1-吡咯烷羧酸,2-[(乙酰氧基)乙酰基]-,1,1-二甲基乙基酯,(2S)- | 105462-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-吡咯烷羧酸,2-[(乙酰氧基)乙酰基]-,1,1-二甲基乙基酯,(2S)-
• 英文名称: tert-butyl (2S)-2-(acetoxyacetyl)pyrrolidine-1-carboxylate
• 英文别名: N-Boc-2(S)-(acetoxyacetyl)pyrrolidine；(S)-1-t-Butoxycarbonyl-2-(2-acetoxy-1-oxoethyl)pyrrolidine；(S)-2-(Acetoxyacetyl)-1-(tert-butoxycarbonyl)pyrrolidine；Boc-2(S)-(acetoxyacetyl)pyrrolidine；Boc-2(S)-(acetoxyacetyl)pyrrolidyne；tert-butyl (2S)-2-(2-acetyloxyacetyl)pyrrolidine-1-carboxylate
• CAS: 105462-68-8
• 化学式: C₁₃H₂₁NO₅
• 分子量: 271.313
• InChiKey: NXLRDTHAZNPPOQ-JTQLQIEISA-N

物化性质

• 沸点：
  364.6±37.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-吡咯烷羧酸,2-[(乙酰氧基)乙酰基]-,1,1-二甲基乙基酯,(2S)- 在 1-氯-N,N,2-三甲基丙烯胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.41h， 生成 2-[(2S)-1-{[(5S)-2-(4-methylbenzyl)-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridin-5-yl]carbonyl}pyrrolidin-2-yl]-2-oxoethyl acetate
  参考文献：
  名称：

  SUBSTITUTED 5,6,7,8-TETRAHYDRO[1,2,4]TRIAZOLO[4,3-A]PYRIDINE-3(2H)-ONES AND 2,5,6,7-TETRAHYDRO-3H-PYRROLO[2,1-C][1,2,4]TRIAZOL-3-ONES, AND USE THEREOF

  摘要：

  该申请涉及新颖的取代5,6,7,8-四氢[1,2,4]三唑并[4,3-a]吡啶-3(2H)-酮和2,5,6,7-四氢-3H-吡咯[2,1-c][1,2,4]三唑-3-酮，其制备方法，以及其单独或组合使用用于治疗和/或预防疾病，以及其用于生产用于治疗和/或预防疾病的药物，特别是用于治疗和/或预防肺部炎症性疾病。

  公开号：

  US20190160048A1
• 作为产物：
  描述：

  (S)-N-(tert-Butoxycarbonyl)proline ethyl carbonate 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.17h， 生成 1-吡咯烷羧酸,2-[(乙酰氧基)乙酰基]-,1,1-二甲基乙基酯,(2S)-
  参考文献：
  名称：

  4-Phenylbutanoyl-2( S )-acylpyrrolidines and 4-phenylbutanoyl- l -prolyl-2( S )-acylpyrrolidines as prolyl oligopeptidase inhibitors

  摘要：

  New 4-phenylbutanoyl-2(S)-acylpyrrolidines and 4-phenylbutanoyl-L-prolyl-2(S)-acylpyrrolidines were synthesized. Their inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. In the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were the best inhibitors having IC50 values of 30 and 23 nM, respectively. This series of compounds shows that that P1 pyrrolidine ring, which is common in most POP inhibitors, can be replaced by either a cyclopentyl ring or a phenyl ring, causing only a slight decrease in the inhibitory activity. In the series of 4-phenylbutanoyl-L-prolyl-2(S)- acyl-pyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were not as active as in the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, The hydroxyacetyl derivative did however show high inhibitors activity. This compound is structurally similar to JTP-4819, which is one of the most potent prolyl oligopeptidase inhibitors. The acyl group in the two series of new compounds seems to bind to different sites of the enzyme, since the second series of ne compounds did not show the same cyclopentanecarbonyl or benzoyl specificity as the first series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00061-5

文献信息

• Compound having prolyl endopeptidase inhibitory activity and
  申请人：Japan Tobacco Inc.

