N-(3-mercapto-2-methylpropanoyl)-N-cyclopentyl glycine | 78773-73-6

• 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-mercapto-2-methylpropanoyl)-N-cyclopentyl glycine
• 英文别名: N-cyclopentyl-N-(3-mercapto-2-methylpropanoyl)glycine；(S)-[Cyclopentyl-(3-mercapto-2-methyl-propionyl)-amino]-acetic acid；2-[cyclopentyl-(2-methyl-3-sulfanylpropanoyl)amino]acetic acid
• CAS: 78773-73-6
• 化学式: C₁₁H₁₉NO₃S
• 分子量: 245.343
• InChiKey: ALRGMGVUAWHELZ-UHFFFAOYSA-N

物化性质

• 沸点：
  431.8±38.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-mercapto-2-methylpropanoyl)-N-cyclopentyl glycine 在 2,2'-二硫二吡啶 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以27%的产率得到4-Cyclopentyl-6,7-dihydro-6-methyl-1,4-thiazepin-2,5-(3H,4H)-dione
  参考文献：
  名称：

  血管紧张素转换酶抑制剂：具有降压活性的新型口服活性1,4-噻嗪-2,5-二酮，1,4-噻嗪-2,5-二酮和1,4-苯并噻嗪-2,5-二酮。

  摘要：

  一系列1,4-噻嗪-2,5-二酮，1,4-噻嗪-2,5-二酮和1,4-苯并硫氮杂-2,5-二酮的制备及其抑菌活性检查了体内和体外的血管紧张素转换酶（ACE）。这些化合物被假定为前药，因为它们在与大鼠血浆一起温育或经0.1 N HCl水溶液或磷酸盐缓冲液（pH 7.4）处理时会发生快速的开环反应，以产生相应的无生物活性的SH化合物。噻嗪类23-25和30在向大鼠口服给药时是ACE的有效抑制剂，其效力与卡托普利（1）相当。大鼠中最活跃的噻嗪类化合物分别为42和45。在所研究的苯并硫氮平中，22a在有意识的正常血压大鼠中抑制ACE的活性最高，ID50 = 0.15 mg / kg，po。

  DOI：

  10.1021/jm00155a032
• 作为产物：
  描述：

  N-环戊基甘氨酸乙酯 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-(3-mercapto-2-methylpropanoyl)-N-cyclopentyl glycine
  参考文献：
  名称：

  血管紧张素转化酶抑制剂：N-取代的单环和双环氨基酸衍生物。

  摘要：

  N-（3-巯基丙酰基）-N-芳基甘氨酸（14a-x），-N-芳基丙氨酸（15a，b），-N-环烷基甘氨酸（16a-k）和-1,2,3,4-的合成描述了四氢异喹啉-3-羧酸（17a-d），-1,2,3,4-四氢喹啉-2-羧酸（18a-f）和-二氢吲哚-2-羧酸（19a-k）。报道了每种化合物对血管紧张素转化酶（ACE）的体外抑制作用，并讨论了每个系列的结构-活性关系。讨论了ACE的体内抑制作用和各系列代表性化合物的降压作用。最有效的化合物19d的体外ACE IC50为2.6 X 10（-9）M，并且以10 mg / kg po的剂量在85 mm的自发性高血压大鼠中降低了血压。

  DOI：

  10.1021/jm00363a011

文献信息

• 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.

  结构化合物：##STR1## 其中 R.sub.1、R.sub.2、R.sub.3、R.sub.4、R.sub.5 和 R.sub.6 为氢、烷基、烯基、炔基、苯基-烷基或环烷基，n 为0至4之间的整数，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、杂环芳基、杂环芳基-烷基、杂环烷基、杂环烷基-烷基、烷氧基烷基、烷基硫基烷基、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、融合杂环芳基-环烷基或融合杂环芳基-环烷基-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、羧酰烷酰基、羟基烷酰基、氨基-烷酰基、氰基、胺基、羧酯基、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；当 Y 为羟基时，它们的非毒性、药学上可接受的碱金属、碱土金属和胺盐。
• Antihypertensive compounds
  申请人：USV Pharmaceutical Corporation

  公开号：US04507316A1

  公开（公告）日：1985-03-26

  Provided are antihypertensive compounds of the formula ##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, and may be the same or different, m is an integer from 0 to 2 inclusive, n is an integer from 0 to 4 inclusive, M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl. Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, and R.sub.7 is alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclic, ##STR2## wherein R is hydrogen, alkyl, or aryl, and where Y is hydroxy, their pharmaceutically acceptable, nontoxic alkali metal, alkaline earth metal, and amine salts.

