UCB 597 | 13877-96-8

• 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: UCB 597
• 英文别名: 1-phenyl-cyclohexanecarboxylic acid-[2-(2-diethylamino-ethoxy)-ethyl ester]；1-Phenyl-cyclohexancarbonsaeure-[2-(2-diaethylamino-aethoxy)-aethylester]；2-(2-diethylaminoethoxy)-ethyl-1-phenyl-1-cyclohexane carboxylate；1-Phenyl-cyclohexanecarboxylic acid 2-(2-diethylamino-ethoxy)-ethyl ester；2-[2-(diethylamino)ethoxy]ethyl 1-phenylcyclohexane-1-carboxylate
• CAS: 13877-96-8
• 化学式: C₂₁H₃₃NO₃
• 分子量: 347.498
• InChiKey: ONLSYSOUHYDKMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-苯基-1-环己羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 UCB 597
  参考文献：
  名称：

  Novel 1-phenylcycloalkanecarboxylic acid derivatives as potential anticonvulsant agents

  摘要：

  A series of analogues based on the anticonvulsant carbetapentane (1, 2-[2-(diethylamino)ethoxy]ethyl 1-phenyl-1-cyclopentylcarboxylate) was prepared as potential novel anticonvulsant drugs. Structure-activity relationships of analogues in which the ester function and cyclopentane moieties were modified have been investigated by evaluating their ability to prevent seizures in the rat maximal electroshock test. These compounds (11, ED50 = 16-mu-mol/kg; 12, ED50 = 86-mu-mol/kg, and 23, ED50 = 173-mu-mol/kg) were effective anticonvulsants. Compound 11, an alkyl ether derivative of 1, was more potent than the parent compound (ED50 = 48-mu-mol/kg) and also showed a 2-fold increase in potency compared to that of the prototypic anticonvulsant drug diphenylhydantoin.

  DOI：

  10.1021/jm00115a002

文献信息

• Organic esters of 2-(2-diethylaminoethoxy)-ethanol and their process of preparation
  申请人：UNION CHIMIQUE BELGE SA

  公开号：US02842585A1

  公开（公告）日：1958-07-08

  The invention comprises esters of the general formula wherein R is 1-phenyl-cyclopentyl, 1-phenyl-cyclohexyl, 4-phenyl-4-tetrahydropyranyl, 1-phenyl-cyclopropyl, diphenylmethyl, phenyl-cyclohexyl - methyl, phenyl - (2 - thenyl)-methyl, phenyl - furfuryl - methyl, or 1-(alpha - cyclohexyl - p - methoxybenzyl) - 4-piperazinyl, and their hydrochlorides and acid citrates; and their preparation by esterification of 2 - (21 - diethylaminoethoxy) - ethanol with either the appropriate carboxylic acid halide RCOHal, with or without the use of a hydrogen chloride acceptor, or the methyl or ethyl ester of the appropriate carboxylic acid RCOOH. It is stated that other methods of esterification may be used. Salts are prepared by reacting the esters with either hydrogen chloride or citric acid in a medium such as ether or acetone. In examples, which describe the preparation of all of the above esters, the first of the above esterification methods is carried out in boiling toluene or boiling pyridine and the second by adding sodium to the reaction components of which the amino alcohol is in excess and distilling off the methanol or ethanol formed together with the excess amino alcohol. The products are useful as spasmolytics. Methyl-phenyl-furfuryl-acetate is obtained from furfuryl chloride and the sodium salt of phenyl acetonitrile followed by saponification of the phenyl-furfuryl-acetonitrile and esterification of the carboxyl group with excess of diazomethane in an ethereal medium. Ethyl - 1 - (alpha - cyclohexyl - p - methoxybenzyl) - 4 - piperazine - carboxylate is obtained from monocarbethoxy-piperazine and alphacyclohexyl-p-methoxy benzyl chloride.

  该发明涉及一般式的酯，其中R为1-苯基-环戊基，1-苯基-环己基，4-苯基-4-四氢吡喃基，1-苯基-环丙基，二苯甲基，苯基-环己基-甲基，苯基-（2-苯基乙基）-甲基，苯基-呋喃甲基，或1-（α-环己基-p-甲氧基苯基）-4-哌嗪基及其盐酸盐和柠檬酸盐；它们通过将2-（21-二乙氨基乙氧基）乙醇与适当的羧酸卤化物RCOHal酯化而成，有或没有使用氢氯酸受体，或适当羧酸RCOOH的甲酯或乙酯。据称可以使用其他酯化方法。盐通过将酯与氢氯酸或柠檬酸在乙醚或丙酮等介质中反应制备。在描述上述所有酯制备的示例中，第一种酯化方法在沸腾甲苯或沸腾吡啶中进行，第二种方法是在反应组分中加入钠，其中氨基醇过量，并蒸馏出与过量氨基醇一起形成的甲醇或乙醇。这些产品可用作平滑肌松弛剂。从呋喃基氯化物和苯基乙腈的钠盐中获得甲基苯基呋喃基乙酸酯，然后皂化苯基呋喃基乙腈并在乙醚介质中使用过量的重氮甲烷酯化羧基。从单羧乙酰哌嗪和α-环己基-p-甲氧基苯基氯化物中获得乙基-1-（α-环己基-p-甲氧基苯基）-4-哌嗪基羧酸酯。
• Novel 1-phenylcycloalkanecarboxylic acid derivatives as potential anticonvulsant agents
  作者：Silvia N. Calderon、Amy Hauck Newman、Frank C. Tortella

  DOI：10.1021/jm00115a002

  日期：1991.11

  A series of analogues based on the anticonvulsant carbetapentane (1, 2-[2-(diethylamino)ethoxy]ethyl 1-phenyl-1-cyclopentylcarboxylate) was prepared as potential novel anticonvulsant drugs. Structure-activity relationships of analogues in which the ester function and cyclopentane moieties were modified have been investigated by evaluating their ability to prevent seizures in the rat maximal electroshock test. These compounds (11, ED50 = 16-mu-mol/kg; 12, ED50 = 86-mu-mol/kg, and 23, ED50 = 173-mu-mol/kg) were effective anticonvulsants. Compound 11, an alkyl ether derivative of 1, was more potent than the parent compound (ED50 = 48-mu-mol/kg) and also showed a 2-fold increase in potency compared to that of the prototypic anticonvulsant drug diphenylhydantoin.