2-氨基-5-(2,4-二氯苯基)-1,3,4-噻二唑 | 28004-63-9

• 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: 2-氨基-5-(2,4-二氯苯基)-1,3,4-噻二唑
• 中文别名: 5-(2,4-二氯苯基)-1,3,4-噻二唑-2-胺
• 英文名称: 5-(2,4-dichloro-phenyl)-[1,3,4]thiadiazol-2-ylamine
• 英文别名: 2-amino-5-(2,4-dichlorophenyl)-1,3,4-thiadiazole；5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-amine
• CAS: 28004-63-9
• 化学式: C₈H₅Cl₂N₃S
• mdl: MFCD00475836
• 分子量: 246.12
• InChiKey: KNZULSYPOPMUED-UHFFFAOYSA-N

物化性质

• 熔点：
  240-242℃ (ethanol water )
• 溶解度：
  4.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  储存条件：2-8°C，避光保存，并存放在惰性气体环境中。

反应信息

• 作为反应物：
  描述：

  2-氨基-5-(2,4-二氯苯基)-1,3,4-噻二唑 在 哌啶 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 8.0h， 生成 2-(2,4-dichlorophenyl)-6-(4-methylphenyl)-7-phenyl-7H-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5-thione
  参考文献：
  名称：

  Gogoi, Probin Chandra; Dutta, Mantu Moni; Kataky, Jiban Chandra Sarmah, Heterocycles, 1991, vol. 32, # 10, p. 1897 - 1912

  摘要：

  DOI：
• 作为产物：
  描述：

  [(2,4-二氯苯基)亚甲基氨基]硫脲 在 碘 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以78%的产率得到2-氨基-5-(2,4-二氯苯基)-1,3,4-噻二唑
  参考文献：
  名称：

  噻二唑类似物的合成，体外α-葡萄糖苷酶抑制潜能及分子对接研究

  摘要：

  α-葡萄糖苷酶是一种分解代谢酶，通过提供能量来维持健康功能来调节人体的血浆葡萄糖水平。2-氨基噻二唑（1 - 13）和2-氨基噻二唑基席夫碱（14 - 22）的合成，其特征在于，1 H NMR和HREI-MS并筛选α葡萄糖苷酶抑制活性。与具有IC 50值为39.60±0.70μM的标准阿卡波糖相比，所有二十二（22）个类似物均表现出不同程度的α-葡萄糖苷酶抑制潜力，IC 50值为2.30±0.1至38.30± 0.7μM。间的系列8个衍生物1，2，6，7，14，17，19和20显示出杰出的α葡萄糖苷酶抑制潜力与IC 50倍的3.30±0.1的值，5.80±0.2，2.30±0.1，2.70±0.1，2.30±0.1，5.50±0.1，4.70分别为±0.2和5.50±0.2μM，比标准药物阿卡波糖好几倍。其余类似物表现出良好至优异的α-葡萄糖苷酶抑制作用。已经为所有化合物建立了结构活性关系

  DOI：

  10.1016/j.bioorg.2018.03.022

文献信息

• FeCl3-promoted synthesis of 1,3,4-thiadiazoles under combined microwave and ultrasound irradiation in water
  作者：Huangdi Feng、Xili Ying、Yanqing Peng、Erik V. Van der Eycken、Chuanduo Liu、Shanshan Zhao、Gonghua Song

  DOI：10.1007/s00706-012-0846-x

  日期：2013.5

  AbstractAn eco-friendly and efficient synthesis of substituted 1,3,4-thiadiazole derivatives has been developed. This aqueous heterogeneous approach proceeds smoothly and quickly under combined microwave and ultrasound irradiation in the presence of FeCl3. Graphical Abstract

  摘要已经开发了一种环保，高效的取代1,3,4-噻二唑衍生物的合成方法。在FeCl 3的存在下，在微波和超声联合照射下，这种水相非均质方法可以平稳，快速地进行。 图形概要
• Synthesis and evaluation of novel 1,3,4-thiadiazole{ uoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents
  作者：Demirci, Aslı、Karayel, Kaan Gökçe、Tatar, Esra、Okullu, Sinem ÖKTEM、Unübol, Nihan、Taşli, Pakize Neslihan、Kocagöz, Zühtü Tanıl、Sahin, Fikrettin、Küçükgüzel, Ilkay

