4-ethoxycarbonylphenoxy-(4'-chlorophenyl)-methane | 56441-54-4

• 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-ethoxycarbonylphenoxy-(4'-chlorophenyl)-methane
• 英文别名: ethyl 4-(4'-chlorobenzyloxy)benzoate；4-(4-Chlorbenzyloxy)-benzoesaeureaethylester；Ethyl 4-[(4-chlorobenzyl)oxy]benzoate；ethyl 4-[(4-chlorophenyl)methoxy]benzoate
• CAS: 56441-54-4
• 化学式: C₁₆H₁₅ClO₃
• mdl: MFCD28101793
• 分子量: 290.746
• InChiKey: SPWPPXQXMUOYDD-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C(Solv: ethanol (64-17-5))
• 沸点：
  412.0±25.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-ethoxycarbonylphenoxy-(4'-chlorophenyl)-methane 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 4-((4-chlorobenzyl)oxy)benzohydrazide
  参考文献：
  名称：

  Synthesis and Anticonvulsant Activity Evaluation of 4-butyl-5-(4- alkoxyphenyl)-2H-1,2,4-triazole-3(4H)-ones

  摘要：

  设计并合成了一系列4-丁基-5-(4-烷氧基苯基)-2H-1,2,4-三唑-3(4H)-酮(6a-6u)，并通过最大电击试验和旋转体试验评估了这些化合物的抗惊厥作用和神经毒性。在合成的化合物中，4-丁基-5-(4-(2-氟苄基)苯基)-2H-1,2,4-三唑-3 (4H)-酮（6k）的药效最强，ED50 值为 27.4 mg/kg，保护指数（PI = TD50/ED50）值为 12.0。除了抗 MES 的药效外，化合物 6k 对戊烯四唑（PTZ）、3-巯基丙酸（3-MP）和双谷氨酸（BIC）诱导的癫痫发作也有很强的抑制作用，这表明其抗惊厥活性可能涉及包括增强 GABA 能活性在内的作用机制。

  DOI：

  10.2174/1570180810666131122003939
• 作为产物：
  描述：

  4-氯苯甲酸乙酯 生成 4-ethoxycarbonylphenoxy-(4'-chlorophenyl)-methane
  参考文献：
  名称：

  WEBER, KARL-HEINZ;STRANSKY, WERNER;WALTHER, GERHARD;KUFNER-MUHL, ULRIKE;H+

  摘要：

  DOI：

文献信息

• Phenyl alkyleneoxy phenyl alkanoic acid esters
  申请人：Beecham Group Limited

  公开号：US03983164A1

  公开（公告）日：1976-09-28

  Pharmaceutical compositions having hypolipidaemic and/or hypoglycaemic activity, contain a substituted (4-carboxyphenoxy) phenyl alkane derivative.

  具有降脂和/或降糖活性的药物组合物，包含一种取代的（4-羧基苯氧基）苯基烷衍生物。
• Substituted (4-carboxyphenoxy) phenyl alkane compounds
  申请人：Beecham Group Limited

  公开号：US04067892A1

  公开（公告）日：1978-01-10

  Pharmaceutical compositions having hypolipidaemic and/or hypoglycaemic activity, contain a substituted (4-carboxyphenoxy) phenyl alkane derivative.

  具有降脂和/或降血糖活性的药物组合物，包含一种取代的（4-羧基苯氧基）苯基烷衍生物。
• Polycyclic oxy-aromatic acid
  申请人：Beecham Group Limited

  公开号：US04098816A1

  公开（公告）日：1978-07-04

  Pharmaceutical compositions having hypolipidaemic and/or hypoglycaemic activity, contain a substituted (4-carboxyphenoxy) phenyl alkane derivative.

  具有降脂和/或降糖活性的药物组合物，包含一种取代的（4-羧基苯氧基）苯基烷衍生物。
• 5-[4-(Benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives and related analogs: new reversible, highly potent, and selective monoamine oxidase type B inhibitors
  作者：Fathi Mazouz、Salah Gueddari、Claude Burstein、Daniel Mansuy、Rene Milcent

  DOI：10.1021/jm00061a006

  日期：1993.4

  Thirty-three new 5-[4-(benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives including related analogues, designed as inhibitors of monoamine oxidase type B (MAO B), were synthesized and investigated both in vitro and ex vivo for their abilities to inhibit selectively rat brain MAO B over MAO A. Three inhibitors were found to act as reversible, highly potent, and selective MAO B inhibitors, namely the nitrile derivative 5-[4-(benzyloxy)phenyl]-3-(2-cyanoethyl)-1,3,4-oxadiazol-2(3H)-one (12a) and two closely related homologues, the corresponding oxadiazolethione 13a and the alcohol 14b. Their IC50(MAO B) values are in the low nanomolar range of 1.4-4.6 nM and their selectivities, estimated by the ratio of IC50 values (A/B), are from 3200 to >71 400. Compound 12a exhibited the highest activity against MAO B. Its IC50 was evaluated to be 1.4 nM with a quasitotal selectivity (>71 400) toward this enzyme. In ex vivo studies, 12a showed a reversible and short duration of action. MAO B was markedly inhibited with the oral dose of 1 mg/kg without any alteration of MAO A, and the inhibition almost did not exceed 24 h. Its ED50 (1 h after oral administration) was evaluated to be 0.56 mg (1.7 mumol)/kg. Remarkably, MAO A was not affected at doses as high as 1500 mg/kg, po. In addition, no apparent toxicity or behavioral anomaly was observed during the treatment even at the maximum administrated dose. SAR studies emphasize the existence of three binding sites to the enzyme with a special importance of the terminal phenyl. Analysis of the inhibition kinetics indicated that 12a acts in a two-step mechanism as a competitive, slow, and tight-binding inhibitor of MAO B with a K(i) value of 0.22 muM and an overall K(i)* value at equilibrium of 0.7 nM.
• Hypolipidemic analogs of ethyl 4-benzyloxybenzoate
  作者：Keith H. Baggaley、Robin Fears、Richard M. Hindley、Brian Morgan、Elspeth Murrell、David E. Thorne

  DOI：10.1021/jm00221a007

  日期：1977.11

  A series of compounds related to ethyl 4-benzyloxybenzoate was synthesized and evaluated for potential hypolipidemic activity in rats. Structure--activity relationships are discussed in terms of cholesterol-lowering activity together with effects on weight gain and liver lipids. A number of the compounds inhibited cholesterol and free fatty acid biosynthesis from [1-14C]acetate in rat liver slices in vitro. Ethyl 4-benzyloxybenzoate, ethyl-4-benzyloxybenzoic acid, ethyl 4-p-bromobenzyloxybenzoates, and 4-o-methoxybenzyloxyphenyl acetate exhibited the most favorable spectrum of activity.