2-Chloroacetamido-4-(2',5'-dimethoxy)phenylthiazole | 91402-37-8

• 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: 2-Chloroacetamido-4-(2',5'-dimethoxy)phenylthiazole
• 英文别名: 2-chloro-N-[4-(2,5-dimethoxyphenyl)-1,3-thiazol-2-yl]acetamide
• CAS: 91402-37-8
• 化学式: C₁₃H₁₃ClN₂O₃S
• mdl: MFCD04621532
• 分子量: 312.777
• InChiKey: VTOORQMYSUAQLB-UHFFFAOYSA-N

物化性质

• 熔点：
  142 °C(Solv: ethanol (64-17-5))
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Chloroacetamido-4-(2',5'-dimethoxy)phenylthiazole 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 反应 12.0h， 生成 2-sec-Butylamino-N-[4-(2,5-dimethoxy-phenyl)-thiazol-2-yl]-acetamide; hydrochloride
  参考文献：
  名称：

  Lakhan; Singh, Journal of the Indian Chemical Society, 1984, vol. 61, # 6, p. 526 - 529

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二甲氧基苯乙酮 在 碘 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 2-Chloroacetamido-4-(2',5'-dimethoxy)phenylthiazole
  参考文献：
  名称：

  Local anaesthetics. Part III. Local anaesthetic activity and synthesis of 2-(N-substituted or N,N-disubstituted aminoacetamido)-4-aryl thiazoles.

  摘要：

  一些新的2-(N取代或N,N双取代氨基乙酰氨基)-4-对硝基苯、4-邻硝基苯和4-(2',5'-二甲氧基)苯噻唑被合成。它们的盐酸盐通过青蛙坐骨神经丛法筛选局部麻醉活性，并与盐酸普鲁卡因的活性进行了比较。其中，2-(N取代氨基乙酰氨基)-4-邻硝基苯噻唑盐酸盐的活性最强：在麻醉起效时间上几乎是盐酸普鲁卡因的两倍。

  DOI：

  10.1271/bbb1961.48.1441

文献信息

• Local anaesthetics. Part III. Local anaesthetic activity and synthesis of 2-(N-substituted or N,N-disubstituted aminoacetamido)-4-aryl thiazoles.
  作者：Ram LAKHAN、Om Prakash SINGH

  DOI：10.1271/bbb1961.48.1441

  日期：——

  Some new 2-(N-substituted or N, N-disubstituted aminoacetamido)-4-p-nitrophenyl, 4-m-nitrophenyl and 4-(2', 5'-dimethoxy)phenyl thiazoles were synthesised. Their hydrochlorides were screened for local anaesthetic activity by Frog's sciatic plexus method and this activity compared with that of procaine hydrochloride. Among them, the 2-(N-substituted aminoacetamido)-4-m-nitrophenylthiazole hydrochlorides are the most potent: almost twice in terms of the onset of anaesthesia in comparison with procaine-HCl.

  一些新的2-(N取代或N,N双取代氨基乙酰氨基)-4-对硝基苯、4-邻硝基苯和4-(2',5'-二甲氧基)苯噻唑被合成。它们的盐酸盐通过青蛙坐骨神经丛法筛选局部麻醉活性，并与盐酸普鲁卡因的活性进行了比较。其中，2-(N取代氨基乙酰氨基)-4-邻硝基苯噻唑盐酸盐的活性最强：在麻醉起效时间上几乎是盐酸普鲁卡因的两倍。
• Synthesis of novel thiazoles bearing lupeol derivatives as potent anticancer and anti-inflammatory agents
  作者：Kummari Narendar、B. Sambasiva Rao、Satyakrishna Tirunavalli、Surender Singh Jadav、Sai Balaji Andugulapati、Vaikundamoorthy Ramalingam、K. Suresh Babu

  DOI：10.1080/14786419.2023.2166042

  日期：——

  terpenoids and possess excellent anticancer, anti-inflammatory, anti-diabetic activities etc. In the present study, the different thiazoles and oxazoles bearing lupeol derivatives were prepared to enhance their biological activity. Initially, the in vitro cytotoxic activity results showed that the synthesized lupeol derivatives (9a–9j and 10a–10e) showed significant activity against various cancer cells

   抽象的 羽扇豆醇是萜类化合物中最重要的代谢产物之一，具有优异的抗癌、抗炎、抗糖尿病等活性。本研究制备了带有羽扇豆醇衍生物的不同噻唑类和恶唑类化合物，以增强其生物活性。最初，体外细胞毒活性结果表明，合成的羽扇豆醇衍生物（ 9a-9j和10a-10e ）对多种癌细胞表现出显着的活性，化合物9h和10b对CAL27细胞表现出优异的活性。此外，这些化合物9h和10b将细胞周期阻滞在S期，并通过下调BcL2和波形蛋白表达以及上调Bax基因表达来诱导CAL27细胞的晚期细胞凋亡。此外，羽扇豆醇衍生物通过抑制 LPS 诱导的 Raw 264.7 细胞中 IL-6 细胞因子的分泌，表现出剂量依赖性抗炎活性。总之，这些结果清楚地表明带有羽扇豆醇衍生物的噻唑和恶唑可以用作针对癌症和炎症性疾病的化疗药物。
• LAKHAN, RAM;SINGH, OM, PRAKASH, J. INDIAN CHEM. SOC., 1984, 61, N 6700002/526-529, 526-529
  作者：LAKHAN, RAM、SINGH, OM, PRAKASH

  DOI：——

  日期：——
• Lakhan; Singh, Journal of the Indian Chemical Society, 1984, vol. 61, # 6, p. 526 - 529
  作者：Lakhan、Singh

  DOI：——

  日期：——
• Synthesis and Evaluation of Aminothiazole Hybrids as Potential Acetylcholinesterase Inhibitors
  作者：Arti Soni、Ashwani Kumar、Vivek Kumar、Ravi Rawat、Volkan Eyupoglu

  DOI：10.14233/ajchem.2024.31241

  日期：——

  This study aimed to synthesize aminothiazole derivatives with 1,3,4-oxadiazole moiety and evaluated their acetylcholinesterase (AChE) and antioxidant activity in order to check their potency against Alzheimer's disease. Inhibition screening against AChE indicated that  synthesized derivatives expressed well to moderate AChE inhibitory activity in vitro. Of the examined synthetic compounds (3a-i), compound 3d expressed the best inhibition with IC50-0.35 µM. The antioxidant activity of all the synthesized compounds was also  analyzed by the DPPH assay. Finally, in molecular docking analysis, the best docking score was displayed by the most active compound  3d supported the in vitro inhibition results. Compound 3d emerged to be promising lead for the further development of anti- Alzheimer’s drugs.