4-<4-(2-chloroethyl)phenyl>thiazol-2-one | 117922-88-0

• 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-<4-(2-chloroethyl)phenyl>thiazol-2-one
• 英文别名: 4-(4-(2-Chloroethyl)phenyl)thiazol-2-one；4-[4-(2-chloroethyl)phenyl]-3H-1,3-thiazol-2-one
• CAS: 117922-88-0
• 化学式: C₁₁H₁₀ClNOS
• 分子量: 239.725
• InChiKey: BOQVSBOOMDJUEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-<4-(2-chloroethyl)phenyl>thiazol-2-one 、 2-哌嗪-1-基-喹噁啉 在 sodium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以71%的产率得到4-{4-[2-(4-(quinoxalin-2-yl)piperazin-1-yl)ethyl]phenyl}thiazol-2-ol
  参考文献：
  名称：

  Design, synthesis, and preliminary in vitro and in vivo pharmacological evaluation of 4-{4-[2-(4-(2-substitutedquinoxalin-3-yl)piperazin-1-yl)ethyl]phenyl}thiazoles as atypical antipsychotic agents

  摘要：

  A series of 4-{4-[2-(4-(2-substitutedquinoxalin-3-yl)piperazin-1-yl)ethyl] phenyl} thiazoles were synthesized in an effort to prepare novel atypical antipsychotic agents. The compounds were designed, synthesized, and characterized by spectral data (IR, H-1 NMR, and MS) and the purity was ascertained by microanalysis. The D-2 and 5-HT2A affinity of the synthesized compounds was screened in vitro by radioligand displacement assays on membrane homogenates isolated from rat striatum and rat cortex, respectively. Furthermore, all the synthesized final compounds (10a-g; 11a-g; 12a-g) were screened for their in vivo pharmacological activity in Swiss albino mice. D-2 antagonism studies were performed using climbing mouse assay model and 5-HT2A antagonism studies were performed using quipazine-induced head twitches in mice. It was observed that none of the new chemical entities exhibited catalepsy and 12d, 11f, and 10a were found to be the most active compounds with 5-HT2A/D-2 ratio of 1.23077, 1.14286, and 1.12857, respectively, while the standard drug risperidone exhibited 5-HT2A/D-2 ratio of 1.0989. Among the twenty one new chemical entities, three compounds (12d, 11f, and 10a) were found to exhibit better atypical antipsychotic activity as they were found to have higher Meltzer index than the standard drug risperidone.

  DOI：

  10.1007/s00044-012-0164-1
• 作为产物：
  描述：

  邻氯乙苯 在 aluminum (III) chloride 作用下， 生成 4-<4-(2-chloroethyl)phenyl>thiazol-2-one
  参考文献：
  名称：

  Design, synthesis, and preliminary in vitro and in vivo pharmacological evaluation of 2-{4-[4-(2,5-disubstituted thiazol-4-yl)phenylethyl]piperazin-1-yl}-1,8-naphthyridine-3-carbonitriles as atypical antipsychotic agents

  摘要：

  A series of 2-{4-[4-(2,5-disubstituted thiazolyl) phenylethyl] piperazin-1-yl}-1,8-naphthyridine-3-carbonitriles were synthesized in an effort to prepare novel atypical antipsychotic agents. The compounds were synthesized either by microwave irradiation technique or by conventional synthesis and were characterized by spectral data (IR, H-1 NMR, and MS) and the purity was ascertained by microanalysis. The D-2 and 5-HT2A affinity of the synthesized compounds was screened in vitro by radioligand displacement assays on membrane homogenates isolated from rat striatum and rat cortex, respectively. Furthermore, all the synthesized compounds were screened for their in vivo pharmacological activity in Swiss albino mice. The D-2 antagonism studies were performed using climbing mouse assay model and 5-HT2A antagonism studies were performed using quipazine-induced head twitches in mice. It was observed that none of the new chemical entities exhibited catalepsy and 10f is the most active among the synthesized compounds with 5-HT2A/D-2 ratio of 1.1286 although the standard drug risperidone exhibited 5-HT2A/D-2 ratio of 1.0989.

  DOI：

  10.3109/14756366.2010.537658

文献信息

• Arylpiperazinyl-alkylene-phenyl-heterocyclic compounds
  申请人：Pfizer Inc.

