4-[4-(2-Chloroethyl)phenyl]-5-methyl-1,3-thiazol-2-amine | 250210-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[4-(2-Chloroethyl)phenyl]-5-methyl-1,3-thiazol-2-amine
• CAS: 250210-21-0
• 化学式: C₁₂H₁₃ClN₂S
• 分子量: 252.768
• InChiKey: CXATZVWCSAGSIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[4-(2-Chloroethyl)phenyl]-5-methyl-1,3-thiazol-2-amine 、 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78%的产率得到5-methyl-4-{4-[2-(4-(quinoxalin-2-yl)piperazin-1-yl)ethyl]phenyl}thiazol-2-amine
  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， 以 二氯甲烷 、 丙酮 为溶剂， 生成 4-[4-(2-Chloroethyl)phenyl]-5-methyl-1,3-thiazol-2-amine
  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

文献信息

• 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.
• Design, synthesis, and preliminary <i>in vitro</i> and <i>in vivo</i> 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
  作者：Kondapalli Venkata Gowri Chandra Sekhar、Vajja Samabasiva Rao、Winnie Deuther-Conrad、Aravalli Satish Reddy、Peter Brust、Mutyala Murali Krishna Kumar

  DOI：10.3109/14756366.2010.537658

  日期：2011.8.1

  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.
• 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
  作者：Kondapalli Venkata Gowri Chandra Sekhar、Vajja Sambasiva Rao、Winnie Deuther-Conrad、Divya Sridhar、Hunsur Nagendra Nagesh、Vellas Sreedhar Kumar、Peter Brust、Muthyala Murali Krishna Kumar

  DOI：10.1007/s00044-012-0164-1

  日期：2013.4

  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.