(3S)-3-乙炔基奎宁环-3-醇 | 160127-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 中文名称: (3S)-3-乙炔基奎宁环-3-醇
• 英文名称: (S)-(-)-3-ethynyl-3-hydroxy quinuclidine
• 英文别名: (S)-3-hydroxy-3-ethynylquinuclidine；(5S)-5-ethynyl-1-azabicyclo[2.2.2]octan-5-ol；(3R)-3-ethynyl-3-quinuclidinol；(3s)-3-Ethynyl-3-quinuclidinol；(3S)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-ol
• CAS: 160127-75-3
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: YRTHQTAVIFQEEG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-溴苯氧基)苯甲酸甲酯 、 (3S)-3-乙炔基奎宁环-3-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以83%的产率得到methyl 4-[4-[2-[(3S)-3-hydroxyquinuclidin-3-yl]ethynyl]phenoxy]benzoate
  参考文献：
  名称：

  Selective non zinc binding inhibitors of MMP13

  摘要：

  Directed screening has identified a novel series of MMP13 inhibitors that possess good levels of activity whilst possessing excellent selectivity over related MMPs. The binding mode of the series has been solved by co-crystallisation and demonstrates an interesting mode of inhibition without interaction with the catalytic zinc atom. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.075
• 作为产物：
  描述：

  3-乙炔基奎宁环-3-醇 在 氢氧化钾 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 53.0h， 生成 (3S)-3-乙炔基奎宁环-3-醇
  参考文献：
  名称：

  猪肝酯酶对三联喹啉醇酯的生物催化拆分

  摘要：

  动力学拆分炔烃酯已使用猪肝酯酶。已经分离出具有高对映体纯度的3-乙炔基-3-羟基喹核苷的（R）和（S）异构体。

  DOI：

  10.1016/0957-4166(95)00172-l

文献信息

• Substituted bicyclic derivatives useful as anticancer agents
  申请人：——

  公开号：US20010034351A1

  公开（公告）日：2001-10-25

  The invention relates to compounds of the formula 1 1 and to pharmaceutically acceptable salts and solvates thereof, wherein A, X, R 1 , R 3 and R 4 are as defined herein. The invention also relates to methods of treating abnormal cell growth in mammals with administering the compounds of formula 1 and to pharmaceutical compositions for treating such disorders which contain the compounds of formula 1. The invention also relates to methods of preparing the compounds of formula 1.

  本发明涉及公式11的化合物及其药学上可接受的盐和溶剂化物，其中A、X、R1、R3和R4的定义如本文所述。本发明还涉及使用公式1的化合物治疗哺乳动物中的异常细胞生长的方法，并涉及含有公式1的化合物的治疗此类疾病的制药组合物。本发明还涉及制备公式1的化合物的方法。
• Quinuclidine compounds and drugs containing the same as the active ingredient
  申请人：Eisai Co., Ltd.

  公开号：US06599917B1

  公开（公告）日：2003-07-29

  The present invention provides an excellent squalene synthesizing enzyme inhibitor. Specifically, it provides a compound (I) represented by the following formula, a salt thereof or a hydrate of them. In which R1 represents (1) hydrogen atom or (2) hydroxyl group; HAr represents an aromatic heterocycle which may be substituted with 1 to 3 groups; Ar represents an optionally substituted aromatic ring; W represents a chain represented by (1) —CH2—CH2— which may be substituted, (2) —CH═CH— which may be substituted, (3) —C≡C—, (4) —NH—CO—, (5) —CO—NH—, (6) —NH—CH2—, (7) —CH2—NH—, (8) —CH2—CO—, (9) —CO—CH2—, (10) —NH—S(O)l—, (11) —S(O)l—NH—, (12) —CH2—S(O)— or (13) —S(O)l—CH2— (l denotes 0, 1 or 2); and X represents a chain represented by (1) a single bond, (2) an optionally substituted C1-6 alkylene chain, (3) an optionally substituted C2-6 alkenylene chain, (4) an optionally substituted C2-6 alkynylene chain, (5) a formula —Q— (wherein Q represents oxygen atom, sulfur atom, CO or N(R2) (wherein R2 represents a C1-6 alkyl group or a C1-6 alkoxy group)), (6) —NH—CO—, (7) —CO—NH—, (8) —NH—CH2—, (9) —CH2—NH—, (10) —CH2—CO—, (11) —CO—CH2—, (12) —NH—S(O)m—, (13) —S(O)m—NH—, (14) —CH2—S(O)m—, (15) —S(O)m—CH2— (wherein m denotes 0, 1 or 2) or (16) —(CH2)n—O— (wherein n denotes an integer from 1 to 6).

