[(4'-cyano-1,1'-biphenyl-4-yl)oxy]butyric acid | 191228-84-9

• 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-yl)oxy]butyric acid
• 英文别名: 4-[4-(4-cyanophenyl)phenoxy]butanoic acid；4-(4'-cyanobiphenyl-4-yloxy)butyric acid
• CAS: 191228-84-9
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: VVJXIHILLDWWOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  [(4'-cyano-1,1'-biphenyl-4-yl)oxy]butyric acid 在 N-甲基吗啉 、 氯化亚砜 、 盐酸羟胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 4-[4-(4-cyanophenyl)phenoxy]butanohydroxamic acid
  参考文献：
  名称：

  Discovery of Potent Nonpeptide Inhibitors of Stromelysin Using SAR by NMR

  摘要：

  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.

  DOI：

  10.1021/ja9702778
• 作为产物：
  描述：

  氰基联苯酚 在 氢氧化钾 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 甲醇 、 丁酮 为溶剂， 反应 0.08h， 生成 [(4'-cyano-1,1'-biphenyl-4-yl)oxy]butyric acid
  参考文献：
  名称：

  Formation of smectic and columnar liquid crystalline phases by cyclotriveratrylene (CTV) and cyclotetraveratrylene (CTTV) derivatives incorporating calamitic structural units

  摘要：

  新型的液晶寡聚介质，由五个、六个或八个 calamitic 4-氰基联苯、2-烷基-5-苯基-1,3,4-噻二唑或5-辛基-2-苯基嘧啶单元通过不同长度的间隔基与一个环三苯基中心核(CTV衍生物,2,3,7,8,12,13-六取代的10,15-二氢-5H-三苯并[a,d,g]环壬烯)或一个环四苯基中心核(CTTV衍生物,2,3,6,7,10,11,14,15-八取代的5,10,15,20-四氢四苯并[a,d,g,j]环十二碳四烯)共价连接而成，已被合成。这些化合物通过偏光显微镜、差示扫描量热法进行研究，其中一些还通过X射线衍射进行了研究。许多CTV衍生物显示出液晶性质。含长间隔基单元的氰基联苯衍生物具有固-液同质相(SA相)，可以很容易地过冷。噻二唑衍生物和嘧啶衍生物只有在间隔基单元相当短时才具有液晶相。噻二唑衍生物在CTV核与calamitic介质之间具有奇数连接原子时形成SA相，而具有偶数间隔基的噻二唑衍生物则显示柱状液晶相。我们提出，这些寡聚介质观察到的柱状液晶相并非因其能形成近似圆盘状的形态，而是代表带状相，这是由中心锥状核和棒状介质基团的不同空间填充引起的立体障碍造成的。假定具有偶数间隔基的分子呈现类似曲折(香蕉状)的平均形状，是形成带状相的原因。此外，一个具有八个附加苯基噻二唑介质的CTTV衍生物显示柱状液晶相。相应的氰基联苯衍生物发现有向列相，而嘧啶衍生物则不具有液晶性。

  DOI：

  10.1039/a702034a

文献信息

• Formation of smectic and columnar liquid crystalline phases by cyclotriveratrylene (CTV) and cyclotetraveratrylene (CTTV) derivatives incorporating calamitic structural units
  作者：Ralph Lunkwitz、Carsten Tschierske、Siegmar Diele

  DOI：10.1039/a702034a

  日期：——

  Novel liquid crystalline oligomesogens, which consist of five, six or eight calamitic 4-cyanobiphenyl, 2-alkyl-5-phenyl-1,3,4-thiadiazole or 5-octyl-2-phenylpyrimidine units covalently linked by spacers of different length with a cyclotribenzylene central core (CTV derivatives, 2,3,7,8,12,13-hexa-substituted 10,15-dihydro-5H-tribenzo[a,d,g]cyclononenes) or a cyclotetrabenzylene central core (CTTV derivatives, 2,3,6,7,10,11,14,15-octa-substituted 5,10,15,20-tetrahydrotetrabenzo[a,d,g,j]cyclododecenes) have been synthesized. These compounds were investigated by polarizing microscopy, differential scanning calorimetry and some of them were also studied by X-ray diffraction. Many of the CTV derivatives show liquid crystalline properties. The cyanobiphenyl derivatives incorporating long spacer units have enantiotropic SA phases which can easily be supercooled. The thiadiazole derivatives and the pyrimidine derivatives have liquid crystalline phases only if the spacer units are rather short. Thiadiazole derivatives with an odd number of connecting atoms between the CTV core and the calamitic mesogens form SA phases, whereas those with even-numbered spacers display columnar mesophases. We propose that the columnar mesophases observed for these oligomesogens do not result from their ability to adopt a nearly disc-like shape. Instead, they represent ribbon phases which result from a steric frustration caused by the different space filling of the central cone-like core and the rod-like mesogenic groups. A chevron-like (banana-like) average shape of the molecules with even-numbered spacers is assumed to be responsible for the formation of the ribbon phases.Also a CTTV derivative with eight appended phenylthiadiazole mesogens displays a columnar mesophase. A nematic phase was found for the corresponding cyanobiphenyl derivative, whereas the pyrimidine derivative is not liquid crystalline.

  新型的液晶寡聚介质，由五个、六个或八个 calamitic 4-氰基联苯、2-烷基-5-苯基-1,3,4-噻二唑或5-辛基-2-苯基嘧啶单元通过不同长度的间隔基与一个环三苯基中心核(CTV衍生物,2,3,7,8,12,13-六取代的10,15-二氢-5H-三苯并[a,d,g]环壬烯)或一个环四苯基中心核(CTTV衍生物,2,3,6,7,10,11,14,15-八取代的5,10,15,20-四氢四苯并[a,d,g,j]环十二碳四烯)共价连接而成，已被合成。这些化合物通过偏光显微镜、差示扫描量热法进行研究，其中一些还通过X射线衍射进行了研究。许多CTV衍生物显示出液晶性质。含长间隔基单元的氰基联苯衍生物具有固-液同质相(SA相)，可以很容易地过冷。噻二唑衍生物和嘧啶衍生物只有在间隔基单元相当短时才具有液晶相。噻二唑衍生物在CTV核与calamitic介质之间具有奇数连接原子时形成SA相，而具有偶数间隔基的噻二唑衍生物则显示柱状液晶相。我们提出，这些寡聚介质观察到的柱状液晶相并非因其能形成近似圆盘状的形态，而是代表带状相，这是由中心锥状核和棒状介质基团的不同空间填充引起的立体障碍造成的。假定具有偶数间隔基的分子呈现类似曲折(香蕉状)的平均形状，是形成带状相的原因。此外，一个具有八个附加苯基噻二唑介质的CTTV衍生物显示柱状液晶相。相应的氰基联苯衍生物发现有向列相，而嘧啶衍生物则不具有液晶性。
• 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。
• Polypeptide protracting tags
  申请人：Dorwald Florencio Zaragoza

  公开号：US20090111730A1

  公开（公告）日：2009-04-30

  Method for increasing (protracting) half-life of LGP analogs in plasma and novel derivatives of such peptides based on covalently linking them to a tetrazole moiety which acts as a carboxylic acid bioisostere.

  一种增加LGP类似物在血浆中半衰期的方法以及基于共价连接到四唑基团的新型衍生物，该四唑基团作为羧酸生物异构体。