4-bromo-4'-[(tert-butyldimethylsilyl)oxy]biphenyl | 116934-63-5

• 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-bromo-4'-[(tert-butyldimethylsilyl)oxy]biphenyl
• 英文别名: 4-bromo-4'-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,1'-biphenyl；((4'-bromo-[1,1'-biphenyl]-4-yl)oxy)(tert-butyl)dimethylsilane；4'-bromo-4-(t-butyl dimethylsiloxy)biphenyl；4-Bromo-4'-(tert-butyldimethylsilyloxy)biphenyl；[4-(4-bromophenyl)phenoxy]-tert-butyl-dimethylsilane
• CAS: 116934-63-5
• 化学式: C₁₈H₂₃BrOSi
• 分子量: 363.37
• InChiKey: NTIMUJCWXCWLNK-UHFFFAOYSA-N

物化性质

• 沸点：
  377.0±25.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-4'-[(tert-butyldimethylsilyl)oxy]biphenyl 在 仲丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 环己烷 、 甲苯 为溶剂， 反应 10.08h， 生成 4'-(1-Aza-bicyclo[2.2.2]oct-2-en-3-yl)-biphenyl-4-ol
  参考文献：
  名称：

  Biphenylquinuclidines as inhibitors of squalene synthase and growth of parasitic protozoa

  摘要：

  In this paper we describe the preparation of some biphenylquinuclidine derivatives and their evaluation as inhibitors of squalene synthase in order to explore their potential in the treatment of the parasitic diseases leishmaniasis and Chagas disease. The compounds were screened against recombinant Leishmania major squalene synthase and against Leishmania mexicana promastigotes, Leishmania donovani intracellular amastigotes and Trypanosoma cruzi intracellular amastigotes. Compounds that inhibited the enzyme, also reduced the levels of steroids and caused growth inhibition of L. mexicana promastigotes. However there was a lower correlation between inhibition of the enzyme and growth inhibition of the intracellular parasites, possibly due to delivery problems. Some compounds also showed growth inhibition of T brucei rhodesiense trypomastigotes, although in this case alternative modes of action other than inhibition of SQS are probably involved. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.060
• 作为产物：
  描述：

  4-羟基-4'-溴联苯 、 叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以96%的产率得到4-bromo-4'-[(tert-butyldimethylsilyl)oxy]biphenyl
  参考文献：
  名称：

  C-Aryl glucoside SGLT2 inhibitors containing a biphenyl motif as potential anti-diabetic agents

  摘要：

  A series of highly active C-aryl glucoside SGLT2 inhibitors containing a biphenyl motif were designed and synthesized for biological evaluation. Among the compounds tested, compound 16l demonstrated high inhibitory activity against SGLT2 (IC50 = 1.9 nM) with an excellent pharmacokinetic profile. Further study indicated that the in vivo efficacy of compound 16l was comparable to that of dapagliflozin, suggesting that further development would be worthwhile. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.040

文献信息

• Synthesis and Activity of a Novel Series of 3-Biarylquinuclidine Squalene Synthase Inhibitors
  作者：George R. Brown、David S. Clarke、Alan J. Foubister、Susan Freeman、Peter J. Harrison、Michael C. Johnson、Keith B. Mallion、John McCormick、Fergus McTaggart、Alan C. Reid、Graham J. Smith、Melvyn J. Taylor

  DOI：10.1021/jm950907l

  日期：1996.1.1

  Quinuclidines with a 3-biaryl substituent are a new class of potent, orally active squalene synthase (SQS) inhibitors. Variants around these rigid structures indicate key structural requirements for cationic SQS inhibitors. Thus the lower in vitro potency found for quinuclidines bearing 3-substituents, which did not overlay the biphenyl group of 3-(biphenyl-4-yl)-3-hydroxyquinuclidine (2) (IC50 = 16

  具有3-联芳基取代基的喹核苷是一类新的有效的，口服活性的角鲨烯合酶（SQS）抑制剂。这些刚性结构周围的变化指示出阳离子SQS抑制剂的关键结构要求。因此，暗示了带有3个取代基的喹核苷的体外效价较低，该奎尼啶没有覆盖3-（联苯基-4-基）-3-羟基喹核苷（2）的联苯基团（IC50 = 16 nM，大鼠微粒体SQS）。 3取代基的方向性要求。类似地，3-三联苯类似物6的较低效能（IC50 = 370 nM）表明该取代基的尺寸受到限制。在具有奎宁环和联苯环之间连接基团的化合物中，亲脂性较低的连接基团的耐受性较差（例如，17，CH2CH2，IC50 = 5 nM与19，NHCO，IC50 = 1.2 microM）。用更具极性的吡啶杂环取代2的远端苯环会导致体外效能降低。通常，大鼠体内的良好体内活性仅限于3-羟基类似物，其中3- [4-（吡啶-4-基）苯基]衍生物39（IC50 = 161 nM）显示出最佳的抑制作用（口服给药后）
• Silacyclohexane compounds, preparation thereof, liquid crystal
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US06004478A1

