1-乙酰基-2-吡咯烷甲酰胺 | 30130-35-9

• 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: 1-乙酰基-2-吡咯烷甲酰胺
• 中文别名: 1-乙酰基-2-吡咯烷羧酰胺
• 英文名称: N-acetylprolinamide
• 英文别名: 1-acetyl-DL-prolin-amide；1-Acetyl-DL-prolin-amid；N-Acetyl-prolinamid；Acetyl-prolinamid；Acetylprolinamid；1-acetylpyrrolidine-2-carboxamide
• CAS: 30130-35-9
• 化学式: C₇H₁₂N₂O₂
• mdl: MFCD03939870
• 分子量: 156.184
• InChiKey: CXURPNUIYCJENH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-乙酰基-2-吡咯烷甲酰胺 在 盐酸 、 甲醇 、 氨 、 sodium ethanolate 、 triethyloxonium fluoroborate 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 嘧啶,5-苯基-2-(2-吡咯烷基)-
  参考文献：
  名称：

  Intramolecular Diels-Alder reactions of pyrimidines and a computational study toward their structure and reactivity

  摘要：

  The syntheses of 2-[(prop-2-ynyloxy)carbonyl]pyrimidine (1), 5-[(prop-2-ynyloxy)carbonyl]pyrimidine (2), 5-phenyl-2-[2-(1-prop-2-ynylpyrryl)]pyrimidine (8),5-phenyl-2-[2-(1-prop-2-ynylpyrrolidinyl)]pyrimidine (9) and 2-[2-(prop-2-ynyloxy)phenyl]-4,6-R2-5-R1-pyrimidine (R1 = H, Cl, Ph; R2 = H, Me) (14a-d) are described. Upon heating, the compounds 1, 9, and 14 undergo an intramolecular Diels-Alder reaction and a subsequent retro Diels-Alder reaction to yield the annelated pyridines 15, 16, and 17, respectively. The compounds 2 and 8 did not react. The nonreactivity of the compounds 2 and 8 is ascribed to conjugation of the pyrimidine aromatic system with part of the dienophilic side chain, giving rise to conformations in which the diene and dienophile moieties cannot interact. For the compounds 1, 9, and 14 conjugation is absent, due to steric hindrance. To support this, semiempirical (MDNO-PM3) and molecular mechanics (MMX, CHEMX) calculations were performed. The HOMO-LUMO energy separation of the compounds did not consequently reflect the observed reactivity. However, the probability of the compounds to be in a reactive conformation appeared to correlate with the observed rate of reaction (9 > 14a > 1 >> 2, 8).

  DOI：

  10.1021/jo00037a011
• 作为产物：
  描述：

  (S)-吡咯烷-2-羧酸乙酯盐酸盐 在 N-甲基吗啉 、 氨 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 240.25h， 生成 1-乙酰基-2-吡咯烷甲酰胺
  参考文献：
  名称：

  Proline-based topologic pyracetam analogs and their nootropic activity

  摘要：

  DOI：

  10.1007/bf00831694

文献信息

• [EN] PYRIDONEMORPHINAN ANALOGS AND BIOLOGICAL ACTIVITY ON OPIOID RECEPTORS<br/>[FR] ANALOGUES DE PYRIDONEMORPHINANE ET ACTIVITÉ BIOLOGIQUE SUR DES RÉCEPTEURS DES OPIOÏDES
  申请人：PURDUE PHARMA LP

  公开号：WO2014091295A1

  公开（公告）日：2014-06-19

  The application is directed to compounds of Formula (I-A) and pharmaceutically acceptable salts and solvates thereof, wherein Formula (II), R1a, R2a, R3a, R4 and Za are defined as set forth in the specification. The invention is also directed to use of compounds of Formula I-A to treat disorders responsive to the modulation of one or more opioid receptors, or as synthetic intermediates. Certain compounds of the present invention are especially useful for treating pain.

  该应用程序涉及公式（I-A）的化合物及其药用可接受的盐和溶剂化合物，其中公式（II），R1a，R2a，R3a，R4和Za的定义如规范所述。该发明还涉及使用公式I-A的化合物来治疗对调节一个或多个阿片受体敏感的疾病，或作为合成中间体。本发明的某些化合物特别适用于治疗疼痛。
• New Aza-Bicyclohexane Compounds Useful As Inhibitors Of Thrombin
  申请人：Branalt Jonas

  公开号：US20090012087A1

  公开（公告）日：2009-01-08

  This invention relates to novel pharmaceutically useful compounds of formula (I), in particular compounds that are competitive inhibitors of trypsin-like serine proteases, especially thrombin, their use as medicaments, pharmaceutical compositions containing them and synthetic routes to their production.

  这项发明涉及具有以下结构的新型药用化合物（I），特别是作为胰蛋白酶样丝氨酸蛋白酶的竞争性抑制剂，尤其是凝血酶，它们作为药物的用途，包含它们的药物组合物以及它们的合成路线。
• Novel Compounds 148
  申请人：Branalt Jonas

  公开号：US20090318517A1

  公开（公告）日：2009-12-24

  This invention relates to novel pharmaceutically useful compounds of formula (I), in particular compounds that are competitive inhibitors of trypsin-like serine proteases, especially thrombin, their use as medicaments, pharmaceutical compositions containing them and synthetic routes to their production.

  本发明涉及一种新的具有药用价值的化合物，其化学式为（I），特别是一种竞争性抑制剂，可作为药物使用，特别是对于类似胰酶的丝氨酸蛋白酶，尤其是凝血酶的化合物，包括它们的使用作为药物，含有这些化合物的制药组合物以及制备它们的合成路线。
• [EN] PHARMACEUTICALLY ACTIVE PYRROLIDINE DERIVATIVES AS BAX INHIBITORS<br/>[FR] DERIVES DE LA PYRROLIDINE PHARMACEUTIQUEMENT ACTIFS COMME INHIBITEURS DE BAX
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2001074769A1

  公开（公告）日：2001-10-11

  The present invention is related to new substituted pyrrolidine derivatives of formula (I). Said compounds are preferably for use as pharmaceutically active compounds. Specifically, pyrrolidine derivatives of formula (I) are useful in the treatment and/or prevention of neurodegenerative disorders, diseases associated with polygultamine tracts, epilepsy, ischemia, infertility, cardiovascular disorders renal hypoxia, hepatitis and AIDS. Said pyrrolidine derivatives display a modulatory and most notably a down-regulating - up to an inhibitory - activity with respect to the cellular death agonist Bax and/or the activation pathways leading to Bax and allows therefore to block the release of cytochrome (c). The present invention is furthermore related to novel pharmaceutically activity substituted pyrrolidine derivatives as well as to methods of their preparation, wherein X is selected from the group consisting of O, S, CR?6R7, NOR6, NNR6R7¿; A is selected from the group consisting of -(C=O)-, -(C=O)-O-, -C(=NH)-, -(C=O)-NH-, -(C=S)-NH, -SO¿2?-, -SO2NH-; -CH2-; B is either a group -(C=O)-NR?8R9¿ or represents a heterocyclic residue having the formula (II) wherein Q is NR10, O or S; n is an integer selected of 0, 1 or 2; Y, Z and E form together with the 2 carbons to which they are attached a 5-6 membered aryl or heteroaryl ring.

  本发明涉及公式（I）的新取代吡咯烷衍生物。所述化合物优选用作药物活性化合物。具体而言，公式（I）的吡咯烷衍生物在神经退行性疾病、与多谷氨酸重复序列相关的疾病、癫痫、缺血、不孕症、心血管疾病、肾脏缺氧、肝炎和艾滋病的治疗和/或预防中有用。所述吡咯烷衍生物显示出调节性，尤其是对于细胞死亡促进剂Bax和/或导致Bax的激活途径具有下调至抑制性的活性，并因此允许阻止细胞色素（c）的释放。本发明还涉及新型药物活性取代吡咯烷衍生物以及其制备方法，其中X选自O，S，CR?6R7，NOR6，NNR6R7¿的群；A选自-(C=O)-，-(C=O)-O-，-C（=NH）-，-(C=O)-NH-，-(C=S)-NH，-SO¿2?，-SO2NH-；-CH2-；B是一个-(C=O)-NR?8R9¿基团或代表具有公式（II）的杂环残基，其中Q是NR10，O或S；n是选择的0、1或2的整数；Y、Z和E与它们所连接的2个碳一起形成一个5-6成员芳基或杂芳基环。
• [EN] MACROLIDE ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES A BASE DE MACROLIDES
  申请人：GLAXO GROUP LTD

  公开号：WO2002050091A1

  公开（公告）日：2002-06-27

  The present invention relates to 11,12 η lactone ketolides of formula (I) wherein R, R?1, R2, R3¿ are as defined herein and pharmaceutically acceptable salts and solvates thereof, to process for their preparation and their use in therapy or prophylaxis of systemic or topical bacterial infections in a human or animal body.

  本发明涉及式（I）的11,12-η内酯酮类化合物，其中R，R?1，R2，R3¿如本文所定义，并且其药学上可接受的盐和溶剂合物，以及其制备过程和在治疗或预防人类或动物体内的全身性或局部细菌感染中的应用。