4'-cyano-<1,1'-biphenyl>-4-carboxylic acid chloride | 71023-27-3

• 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: 4'-cyano-<1,1'-biphenyl>-4-carboxylic acid chloride
• 英文别名: 4′-cyano-1,1′-biphenyl-4-carboxylic acid chloride；4'-cyano-4-biphenylylcarbonyl chloride；4-(4-Cyanophenyl)benzoyl chloride
• CAS: 71023-27-3
• 化学式: C₁₄H₈ClNO
• 分子量: 241.677
• InChiKey: STZOTSLZVGSAKO-UHFFFAOYSA-N

物化性质

• 沸点：
  404.9±38.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-cyano-<1,1'-biphenyl>-4-carboxylic acid chloride 以 四氢呋喃 为溶剂， 反应 12.17h， 生成 5-chloro-N-(5-chloropyridin-2-yl)-2-[[4-[4-(N,N-dimethylcarbamimidoyl)phenyl]benzoyl]amino]benzamide
  参考文献：
  名称：

  Design, synthesis, and SAR of anthranilamide-based factor Xa inhibitors incorporating substituted biphenyl P4 motifs

  摘要：

  Anthranilamides 4 and 5 were designed and synthesized as selective and orally bioavailable factor Xa inhibitors. Structural modifications aimed at lowering their lipophilicity were performed at the central phenyl ring and at the S4 binding biphenyl region by incorporating water solublizing substituents. The resulting compounds (e.g., 7, 8, 14, 30a, and 32b) are highly potent in vitro, and show improved activity in human plasma-based thrombin generation assay. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2003.11.079
• 作为产物：
  描述：

  4-氰基-4-联苯羧酸 在 氯化亚砜 作用下， 反应 1.0h， 生成 4'-cyano-<1,1'-biphenyl>-4-carboxylic acid chloride
  参考文献：
  名称：

  Design, synthesis, and SAR of anthranilamide-based factor Xa inhibitors incorporating substituted biphenyl P4 motifs

  摘要：

  Anthranilamides 4 and 5 were designed and synthesized as selective and orally bioavailable factor Xa inhibitors. Structural modifications aimed at lowering their lipophilicity were performed at the central phenyl ring and at the S4 binding biphenyl region by incorporating water solublizing substituents. The resulting compounds (e.g., 7, 8, 14, 30a, and 32b) are highly potent in vitro, and show improved activity in human plasma-based thrombin generation assay. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2003.11.079

文献信息

• 5-membered heterocyclic compounds, processes for preparing them and
  申请人：Dr. Karl Thomae GmbH

  公开号：US05463071A1

  公开（公告）日：1995-10-31

  Compounds of the formula ##STR1## wherein X.sub.1 to X.sub.5 are as defined herein, the tautomers, the stereoisomers including the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases. The compounds are useful for inhibiting undesirable cell aggregation.

  式为##STR1##的化合物，其中X.sub.1至X.sub.5如本文所定义，其互变异构体、立体异构体包括其混合物以及其盐，特别是其与无机或有机酸或碱形成的生理上可接受的盐。这些化合物对抑制不良细胞聚集是有用的。
• Substituted amino alcohols as chiral dopants
  申请人：Fraunhofer-Gesellschaft zur Förderung der Angewandten Forschung E.V.

  公开号：US09273247B2

  公开（公告）日：2016-03-01

  The invention relates to the use of a substituted, chiral amino alcohol, comprising one or more structural units of the following formula (1), wherein the abbreviations A, Y, R1 and R3 to R5 have the following meanings: is a covalent bond or a hydrocarbon group, Y is a covalent bond or a hydrocarbon group that can have an oxygen atom at one of its ends through which it is bonded to R1, R1 is an aliphatic or heterocyclic or aromatic radical, the carbon chain of which may be interrupted by one or more B groups, R5 is selected from the group consisting of (a) aliphatic radicals, wherein individual carbon atoms may be replaced by oxygen atoms or carbonyl groups, and wherein the carbon chains of same radicals may be optionally interrupted by a B group, and (b) araliphatic, cycloaliphatic, aromatic and heterocyclic radicals, wherein the carbon chain can be interrupted by one or more B structural elements and/or by one or more D coupling groups, R3, R4 are hydrogen or aliphatic or araliphatic substituents, which are independent of one another, wherein the carbon chain can be interrupted by one or more B groups, B is selected from polymerizable or crosslinkable structural elements from the group comprising C1-C16-alkenyl, C1-C16-alkenyloxy, —C═C—, —CH═CH—COO—, —CH═CH—, —CX═CH—COO— with X═C1-C16-alkyl, and the trans-form of —OOC—CH═CH—COO—, and D is selected from —O—, —NH—, —N(CH3)—, —N(C2H5)—, —SO2—, —CO—, —COO—, —CH═CH—, —OCOO—, —OCH2—, CH═N, —CF2CF2—, as a chiral dopant in liquid crystal (mixtures), e.g., in electro-optical systems.