  提供了以下化学式的降压化合物：##STR1## 其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5和R.sub.6为氢，烷基，烯基，炔基，苯基-烷基或环烷基，可以相同或不同，m是0到2的整数，n是0到4的整数，M是烯基，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，杂环芳基，杂环芳基-烷基，杂环环烷基，杂环环烷基-烷基，融合芳基-环烷基，融合芳基-环烷基-烷基，融合杂环芳基-环烷基，融合杂环芳基-环烷基-烷基，烷氧基烷基，烷硫基烷基，烷基氨基烷基或二烷基氨基烷基。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是烷基，芳基，芳基-烷基，环烷基，环烷基-烷基，杂环，##STR2##其中R为氢，烷基或芳基，Y为羟基，它们的药学上可接受，无毒的碱金属，碱土金属和胺盐。
• Antihypertensive lactams
  申请人：——

  公开号：US04766210A1

  公开（公告）日：1988-08-23

  Antihypertensive compounds of the structure ##STR1## wherein: n is an integer from 0 to 2 inclusive, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 are independently hydrogen, alkyl having from 1 to 6 carbon atoms, alkenyl having from 2 to 6 carbon atoms, alkynyl having from 2 to 6 carbon atoms, cycloalkyl having from 3 to 16 carbon atoms, phenyl, benzyl, tolyl, naphthyl, phenethyl, indanyl, tetrahydronaphthyl, decahydronaphthyl, pyridyl, quinolyl, pyrrolidyl, pyrrolyl, morpholinyl, thiomorpholinyl, furyl, furfuryl, tetrahydrofurfuryl, benzimidazole, thienyl, imidolyl, or tetrahydroindolyl, and where the R.sub.1 to R.sub.7 groups are alkyl, said groups carrying a substituent selected from hydroxy, alkoxy, amino, carboxy, or carbalkoxy, the alkyl group in alkoxy and carbalkoxy having from 1 to 6 carbon atoms, or R.sub.2 taken together with R.sub.3 and the carbons to which they are attached is tetrahydronapthyl or phenyl, and when phenyl R.sub.1 and R.sub.4 are absent, or R.sub.6 and R.sub.7 taken together with the carbon to which R.sub.6 is attached and the nitrogen to which R.sub.7 is attached form a heterocycle selected from pyrrolidyl, thiazolidine, tetrahydro-isoquinoline, thiomorpholine, or 2,2,5,5-tetramethylthiazolidinie, and Y is .dbd.O, .dbd.S, .dbd.NR.sub.1, .dbd.NOR.sub.1 or .dbd.N--NH.sub.2, R.sub.1 being the same as defined above.

  结构式为##STR1##的降压化合物，其中：n是0至2的整数，R.sub.1、R.sub.2、R.sub.3、R.sub.4、R.sub.5、R.sub.6和R.sub.7独立地为氢、碳数为1到6的烷基、碳数为2到6的烯基、碳数为2到6的炔基、碳数为3到16的环烷基、苯基、苄基、甲苯基、萘基、苯乙基、茚基、四氢萘基、十氢萘基、吡啶基、喹啉基、吡咯烷基、吡咯基、吗啉基、硫代吗啉基、呋喃基、呋喃甲基、四氢呋喃基、苯并咪唑基、噻吩基、咪唑基或四氢吲哚基，其中R.sub.1至R.sub.7基为烷基，所述基带有从羟基、烷氧基、氨基、羧基或羧烷氧基中选择的取代基，烷氧基和羧烷氧基中的烷基含有1到6个碳原子，或R.sub.2与R.sub.3及它们所连接的碳一起取代为四氢萘基或苯基，当苯基R.sub.1和R.sub.4不存在时，或R.sub.6和R.sub.7与R.sub.6所连接的碳和R.sub.7所连接的氮一起形成从吡咯基、噻唑环、四氢异喹啉、硫代吗啉或2,2,5,5-四甲基噻唑环中选择的杂环，且Y为.dbd.O、.dbd.S、.dbd.NR.sub.1、.dbd.NOR.sub.1或.dbd.N--NH.sub.2，其中R.sub.1与上述定义相同。
• Antihypertensive amide compounds
  申请人：Rorer Pharmaceutical Corporation

  公开号：US04839367A1

  公开（公告）日：1989-06-13

  Provided are antihypertensive compounds of the formula ##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, and may be the same or different, m is an integer from 0 to 2 inclusive, n is an integer from 0 to 4 inclusive, M is alkyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl, Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, and R.sub.7 is alkyl, aryl, aralkyl, cycloalkyl, cycloalkyl-alkyl, heterocyclic, --CO--SR, --CS--SR, ##STR2## CH.sub.2 CO.sub.R, --CHM--CO.sub.2 R, --CH.sub.2 --CO--SR, --CN, ##STR3## --CO--NH--CH.sub.2 CO.sub.2 R, ##STR4## or --CO--CO.sub.2 CO.sub.2 R, wherein R is hydrogen, alkyl, or aryl, and where Y is hydroxy, their pharmaceutically acceptable, nontoxic alkali metal, alkaline earth metal, and amine salts.

