5-(4-硝基苄基)-1,3,4-噻二唑-2-胺 | 247225-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(4-硝基苄基)-1,3,4-噻二唑-2-胺
• 英文名称: 5-(4-nitrobenzyl)-1,3,4-thiadiazol-2-amine
• 英文别名: 5-[(4-nitrophenyl)methyl]-1,3,4-thiadiazol-2-amine
• CAS: 247225-84-9
• 化学式: C₉H₈N₄O₂S
• mdl: MFCD00450189
• 分子量: 236.254
• InChiKey: IVPDFKYKTMICSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(4-硝基苄基)-1,3,4-噻二唑-2-胺 在 N-甲基吗啉 、 盐酸 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.92h， 生成 N-[1-(methoxymethyl)-2-[[5-[(4-nitrophenyl)methyl]-1,3,4-thiadiazol-2-yl]amino]-2-oxoethyl]cyclopentanecarboxamide
  参考文献：
  名称：

  BAY-805 的发现和表征，泛素特异性蛋白酶 USP21 的强效选择性抑制剂

  摘要：

  USP21 属于去泛素化酶 (DUB) 的泛素特异性蛋白酶 (USP) 亚家族。由于其与肿瘤发展和生长的相关性，USP21 已被报道为一种有前途的新型癌症治疗靶点。在此，我们介绍了第一个高效和选择性 USP21 抑制剂的发现。经过高通量筛选和随后的基于结构的优化，我们确定 BAY-805 是一种非共价抑制剂，对 USP21 具有低纳摩尔亲和力，对其他 DUB 靶标以及激酶、蛋白酶和其他常见脱靶具有高选择性. 此外，表面等离子共振 (SPR) 和细胞热位移分析 (CETSA) 证明了 BAY-805 的高亲和力靶点参与，导致在基于细胞的报告分析中强烈的 NF-κB 激活。据我们所知，

  DOI：

  10.1021/acs.jmedchem.2c01933
• 作为产物：
  描述：

  对硝基苯乙腈 、 氨基硫脲 在 三氟乙酸 作用下， 以75%的产率得到5-(4-硝基苄基)-1,3,4-噻二唑-2-胺
  参考文献：
  名称：

  BAY-805 的发现和表征，泛素特异性蛋白酶 USP21 的强效选择性抑制剂

  摘要：

  USP21 属于去泛素化酶 (DUB) 的泛素特异性蛋白酶 (USP) 亚家族。由于其与肿瘤发展和生长的相关性，USP21 已被报道为一种有前途的新型癌症治疗靶点。在此，我们介绍了第一个高效和选择性 USP21 抑制剂的发现。经过高通量筛选和随后的基于结构的优化，我们确定 BAY-805 是一种非共价抑制剂，对 USP21 具有低纳摩尔亲和力，对其他 DUB 靶标以及激酶、蛋白酶和其他常见脱靶具有高选择性. 此外，表面等离子共振 (SPR) 和细胞热位移分析 (CETSA) 证明了 BAY-805 的高亲和力靶点参与，导致在基于细胞的报告分析中强烈的 NF-κB 激活。据我们所知，

  DOI：

  10.1021/acs.jmedchem.2c01933

文献信息

• Novel Substituted Imidazo[2,1‐ <i>b</i> ][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their <i>In Vitro</i> Antifungal Activities
  作者：Mustafa Er、Hakan Tahtaci、Tuncay Karakurt、Abdurrahman Onaran

  DOI：10.1002/jhet.3653

  日期：2019.9

  imidazo[2,1‐b][1,3,4]thiadiazole derivatives were synthesized. To this end, first 2‐amino‐1,3,4‐thiadiazole derivatives (compounds 2a and 2b), the starting materials, were synthesized with high yields (82% and 79%, respectively). Then imidazo[2,1‐b][1,3,4]thiadiazole derivatives (4–16), the target compounds, were synthesized from reactions of 2‐amino‐1,3,4‐thiadiazole derivatives (2a and 2b) with 2‐bromoacetophenone

  在这项研究中，合成了一系列新的取代的咪唑并[2,1– b ] [1,3,4]噻二唑衍生物。为此，首先以高收率（分别为82％和79％）合成了起始原料2-氨基-1,3,4-噻二唑（化合物2a和2b）。然后咪唑并[2,1- b ] [1,3,4]噻二唑衍生物（4 - 16），目标化合物中，从2-氨基-1,3,4-噻二唑衍生物的反应（合成图2a和图2b）含2-溴苯乙酮衍生物（3a - 3i）（收率52％至71％）。所有合成的化合物的特征均是11 H NMR，13 C NMR，傅里叶变换红外，元素分析，质谱，和X射线衍射分析（化合物4 - 12，14，和15）的技术。体外对所有合成的化合物进行抗真菌活性测试。确定了针对某些植物病原体的目标化合物的抑制区，抑制百分比，最小杀真菌活性，最小抑制浓度和致死剂量值。根据生物学活性测试的结果，所有合成的化合物均显示出中等至高水平的抗真菌活性。进行理论计算以支持
• Microwave-assisted synthesis and antimicrobial activity of some imidazo[2,1-b][1,3,4]thiadiazole derivatives
  作者：Sharad Dhepe、Sujeet Kumar、R. Vinayakumar、Sureshbabu A. Ramareddy、Subhas S. Karki

  DOI：10.1007/s00044-011-9671-8

  日期：2012.8

  Mass spectroscopy. Antibacterial and antifungal activity was performed using cup plate method against Staphylococcus aureus, Klebsiella, and Candida albicans microorganisms. 2-(4-nitro benzyl)-6-(4-bromo phenyl)imidazo[2,1-b][1,3,4]thiadiazole (4Ce) was the only derivative which showed activity against Klebsiella at low micromolar concentration (5 μg/ml) with moderate zone of inhibition. And 2-(4-nitro

