(S)-3-哌啶甲酸甲酯盐酸盐 | 164323-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (S)-3-哌啶甲酸甲酯盐酸盐
• 中文别名: (S)-哌啶-3-羧酸甲酯盐酸盐；S-3-哌啶甲酸甲酯盐酸盐
• 英文名称: (S)-(+)-nipecotic acid methyl ester hydrochloride
• 英文别名: (S)-methyl nipecotate hydrochloride；(S)-piperidine-3-carboxylic acid methyl ester hydrochloride；(S)-Methyl piperidine-3-carboxylate hydrochloride；methyl (3S)-piperidine-3-carboxylate;hydrochloride
• CAS: 164323-84-6
• 化学式: C₇H₁₃NO₂*ClH
• 分子量: 179.647
• InChiKey: BQQZKNAQDKIGGZ-RGMNGODLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (S)-3-哌啶甲酸甲酯盐酸盐 在 N-甲基吗啉 、 lithium hydroxide 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 反应 21.5h， 生成 N^α-Boc-D-Lys(Cbz)-(S)-(+)-Nip-β-Ala-OBn
  参考文献：
  名称：

  Design and Evaluation of Nonpeptide Fibrinogen .gamma. Chain-Based GPIIB/IIIA Antagonists

  摘要：

  Two series of nonpeptide turn mimetics were designed by analysis of the solution NMR structure of the 385-411 sequence of the gamma-chain of fibrinogen. These compounds, based on the KQAGD (Lys-Gln-Ala-Gly-Asp, 406-410) sequence, were synthesized and studied in vitro. The most interesting compound from our study, RWJ 50042 (25), exhibits potent inhibition of fibrinogen binding to GPIIb/IIIa (IC50 = 0.009 mu M), as well as thrombin- or collagen-induced platelet aggregation (IC50 = 0.76, 0.14 mu M). Since the 400-411 sequence is required for gamma-chain bioactivity and is a unique recognition sequence among ligands for integrins, vis-a-vis other RGD (Arg-Gly-Asp)-presenting proteins, these turn mimetics may represent a new, selective approach to antagonism of the fibrinogen receptor.

  DOI：

  10.1021/jm00010a002
• 作为产物：
  描述：

  甲醇 、 (S)-3-哌啶甲酸 在 氯化亚砜 作用下， 反应 5.0h， 生成 (S)-3-哌啶甲酸甲酯盐酸盐
  参考文献：
  名称：

  用于发现有效NDM-1抑制剂的D-卡托普利的结构导向优化

  摘要：

  长期以来，β-内酰胺类抗生素一直是治疗细菌感染的主要手段。新德里金属β-内酰胺酶1（NDM-1）能够水解几乎所有β-内酰胺抗生素，甚至可以水解临床上使用的丝氨酸-β-内酰胺酶抑制剂。NDM-1基因在致病细菌中的广泛和快速传播引起了广泛的关注，因此迫切需要高效的NDM-1抑制剂。在这里我们报告一系列的D-卡托普利衍生物的结构指导设计，可以在体外和细胞水平抑制NDM-1的活性。结构比较表明了抑制作用增强的机制，并为进一步的抑制剂优化提供了见识。

  DOI：

  10.1016/j.bmc.2020.115902

文献信息

• 哌嗪脲基类衍生物、其制备方法及其在医药上的应用
  申请人：江苏恒瑞医药股份有限公司

  公开号：CN112778299B

  公开（公告）日：2023-07-14

  本公开涉及哌嗪脲基类衍生物、其制备方法及其在医药上的应用。特别地，本公开涉及通式(I)所示的哌嗪脲基类衍生物、其制备方法、含有该衍生物的药物组合物，以及其作为衣壳蛋白抑制剂，特别是在预防和/或治疗乙型肝炎、流感、疱疹和艾滋病等疾病中的用途。其中通式(I)中的各基团的定义与说明书中的定义相同。
• [EN] ALPHA V BETA 6 AND ALPHA V BETA 1 INTEGRIN INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'INTÉGRINE ALPHA V BÊTA 6 ET ALPHA V BÊTA 1 ET LEURS UTILISATIONS
  申请人：DICE MOLECULES SV INC

  公开号：WO2022192545A1

  公开（公告）日：2022-09-15

  Provided herein are alpha V beta 6 and alpha V beta 1 integrin inhibitors, methods of making such alpha V beta 6 and alpha V beta 1 integrin inhibitors, pharmaceutical compositions of alpha V beta 6 and alpha V beta 1 integrin inhibitors, and methods of treating and/or preventing various medical disorders in a subject by administering to the subject in need thereof alpha V beta 6 and alpha V beta 1 integrin inhibitors.

