PhCO-GlyN(CH2)4 | 95204-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: PhCO-GlyN(CH2)4
• 英文别名: N-[2-oxo-2-(pyrrolidin-1-yl)ethyl]benzamide；Benzamide, N-(2-oxo-2-(1-pyrrolidinyl)ethyl)-；N-(2-oxo-2-pyrrolidin-1-ylethyl)benzamide
• CAS: 95204-52-7
• 化学式: C₁₃H₁₆N₂O₂
• mdl: MFCD01667732
• 分子量: 232.282
• InChiKey: CXSUVQOSBPNFDM-UHFFFAOYSA-N

物化性质

• 沸点：
  494.4±28.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  PhCO-GlyN(CH2)4 在 甲醇 、 sodium methylate 、 sodium acetate 、 二氧化氮 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 生成 2-diazo-1-(pyrrolidin-1-yl)ethanone
  参考文献：
  名称：

  肽键的亚硝化。吡咯烷和α-氨基酯裂解亚硝化肽

  摘要：

  已经研究了几种α-氨基酸和多肽（包含Gly，L-Ala，L-Leu，L-或DL-Phe和/或L-或D-Val）与空气稀释的氮氧化物的反应模拟被污染的城市空气可能在肺组织中产生的肽键的N-亚硝化。大多数N-保护的α-氨基酸可提供定量的N-亚硝基衍生物。受N保护的二肽提供二亚硝化肽，二亚硝化化合物和单亚硝化化合物的混合物，选择性单亚硝化产物，或根本不发生反应，这主要取决于空间效应。对于一些更高的肽，观察到相同的趋势。保留了原料的手性的（多）亚硝化肽的特征是1 H和13在温和的条件下，经吡咯烷和氨基酯裂解，得到13 C NMR光谱，得到（新的）酰胺或肽以及重氮衍生物。

  DOI：

  10.1016/s0040-4020(01)82437-6
• 作为产物：
  描述：

  苯甲酰氯 在 硫酸 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 PhCO-GlyN(CH2)4
  参考文献：
  名称：

  Synthesis, biological activity screening and molecular modeling study of acylaminoacetamide derivatives

  摘要：

  In this study, non-rigid analogs of thalidomide have been designed in order to develop potentially active, more effective and safer lead molecules for disorders caused or contributed by inflammation. Five different series of acylaminoacetamide compounds were synthesized, and the biological inhibitory potency of the title compounds has been determined by evaluating their effects on COX-2 isoenzyme expression and PGE(2) production in A549 (human lung adenocarcinoma) cell lines. Among the studied series, N-[2-(isopropylamino)-2-oxoethyl]isonicotinamide is the most active inhibitory compound on COX-2 isoenzyme expression, and N-[2-oxo-2-(pyrolydine-1-yl)etyl]isonicotinamide is the most active inhibitory compound on the biosynthesis of PGE(2). Molecular docking studies and molecular dynamics simulations were also applied to investigate non-covalent interactions of the most active compounds inside the active side of the crystal structure of murine cyclooxygenase 2 (mCOX-2) isoenzyme.

  DOI：

  10.1007/s00044-015-1419-4

文献信息

• Acylated Gly-(2-cyano)pyrrolidines as inhibitors of fibroblast activation protein (FAP) and the issue of FAP/prolyl oligopeptidase (PREP)-selectivity
  作者：Oxana Ryabtsova、Koen Jansen、Sebastiaan Van Goethem、Jurgen Joossens、Jonathan D. Cheng、Anne-Marie Lambeir、Ingrid De Meester、Koen Augustyns、Pieter Van der Veken

  DOI：10.1016/j.bmcl.2012.03.107

  日期：2012.5

  A series of N-acylated glycyl-(2-cyano) pyrrolidines were synthesized with the aim of generating structure-activity relationship (SAR) data for this class of compounds as inhibitors of fibroblast activation protein (FAP). Specifically, the influence of (1) the choice of the N-acyl group and (2) structural modification of the 2-cyanopyrrolidine residue were investigated. The inhibitors displayed inhibitory potency in the micromolar to nanomolar range and showed good to excellent selectivity with respect to the proline selective dipeptidyl peptidases (DPPs) DPP IV, DPP9 and DPP II. Additionally, selectivity for FAP with respect to prolyl oligopeptidase (PREP) is reported. Not unexpectedly, the latter data suggest significant overlap in the pharmacophoric features that define FAP or PREP-inhibitory activity and underscore the importance of systematically evaluating the FAP/PREP-selectivity index for inhibitors of either of these two enzymes. Finally, this study forwards several compounds that can serve as leads or prototypic structures for future FAP-selective-inhibitor discovery. (C) 2012 Elsevier Ltd. All rights reserved.
• MORPHOLINONE COMPOUNDS AS FACTOR IXA INHIBITORS
  申请人：Mochida Pharmaceutical Co., Ltd.

  公开号：EP2473491A1

  公开（公告）日：2012-07-11
• KDM1A INHIBITORS FOR THE TREATMENT OF DISEASE
  申请人：Imago Biosciences Inc.

  公开号：EP3030323B1

  公开（公告）日：2019-04-24
• Substrates and Inhibitors of Antiplasmin Cleaving Enzyme and Fibroblast Activation Protein and Methods of Use
  申请人：McKee Patrick A.

  公开号：US20110144037A1

  公开（公告）日：2011-06-16

  The presently disclosed and claimed inventive concepts include inhibitors of antiplasmin cleaving enzyme (APCE) and fibroblast activation protein alpha (FAP) which can be used in various therapies related to disorders of fibrin and α 2 -antiplasmin and abnormal cell proliferation. The presently disclosed and claimed inventive concepts also include substrates of APCE and FAP, which may be used, for example, in screening methods for identifying such inhibitors. The presently disclosed and claimed inventive concepts further include, but are not limited to, methods of treating or inhibiting atherosclerosis and thrombus disorders by altering the ratios of types of plasma α 2 -antiplasmin and to methods of treating conditions involving abnormal cell proliferation such as cancers.
• [EN] MORPHOLINONE COMPOUNDS AS FACTOR IXA INHIBITORS<br/>[FR] COMPOSÉS MORPHOLINONES COMME INHIBITEURS DU FACTEUR IXA
  申请人：MOCHIDA PHARM CO LTD

  公开号：WO2011025565A1

  公开（公告）日：2011-03-03

  The present invention provides compounds having the formula (I) or a pharmaceutically acceptable salt or a solvate thereof, pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes.