5-(3-methoxybenzyl)-1,3,4-thiadiazol-2-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(3-methoxybenzyl)-1,3,4-thiadiazol-2-amine
• 英文别名: 5-[(3-Methoxyphenyl)methyl]-1,3,4-thiadiazol-2-amine
• 化学式: C₁₀H₁₁N₃OS
• mdl: MFCD02664081
• 分子量: 221.283
• InChiKey: ZCGKFLJMXCVTPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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

反应信息

• 作为反应物：
  描述：

  5-(3-methoxybenzyl)-1,3,4-thiadiazol-2-amine 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 19.5h， 生成 3-[2-(3-methoxybenzyl)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：

  3-甲氧基苯乙酸 、 氨基硫脲 在 三氯氧磷 作用下， 以 水 为溶剂， 生成 5-(3-methoxybenzyl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  作为碳酸酐酶抑制剂的 1,3,4-噻二唑-噻唑烷酮杂化物的设计、合成以及体外和计算机研究

  摘要：

  在本研究中，合成了一系列1,3,4-噻二唑-噻唑烷酮衍生物（7a-j ）作为碳酸酐酶抑制剂。测定了这些合成化合物的体外碳酸酐酶抑制活性，结果表明化合物7i (IC 50 = 0.402 ± 0.017 μM) 比标准参考乙酰唑胺 (IC 50 = 0.998 ± 0.046 μM)更有效。此外，还进行了动力学分析来观察与目标酶的结合方式，结果表明化合物7i以竞争的方式与目标绑定。对所有化合物进行了抗DPPH抗氧化活性和对A549（人肺癌细胞）抗癌活性的筛选，MTT测定结果表明化合物7a和7d具有更强的生长抑制作用。此外，根据分子对接研究，化合物7i在受体结合口袋内表现出良好的构象状态和氢键相互作用。因此，新型化合物7i可用作有效且选择性碳酸酐酶抑制剂的有前途的药效团。

  DOI：

  10.1039/d3nj01547e

文献信息

• Design, synthesis, and <i>in vitro</i> and <i>in silico</i> studies of 1,3,4-thiadiazole-thiazolidinone hybrids as carbonic anhydrase inhibitors
  作者：Narges Hosseini Nasab、Hussain Raza、Young Seok Eom、Mubashir Hassan、Andrzej Kloczkowski、Lloyd Christopher Chetty、Hendrik Gert Kruger、Song Ja Kim

  DOI：10.1039/d3nj01547e

  日期：——

  In this study, a series of 1,3,4-thiadiazole-thiazolidinone derivatives (7a–j) were synthesized as carbonic anhydrase inhibitors. The in vitro carbonic anhydrase inhibitory activity of these synthesized compounds was determined and the results revealed that compound 7i (IC50 = 0.402 ± 0.017 μM) is more potent than the standard reference acetazolamide (IC50 = 0.998 ± 0.046 μM). Moreover, kinetic analysis

  在本研究中，合成了一系列1,3,4-噻二唑-噻唑烷酮衍生物（7a-j ）作为碳酸酐酶抑制剂。测定了这些合成化合物的体外碳酸酐酶抑制活性，结果表明化合物7i (IC 50 = 0.402 ± 0.017 μM) 比标准参考乙酰唑胺 (IC 50 = 0.998 ± 0.046 μM)更有效。此外，还进行了动力学分析来观察与目标酶的结合方式，结果表明化合物7i以竞争的方式与目标绑定。对所有化合物进行了抗DPPH抗氧化活性和对A549（人肺癌细胞）抗癌活性的筛选，MTT测定结果表明化合物7a和7d具有更强的生长抑制作用。此外，根据分子对接研究，化合物7i在受体结合口袋内表现出良好的构象状态和氢键相互作用。因此，新型化合物7i可用作有效且选择性碳酸酐酶抑制剂的有前途的药效团。
• 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
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Filippo Prencipe、Jan Balzarini、Sandra Liekens、Francisco Estévez

  DOI：10.1016/j.ejmech.2015.06.042

  日期：2015.8

  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.
• Design and synthesis of thiadiazole-oxadiazole-acetamide derivatives: Elastase inhibition, cytotoxicity, kinetic mechanism, and computational studies
  作者：Narges Hosseini Nasab、Hussain Raza、Young Seok Eom、Mubashir Hassan、Andrzej Kloczkowski、Song Ja Kim

  DOI：10.1016/j.bmc.2023.117292

  日期：2023.5

  Considering the biological significance of 1,3,4-thiadiazole/oxadiazole heterocyclic scaffolds, a novel series of 1,3,4-thiadiazole-1,3,4-oxadiazole-acetamide derivatives (7a–j) was designed and synthesized using molecular hybridization. The inhibitory effects of the target compounds on elastase were evaluated, and all of these molecules were found to be potent inhibitors compared to the standard reference

  考虑到 1,3,4-噻二唑/恶二唑杂环支架的生物学意义，设计并合成了一系列新的 1,3,4-噻二唑-1,3,4-恶二唑-乙酰胺衍生物 ( 7a - j )杂交。评估了目标化合物对弹性蛋白酶的抑制作用，发现与标准参考齐墩果酸相比，所有这些分子都是有效的抑制剂。化合物7f表现出优异的抑制活性 (IC 50 = 0.06 ± 0.02 μM)，其活性是齐墩果酸 (IC 50  = 12.84 ± 0.45 μM) 的 214 倍。还对最有效的化合物进行了动力学分析 ( 7f) 确定与目标酶结合的模式，发现7f以竞争方式抑制酶。此外，使用 MTT 测定法评估它们对 B16F10 黑色素瘤细胞系活力的毒性，即使在高浓度下，所有化合物也没有对细胞产生任何毒性作用。所有化合物的分子对接研究也证明了它们良好的对接分数，其中，化合物7f在受体结合口袋内具有良好的构象状态，氢键相互作用，这与实验抑制研究一致。