  开发了一种简单有效的方法，用于在微波（MW）活化下使用2-氨基-5-取代-1合成2,6-二取代-咪唑并[2,1-b] [1,3,4]噻二唑， 3,4-噻二唑和适当的溴代酮为原料。所有反应都证明了MW反应的好处：操作方便，反应时间短，产率高。通过IR，NMR和质谱对所有衍生物进行表征。使用杯板法对金黄色葡萄球菌，克雷伯菌和白色念珠菌微生物进行抗菌和抗真菌活性。2-（4-硝基苄基）-6-（4-溴苯基）咪唑并[2,1-b] [1,3,4]噻二唑（4Ce）是唯一对克雷伯菌具有活性的衍生物在低微摩尔浓度（5μg/ ml）下具有中等抑制区域。而2-（4-硝基苄基）-6-（4-氟苯基）咪唑并[2,1-b] [1,3,4]噻二唑（4Cf）作为最有效的抗真菌活性衍生物，相对于50μg/ ml与标准氟康唑比较的白色念珠菌。
• Synthesis, crystal structures, and biological activity of zinc(II) complexes derived from 2-amino-1,3,4-thiadiazole derivatives
  作者：Hui-Long Zhu、Yu-Wei Liu、Zong-Ming Tang、Fu-Jun Yin、Wei-Wei Liu、Zhi-Ling Cao、Juan Bao、Meng Li、Ling-Yan Qin、Da-Hua Shi

  DOI：10.1080/15533174.2016.1149723

  日期：2017.1.2

  Two new similar zinc(II) complexes, [ZnCl2L12] and [ZnCl2L22], derived from the 2-amino-1,3,4-thiadiazole derivatives, were prepared and structurally characterized by X-ray diffraction. The Zn atom in each complex has a tetrahedral coordination and is coordinated by two N atoms of the ligands and two Cl atoms. The urease inhibitory activities of the complexes and the ligands were evaluated.

  制备了由2-氨基-1,3,4-噻二唑衍生物衍生的两种新的相似的锌（II）络合物[ZnCl 2 L1 2 ]和[ZnCl 2 L2 2 ]，并通过X射线衍射对其结构进行了表征。每个络合物中的Zn原子具有四面体配位，并由两个N配体原子和两个Cl原子配位。评价了复合物和配体的脲酶抑制活性。
• Divergent effects of compounds on the hydrolysis and transpeptidation reactions of γ-glutamyl transpeptidase
  作者：Stephanie Wickham、Nicholas Regan、Matthew B. West、Vidya Prasanna Kumar、Justin Thai、Pui Kai Li、Paul F. Cook、Marie H. Hanigan

  DOI：10.3109/14756366.2011.597748

  日期：2012.8.1

  A novel class of inhibitors of the enzyme gamma-glutamyl transpeptidase (GGT) were evaluated. The analog OU749 was shown previously to be an uncompetitive inhibitor of the GGT transpeptidation reaction. The data in this study show that it is an equally potent uncompetitive inhibitor of the hydrolysis reaction, the primary reaction catalyzed by GGT in vivo. A series of structural analogs of OU749 were evaluated. For many of the analogs, the potency of the inhibition differed between the hydrolysis and transpeptidation reactions, providing insight into the malleability of the active site of the enzyme. Analogs with electron withdrawing groups on the benzosulfonamide ring, accelerated the hydrolysis reaction, but inhibited the transpeptidation reaction by competing with a dipeptide acceptor. Several of the OU749 analogs inhibited the transpeptidation reaction by slow onset kinetics, similar to acivicin. Further development of inhibitors of the GGT hydrolysis reaction is necessary to provide new therapeutic compounds.
• Novel 2-amino-1,3,4-thiadiazoles and their acyl derivatives: Synthesis, structural characterization, molecular docking studies and comparison of experimental and computational results
  作者：Mustafa Er、Gamze Isildak、Hakan Tahtaci、Tuncay Karakurt

  DOI：10.1016/j.molstruc.2016.01.045

  日期：2016.4

  This study aims to synthesize and characterize compounds containing 2-amino-1,3,4-thiadiazole and compare experimental results to theoretical results. For this purpose, firstly mono, di and tetra 2-amino-1,3,4-thiadiazole compounds (2a-c, 14, 20 and 25) were synthesized in relatively high yields (74-87%). The target compounds (3-11, 15-17, 21-23 and 26-28) were then synthesized in moderate to high yields (65-85%) from the reactions of 2-amino-1,3,4-thiadiazole compounds with various acyl chloride derivatives.The structures of all synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR, elemental analyses and mass spectroscopy techniques. The structures of 2b (C9H8N4O2S) and 2c (C11H13N3O2S) were also elucidated by X-ray diffraction analysis.Lastly, IR spectrum, H-1 NMR and C-13 NMR chemical shift values, frontier molecular orbital (FMO) values of these molecules containing heteroatoms were examined using the Becke-3- Lee-Yang-Parr (B3LYP) method with the 6-31G(d) basis set. Two different molecular structures containing 2-amino-1,3,4-thiadiazole (2b, 2c) were used in our study to examine these properties. Also, compounds 2b and 2c form a stable complex with beta-Lactamase as can be understood from the binding affinity values and the results show that the compound might inhibit the beta-Lactamase enzyme. It was found that theoretical and experimental results obtained in the experiment were compatible with each other and with the values found in the literature. (C) 2016 Elsevier B.V. All rights reserved.