4-phenyl-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)thiazole | 957754-13-1

• 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-phenyl-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)thiazole
• 英文别名: 4-phenyl-N-(1-pyridin-2-ylethylideneamino)-1,3-thiazol-2-amine
• CAS: 957754-13-1
• 化学式: C₁₆H₁₄N₄S
• 分子量: 294.38
• InChiKey: YNPDCRSCSRUBQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-乙酰基吡啶 在 溶剂黄146 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 4-phenyl-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)thiazole
  参考文献：
  名称：

  肼基芳基噻唑基吡啶支架：合成，结构表征，体外α-葡萄糖苷酶抑制活性和计算机研究

  摘要：

  阿卡波糖，米格列醇和伏格列波糖是α-葡萄糖苷酶的抑制剂，并在临床上用于II型糖尿病的治疗。但是，许多不利影响也与之相关。因此，开发新的治疗剂是药物化学研究的最大兴趣。当前的研究是基于新α-葡萄糖苷酶抑制剂的鉴定。为此，通过两步反应合成了基于肼基芳基噻唑的吡啶衍生物1–39，并通过光谱技术EI-MS，HREI-MS，1 H-和13 C NMR进行了全面表征。然而，NOESY证实了亚胺键的立体化学。所有化合物均经过体外α葡萄糖苷酶抑制活性，并发现有源很多倍（IC 50  = 1.40±0.01-236.10±2.20  μ M）相比，具有IC的标准阿卡波糖50的856.45±5.60值 μ M的限定的结构-活性关系是为了推测取代基对抑制活性的影响而进行的实验，预测与负诱导作用较小的取代基相比，负诱导作用较大的取代基在活性中起重要作用。但是，为了更好地了解配体酶的相互作用，还进行了分子对接研究。

  DOI：

  10.1016/j.ejmech.2017.06.041

文献信息

• Exploring 4-substituted-2-thiazolylhydrazones from 2-, 3-, and 4-acetylpyridine as selective and reversible hMAO-B inhibitors
  作者：Paola Chimenti、Anél Petzer、Simone Carradori、Melissa D’Ascenzio、Romano Silvestri、Stefano Alcaro、Francesco Ortuso、Jacobus P. Petzer、Daniela Secci

  DOI：10.1016/j.ejmech.2013.05.032

  日期：2013.8

  A series of 4-substituted-2-thiazolylhydrazone derivatives have been synthesized and tested in vitro for their human monoamine oxidase (hMAO) A and B inhibitory activity. Our findings confirmed that the substitution at C4 of the thiazole ring was important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Moreover, these derivatives were endowed with a reversible mechanism of enzyme inhibition. Molecular modelling studies were performed to rationalize the recognition of all inhibitors with respect to hMAO-A and -B isoforms. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Study of in vitro biological activity of thiazoles on Leishmania (Leishmania) infantum
  作者：Vinícius Vasconcelos Gomes de Oliveira、Mary Angela Aranda de Souza、Rafaela Ramos Mororó Cavalcanti、Marcos Veríssimo de Oliveira Cardoso、Ana Cristina Lima Leite、Valdemiro Amaro da Silva Junior、Regina Célia Bressan Queiroz de Figueiredo

  DOI：10.1016/j.jgar.2020.02.028

  日期：2020.9

  Objectives: In the prospection of possible agents against neglected diseases, thiazole compounds are presented as promising candidates and are known to have activity against trypanosomatid parasites. Thus, this work aimed to evaluate the effects of thiazole compounds on Leishmania infantum, the aetiological agent of visceral leishmaniasis.Methods: Thiazole compounds (five thiazoacetylpyridines [TAPs-01, -04, -05, -06, -09) and five thiazopyridines [TPs-01, -04, -05, -06, -09]) were tested regarding their leishmanicidal activity on both promastigote and amastigote forms of L. infantum. Cytotoxicity was tested using peritoneal macrophages of BALB/c mice. Ultrastructural analyses were performed to identify possible intracellular targets of the most effective compound on promastigote forms. To observe routes that can clarify the possible mechanism of action of the compounds on the intracellular amastigote forms, the nitrite dosage was performed.Results: All compounds inhibited the growth of promastigote and presented low cytotoxicity, being more selective to the parasite than to mammalian cells. All compounds tested were able to decrease macrophage infection. There was a significant decrease in the survival rate of the amastigote when compared with the untreated cells, with TAP-04 presenting the best index. TAP-04 induced ultrastructural changes that are related to cell death by apoptosis. None of the macrophage groups infected with L. infantum and subsequently treated showed increased nitrite release.Conclusions: The low toxicity to mammalian cells and the leishmanicidal activity observed demonstrate that the synthesis of drugs based in thiosemicarbazone nucleus, thiazole and pyridine derivatives are promising for the treatment of visceral leishmaniasis. (C) 2020 The Authors. Published by Elsevier Ltd on behalf of International Society for Antimicrobial Chemotherapy.
• Hydrazinyl arylthiazole based pyridine scaffolds: Synthesis, structural characterization, in vitro α-glucosidase inhibitory activity, and in silico studies
  作者：Farman Ali、Khalid Mohammed Khan、Uzma Salar、Muhammad Taha、Nor Hadiani Ismail、Abdul Wadood、Muhammad Riaz、Shahnaz Perveen

  DOI：10.1016/j.ejmech.2017.06.041

  日期：2017.9

  All compounds were subjected to in vitro α-glucosidase inhibitory activity and found many folds active (IC50 = 1.40 ± 0.01–236.10 ± 2.20 μM) as compared to the standard acarbose having IC50 value of 856.45 ± 5.60 μM. A limited structure-activity relationship was carried out in order to make a presumption about the substituent's effect on inhibitory activity which predicted that substituents of more

  阿卡波糖，米格列醇和伏格列波糖是α-葡萄糖苷酶的抑制剂，并在临床上用于II型糖尿病的治疗。但是，许多不利影响也与之相关。因此，开发新的治疗剂是药物化学研究的最大兴趣。当前的研究是基于新α-葡萄糖苷酶抑制剂的鉴定。为此，通过两步反应合成了基于肼基芳基噻唑的吡啶衍生物1–39，并通过光谱技术EI-MS，HREI-MS，1 H-和13 C NMR进行了全面表征。然而，NOESY证实了亚胺键的立体化学。所有化合物均经过体外α葡萄糖苷酶抑制活性，并发现有源很多倍（IC 50  = 1.40±0.01-236.10±2.20  μ M）相比，具有IC的标准阿卡波糖50的856.45±5.60值 μ M的限定的结构-活性关系是为了推测取代基对抑制活性的影响而进行的实验，预测与负诱导作用较小的取代基相比，负诱导作用较大的取代基在活性中起重要作用。但是，为了更好地了解配体酶的相互作用，还进行了分子对接研究。