  本发明提供了一种优异的角鲨烯合成酶抑制剂。具体地，提供了以下式子所表示的化合物(I)、其盐或其水合物。其中，R1代表(1)氢原子或(2)羟基；HAr代表一种芳香杂环，可以被1-3个基团取代；Ar代表一个可选取代的芳香环；W代表一个由(1) -CH2-CH2-表示的链，该链可以被取代，(2) -CH═CH-表示的链，该链可以被取代，(3) -C≡C-，(4) -NH-CO-，(5) -CO-NH-，(6) -NH-CH2-，(7) -CH2-NH-，(8) -CH2-CO-，(9) -CO-CH2-，(10) -NH-S(O)l-，(11) -S(O)l-NH-，(12) -CH2-S(O)-或(13) -S(O)l-CH2- (其中l表示0、1或2)；X代表一个由(1)单键，(2)可选取代的C1-6烷基链，(3)可选取代的C2-6烯基链，(4)可选取代的C2-6炔基链，(5)公式-Q- (其中Q表示氧原子、硫原子、CO或N(R2) (其中R2表示C1-6烷基或C1-6烷氧基))，(6) -NH-CO-，(7) -CO-NH-，(8) -NH-CH2-，(9) -CH2-NH-，(10) -CH2-CO-，(11) -CO-CH2-，(12) -NH-S(O)m-，(13) -S(O)m-NH-，(14) -CH2-S(O)m-，(15) -S(O)m-CH2- (其中m表示0、1或2)或(16) -(CH2)n-O- (其中n表示1-6的整数)的链。
• N-ARYL-SUBSTITUTED CYCLIC AMINE DERIVATIVE AND MEDICINE CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP1375496B1

  公开（公告）日：2007-07-04
• Novel optimised quinuclidine squalene synthase inhibitors
  作者：George R. Brown、Alan J. Foubister、Susan Freeman、Fergus McTaggart、Donald J. Mirrlees、Alan C. Reid、Graham J. Smith、Melvyn J. Taylor、Douglas A. Thomason、Paul R.O. Whittamore

  DOI：10.1016/s0960-894x(97)00053-x

  日期：1997.3

  Optimised quinuclidine squalene synthase (SQS) inhibitors are reported; 3-[2-(2-allyl-4-(2-ethoxy carbonylethyl)phenyl)ethynyl]quinuclidin-3-ol 1c, is a potent inhibitor of rat (KI = 6 nM) and human (KI = 43 nM) microsomal SQS; the oral ED(50) of 1c, for the inhibition of rat cholesterol biosynthesis was 1.3+/-0.45 mg/kg and for the R-enantiomer 1m, 0.8+/-0.2 mg/kg, with the corresponding R-carboxylic acid 6a, being 0.9+/-0.25 mg/kg. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Selective non zinc binding inhibitors of MMP13
  作者：Chris De Savi、Andrew D. Morley、Attilla Ting、Ian Nash、Kostas Karabelas、Christine M. Wood、Michael James、Stephen J. Norris、Galith Karoutchi、Neil Rankine、Gordon Hamlin、Philip A. MacFaul、David Ryan、Sarah V. Baker、David Hargreaves、Stefan Gerhardt

  DOI：10.1016/j.bmcl.2011.05.075

  日期：2011.7

  Directed screening has identified a novel series of MMP13 inhibitors that possess good levels of activity whilst possessing excellent selectivity over related MMPs. The binding mode of the series has been solved by co-crystallisation and demonstrates an interesting mode of inhibition without interaction with the catalytic zinc atom. (C) 2011 Elsevier Ltd. All rights reserved.