  本文提供了αVβ6和αVβ1整合素抑制剂，制备这种αVβ6和αVβ1整合素抑制剂的方法，αVβ6和αVβ1整合素抑制剂的药物组合物，以及通过向需要此类抑制剂的受试者投与αVβ6和αVβ1整合素抑制剂来治疗和/或预防各种医学疾病的方法。
• New N -phenyl-4,5-dibromopyrrolamides and N -Phenylindolamides as ATPase inhibitors of DNA gyrase
  作者：Nace Zidar、Tihomir Tomašič、Helena Macut、Anja Sirc、Matjaž Brvar、Sofia Montalvão、Päivi Tammela、Janez Ilaš、Danijel Kikelj

  DOI：10.1016/j.ejmech.2016.03.079

  日期：2016.7

  Following the withdrawal of novobiocin, the introduction of a new ATPase inhibitor of DNA gyrase to the clinic would add the first representative of this mechanistic class to the antibacterial pipeline. This would be of great importance because of the well-known problems associated with antibacterial resistance. Using structure-based design and starting from the recently determined crystal structure of the N-phenyl-4,5-dibromopyrrolamide inhibitor-DNA gyrase B complex, we have prepared 28 new N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides and evaluated them against DNA gyrase from Escherichia coli. The most potent compound was 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl) amino)-2-oxoacetic acid (9a), with an IC50 of 0.18 mu M against E. coli gyrase. A selected set of compounds was evaluated against DNA gyrase from Staphylococcus aureus and against topoisomerase IV from E. coli and S. aureus, but the activities were weaker. The binding affinity of 2-((4-(4,5-dibromo-1H-pyrrole-2carboxamido)phenyl)amino)-2-oxoacetic acid (9a) to E. coli gyrase was studied using surface plasmon resonance. In the design of the present series, the focus was on the optimisation of biological activities of compounds especially by varying their size, the position and orientation of key functional groups, and their acid base properties. The structure activity relationship (SAR) was examined and the results were rationalised with molecular docking. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Discovery of molecular switches within the ADX-47273 mGlu5 PAM scaffold that modulate modes of pharmacology to afford potent mGlu5 NAMs, PAMs and partial antagonists
  作者：Jeffrey P. Lamb、Darren W. Engers、Colleen M. Niswender、Alice L. Rodriguez、Daryl F. Venable、P. Jeffrey Conn、Craig W. Lindsley

  DOI：10.1016/j.bmcl.2010.11.119

  日期：2011.5

  This Letter describes a chemical lead optimization campaign directed at a weak mGlu(5) NAM discovered while developing SAR for the mGlu(5) PAM, ADX-47273. An iterative parallel synthesis effort discovered multiple, subtle molecular switches that afford potent mGlu(5) NAMs, mGlu(5) PAMs as well as mGlu(5) partial antagonists. (C) 2010 Elsevier Ltd. All rights reserved.
• Design and Evaluation of Nonpeptide Fibrinogen .gamma. Chain-Based GPIIB/IIIA Antagonists
  作者：William J. Hoekstra、Mary Pat Beavers、Patricia Andrade-Gordon、Mary F. Evangelisto、Patricia M. Keane、Jeffery B. Press、Karen A. Tomko、Francis Fan、Marek Kloczewiak

  DOI：10.1021/jm00010a002

  日期：1995.5

  Two series of nonpeptide turn mimetics were designed by analysis of the solution NMR structure of the 385-411 sequence of the gamma-chain of fibrinogen. These compounds, based on the KQAGD (Lys-Gln-Ala-Gly-Asp, 406-410) sequence, were synthesized and studied in vitro. The most interesting compound from our study, RWJ 50042 (25), exhibits potent inhibition of fibrinogen binding to GPIIb/IIIa (IC50 = 0.009 mu M), as well as thrombin- or collagen-induced platelet aggregation (IC50 = 0.76, 0.14 mu M). Since the 400-411 sequence is required for gamma-chain bioactivity and is a unique recognition sequence among ligands for integrins, vis-a-vis other RGD (Arg-Gly-Asp)-presenting proteins, these turn mimetics may represent a new, selective approach to antagonism of the fibrinogen receptor.