  DOI：10.3906/kim-1710-35

  日期：——

  A series of 5-substituted-1,3,4-thiadiazole-based fluoroquinolone derivatives were designed as potential antibacterial and anticancer agents using a molecular hybridization approach. The target compounds 16-25 were synthesized by reacting the corresponding $N$-(5-substituted-1,3,4-thiadiazol-2-yl)-2-chloroacetamides with ciprofloxacin or norfloxacin. The purity and identity of the synthesized compounds were determined by the use of chromatographic and spectral techniques (NMR, IR, MS, etc.) besides elemental analysis. Antibacterial, antituberculosis, and anticancer activity of the target compounds were evaluated against selected strains and cancer cell lines. Compound 20 was appreciated as the most active agent representing antibacterial activity against Escherichia coli and Staphylococcus aureus with MIC values of 4 $\mu $g/mL and 2 $\mu $g/mL, respectively. Amongst the synthesized fluoroquinolone derivatives, compounds 19 and 20were found to have modest antitubercular activity with 8 $\mu $g/mL MIC values for each. Most potent derivative, compound 20 was docked against Staphylococcus aureus and Mycobacterium tuberculosis DNA gyrase enzymes to visualize the possible conformation of the compound. Additionally, anticancer activities of target compounds were evaluated on seven different cancer cell lines.

  一系列5-取代-1,3,4-噻二唑基氟喹诺酮衍生物被设计为潜在的抗菌和抗癌药物，采用分子杂交方法。目标化合物16-25是通过将相应的 $N$-（5-取代-1,3,4-噻二唑-2-基）-2-氯乙酰胺与环丙沙星或诺氟沙星反应合成的。合成化合物的纯度和身份通过色谱和光谱技术（NMR、IR、MS等）以及元素分析确定。目标化合物的抗菌、抗结核和抗癌活性针对选定的菌株和癌细胞系进行了评估。化合物20被认为是最活跃的抗菌剂，对大肠杆菌和金黄色葡萄球菌的MIC值分别为4 $\mu $g/mL和2 $\mu $g/mL。在合成的氟喹诺酮衍生物中，化合物19和20被发现具有适度的抗结核活性，每个化合物的MIC值为8 $\mu $g/mL。最强大的衍生物，化合物20与金黄色葡萄球菌和结核分枝杆菌DNA拓扑异构酶酶对接，以可视化化合物的可能构象。此外，目标化合物的抗癌活性在七种不同的癌细胞系上进行了评估。
• Novel 4-Thiazolidinones as Non-Nucleoside Inhibitors of Hepatitis C Virus NS5B RNA-Dependent RNA Polymerase
  作者：Gizem Çakır、İlkay Küçükgüzel、Rupa Guhamazumder、Esra Tatar、Dinesh Manvar、Amartya Basu、Bhargav A. Patel、Javairia Zia、Tanaji T. Talele、Neerja Kaushik-Basu

  DOI：10.1002/ardp.201400247

  日期：2015.1

  In continuation of our efforts to develop new derivatives as hepatitis C virus (HCV) NS5B inhibitors, we synthesized novel 5‐arylidene‐4‐thiazolidinones. The novel compounds 29–42, together with their synthetic precursors 22–28, were tested for HCV NS5B inhibitory activity; 12 of these compounds displayed IC50 values between 25.3 and 54.1 µM. Compound 33, an arylidene derivative, was found to be the

