N-环戊基甘氨酸叔丁酯 | 78773-69-0

• 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
• 中文名称: N-环戊基甘氨酸叔丁酯
• 英文名称: tert-butyl N-(cyclopentyl)glycinate
• 英文别名: N-cyclopentylglycine tert-butyl ester；Tert-butyl 2-(cyclopentylamino)acetate
• CAS: 78773-69-0
• 化学式: C₁₁H₂₁NO₂
• mdl: MFCD12148674
• 分子量: 199.293
• InChiKey: AJWUSVUOAIUDGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  266.7±23.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.909
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-环戊基甘氨酸叔丁酯 在 氨 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 16.5h， 生成 N-(3-mercapto-2-methyl propanoyl)-N-cyclopentyl glycine-t-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
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 环戊胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到N-环戊基甘氨酸叔丁酯
  参考文献：
  名称：

  Antihypertensive amides

  摘要：

  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。

  公开号：

  US04256761A1

文献信息

• Fluoro-amide derivatives
  申请人：ICI Americas Inc.

  公开号：US05270301A1

  公开（公告）日：1993-12-14

  The present invention relates to certain fluoro-amide derivatives, as described herein, which are human leukocyte elastase (HLE) inhibitors making them useful whenever such inhibition is desired, such as for research tools in pharmacological, diagnostic and related studies and in the treatment of diseases in mammals in which HLE is implicated, including treatment of tissue degenerative diseases such as pulmonary emphysema. The invention also includes intermediates useful in the synthesis of these fluoro-amide derivatives, processes for preparing them, pharmaceutical compositions containing such peptide derivatives and methods for their use.

  本发明涉及某些氟酰胺衍生物，如下所述，这些衍生物是人类白细胞弹性蛋白酶（HLE）抑制剂，使它们在需要此类抑制时具有用途，例如作为药理学、诊断和相关研究中的研究工具，以及在HLE参与的哺乳动物疾病治疗中，包括治疗肺气肿等组织退行性疾病。该发明还包括在合成这些氟酰胺衍生物过程中有用的中间体、制备它们的方法、含有这种肽衍生物的药物组合物以及其使用方法。
• Design, synthesis, and biological evaluation of 2,6,7-substituted pyrrolo[2,3-d]pyrimidines as cyclin dependent kinase inhibitor in pancreatic cancer cells
  作者：Xingpeng Shi、Yanni Quan、Yixuan Wang、Ying Wang、Yanping Li

  DOI：10.1016/j.bmcl.2020.127725

  日期：2021.2

  highly malignant tumor, and more effective treatment is urgently needed to lengthen the life of patients. In this paper a class of new 2,6,7-substituted pyrrolo[2,3-d]pyrimidine derivatives of CDK 4/6 inhibitor ribociclib (1) was designed and synthesized to investigate their effect on the proliferation of pancreatic cancer cells. The structure–activity relationship (SAR) of synthetic compounds was

  胰腺癌是高度恶性的肿瘤，迫切需要更有效的治疗以延长患者的寿命。本文设计并合成了一类新的CDK 4/6抑制剂ribociclib（1）的2,6,7-取代的吡咯并[2,3- d ]嘧啶衍生物，以研究其对胰腺癌细胞增殖的影响。基于合成化合物的体外抗增殖活性和CDK4抑制活性，分析了它们的结构活性关系（SAR）。一系列6-苯胺基羰基取代的吡咯并[2,3的d ]嘧啶衍生物（25，41 - 48）显示在MTT测定针对两种增殖癌细胞系（MIA PACA-2和BxPC-3）的显著增加的效力尽管它们的CDK4抑制活性在一个变化范围内相比均降低1。在人激酶谱分析中，最有效的化合物41被鉴定为高度选择性和有效的CDK 4/6抑制剂，它还具有良好的体外药代动力学特性，可用于进一步的体内评估。同时，有41位患者表现出与mTOR抑制剂联合治疗胰腺癌的潜力。或者，将磺酰胺片段引入吡咯并[2,3- d]嘧啶为未来优化提供新的CDK9抑制剂提供了线索。
• 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。
• Peptide derivatives
  申请人：Zeneca Inc.

  公开号：US05723442A1

  公开（公告）日：1998-03-03

  The present invention relates to certain peptide derivatives, as described herein, which are human leukocyte elastase (HLE) inhibitors making them useful whenever such inhibition is desired, such as for research tools in pharmacological, diagnostic and related studies and in the treatment of diseases in mammals in which HLE is implicated, including treatment of tissue degenerative diseases such as pulmonary emphysema. The invention also includes intermediates useful in the synthesis of these peptide derivatives, processes for preparing them, pharmaceutical compositions containing such peptide derivatives and methods for their use.

  本发明涉及某些肽衍生物，如下所述，这些肽衍生物是人类白细胞弹性蛋白酶（HLE）抑制剂，使它们在需要进行此类抑制时非常有用，例如用作药理学、诊断和相关研究工具以及治疗哺乳动物中HLE参与的疾病，包括治疗肺气肿等组织退行性疾病。该发明还包括合成这些肽衍生物的中间体，制备它们的方法，含有此类肽衍生物的药物组合物以及其使用方法。
• Angiotensin-converting enzyme inhibitors: new orally active 1,4-thiazepine-2,5-diones, 1,4-thiazine-2,5-diones, and 1,4-benzothiazepine-2,5-diones possessing antihypertensive activity
  作者：Jerry W. Skiles、John T. Suh、Bruce E. Williams、Paul R. Menard、Jeffrey N. Barton、Bernard Loev、Howard Jones、Edward S. Neiss、Alfred Schwab

  DOI：10.1021/jm00155a032

  日期：1986.5

  most active thiazines in rats, po, were 42 and 45. Of the benzothiazepines studied, 22a was the most active in inhibiting ACE in the conscious normotensive rat, ID50 = 0.15 mg/kg, po. The acute antihypertensive effects of oral administration of a number of these compounds on mean arterial pressure and heart rate were studied in spontaneously hypertensive rats (SHR) maintained on a sodium-deficient diet

  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。