2-{4-[4-(5-methyl-2-(methylamino)thiazol-4-yl)phenethyl]piperazin-1-yl}-1,8-naphthyridine-3-carbonitrile | 1316314-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-{4-[4-(5-methyl-2-(methylamino)thiazol-4-yl)phenethyl]piperazin-1-yl}-1,8-naphthyridine-3-carbonitrile
• 英文别名: 2-[4-[2-[4-[5-Methyl-2-(methylamino)-1,3-thiazol-4-yl]phenyl]ethyl]piperazin-1-yl]-1,8-naphthyridine-3-carbonitrile
• CAS: 1316314-98-3
• 化学式: C₂₆H₂₇N₇S
• 分子量: 469.613
• InChiKey: CLTWMQRXALTGMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  邻氯乙苯 在 aluminum (III) chloride 、 sodium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 2-{4-[4-(5-methyl-2-(methylamino)thiazol-4-yl)phenethyl]piperazin-1-yl}-1,8-naphthyridine-3-carbonitrile
  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

• 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.