  提供的是抗高血压化合物的公式，其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5和R.sub.6为氢，烷基，烯基，炔基，苯基-烷基或环烷基，可以相同或不同，m为0到2的整数，n为0到4的整数，M为烷基，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，杂环芳基，杂环芳基-烷基，杂环环烷基，杂环环烷基-烷基，融合芳基-环烷基，融合芳基-环烷基-烷基，融合杂环芳基-环烷基，融合杂环芳基-环烷基-烷基，烷氧基烷基，烷硫基烷基，烷基氨基烷基或二烷基氨基烷基，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为烷基，芳基，芳基-烷基，环烷基，环烷基-烷基，杂环，--CO--SR，--CS--SR，##STR2## CH.sub.2 CO.sub.R，--CHM--CO.sub.2 R，--CH.sub.2 --CO--SR，--CN，##STR3## --CO--NH--CH.sub.2 CO.sub.2 R，##STR4## 或--CO--CO.sub.2 CO.sub.2 R，其中R为氢，烷基或芳基，且当Y为羟基时，它们的药学上可接受，无毒的碱金属，碱土金属和胺盐。
• Antihypertensive 1,4-thiazepine-ones, 1,4-thiazonine-ones, and method of
  申请人：USV Pharmaceutical Corporation

  公开号：US04287203A1

  公开（公告）日：1981-09-01

  Antihypertensive compounds of the structure ##STR1## wherein: n is an integer from 0 to 2 inclusive, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 are independently hydrogen, alkyl having from 1 to 6 carbon atoms, alkenyl having from 2 to 6 carbon atoms, alkynyl having from 2 to 6 carbon atoms, cycloalkyl having from 3 to 16 carbon atoms, phenyl, benzyl, tolyl, naphthyl, phenethyl, indanyl, tetrahydronaphthyl, decanydronaphthyl, pyridyl, quinolyl, pyrrolidyl, pyrrolyl, morpholinyl, thiomorpholinyl, furyl, furfuryl, tetrahydrofurfuryl, benzimidazole, thienyl, imidolyl, or tetrahydroindolyl, and where the R.sub.1 to R.sub.7 groups are alkyl, said groups carrying a substituent selected from hydroxy, alkoxy, amino, carboxy, or carbalkoxy, the alkyl group in alkoxy and carbalkoxy having from 1 to 6 carbon atoms, or R.sub.2 taken together with R.sub.3 and the carbons to which they are attached is tetrahydronaphthyl or phenyl, and when phenyl R.sub.1 and R.sub.4 are absent, or R.sub.6 and R.sub.7 taken together with the carbon to which R.sub.6 is attached and the nitrogen to which R.sub.7 is attached form a heterocycle selected from pyrrolidyl, thiazolidine, tetrahydro-isoquinoline, thiomorpholine, or 2,2,5,5-tetramethylthiazolidinie, and Y is .dbd.O, .dbd.S, .dbd.NR.sub.1, .dbd.NOR.sub.1 or .dbd.N--NH.sub.2, R.sub.1 being the same as defined above.

  结构式 ##STR1## 的降压化合物，其中：n是0到2之间的整数，R.sub.1、R.sub.2、R.sub.3、R.sub.4、R.sub.5、R.sub.6和R.sub.7独立地为氢、具有1到6个碳原子的烷基、具有2到6个碳原子的烯基、具有2到6个碳原子的炔基、具有3到16个碳原子的环烷基、苯基、苄基、甲苯基、萘基、苯乙基、吲哚基、四氢萘基、十氢萘基、吡啶基、喹啉基、吡咯烷基、吡咯基、吗啉基、硫代吗啉基、呋喃基、呋喃甲基、四氢呋喃基、苯并咪唑基、噻吩基、咪唑基或四氢吲哚基，其中R.sub.1到R.sub.7基团是烷基，其携带从羟基、烷氧基、氨基、羧基或羧基烷氧基中选择的取代基，烷氧基和羧基烷氧基中的烷基具有1到6个碳原子，或R.sub.2与R.sub.3及它们所连接的碳原子一起取代四氢萘基或苯基，当苯基R.sub.1和R.sub.4不存在时，或者当R.sub.6和R.sub.7与R.sub.6连接的碳原子和R.sub.7连接的氮原子一起形成从吡咯烷基、噻唑烷、四氢异喹啉、硫代吗啉或2,2,5,5-四甲基噻唑啉中选择的杂环时，Y为.dbd.O、.dbd.S、.dbd.NR.sub.1、.dbd.NOR.sub.1或.dbd.N--NH.sub.2，其中R.sub.1如上所定义。