2-氯-1-[4-(2-氯乙基)苯基]乙酮 | 129865-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氯-1-[4-(2-氯乙基)苯基]乙酮
• 英文名称: 2-Chloro-1-[4-(2-chloroethyl)phenyl]ethanone
• CAS: 129865-49-2
• 化学式: C₁₀H₁₀Cl₂O
• 分子量: 217.095
• InChiKey: QLYFKDQYNRUTND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-氯-1-[4-(2-氯乙基)苯基]乙酮 在 sodium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 48.0h， 生成 4-{4-[2-(4-(2-methoxyquinoxalin-3-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 、 氯乙酰氯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 2-氯-1-[4-(2-氯乙基)苯基]乙酮
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.10.035

文献信息

• Design, synthesis and antimycobacterial evaluation of 1-(4-(2-substitutedthiazol-4-yl)phenethyl)-4-(3-(4-substitutedpiperazin-1-yl)alkyl)piperazine hybrid analogues
  作者：Hunsur Nagendra Nagesh、Amaroju Suresh、Sirigina Devesh Sathya Sri Sairam、Dharmarajan Sriram、Perumal Yogeeswari、Kondapalli Venkata Gowri Chandra Sekhar

  DOI：10.1016/j.ejmech.2014.07.067

  日期：2014.9

  A series of twenty six new 1-(4-(2-substitutedthiazol-4-yl)phenethyl)-4-(3-(4-substitutedpiperazin-1-yl)alkyl)piperazine analogues were synthesized by seven steps and evaluated for their anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain. Among the tested compounds, 7j, 7p, and 7r exhibited moderate activity (MIC = 6.25 μg/mL) and compounds 7a, 7f, 7g, 7n and 7v exhibited good activity (MIC = 3.125 μg/mL), while 7h displayed excellent activity (MIC = 1.56 μg/mL) by inhibiting 99% growth of M. tuberculosis H37Rv strain. In addition, all the active compounds were subjected to cytotoxic studies against mouse macrophage (RAW264.7) cell lines and the selectivity index values for most of the compounds is >10 indicating suitability of compounds in an endeavour to attain lead molecule for further drug development.
• 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.
• 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 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.