  公开号：US04891375A1

  公开（公告）日：1990-01-02

  Arylpiperazinyl-alkylenephenyl-p-heterocyclic compounds, and the pharmaceutically acceptable acid addition salts thereof are neuroleptic agents. They are useful in the treatment of psychotic disorders.

  芳基哌嗪基-烷基苯基-p-杂环化合物及其药用可接受的酸盐是神经阻滞剂。它们在治疗精神疾病中很有用。
• Synthesis and preliminary pharmacological investigations of 1-(1,2-dihydro-2-acenaphthylenyl)piperazine derivatives as potential atypical antipsychotic agents in mice
  作者：P Srinivas、A.R Subramanian、P Brust、S.A.V Raghavan、J.B Rangisetty、C.N.V.H.B Gupta、N Sridhar、A Veeranjaneyulu、P Parimoo

  DOI：10.1016/s0014-827x(99)00058-0

  日期：1999.8

  antipsychotic agents, one strategy is that the dopaminergic system can be modulated through manipulation of the serotonergic system. The synthesis and preliminary pharmacological evaluation of a series of potential atypical antipsychotic agents based on the structure of 1-(1,2-dihydro-2-acenaphthylenyl)piperazine (7) is described. Compound 7e, 5-2-[4-(1,2-dihydro-2-acenaphthylenyl)piperazinyl]ethyl}-2

  在开发新的非典型抗精神病药的研究中，一种策略是可以通过操纵血清素能系统来调节多巴胺能系统。描述了基于1-（1,2-二氢-2-ac烯基）哌嗪（7）结构的一系列潜在的非典型抗精神病药的合成和初步药理学评估。来自该系列的化合物7e，5- 2- [4-（1,2-二氢-2-ac烯基）哌嗪基]乙基} -2,3-二氢dro-1H-吲哚-2-酮在5-HT1A和5-HT2A受体对D2受体的亲和力适中。7e表现出由氟哌啶醇引起的僵直症的高度逆转，表明其非典型的抗精神病药性。
• Synthesis and preliminary pharmacological evaluation of N-2-(4-(4-(2-substitutedthiazol-4-yl) piperazin-1-yl)-2-oxoethyl)acetamides as novel atypical antipsychotic agents
  作者：K.V.G. Chandra Sekhar、V.S. Rao、Devambatla Ravi Kumar Vyas、M. Murali Krishna Kumar

  DOI：10.1016/j.bmcl.2008.10.035

  日期：2008.12

  A series of N-2-(4-(4-(2-substitutedthiazol-4-yl) piperazin-1-yl)-2-oxoethyl)acetamides were synthesized in an effort to prepare novel atypical antipsychotic agents. The compounds were synthesized by either microwave irradiation technique or by conventional synthesis and were characterized by spectral data (IR, H-1 NMR, and MS) and the purity was ascertained by microanalysis. All the synthesized compounds were screened for their in vivo pharmacological activity in Swiss albino mice. D-2 antagonism studies were performed using climbing mouse assay model and 5-HT2A antagonism studies were performed using quipazine induced head twitches in mice. It was observed that none of the new chemical entities exhibited catalepsy. AG 3 was found to be the most active compound. (C) 2008 Elsevier Ltd. All rights reserved.
• 1-Naphthylpiperazine derivatives as potential atypical antipsychotic agents
  作者：John A. Lowe、Thomas F. Seeger、Arthur A. Nagel、Harry R. Howard、Patricia A. Seymour、James H. Heym、Frank E. Ewing、Michael E. Newman、Anne W. Schmidt

  DOI：10.1021/jm00110a016

  日期：1991.6

  The design and synthesis of a series of potential atypical antipsychotic agents based on the structure of 1-naphthylpiperazine are described. The incorporation of dopamine antagonist activity into the parent structure was achieved with heterocyclic surrogates for the catechol moiety of dopamine. Compound 4b from this series showed a biochemical profile that translated to behavioral activity in the rat predictive of an antipsychotic agent with a low propensity to cause extrapyramidal side effects in man.
• US4891375A
  申请人：——

  公开号：US4891375A

  公开（公告）日：1990-01-02