  为了继续努力开发新的衍生物作为丙型肝炎病毒 (HCV) NS5B 抑制剂，我们合成了新的 5-亚芳基-4-噻唑烷酮。测试了新化合物 29-42 及其合成前体 22-28 的 HCV NS5B 抑制活性；其中 12 种化合物的 IC50 值介于 25.3 和 54.1 µM 之间。化合物 33 是​​一种亚芳基衍生物，被发现是该系列中活性最高的化合物，IC50 值为 25.3 µM。对 NS5B 的拇指口袋 II 进行了分子对接研究，以假设这些化合物的结合模式。
• Synthesis and anti-inflammatory activity of some new thiadiazole linked pyrazole benzene sulphonamides as cyclooxygenase inhibitors
  作者：Jahangir Alam、Ozair Alam、Rahmat Ali、Mohd Naim、Suroor Khan

  DOI：10.13005/ojc/310404

  日期：2015.12.30

  A new series of thiadiazole linked pyrazole benzenesulfonamide derivatives were synthesized by the condensation of aldehydic pyrazole with aryl substituted thiadiazole amine followed by Schiff base reaction. The synthesized compounds (6a-o) were characterized by IR, NMR, and Mass spectral data, further evaluated their in-vivo anti-inflammatory, analgesic and in-vitro COX-II inhibition assay. The compounds 6b and 6m showed most significant in-vivo anti-inflammatory with 72.33 and 71.17% inhibition along analgesic activity having 67.89% and 71.37 % respectively. Their selectivity against COX-II enzyme with selectivity index 67.81 and 66.38 was established for 6b and 6m, which is compared with Celecoxib. During the gastric ulceration study, selected compounds couldn’t observed any ulcerogenic effect on gastric mucosa.The in-silico pharmacokinetic profile and molecular docking study exposed very good binding affinity towards the cycloxygenase (COX-II) enzyme (PDB Id: 3PGH), therefore the compounds 6b and 6m are used as promising lead candidates for the support of drug development.

  通过醛基吡唑与芳基取代的噻二唑胺缩合，随后进行希夫碱反应，合成了一系列新的噻二唑联吡唑苯磺酰胺衍生物。合成的化合物（6a-o）通过IR、NMR和质谱数据进行表征，并进一步评估了其在体内的抗炎、镇痛作用及体外COX-II抑制活性。化合物6b和6m显示出最显著的体内抗炎活性，抑制率分别为72.33%和71.17%，同时具有镇痛活性，分别为67.89%和71.37%。它们对COX-II酶的选择性指数分别为67.81和66.38，与塞来昔布相比。在胃溃疡研究中，选定的化合物未观察到对胃黏膜的溃疡形成作用。通过计算机模拟的药代动力学特征和分子对接研究显示，这些化合物对环氧合酶（COX-II）酶（PDB ID：3PGH）具有非常好的结合亲和力，因此，化合物6b和6m被视为有前途的先导候选物，用于支持药物开发。
• Thiadiazole Derivatives as Potential Anticonvulsant Agents
  作者：Pooja Mullick、Suroor A. Khan、Surajpal Verma、Ozair Alam

  DOI：10.5012/bkcs.2011.32.3.1011

  日期：2011.3.20

  A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR, $^1H$ NMR, $^13}C$ NMR and mass spectral data confirmed the structure of the synthesized compounds. The derivatives of these moieties were evaluated for anticonvulsant activity by MES model and neurotoxicity by rotarod method. The synthesized compounds showed good potential for anticonvulsant activity besides this, the compounds also showed neurotoxic effect. It was observed that compounds with $OCH_3$ at 3, 4 position of phenyl ring [5(a-l)] showed less protection against convulsions as compared to compounds having unsubstituted phenyl ring [4(a-l)].

  一系列噻二唑衍生物通过不同取代的苯甲酸环合得到不同取代的噻唑烷-4-酮。元素分析、红外、$^1H$ NMR、$^13}C$ NMR 和质谱数据证实了合成化合物的结构。这些基团的衍生物通过MES模型评估了它们的抗惊厥活性，并通过旋转棒方法评估了神经毒性。所合成的化合物显示出良好的抗惊厥活性潜力，此外，这些化合物还表现出神经毒性效应。观察发现，相比于具有未取代苯环的化合物[4(a-l)]，在苯环3, 4位带有$OCH_3$的化合物[5(a-l)]对抗惊厥的保护作用较弱。