4-carboxybenzylidene-4-chloroaniline | 3939-35-3

• 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-carboxybenzylidene-4-chloroaniline
• 英文别名: 4-Chlor-N-<4-carboxy-benzyliden>-anilin；4-Chlor-N-(4-carboxy-benzyliden)-anilin；4-[(4-Chlorophenyl)iminomethyl]benzoic acid
• CAS: 3939-35-3
• 化学式: C₁₄H₁₀ClNO₂
• 分子量: 259.692
• InChiKey: VJMFMCHWBCLVMR-UHFFFAOYSA-N

物化性质

• 熔点：
  264 °C
• 沸点：
  446.4±30.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-carboxybenzylidene-4-chloroaniline 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以26.8 g的产率得到4-[(4-chlorophenylamino)methyl]benzoic acid
  参考文献：
  名称：

  Human Glucagon Receptor Antagonists with Thiazole Cores. A Novel Series with Superior Pharmacokinetic Properties

  摘要：

  The aim of the work presented here was to design and synthesize potent human glucagon receptor antagonists with improved pharmacokinetic (PK) properties for development of pharmaceuticals for the treatment of type 2 diabetes. We describe the preparation of compounds with cyclic cores (5-aminothiazoles), their binding affinities for the human glucagon and GIP receptors, as well as affinities for rat, mouse, pig, dog, and monkey glucagon receptors. Generally, the compounds had slightly less glucagon receptor affinity compared to compounds of the previous series, but this was compensated for by much improved PK profiles in both rats and dogs with high oral bioavailabilities and sustained high plasma exposures. The compounds generally showed species selectivity for glucagon receptor binding with poor affinities for the rat, mouse, rabbit, and pig receptors. However, dog and monkey glucagon receptor affinities seem to reflect the human situation. One compound of this series, 18, was tested intravenously in an anesthetized glucagon-challenged monkey model of hyperglucagonaemia and hyperglycaemia and was shown dose-dependently to decrease glycaemia. Further, high plasma exposures and a long plasma half-life (5.2 h) were obtained.

  DOI：

  10.1021/jm8016249
• 作为产物：
  描述：

  对氯苯胺 、 对醛基苯甲酸 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以69%的产率得到4-carboxybenzylidene-4-chloroaniline
  参考文献：
  名称：

  氢键和甲亚胺基团取向对苄叉苯胺化合物液晶性能的影响

  摘要：

  这项研究研究了取代基和氢键，亚胺键的取向对亚苄基苯胺化合物作为液晶的行为的影响。通过苯胺及其取代的衍生物与4-甲酰基苯甲酸反应，合成了化合物4-羧基亚苄基-4-X-苯胺（X = H，F，Cl，Br，CH 3，OCH 3）1a-6a。苯甲醛及其取代的衍生物与4-氨基苯甲酸的无水乙醇反应，合成了化合物4-X-亚苄基-4-羧基苯胺（X = H，F，Cl，Br，CH 3，OCH 3）1b-6b作为溶剂。通过FT IR和1 H NMR光谱对合成的化合物进行表征，使用差示扫描量热法（DSC）和偏振光学显微镜（POM）技术研究液晶性能。根据介晶性质，已证明化合物2b-4b是双晶的，具有近晶相和向列相，化合物5b，6b是单晶的，具有向列相，而化合物1a-6a和1b没有显示出中间相。对于化合物1a – 6a的氢键结合和亚胺键的反转（与化合物1b – 6b相比）导致其介晶特性不存在。

  DOI：

  10.17344/acsi.2019.5648

文献信息

• The Effect of Hydrogen Bonding and Azomethine Group Orientation on Liquid Crystal Properties in Benzylidene Aniline Compounds
  作者：Abdullah Hussein Kshash

  DOI：10.17344/acsi.2019.5648

  日期：——

  behavior of benzylidene aniline compounds as liquid crystals (LC). Compounds 4-carboxy benzylidene-4-X-aniline (X = H, F, Cl, Br, CH 3 , OCH 3 ) 1a – 6a were synthesized by the reaction of aniline and its substituted derivatives with 4-formylbenzoic acid. Compounds 4-X-benzylidene-4-carboxy aniline (X = H, F, Cl, Br, CH 3 , OCH 3 ) 1b – 6b were synthesized by the reaction of benzaldehyde and its substituted

  这项研究研究了取代基和氢键，亚胺键的取向对亚苄基苯胺化合物作为液晶的行为的影响。通过苯胺及其取代的衍生物与4-甲酰基苯甲酸反应，合成了化合物4-羧基亚苄基-4-X-苯胺（X = H，F，Cl，Br，CH 3，OCH 3）1a-6a。苯甲醛及其取代的衍生物与4-氨基苯甲酸的无水乙醇反应，合成了化合物4-X-亚苄基-4-羧基苯胺（X = H，F，Cl，Br，CH 3，OCH 3）1b-6b作为溶剂。通过FT IR和1 H NMR光谱对合成的化合物进行表征，使用差示扫描量热法（DSC）和偏振光学显微镜（POM）技术研究液晶性能。根据介晶性质，已证明化合物2b-4b是双晶的，具有近晶相和向列相，化合物5b，6b是单晶的，具有向列相，而化合物1a-6a和1b没有显示出中间相。对于化合物1a – 6a的氢键结合和亚胺键的反转（与化合物1b – 6b相比）导致其介晶特性不存在。
• Human Glucagon Receptor Antagonists with Thiazole Cores. A Novel Series with Superior Pharmacokinetic Properties
  作者：Peter Madsen、János T. Kodra、Carsten Behrens、Erica Nishimura、Claus B. Jeppesen、Lone Pridal、Birgitte Andersen、Lotte B. Knudsen、Carmen Valcarce-Aspegren、Mette Guldbrandt、Inge T. Christensen、Anker S. Jørgensen、Lars Ynddal、Christian L. Brand、Morten Aa. Bagger、Jesper Lau

  DOI：10.1021/jm8016249

  日期：2009.5.14

  The aim of the work presented here was to design and synthesize potent human glucagon receptor antagonists with improved pharmacokinetic (PK) properties for development of pharmaceuticals for the treatment of type 2 diabetes. We describe the preparation of compounds with cyclic cores (5-aminothiazoles), their binding affinities for the human glucagon and GIP receptors, as well as affinities for rat, mouse, pig, dog, and monkey glucagon receptors. Generally, the compounds had slightly less glucagon receptor affinity compared to compounds of the previous series, but this was compensated for by much improved PK profiles in both rats and dogs with high oral bioavailabilities and sustained high plasma exposures. The compounds generally showed species selectivity for glucagon receptor binding with poor affinities for the rat, mouse, rabbit, and pig receptors. However, dog and monkey glucagon receptor affinities seem to reflect the human situation. One compound of this series, 18, was tested intravenously in an anesthetized glucagon-challenged monkey model of hyperglucagonaemia and hyperglycaemia and was shown dose-dependently to decrease glycaemia. Further, high plasma exposures and a long plasma half-life (5.2 h) were obtained.