  公开（公告）日：1999-12-21

  A silacyclohexane compound of the formulas (I) ##STR1## wherein R represents an organic residue, ##STR2## represents an unsubstituted or substituted silicon-containing cyclohexylene group or a 1,4-cyclohexylene group, ##STR3## represents an unsubstituted or substituted phenylene, an unsubstituted or substituted silicon-containing cyclohexylene group or trans-4-sila-1,4-cyclohexylene group, or a 1,4-cyclohexylene group provided that at least one of these residues represents a silicon-containing cyclohexylene group, j, k and l are, respectively, 0 or 1, L.sub.1 and L.sub.2, respectively, represent H or F, m and n are, respectively, 0, 1 or 2 provided that m+n=2, 3 or 4, and X represents H, F or Cl. A liquid crystal composition comprising the silacyclohexane compound of the above formula is also described, along with a liquid crystal device comprising the composition.

  化学式（I）的硅环己烷化合物##STR1##其中R代表有机残基，##STR2##代表未取代或取代的含硅环己基团或1,4-环己基团，##STR3##代表未取代或取代的苯基、未取代或取代的含硅环己基团或反-4-硅-1,4-环己基团，或1,4-环己基团，其中至少一个这些残基代表含硅环己基团，j、k和l分别为0或1，L.sub.1和L.sub.2分别代表H或F，m和n分别为0、1或2，但要求m+n=2、3或4，X代表H、F或Cl。还描述了包括上述化学式的硅环己烷化合物的液晶组合物，以及包括该组合物的液晶器件。
• Biphenyl quinuclidines
  申请人：Zeneca Limited

  公开号：US05792777A1

  公开（公告）日：1998-08-11

  Biphenylylquinuclidine compounds of the formula I: ##STR1## and pharmaceutically-acceptable salts thereof; wherein R.sup.1 is hydrogen or hydroxy; R.sup.2 is hydrogen; or R.sup.1 and R.sup.2 are joined together so that CR.sup.1 -CR.sup.2 is a double bond; and one or both ring A and ring B may be optionally unsubstituted or independently substituted by one or more substituents selected from halogeno, hydroxy, amino, nitro, cyano, carboxy, carbamoyl, (1-6C)alkyl, (1-6C)alkoxy, (1-6C)alkylamino, di-\x9b(1-6C)alkyl!amino, N-\x9b(1-6C)alkyl!carbamoyl, N,N-di-\x9b(1-6C)alkyl!carbamoyl, (1-6C)alkoxycarbonyl, (1-6C)alkylthio, (1-6C)alkylsulphinyl, (1-6C)alkylsulphonyl and halogeno-(1-6C)alkyl; are inhibitors of squalene synthase and are hence useful in treating diseases or medical conditions such as hypercholesterolemia, atherosclerosis and fungal diseases. Methods of using these compounds to treat such conditions, novel compounds, processes for making these compounds and pharmaceutical compositions containing them are claimed.

  苯基喹啉化合物的化学式 I：##STR1## 及其药用可接受的盐；其中 R.sup.1 为氢或羟基；R.sup.2 为氢；或 R.sup.1 和 R.sup.2 结合在一起，使得 CR.sup.1 -CR.sup.2 为双键；环 A 和/或环 B 可能是未取代的，也可以独立地被一个或多个卤素、羟基、氨基、硝基、氰基、羧基、氨甲酰基、(1-6C)烷基、(1-6C)烷氧基、(1-6C)烷基氨基、二-(1-6C)烷基氨基、N-(1-6C)烷基)氨甲酰基、N,N-二-(1-6C)烷基)氨甲酰基、(1-6C)烷氧羰基、(1-6C)烷基硫醚基、(1-6C)烷基磺氧基、(1-6C)烷基磺酰基和卤素-(1-6C)烷基取代；这些化合物是角鲨烯合成酶的抑制剂，因此在治疗高胆固醇血症、动脉粥样硬化和真菌病等疾病或医疗状况中有用。声明了使用这些化合物治疗这些疾病的方法、新化合物、制备这些化合物的方法以及含有它们的药物组合物。
• 17-Beta-hydroxysteroid dehydrogenase-II inhibitors
  申请人：——

