5-(4'-cyanobiphenyl-4-yloxy)pentanoic acid | 164929-09-3

• 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: 5-(4'-cyanobiphenyl-4-yloxy)pentanoic acid
• 英文别名: [(4'-cyano-1,1'-biphenyl-4-yl)oxy]valeric acid；5-(4-(4-cyanophenyl)phenoxy)pentanoic acid；5-[4-(4-cyanophenyl)phenoxy]pentanoic acid
• CAS: 164929-09-3
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: AQQWRBMYPWZPJA-UHFFFAOYSA-N

物化性质

• 沸点：
  530.0±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4'-cyanobiphenyl-4-yloxy)pentanoic acid 在 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  An enthalpic basis of additivity in biphenyl hydroxamic acid ligands for stromelysin-1

  摘要：

  Fragment based drug discovery remains a successful tool for pharmaceutical lead discovery. Although based upon the principle of thermodynamic additivity, the underlying thermodynamic basis is poorly understood. A thermodynamic additivity analysis was performed using stromelysin-1 and a series of biphenyl hydroxamate ligands identified through fragment additivity. Our studies suggest that, in this instance, additivity arises from enthalpic effects, while interaction entropies are unfavorable; this thermodynamic behavior is masked by proton transfer. Evaluation of the changes in constant pressure heat capacities during binding suggest that solvent exclusion from the binding site does not account for the dramatic affinity enhancements observed. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.032
• 作为产物：
  描述：

  5-溴戊酸乙酯 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-(4'-cyanobiphenyl-4-yloxy)pentanoic acid
  参考文献：
  名称：

  Synthesis and Phase Behavior of Side-Group Liquid Crystalline Polymers in Nematic Solvents

  摘要：

  A model system of side-group liquid crystalline polymers (SGLCPs) with systematically varied molecular weight (from 78 to 420 kg/mol; PDI less than or equal to 1.16) and spacer length (8-12 atoms long) was prepared by polymer analogous synthesis. Matching the structure of the mesogenic units to that of the nematic solvent produced excellent solubility, even at molecular weights an order of magnitude greater than in prior literature on SGLCP solutions. Addition of up to 10 wt % polymer did not affect the ordinary and extraordinary refractive indices of the nematic host (4-pentyl-4'-cyanobiphenyl, 5CB), indicating that the order parameter was not significantly affected by the polymer.

  DOI：

  10.1021/ma0348268

文献信息

• Liquid-crystalline heterodimesogens and ABA-heterotrimesogens comprising a bent 3,5-diphenyl-1,2,4-oxadiazole central unit
  作者：Govindaswamy Shanker、Marko Prehm、Carsten Tschierske

  DOI：10.3762/bjoc.8.54

  日期：——

  dimesogens exhibit broad ranges of cybotactic nematic phases (N(cybA) and N(cybC)), in some cases accompanied by additional mesophases (CybA or SmC) at lower temperature. The combination of the 3,5-diphenyl-1,2,4-oxadiazole unit with one cyanobiphenyl core leads to the removal of tilted smectic and cybotactic nematic phases (SmC, N(cybC)), which are replaced by the nontilted CybA phases and nematic phases composed

  三种新型末端连接的ABA-异三聚体和异二聚体，由弯曲的3,5-二苯基-1,2,4-恶二唑中心单元和一或两个棒状4-氰基联苯核或一个2-苯基-1组成，合成了由柔性间隔物连接的 3,4-噻二唑核，并通过光学偏光显微镜 (PM)、差示扫描量热法 (DSC) 和 X 射线衍射 (XRD) 研究了它们的介晶行为。所有 dimesogens 都表现出广泛的细胞内向列相（N(cybA) 和 N(cybC)），在某些情况下，在较低温度下还伴有额外的中间相（CybA 或 SmC）。3,5-二苯基-1,2,4-恶二唑单元与一个氰基联苯核的组合导致倾斜的近晶相和胞内相向列相（SmC，N（cybC））的去除，它们被非倾斜的 CybA 相和由 SmA 型簇 (N(cybA)) 组成的向列相取代。弯曲核介晶的正交晶胞向列相对于实现正交型双轴向列相特别感兴趣。XRD 和光学观察区分了正交 (N(cybA)) 和偏斜 (N(cybC))
• Alkylenedioxythiophenes and poly(alkylenedioxythiophenes) containing mesogenic groups
  申请人：——

