5-(4-ethoxyphenyl)-[1,3,4]thiadiazol-2-ylamine | 247225-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-ethoxyphenyl)-[1,3,4]thiadiazol-2-ylamine
• 英文别名: 5-(4-ethoxyphenyl)-1,3,4-thiadiazol-2-amine
• CAS: 247225-35-0
• 化学式: C₁₀H₁₁N₃OS
• 分子量: 221.283
• InChiKey: IJWTVHRMEPWMSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  5-(4-ethoxyphenyl)-[1,3,4]thiadiazol-2-ylamine 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 19.5h， 生成 3-[2-(4-ethoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]aniline
  参考文献：
  名称：

  Design, synthesis and antiproliferative activity of novel heterobivalent hybrids based on imidazo[2,1- b ][1,3,4]thiadiazole and imidazo[2,1- b ][1,3]thiazole scaffolds

  摘要：

  Heterobivalent ligands constituted by two different pharmacophores that bind to different molecular targets or to two distinct sites on the same molecular target could be one of the methods used for the treatment of cancer. In view of the importance of imidazo[1,2-6][1,3]thiazole and imidazo[1,2-b][1,3,4] thiadiazole as privileged structures for the preparation of novel anticancer agents, we decided to explore the synthesis and biological evaluation of molecular conjugates comprising these fused bicyclic systems tethered at their C-6 position by a meta-(alpha-bromoacryloylamido)phenyl moiety. We found that most of the hybrid compounds displayed high antiproliferative activity toward a wide panel of cancer cell lines, with one-digit micromolar to submicromolar 50% inhibitory concentrations (IC50). We have observed that selected compounds 7d, 7e, 7n and 8c induced apoptosis, which was associated with the release of cytochrome c and cleavage of multiple caspases. Overexpression of the protective mitochondrial protein Bcl-2 did not confer protection to cell death induced by these compounds. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.042
• 作为产物：
  描述：

  对羟基苯甲酸 在 potassium hydroxide 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 5-(4-ethoxyphenyl)-[1,3,4]thiadiazol-2-ylamine
  参考文献：
  名称：

  Synthesis and Mesomorphic Properties of New Columnar Liquid Crystal Containing 1,3,5-triiminebenzene with Pendant 1,3,4-thiadiazole Group

  摘要：

  A novel discotic liquid crystal series based on 1,3,5-benzenetrisazomethine derivatives with three pendant 2-amino-5-(4'-n-alkoxy) phenyl-1,3,4-thiadiazole has been synthesized, which is the first columnar molecules containing 1,3,4-thiadiazole moiety exhibiting a discotic liquid crystal. The molecular structure of compounds was confirmed by FT-IR, H-1-NMR, and mass spectroscopy and elemental analysis. The electron excitation properties of these compounds were investigated by UV-vis absorption spectroscopy. Their liquid crystalline properties were studied by polarizing optical microscopy and differential scanning calorimetry. The formation of a columnar mesophase was found to be dependent on the number of methylene unit in alkoxy side chains.

  DOI：

  10.1080/15421406.2013.864546

文献信息

• N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings as novel antibacterial agents: Design, synthesis, biological evaluation and target identification
  作者：Wenjie Xue、Xueyao Li、Guixing Ma、Hongmin Zhang、Ya Chen、Johannes Kirchmair、Jie Xia、Song Wu

  DOI：10.1016/j.ejmech.2019.112022

  日期：2020.2

  new class of antibacterial agents, as one of its derivatives was identified as an antibacterial agent against S. aureus. However, no potency-directed structural optimization has been performed. In this study, we designed and synthesized 37 derivatives, and evaluated their antibacterial activity against S. aureus ATCC29213, which led to the identification of ten potent antibacterial agents with minimum

  由于发生抗生素抗性，细菌感染性疾病已成为对公共健康的严重威胁。为了克服抗生素抗性，迫切需要新型抗生素。N-噻二唑-4-羟基-2-喹诺酮-3-羧酰胺是一类潜在的新型抗菌剂，因为其衍生物之一被确定为针对金黄色葡萄球菌的抗菌剂。但是，尚未执行效能导向的结构优化。在这项研究中，我们设计和合成了37种衍生物，并评估了它们对金黄色葡萄球菌ATCC29213的抗菌活性，从而鉴定出十种有效抑菌剂，其最低抑菌浓度（MIC）值均低于1μg/ mL。接下来，我们针对一组抗药性临床分离株进行了细菌生长抑制测定，包括耐甲氧西林的金黄色葡萄球菌，以及对HepG2和HUVEC细胞的细胞毒性测定。一种被测试的化合物，称为1-乙基-4-羟基-2-氧代-N-（5-（噻唑-2-基）-1,3,4-噻二唑-2-基）-1,2-二氢喹啉-与万古霉素相比，3-羧酰胺（g37）对被测菌株的抗菌力（MIC：0.25-1μg/ mL对1-64μg/
• Virtual Screening Identification of Nonfolate Compounds, Including a CNS Drug, as Antiparasitic Agents Inhibiting Pteridine Reductase
  作者：Stefania Ferrari、Federica Morandi、Domantas Motiejunas、Erika Nerini、Stefan Henrich、Rosaria Luciani、Alberto Venturelli、Sandra Lazzari、Samuele Calò、Shreedhara Gupta、Veronique Hannaert、Paul A. M. Michels、Rebecca C. Wade、M. Paola Costi

  DOI：10.1021/jm1010572

  日期：2011.1.13

  Folate analogue inhibitors of Leishmania major pteridine reductase (PTR1) are potential antiparasitic drug candidates for combined therapy with dihydrofolate reductase (DHFR) inhibitors To identify new molecules with specificity for PTR1, we carried out a virtual screening of the Available Chemicals Directory (ACD) database to select compounds that could interact with L major PTR1 but not with human DHFR Through two rounds of drug discovery, we successfully identified eighteen drug-like molecule, with low micromolar affinities and high in vitro specificity profiles Their efficacy against Leishmania species was studied in cultured cells of the promastigote stage, using the compounds both alone and in combination with 1 (pyrimethamine, 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine) Six compounds showed efficacy only in combination In toxicity tests against human fibroblasts, several compounds showed low toxicity One compound, 5c (riluzole, 6-(trifluoromethoxy)-1,3-benzothiazol-2-ylamine,), a known drug approved for CNS pathologies, was active in combination and is suitable for early preclinical evaluation of its potential for label extension as a PTR1 inhibitor and antiparasitic drug candidate