboxy; functionally modified carboxy selected from esterified carboxy, carbamoyl, and N-substituted carbamoyl; 5-tetrazolyl; 2-oxazolyl, 4,5-dihydro-2-oxazolyl, or each said grouping substituted by lower alkyl; R and R.sub.o independently represent lower alkyl, (C.sub.3 -C.sub.7)-cycloalkyl-lower alkyl, or aryl-lower alkyl; A represents methylene; or A represents methylene substituted by lower alkyl, by lower alkylthio-lower alkyl, by aryl-lower alkylthio-lower alkyl, by arylthio-lower alkyl, by hydroxy-lower alkyl, by acyloxy-lower alkyl, by lower alkoxy-lower alkyl, by aryl-lower alkyloxy-lower alkyl, by aryloxy-lower alkyl, by amino-lower alkyl, by acylamino-lower alkyl, by guanidino-lower alkyl, by (C.sub.3 -C.sub.7)-cycloalkyl, by (C.sub.3 -C.sub.7)-cycloalkyl-lower alkyl, by aryl or aryl-lower alkyl; pharmaceutically acceptable ester and amide derivatives of any said compounds having a free carboxy group; pharmaceutically acceptable salts; methods for synthesis; pharmaceutical compositions thereof; and use thereof as endopeptidase inhibitors.

  本发明揭示了公式##STR1##的化合物，其中X和Y独立地表示羟甲基；氰基；羧基；功能修饰的羧基，所述功能修饰的羧基被选择为酯化羧基，氨基甲酰基或N-取代的氨基甲酰基；5-四唑基；2-噁唑基，4,5-二氢-2-噁唑基，或所述各个基团被较低的烷基取代；R和R.sub.o独立地表示较低的烷基，（C.sub.3-C.sub.7）-环烷基-较低的烷基，或芳基-较低的烷基；A表示亚甲基；或A表示被较低的烷基，被较低的烷基硫基-较低的烷基，被芳基-较低的烷基硫基-较低的烷基，被芳基硫基-较低的烷基，被羟基-较低的烷基，被酰氧基-较低的烷基，被较低的烷氧基-较低的烷基，被芳基-较低的烷氧基-较低的烷基，被芳氧基-较低的烷基，被氨基-较低的烷基，被酰胺基-较低的烷基，被鸟氨酸基-较低的烷基，被（C.sub.3-C.sub.7）-环烷基，被（C.sub.3-C.sub.7）-环烷基-较低的烷基，被芳基或芳基-较低的烷基取代的亚甲基；任何具有自由羧基的所述化合物的药学上可接受的酯和酰胺衍生物；药学上可接受的盐；合成方法；其制药组合物；以及其作为内肽酶抑制剂的用途。
• Certain n-substituted butyramide derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US05166212A1

  公开（公告）日：1992-11-24

  Disclosed are compound of the formula ##STR1## wherein X and Y independently represent hydroxymethyl; cyano; carboxy; functionally modified carboxy selected from esterified carboxy, carbamoyl, and N-substituted carbamoyl; 5-tetrazolyl; 2-oxazolyl, 4,5-dihydro-2-oxazolyl, or each said grouping substituted by lower alkyl; R and R.sub.o independently represent lower alkyl, (C.sub.3 -C.sub.7)-cycloalkyl-lower alkyl, or aryl-lower alkyl; A represents methylene; or A represents methylene substituted by lower alkyl, by lower alkylthio-lower alkyl, by aryl-lower alkylthio-lower alkyl, by arylthio-lower alkyl, by hydroxy-lower alkyl, by acyloxy-lower alkyl, by lower alkoxy-lower alkyl, by alkyloxy-lower alkyl, by aryloxy-lower alkyl, by amino-lower alkyl by acylamino-lower alkyl, by guanidino-lower amino-lower alkyl, by (C.sub.3 -C.sub.7)-cycloalkyl, by (C.sub.3 -C.sub.7)-cycloalkyl-lower alkyl, by aryl or aryl-lower alkyl; pharmaceutically acceptable ester and amide derivatives of any said compounds having a free carboxy group; pharmaceutically acceptable salts; methods for synthesis; pharmaceutical compositions thereof; and use thereof as endopentidase inhibitors.

  本发明涉及一种化合物，其化学式为##STR1##其中X和Y独立地表示羟甲基;氰基;羧基;功能修饰的羧基，所述功能修饰的羧基选自酯化羧基，氨基甲酰基和N-取代氨基甲酰基; 5-四唑基; 2-噁唑基，4,5-二氢-2-噁唑基，或每个所述基团均被低烷基取代; R和R.sub.o独立地表示低烷基，(C.sub.3-C.sub.7)-环烷基-低烷基或芳基-低烷基; A表示亚甲基; 或A表示被低烷基，被低烷硫基-低烷基，被芳基-低烷硫基-低烷基，被芳基硫基-低烷基，羟基-低烷基，酰氧基-低烷基，低烷氧基-低烷基，烷氧基-低烷基，芳氧基-低烷基，氨基-低烷基，酰胺基-低烷基，鸟氨酸基-低氨基-低烷基，(C.sub.3-C.sub.7)-环烷基，(C.sub.3-C.sub.7)-环烷基-低烷基，芳基或芳基-低烷基取代的亚甲基取代; 具有自由羧基的任何所述化合物的药学上可接受的酯和酰胺衍生物; 药学上可接受的盐; 合成方法; 其药物组成物; 以及作为内肽酶抑制剂的用途。
• KSANDER, GARY M.;DIEFENBACHER, CLIVE G.;YUAN, ANDREW M.;CLARK, F.;SAKANE,+, J. MED. CHEM., 32,(1989) N2, C. 2519-2526
  作者：KSANDER, GARY M.、DIEFENBACHER, CLIVE G.、YUAN, ANDREW M.、CLARK, F.、SAKANE,+

  DOI：——

  日期：——
• N-SUBSTITUTED BUTYRAMIDE DERIVATIVES
  申请人：CIBA-GEIGY AG

  公开号：EP0185079A1

  公开（公告）日：1986-06-25
• US4939261A
  申请人：——

  公开号：US4939261A

  公开（公告）日：1990-07-03