N-(3-acetylthio-2-methylpropanoyl)-N-furfurylglycine tert-butyl ester | 78773-81-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(3-acetylthio-2-methylpropanoyl)-N-furfurylglycine tert-butyl ester
• 英文别名: tert-butyl 2-[(3-acetylsulfanyl-2-methylpropanoyl)-(furan-2-ylmethyl)amino]acetate
• CAS: 78773-81-6
• 化学式: C₁₇H₂₅NO₅S
• 分子量: 355.455
• InChiKey: XTOUFMZFRCJYIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(3-acetylthio-2-methylpropanoyl)-N-furfurylglycine tert-butyl ester 在 羟基甲酸酯 、 乙酸乙酯 、 氯仿 、 水 、 magnesium sulfate 、 crude product 、 Ethyl acetate hexane acetic acid 作用下， 以 苯甲醚 、 三氟乙酸 为溶剂， 反应 2.0h， 以ethyl acetate/n-hexane/acetic acid (40:60:1) to give pure product as a colorless oil (5.5 g, 44.7%)的产率得到N-(3-acetylthio-2-methylpropanoyl)-N-furfurylglycine
  参考文献：
  名称：

  Antihypertensive amides

  摘要：

  结构式为 ##STR1## 的化合物，其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5和R.sub.6分别为氢，烷基，烯基，炔基，苯基-烷基或环烷基，n为0至4的整数，M为杂环或杂环烷基，Y为羟基，烷氧基，氨基或取代氨基，氨基-烷酰基，芳氧基，氨基烷氧基或羟基烷氧基，R.sub.7为氢，烷酰基，羧基烷酰基，羟基烷酰基，氨基-烷酰基，氰基，酰胺基，羧基烷氧基，ZS或 ##STR2## 其中Z为氢，烷基，羟基烷基，氨基烷基或基团 ##STR3## 其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5，R.sub.6，n，M和Y如上所述；其中Y为羟基的无毒，药学上可接受的碱金属，碱土金属和胺盐。

  公开号：

  US04507312A1
• 作为产物：
  描述：

  2-呋喃甲胺 在 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 16.0h， 生成 N-(3-acetylthio-2-methylpropanoyl)-N-furfurylglycine tert-butyl ester
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. New orally active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives

  摘要：

  A variety of N-substituted (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives was synthesized and their ability in inhibiting the activity of angiotensin-converting enzyme (ACE) was examined in vitro and in vivo. The acylthio derivatives prepared are assumed to act as prodrugs since they are much less active than the corresponding free SH compounds in vitro and can be expected to act in vivo only after conversion to the free sulfhydryl compounds. A number of these compounds are potent ACE inhibitors that lowered blood pressure in Na-deficient, conscious spontaneously hypertensive rats (SHR), a high renin model. One of the most active members of the series was (S)-N-cyclopentyl-N-[3-[(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1 -oxopropyl]glycine (REV 3659-(S), pivopril). Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00379a013

文献信息

• Antihypertensive N-benzimidazolyl- and N-imidazolyl-amino acid
  申请人：USV Pharmaceutical Corp.

  公开号：US04565825A1

  公开（公告）日：1986-01-21

  Compounds of the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl, n is an integer from 0 to 4 inclusive, M is heterocyclic or heterocyclic alkyl, Y is hydroxy, alkoxy, amino, or substituted amino, amino-alkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, and R.sub.7 is hydrogen, alkanoyl, carboxylalkanoyl, hydroxyalkanoyl, amino-alkanoyl, cyano, amidino, carbalkoxy, ZS, or ##STR2## wherein Z is hydrogen, alkyl, hydroxyalkyl, aminoalkyl or the radical ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, n, M and Y are as described above; and where Y is hydroxy their nontoxic, pharmaceutically acceptable alkali metal, alkaline earth metal, and amine salts. The compounds of the invention exhibit antihypertensive and angiotensin converting enzyme inhibitory activity.

  结构为##STR1##的化合物，其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5和R.sub.6是氢，烷基，烯基，炔基，苯基-烷基或环烷基，n是0到4的整数，M是杂环或杂环烷基，Y是羟基，烷氧基，氨基或取代氨基，氨基-烷酰基，芳氧基，氨基烷氧基，或羟基烷氧基，R.sub.7是氢，烷酰基，羧酸烷酰基，羟基烷酰基，氨基-烷酰基，氰基，酰胺基，碳酸烷氧基，ZS或##STR2##其中Z是氢，烷基，羟基烷基，氨基烷基或基团##STR3##其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5，R.sub.6，n，M和Y如上所述；并且当Y是羟基时，它们是无毒的，药学上可接受的碱金属，碱土金属和胺盐。该发明的化合物具有降压和血管紧张素转换酶抑制活性。
• Blood pressure lowering n-pyridyl-, n-quinolyl-, and n-piperdyl-n-acyl
  申请人：USV Pharmaceutical Corp.

  公开号：US04588734A1

  公开（公告）日：1986-05-13

  Compounds of the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl, n is an integer from 0 to 4 inclusive, M is heterocyclic or heterocyclic alkyl, Y is hydroxy, alkoxy, amino, or substituted amino, amino-alkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, and R.sub.7 is hydrogen, alkanoyl, carboxylalkanoyl, hydroxyalkanoyl, amino-alkanoyl, cyano, amidino, carbalkoxy, ZS, or ##STR2## wherein Z is hydrogen, alkyl, hydroxyalkyl, aminoalkyl or the radical ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, n, M and Y are as described above; and where Y is hydroxy their nontoxic, pharmaceutically acceptable alkali metal, alkaline earth metal, and amine salts. These compounds possess antihypertensive and angiotensin converting enzyme inhibitory activity.

  结构式为：##STR1## 其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5和R.sub.6是氢，烷基，烯基，炔基，苯基-烷基或环烷基，n是0至4的整数，M是杂环或杂环烷基，Y是羟基，烷氧基，氨基或取代氨基，氨基-烷酰基，芳氧基，氨基烷氧基或羟基烷氧基，R.sub.7是氢，烷酰基，羧酸烷酰基，羟基烷酰基，氨基-烷酰基，氰基，酰胺基，碳酰氧基，ZS或##STR2## 其中Z是氢，烷基，羟基烷基，氨基烷基或基团##STR3## 其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5，R.sub.6，n，M和Y如上所述；如果Y是羟基，则它们是无毒的、药学上可接受的碱金属、碱土金属和胺盐。这些化合物具有降压和血管紧张素转化酶抑制活性。
• US4256761A
  申请人：——

  公开号：US4256761A

  公开（公告）日：1981-03-17
• US4304771A
  申请人：——

  公开号：US4304771A

  公开（公告）日：1981-12-08
• US4548928A
  申请人：——

  公开号：US4548928A

  公开（公告）日：1985-10-22