  公开号：US05536737A1

  公开（公告）日：1996-07-16

  Compounds of the formula ##STR1## wherein R is a hydrogen atom or an acyl; U is --O--, --CHR.sup.1 -- or --NR.sup.2 -- wherein R.sup.1 is a hydrogen atom or a hetero ring, and R.sup.2 is a hydrogen atom or a lower alkoxycarbonyl lower alkyl; V is --O--, --S--, --CHR.sup.3 -- or --NR.sup.4 -- wherein R.sup.3 is a hydrogen atom or a lower alkoxycarbonyl, and R.sup.4 is a hydrogen atom, a lower alkyl or an acyl; W is methyl, a hetero ring or optionally substituted phenyl; X and Y are the same or different and each is --CH.sub.2 -- or --S--; m is an integer of 0 to 6; and n is an integer of 1 to 4, and pharmaceutically acceptable salts thereof. The compounds of the present invention have specifically strong inhibitory activity against prolyl endopeptidase, and suppress decomposition and inactivation of TRH, substance P, neurotensin, vasopressin and the like. Accordingly, the compounds can be used for the prophylaxis and/or treatment of dementia and amnesia including Alzheimer's disease.

  公式为##STR1##的化合物，其中R是氢原子或酰基; U是--O--，--CHR.sup.1--或--NR.sup.2--，其中R.sup.1是氢原子或杂环，R.sup.2是氢原子或低烷氧羰基低烷基; V是--O--，--S--，--CHR.sup.3--或--NR.sup.4--，其中R.sup.3是氢原子或低烷氧羰基，R.sup.4是氢原子，低烷基或酰基; W是甲基，杂环或可选取代苯基; X和Y相同或不同，每个都是--CH.sub.2--或--S--; m是0到6的整数; n是1到4的整数，以及其药学上可接受的盐。本发明的化合物具有特别强的脯氨酰内肽酶抑制活性，并抑制TRH、物质P、神经肽、加压素等的分解和失活。因此，这些化合物可用于预防和/或治疗包括阿尔茨海默病在内的痴呆和健忘症。
• [EN] COMPOUNDS HAVING PROLYL OLIGOPEPTIDASE INHIBITORY ACTIVITY, METHODS FOR THEIR PREPARATION AND THEIR USE<br/>[FR] COMPOSES INHIBITEURS DE LA PROLYL OLIGOPEPTIDASE, PROCEDES DE PREPARATION ET UTILISATION
  申请人：ORION CORP

  公开号：WO2003004468A1

  公开（公告）日：2003-01-16

  Compounds of the formula (I), wherein the symbol aa means a residue of an α-amino acid. The invention is also directed to a method for the preparation of the compounds of formula (I), as well as their use as prolyl oligopeptide inhibitors, for example for the treatment of Alzheimer's disease.

  公式（I）的化合物，其中符号aa表示α-氨基酸的残基。本发明还涉及一种制备公式（I）化合物的方法，以及它们作为脯氨酰寡肽抑制剂的用途，例如用于治疗阿尔茨海默病。
• Compounds having prolyl oligopeptidase inhibitory activity, methods for their preparation and their use
  申请人：Gynther Jukka

  公开号：US20050020677A1

  公开（公告）日：2005-01-27

  Compounds of the formula (I), wherein the symbol aa means a residue of an α-amino acid. The invention is also directed to a method for the preparation of the compounds of formula (I), as well as their use as prolyl oligopeptide inhibitors, for example for the treatment of Alzheimer's disease.

  式(I)的化合物，其中符号aa表示α-氨基酸残基。本发明还涉及一种制备式(I)化合物的方法，以及它们作为脯氨酰寡肽酶抑制剂的用途，例如用于治疗阿尔茨海默病。
• Amino acid derivatives as enzyme inhibitors
  申请人：Merck & Co., Inc.

  公开号：US04626545A1

  公开（公告）日：1986-12-02

  Compounds of the formula ##STR1## and their use as angiotensin converting enzyme inhibitors and antihypertensives are disclosed.

  本发明公开了化学式为##STR1##的化合物及其作为血管紧张素转化酶抑制剂和降压药物的用途。
• Compounds having prolyl oligopeptidase inhibitory activity
  申请人：Gynther Jukka

  公开号：US20060229254A1

  公开（公告）日：2006-10-12

  A compound of formula (I), wherein X, R 1 , R 2 and R 3 are as defined in the disclosure, or a pharmaceutically acceptable salt or ester thereof, useful as a prolyl oligopeptidase inhibitor. The compounds can be used for the treatment of diseases or conditions where prolyl oligopeptidase inhibitors are indicated to be effective, for example for the treatment of neurodegenerative diseases, such as Alzheimer's disease and senile dementia.

  式(I)的化合物，其中X、R1、R2和R3如所披露的定义，或其药学上可接受的盐或酯，可用作脯氨酰寡肽酶抑制剂。这些化合物可用于治疗需要脯氨酰寡肽酶抑制剂具有疗效的疾病或情况，例如用于治疗神经退行性疾病，如阿尔茨海默病和老年性痴呆症。