  公开号：US20040227128A1

  公开（公告）日：2004-11-18

  The invention relates to new 3,4-alkylenedioxythiophenes which are substituted with mesogenic groups, if desired via a bridging group, and their polymeric derivatives (poly-(3,4-alkylenedioxythiophenes)).

  本发明涉及新的3,4-烷基二氧硫杂苯，其被取代为介向基团，如果需要可以通过桥接基团进行，以及它们的聚合物衍生物（聚（3,4-烷基二氧硫杂苯））。
• Biphenyl hydroxamate inhibitors of matrix metalloproteinases
  申请人：Abbott Laboratories

  公开号：US05665777A1

  公开（公告）日：1997-09-09

  Compounds of formula ##STR1## or a pharmaceutically acceptable salt thereof inhibit matrix metalloproteinases and TNF.alpha. secretion and are useful in the treatment of inflammatory disease states. Also disclosed are matrix metalloproteinases and TNF.alpha. secretion inhibiting compositions and a method for inhibiting matrix metalloproteinases and TNF.alpha. secretion.

  式为##STR1##的化合物或其药学上可接受的盐，能够抑制基质金属蛋白酶和TNFα分泌，对治疗炎症性疾病状态有用。还揭示了基质金属蛋白酶和TNFα分泌抑制组合物以及抑制基质金属蛋白酶和TNFα分泌的方法。
• Alkylendioxythiophene und Poly(alkylendioxythiophene) mit mesogenen Gruppen
  申请人：Bayer Chemicals AG

  公开号：EP1440974A2

  公开（公告）日：2004-07-28

  Die Erfindung betrifft neue 3,4-Alkylendioxythiophene gegebenenfalls über ein Bindeglied substituiert mit mesogenen Gruppen und deren polymere Derivate (Poly-(3,4-alkylendioxythiophene)).

  本发明涉及新型 3,4-亚烷基二氧噻吩，可选择通过连接构件被中原基团取代，以及它们的聚合衍生物（聚（3,4-亚烷基二氧噻吩））。
• Discovery of Potent Nonpeptide Inhibitors of Stromelysin Using SAR by NMR
  作者：P. J. Hajduk、G. Sheppard、D. G. Nettesheim、E. T. Olejniczak、S. B. Shuker、R. P. Meadows、D. H. Steinman、G. M. Carrera、P. A. Marcotte、J. Severin、K. Walter、H. Smith、E. Gubbins、R. Simmer、T. F. Holzman、D. W. Morgan、S. K. Davidsen、J. B. Summers、S. W. Fesik

  DOI：10.1021/ja9702778

  日期：1997.6.1

  With the use of an NMR-based method, potent (IC50 < 25 nM) nonpeptide inhibitors of the matrix metalloproteinase stromelysin (MMP-3) were discovered. The method, called SAR by NMR (for structure-activity relationships by nuclear magnetic resonance), involves the identification, optimization, and linking of compounds that bind to proximal sites on a protein. Using this technique, two ligands that bind weakly to stromelysin (acetohydroxamic acid, K-D = 17 mM; 3-(cyanomethyl)-4'-hydroxybiphenyl, K-D = 0.02 mM) were identified. On the basis of NMR-derived structural information, the two fragments were connected to produce a 15 nM inhibitor of this enzyme. This compound was rapidly discovered (less than 6 months) and required only a minimal amount of chemical synthesis. These studies indicate that the SAR by NMR method can be effectively applied to enzymes to yield potent lead inhibitors-an important part of the drug discovery process.