5-((3-nitrobenzyl)thio)-1,3,4-thiadiazol-2-amine | 333459-58-8

• 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: 5-((3-nitrobenzyl)thio)-1,3,4-thiadiazol-2-amine
• 英文别名: 5-[(3-Nitrobenzyl)sulfanyl]-1,3,4-thiadiazol-2-amine；5-[(3-nitrophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-amine
• CAS: 333459-58-8
• 化学式: C₉H₈N₄O₂S₂
• mdl: MFCD03015499
• 分子量: 268.32
• InChiKey: UTVGCLISWGMJMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196 °C(Solv: methanol (67-56-1))
• 沸点：
  513.5±52.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-((3-nitrobenzyl)thio)-1,3,4-thiadiazol-2-amine 在 亚硝酸特丁酯 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以44%的产率得到2-bromo-5-((3-nitrobenzyl)thio)-1,3,4-thiadiazole
  参考文献：
  名称：

  Discovery and development of substituted thiadiazoles as inhibitors of Staphylococcus aureus Sortase A

  摘要：

  High-throughput screening of small-molecule libraries has led to the identification of thiadiazoles as a new class of inhibitors against Staphylococcus aureus sortase A (SrtA). N-(5-((4-nitrobenzyl) thio)-1,3,4-thiadiazol-2-yl)nicotinamide (IC50= 3.8 mu M) was identified as a potent inhibitor of SrtA after synthetic modification of hit compounds. Additional ligands developed in this study displayed affinities in the low micromolar range without affecting bacterial growth in vitro. The study also suggest a new mode of action through covalent binding to the active site cysteine.

  DOI：

  10.1016/j.bmc.2019.115043
• 作为产物：
  描述：

  2-氨基-5-巯基-1,3,4-噻二唑 、 3-硝基溴苄 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 5-((3-nitrobenzyl)thio)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  法呢基硫代水杨酸衍生物作为抗肿瘤药物的合成及体外生物学评价

  摘要：

  摘要合成了具有不同取代的1,3,4-噻二唑的新型法呢基硫代水杨酸（FTA）衍生物5a-m。在大多数测试的癌细胞中，化合物5b，5c，5e和5f显示出优于FTA的抗肿瘤活性。此外，5e诱导肿瘤细胞凋亡，伴随着较低的Bcl-2表达，但在癌细胞中具有较高的Bax和caspase 3表达活性。

  DOI：

  10.1016/j.cclet.2012.08.007

文献信息

• Design, synthesis, and biological evaluation of 1-(5-(benzylthio)-1,3,4-thiadiazol-2-yl)-3-phenylurea derivatives as anticancer agents
  作者：Ayoub Aghcheli、Mahsa Toolabi、Adileh Ayati、Setareh Moghimi、Loghman Firoozpour、Tayebeh Oghabi Bakhshaiesh、Elahe Nazeri、Maryam Norouzbahari、Rezvan Esmaeili、Alireza Foroumadi

  DOI：10.1007/s00044-020-02616-2

  日期：2020.11

  proliferation of tested cancer cells. In particular, 2-F, 4-Cl, and 2,6-diF substituted derivatives (5d, 5g, and 5k) showed promising activities, especially against Hela cancer cells (IC50 = 0.37, 0.73 and 0.95 µM, respectively) which were significantly more potent than sorafenib as the reference drug (IC50 = 7.91 µM). Flow cytometry analysis revealed that the prototype compounds (5d, 5g, and 5k) significantly

  设计并合成了一系列新型的1-（5-（苄硫基）-1,3,4-噻二唑-2-基）-3-苯基脲衍生物（5a-1）作为索拉非尼类似物。评价了合成化合物对四种不同的人类癌细胞（包括MCF-7，HepG2，A549和HeLa细胞系）的体外细胞毒性作用。生物学结果表明，大多数化合物显着阻止了测试癌细胞的增殖。特别是2-F，4-Cl和2,6- di F取代的衍生物（5d，5g和5k）显示出有希望的活性，尤其是针对Hela癌细胞（IC 50 分别为0.37、0.73和0.95 µM），这比索拉非尼作为参考药物的效用要强得多（IC 50  = 7.91 µM）。流式细胞仪分析表明，原型化合物（5d，5g和5k）显着诱导HeLa癌细胞凋亡，并阻止了亚G1期的细胞周期。此外，计算机对接研究证实了原型化合物与VEGFR-2活性位点的结合。
• Synthesis and radioligand‐binding assay of 2,5‐disubstituted thiadiazoles and evaluation of their anticonvulsant activities
  作者：Mahsa Toolabi、Mona Khoramjouy、Ayoub Aghcheli、Adileh Ayati、Setareh Moghimi、Loghman Firoozpour、Soraya Shahhosseini、Rouhallah Shojaei、Ali Asadipour、Kouros Divsalar、Mehrdad Faizi、Alireza Foroumadi