  公开号：US20030087952A1

  公开（公告）日：2003-05-08

  17-beta-hydroxysteroid dehydrogenase-I1 inhibitors having the structural formula 1 wherein the phenyl group labeled A and the group —C(R 4 )(R 6 )Y are oriented cis to each other; W represents 0 or S; R 1 represents —H or optionally substituted —(C 1 -C 4 )alkyl; n represents 0 or an integer of 1-3; and R 2 represents any of a variety of substituents on ring A. R 4 generally represents —H but may be a bond terminating at the ortho position of ring A. Y represents fluorine, —OR 5 , or —SR 5 , and R 5 represents —H. optionally substituted —(C 1 -C 4 )alkyl, optionally substituted -phenyl, optionally substituted —(C 1 -C 4 )alkyl-phenyl, or optionally substituted —(C 1 -C 4 )acyl. R 6 represents any of a variety of groups as defined in the specification and claims, including heteroaryl, arylalkyl, heteroarylalkyl, arylalkenyl, heteroarylalkenyl, alkynyl, arylalkynyl, heteroarylalkynyl, aryl, and indolyl. Pharmaceutically acceptable salts and N-oxides of these materials are also included. Also claimed are pharmaceutical compositions containing these materials and methods of using them.

  具有结构式1的17-β-羟基类固醇脱氢酶I1抑制剂，其中被标记为A的苯基和—C（R4）（R6）Y基团相互顺式取向；W表示0或S；R1表示—H或可选取代的—（C1-C4）烷基；n表示0或1-3的整数；R2表示环A上各种取代基中的任何一种。R4通常表示—H，但可以是终止于环A的邻位的键。Y表示氟，—OR5或—SR5，其中R5表示—H，可选取代的—（C1-C4）烷基，可选取代的苯基，可选取代的—（C1-C4）烷基苯基或可选取代的—（C1-C4）酰基。R6表示规范和权利要求书中定义的各种基团，包括杂环芳基，芳基烷基，杂环芳基烷基，芳基烯基，杂环芳基烯基，炔基，芳基炔基，杂环芳基炔基，芳基和吲哚基。还包括这些材料的药学上可接受的盐和N-氧化物。还声明了含有这些材料的制药组合物和使用它们的方法。
• 17-beta-hydroxysteroid dehydrogenase-II inhibitors
  申请人：Bayer Pharmaceuticals Corporation

  公开号：US06784167B2

  公开（公告）日：2004-08-31

  17-beta-hydroxysteroid dehydrogenase-II inhibitors having the structural formula wherein the phenyl group labeled A and the group —C(R4)(R6)Y are oriented cis to each other; W represents O or S; R1 represents —H or optionally substituted —(C1-C4)alkyl; n represents 0 or an integer of 1-3; and R2 represents any of a variety of substituents on ring A. R4 generally represents —H but may be a bond terminating at the ortho position of ring A. Y represents fluorine, —OR5, or —SR5, and R5 represents —H, optionally substituted —(C1-C4)alkyl, optionally substituted -phenyl, optionally substituted —(C1-C4)alkyl-phenyl, or optionally substituted —(C1-C4)acyl. R6 represents any of a variety of groups as defined in the specification and claims, including heteroaryl, arylalkyl, heteroarylalkyl, arylalkenyl, heteroarylalkenyl, alkynyl, arylalkynyl, heteroarylalkynyl, aryl, and indolyl. Pharmaceutically acceptable salts and N-oxides of these materials are also included. Also claimed are pharmaceutical compositions containing these materials and methods of using them.

  具有以下结构式的17-beta-羟基类固醇脱氢酶-II抑制剂，其中标记为A的苯基和群体—C（R4）（R6）Y定向为顺式构型；W代表O或S；R1代表—H或可选取代的—（C1-C4）烷基；n代表0或1-3的整数；R2代表环A上的各种取代基。R4通常代表—H，但可能是终止于环A的邻位的键。Y代表氟，—OR5或—SR5，R5代表—H，可选取代的—（C1-C4）烷基，可选取代的苯基，可选取代的—（C1-C4）烷基-苯基或可选取代的—（C1-C4）酰基。R6代表规范和权利要求中定义的各种群体，包括杂环芳基，芳基烷基，杂环芳基烷基，芳基烯基，杂环芳基烯基，炔基，芳基炔基，杂环芳基炔基，芳基和吲哚基。还包括这些材料的药学上可接受的盐和N-氧化物。还声明了含有这些材料的制药组合物和使用它们的方法。