N-tetrahydrofurfurylglycine tert-butyl ester | 65042-16-2

• 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-tetrahydrofurfurylglycine tert-butyl ester
• 英文别名: tert-butyl 2-(oxolan-2-ylmethylamino)acetate
• CAS: 65042-16-2
• 化学式: C₁₁H₂₁NO₃
• mdl: MFCD12148623
• 分子量: 215.293
• InChiKey: IRDYMHHSOVBXCN-UHFFFAOYSA-N

物化性质

• 沸点：
  288.6±15.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.909
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tetrahydrofurfurylglycine tert-butyl ester 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.5h， 生成 [(3-Acetylsulfanyl-2-methyl-propionyl)-(tetrahydro-furan-2-ylmethyl)-amino]-acetic acid
  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
• 作为产物：
  描述：

  2-四氢糠胺 、 溴乙酸叔丁酯 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 N-tetrahydrofurfurylglycine 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

• N.sup.2 -Arylsulfonyl-L-argininamides and the pharmaceutically
  申请人：Mitsubishi Chemical Industries, Limited

  公开号：US04140681A1

  公开（公告）日：1979-02-20

  N.sup.2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis in mammals.

  N.2-芳基磺酰-L-精氨酰胺及其药学上可接受的盐被发现作为药物代理在哺乳动物中抑制和抑制血栓形成是有效的。
• Antihypertensive amides
  申请人：USV Pharmaceutical Corporation

  公开号：US04256761A1

  公开（公告）日：1981-03-17

  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 alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycyclo-alkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, dialkylamino-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, or fused heteroaryl-cycloalkyl-alkyl, Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, 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, hyroxyalkyl, 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 non-toxic, pharmaceutically acceptable alkali metal, alkaline earth metal, and amine salts.

  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均为氢、烷基、烯基、炔基、苯基烷基或环烷基，n为0至4的整数，M为烯基、炔基、环烷基、环烷基烷基、多环烷基、多环烷基烷基、芳基、芳基烷基、杂芳基、杂芳基烷基、杂环烷基、杂环烷基烷基、烷氧基烷基、烷硫基烷基、烷基氨基烷基、二烷基氨基烷基、融合芳基环烷基、融合芳基环烷基烷基、融合杂芳基环烷基或融合杂芳基环烷基烷基，Y为羟基、烷氧基、氨基或取代氨基、氨基酰基、芳氧基、氨基烷氧基或羟基烷氧基，R.sub.7为氢、脂肪酰基、羧基脂肪酰基、羟基脂肪酰基、氨基-脂肪酰基、氰基、胍基、羧烷氧基或##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；当Y为羟基时，它们为非毒性、药学上可接受的碱金属、碱土金属和胺盐。
• N.sup.2 -naphthalenesulfonyl-L-argininamides and the pharmaceutically
  申请人：Mitsubishi Chemical Industries Ltd.

  公开号：US04036955A1

  公开（公告）日：1977-07-19

  N.sup.2 -naphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis.

  N.sup.2 -萘磺基-L-精氨酰胺及其药学上可接受的盐已被发现作为药物代理，可有效抑制和抑制血栓形成。
• 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。