  DOI：10.1002/ardp.202000066

  日期：2020.12

  respectively) were the most potent ones in the sleep test and anticonvulsant test, showing a comparable activity with diazepam as the reference drug. The results of in vivo studies, especially the antagonistic effects of flumazenil, and also the radioligand‐binding assay confirmed the involvement of benzodiazepine (BZD) receptors in the anticonvulsant and hypnotic activity of compounds 7 and 11. Finally, the

  在这项研究中，使用适当的合成路线合成了一些 2,5-二取代的 1,3,4-噻二唑，它们的抗惊厥活性通过最大电休克癫痫 (MES) 试验确定，并通过旋转棒评估它们的神经毒性。测试。此外，使用戊巴比妥诱导的睡眠测试来测试他们的催眠活动。化合物 7（在 MES 和睡眠测试中分别为 ED50 = 1.14 和 2.72 μmol/kg）和 11（在 MES 和睡眠测试中分别为 ED50 = 0.65 和 2.70 μmol/kg）是睡眠测试中最有效的化合物，并且抗惊厥试验，显示与作为参考药物的地西泮相当的活性。体内研究结果，尤其是氟马西尼的拮抗作用，以及放射性配体结合试验证实苯二氮卓 (BZD) 受体参与化合物 7 和 11 的抗惊厥和催眠活性。 最后，化合物 11 在 GABAA（γ-氨基丁酸）的 BZD 结合位点的对接研究) 受体证实了该化合物可能与 BZD 受体结合。我们得出结论，在杂环的 2
• Thiazolidine-2,4-dione derivatives as potential α-glucosidase inhibitors: Synthesis, inhibitory activity, binding interaction and hypoglycemic activity
  作者：Mengyue Li、Jinping Sun、Bingwen Liang、Xiaofeng Min、Jinhui Hu、Rihui Wu、Xuetao Xu

  DOI：10.1016/j.bioorg.2024.107177

  日期：2024.3

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• Synthesis and cytotoxic evaluation of new colchicine derivatives bearing 1,3,4-thiadiazole moieties
  作者：Li-Hong Shen、Hong-Yu Li、Hui-Xia Shang、Shu-Ting Tian、Yi-Sheng Lai、Li-Jie Liu

  DOI：10.1016/j.cclet.2013.01.052

  日期：2013.4

  In search of novel anticancer agents, a series of N-methyl colchiceinamide derivatives (7a-7i) containing 1,3,4-thiadiazole moieties were synthesized, and their structures were confirmed by spectral analysis. Cytotoxicity of these compounds was evaluated by MTT assay in vitro against four human tumor cell lines, i.e. A2780, A549, BEL7402, and MCF-7. The results indicated that most of the derivatives showed significant anticancer activities, particularly, compounds 7h and 7i showed more potent cytotoxic activities of all screened cancer cells than colchicine. (C) 2013 Li-Hong Shen. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Synthesis of 2-Amino-5-sulfanyl-1,3,4-thiadiazole Derivatives and Evaluation of Their Antidepressant and Anxiolytic Activity
  作者：Francesca Clerici、Donato Pocar、Maddalena Guido、Antonella Loche、Vincenzo Perlini、Mario Brufani

  DOI：10.1021/jm001027w

  日期：2001.3.1

  Recently a series of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives bearing different substituents were synthesized and screened pharmacologically in order to evaluate their central nervous system activity. The purpose of this study was to evaluate the effects of the title compounds on CNS activity by varying the substituents in the thiadiazole moiety. It was found that some of these compounds possess marked antidepressant and anxiolytic properties comparable in efficiency to the reference drugs Imipramine and Diazepam. The most potent compound 3k was further investigated to complete its pharmacological profile with respect to undesired side effects. Behavioral results showed that 3k is a very promising compound, characterized by a mixed antidepressant-anxiolytic activity accompanied by a therapeutic dose range that is essentially 2 orders of magnitude less than that at which side effects such as sedation and amnesia are evident.