  该发明涉及使用一种取代的手性氨基醇，包括以下式（1）的一个或多个结构单元，其中缩写A、Y、R1和R3至R5具有以下含义：A是共价键或碳氢基团，Y是共价键或碳氢基团，可以在其一端具有氧原子，通过该氧原子与R1键合，R1是脂肪族、杂环或芳香基，其碳链可能被一个或多个B基团中断，R5选自以下组成的群体：（a）脂肪基，其中个别碳原子可被氧原子或羰基取代，同一基团的碳链可能选择性地被B基团中断；（b）芳基脂肪族、环脂肪族、芳香和杂环基，其碳链可被一个或多个B结构元素和/或一个或多个D偶联基中断，R3、R4是氢或脂肪族或芳基脂肪族取代基，彼此独立，其碳链可能被一个或多个B基团中断，B选自以下群体中的可聚合或可交联的结构单元：C1-C16-烯基、C1-C16-烯氧基、—C═C—、—CH═CH—COO—、—CH═CH—、—CX═CH—COO—，其中X=C1-C16-烷基，以及—OOC—CH═CH—COO—的反式形式，D选自—O—、—NH—、—N(CH3)—、—N(C2H5)—、—SO2—、—CO—、—COO—、—CH═CH—、—OCOO—、—OCH2—、CH═N、—CF2CF2—，作为液晶（混合物）中的手性掺杂剂，例如在电光系统中。
• 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
  申请人：Dr. Karl Thomae GmbH

  公开号：EP0525629A2

  公开（公告）日：1993-02-03

  Die Erfindung betrifft 5-gliedrige Heterocyclen der allgemeinen Formel in der X1 bis X5 wie im Anspruch 1 definiert sind, deren Tautomere, deren Stereoisomere einschließlich deren Gemische und deren Salze, insbesondere deren physiologisch verträgliche Salze mit anorganischen oder organischen Säuren oder Basen, welche wertvolle pharmakologische Eigenschaften aufweisen, vorzugsweise aggregationshemmende Wirkungen, die Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung.

  本发明涉及通式如下的五元杂环 其中 X1至X5（如权利要求1所定义）、它们的同分异构体、它们的立体异构体，包括它们的混合物和它们的盐，特别是它们与无机酸或有机酸或碱的生理相容盐，它们显示出有价值的药理特性，最好是有抑制聚集的作用，以及含有这些化合物的药物和它们的制备工艺。
• Discovery, synthesis, and structure–activity relationship of 6-aminomethyl-7,8-dihydronaphthalenes as human melanin-concentrating hormone receptor 1 antagonists
  作者：Makoto Kamata、Toshiro Yamashita、Toshihiro Imaeda、Toshio Tanaka、Jun Terauchi、Maki Miyamoto、Taiichi Ora、Michiko Tawada、Satoshi Endo、Shiro Takekawa、Asano Asami、Nobuhiro Suzuki、Yasutaka Nagisa、Yoshihide Nakano、Kaoru Watanabe、Hitomi Ogino、Koki Kato、Kaneyoshi Kato、Yuji Ishihara

  DOI：10.1016/j.bmc.2011.07.038

  日期：2011.9

  Human melanin-concentrating hormone receptor 1 (hMCHR1) antagonists are promising targets for obesity treatment. We identified the tetrahydronaphthalene derivative 1a with modest binding affinity for hMCHR1 by screening an in-house G protein-coupled receptor (GPCR) ligand library. We synthesized a series of 6-aminomethyl-5,6,7,8-tetrahydronaphthalenes and evaluated their activity as hMCHR1 antagonists. Modification of the biphenylcarbonylamino group revealed that the biphenyl moiety played a crucial role in the interaction of the antagonist with the receptor. The stereoselective effect of the chiral center on binding affinity generated the novel 6-aminomethyl-7,8-dihydronaphthalene scaffold without a chiral center. Optimization of the amino group led to the identification of a potent antagonist 2s (4'-fluoro-N[6-(1-pyrrolidinylmethyl)-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide), which significantly inhibited the nocturnal food intake in rats after oral administration. Pharmacokinetic analysis confirmed that 2s had good oral bioavailability and brain penetrance. This antagonist appears to be a viable lead compound that can be used to develop a promising therapy for obesity. (C) 2011 Elsevier Ltd. All rights reserved.
• A new class of chiral smectic liquid crystals: substituted biphenylylcyclohexylidene ethanols having an axial chirality
  作者：Guy Solladie、Richard Zimmermann

  DOI：10.1021/jo00221a020

  日期：1985.10