4,5-二(4-氯苯基)-1,3-噻唑-2-胺 | 89405-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4,5-二(4-氯苯基)-1,3-噻唑-2-胺
• 英文名称: 4,5-bis-(4-chlorophenyl)-2-aminothiazole
• 英文别名: 4,5-bis(4-chlorophenyl)thiazol-2-ylamine；4,5-Bis(4-chlorophenyl)-1,3-thiazol-2-amine
• CAS: 89405-45-8
• 化学式: C₁₅H₁₀Cl₂N₂S
• 分子量: 321.23
• InChiKey: JKYJLVSUKREJNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4,5-二(4-氯苯基)-1,3-噻唑-2-胺 在 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 1-(2-methylbenzyl)-N-[4,5-bis(4-chlorophenyl)thiazol-2-yl]-piperidine-4-carboxamide
  参考文献：
  名称：

  Benzylpiperidine-Linked Diarylthiazoles as Potential Anti-Alzheimer’s Agents: Synthesis and Biological Evaluation

  摘要：

  A novel series of hybrid molecules were designed and synthesized by fusing the pharmacophoric features of cholinesterase inhibitor donepezil and diarylthiazole as potential multitarget-directed ligands for the treatment of Alzheimer's disease (AD). The compounds showed significant in vitro anticholinesterase (anti-ChE) activity, the most potent compound (44) among them showing the highest activity (IC50 value of 0.30 +/- 0.01 mu M) for AChE and (1.84 +/- 0.03 mu M) for BuChE. Compound 44 showed mixed inhibition of AChE in the enzyme kinetic studies. Some compounds exhibited moderate to high inhibition of AChE-induced A beta(1-42) aggregation and noticeable in vitro antioxidant and antiapoptotic properties. Compound 44 showed significant in vivo anti-ChE and antioxidant activities. Furthermore, compound 44 demonstrated in vivo neuroprotection by decreasing A beta(1-42)-induced toxicity by attenuating abnormal levels of A beta(1-42), p-Tau, cleaved caspase-3, and cleaved PARP proteins. Compound 44 exhibited good oral absorption and was well tolerated up to 2000 mg/kg, po, dose without showing toxic effects.

  DOI：

  10.1021/acs.jmedchem.6b00426
• 作为产物：
  描述：

  1,2-双(4-氯苯基)-2-羟基乙酮 在 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 4,5-二(4-氯苯基)-1,3-噻唑-2-胺
  参考文献：
  名称：

  Dash; Patra; Mahapatra, Journal of the Indian Chemical Society, 1983, vol. 60, # 8, p. 772 - 774

  摘要：

  DOI：

文献信息

• Dash, B.; Patra, M.; Mohapatra, P. K., Journal of the Indian Chemical Society, 1985, vol. 62, # 6, p. 460 - 464
  作者：Dash, B.、Patra, M.、Mohapatra, P. K.

  DOI：——

  日期：——
• Dash; Mahapatra; Panda, Journal of the Indian Chemical Society, 1984, vol. 61, # 11-12, p. 1061 - 1064
  作者：Dash、Mahapatra、Panda、Pattnaik

  DOI：——

  日期：——
• DASH, B.;PATRA, M.;MOHAPATRA, P. K., J. INDIAN CHEM. SOC., 1985, 62, N 6, 460-464
  作者：DASH, B.、PATRA, M.、MOHAPATRA, P. K.

  DOI：——

  日期：——
• DASH, B.;MOHAPATRA, P. K., J. INST. CHEM. (INDIA), 1984, 56, N 1, 11-14
  作者：DASH, B.、MOHAPATRA, P. K.

  DOI：——

  日期：——
• Benzylpiperidine-Linked Diarylthiazoles as Potential Anti-Alzheimer’s Agents: Synthesis and Biological Evaluation
  作者：Mahesh Shidore、Jatin Machhi、Kaushik Shingala、Prashant Murumkar、Mayank Kumar Sharma、Neetesh Agrawal、Ashutosh Tripathi、Zalak Parikh、Prakash Pillai、Mange Ram Yadav

  DOI：10.1021/acs.jmedchem.6b00426

  日期：2016.6.23

  A novel series of hybrid molecules were designed and synthesized by fusing the pharmacophoric features of cholinesterase inhibitor donepezil and diarylthiazole as potential multitarget-directed ligands for the treatment of Alzheimer's disease (AD). The compounds showed significant in vitro anticholinesterase (anti-ChE) activity, the most potent compound (44) among them showing the highest activity (IC50 value of 0.30 +/- 0.01 mu M) for AChE and (1.84 +/- 0.03 mu M) for BuChE. Compound 44 showed mixed inhibition of AChE in the enzyme kinetic studies. Some compounds exhibited moderate to high inhibition of AChE-induced A beta(1-42) aggregation and noticeable in vitro antioxidant and antiapoptotic properties. Compound 44 showed significant in vivo anti-ChE and antioxidant activities. Furthermore, compound 44 demonstrated in vivo neuroprotection by decreasing A beta(1-42)-induced toxicity by attenuating abnormal levels of A beta(1-42), p-Tau, cleaved caspase-3, and cleaved PARP proteins. Compound 44 exhibited good oral absorption and was well tolerated up to 2000 mg/kg, po, dose without showing toxic effects.