5-[(4-chlorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol | 154480-38-3

• 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-[(4-chlorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol
• 英文别名: 2-((4-chlorobenzylidene)amino)-5-mercapto-1,3,4-thiadiazole；2-(4-chlorobenzylideneamino)-5-mercapto-1,3,4-thiadiazole；5-((4-chlorobenzylidene)amino)-1,3,4-thiadiazole-2-thiol；5-[(4-chlorophenyl)methylideneamino]-3H-1,3,4-thiadiazole-2-thione
• CAS: 154480-38-3
• 化学式: C₉H₆ClN₃S₂
• 分子量: 255.752
• InChiKey: DUKBFSWBEKKLEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[(4-chlorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol 在 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 7.0h， 生成 7-(4-Chloro-phenyl)-2-ethylsulfanyl-6-o-tolyl-6,7-dihydro-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5-thione
  参考文献：
  名称：

  Hetero Diels-Alder Synthesis and Fungitoxicity of New 1,3,4-Thiadiazolo[3,2-a]-s-triazine-5(H)-thiones

  摘要：

  Hetero Diels-Alder synthesis involving conjugated azomethines, 5-(arylideneamino)-2-mercapto-1,3,4-thiadiazoles IIa-c, as dienes (azadienes) and aryl isothiocyanates as dienophiles affords 2,6,7-trisubstituted 6,7-dihydro-1,3,4-thiadiazolo[3,2-a]-s-triazine-5(H)-thiones IIIa-f. The azomethines IIa-c on ethylation followed by hetero Diels-Alder reaction furnish 6,7-diaryl-2-(ethylthio)-6,7-dihydro-1,3 thiadiazolo[3,2-a]-s-triazine-5(H)-thiones IVa-f. Fungitoxicities of the compounds II-IV were evaluated in vitro aginst Aspergillus niger and Fusarium oxysporum. Some of the compounds displayed activities comparable with that of the commercial fungicide Dithane M-45. Structure-activity relationships for the screened compounds are discussed.

  DOI：

  10.1021/jf00042a020
• 作为产物：
  描述：

  4-氯苯甲醛 、 2-氨基-5-巯基-1,3,4-噻二唑 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以30.2%的产率得到5-[(4-chlorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol
  参考文献：
  名称：

  含席夫碱部分作为酪氨酸酶抑制剂的1,3,4-噻二唑衍生物的分子对接研究和生物学评估

  摘要：

  设计，合成了带有席夫碱部分的1,3,4-噻二唑衍生物，并评估了它们对酪氨酸酶的抑制活性。一些化合物显示出强效的酪氨酸酶抑制活性，尤其是4-（（（5-mercapto-1,3,4-thiadiazol-2-yl）-imino）methyl）-2-methoxy-phenol（14）表现出优异的抑制作用。其他化合物的IC 50值为0.036μM。初步讨论了结构-活性关系（SARs），对接研究表明化合物14对蘑菇酪氨酸酶具有很强的结合亲和力。羟基可能是活性基团。抑制动力学研究表明，化合物（13和14）通过充当非竞争性抑制剂来抑制酪氨酸酶。化合物14的LD 50值为5000mg / kg。

  DOI：

  10.1016/j.bioorg.2016.09.007

文献信息

• Antimicrobial and antitubercular evaluation of some new 5-amino-1,3,4-thiadiazole-2-thiol derived Schiff bases
  作者：Kasetti Ashok BABU、Indrajeet SINGHVI、Nagasuri RAVINDRA、Afzal Basha SHAIK

  DOI：10.33224/rrch.2020.65.9.01

  日期：——

  In an effort to study the effect of 1,3,4-thidiazole based molecules on bacteria, fungal and tuberculosis species, we synthesized a series of Schiff bases (2a-2m) by reacting a variety of carbonyl compounds with 5-amino-1,3,4- thiadiazole-2-thiol. Molecular structure of these compounds was retrieved by spectral methods and elemental analysis. All these compounds were evaluated for their antibacterial, antifungal and antitubercular activities employing standard biological protocols. The compounds 2m and 2l substituted with the electron withdrawing fluorine and nitro groups showed excellent inhibitory activity against Staphylococcus aureus, Aspergillus niger and Candida tropicalis with an MIC of 8 µg/mL whereas 2i containing the electron releasing dimethylamino group showed potent activity against Proteus vulgaris. Additionally, 2m along with 2j, 2k and 2l also exhibited superior antimycobacterial activity than the standard pyrazinamide. The activity data for these compounds pave the way for the development of new antimicrobial and antitubercular drugs.

  为了研究基于 1,3,4-噻二唑的分子对细菌、真菌和结核菌的影响，我们将多种羰基化合物与 5-氨基-1,3,4-噻二唑-2-硫醇反应，合成了一系列希夫碱（2a-2m）。这些化合物的分子结构是通过光谱方法和元素分析得到的。所有这些化合物的抗菌、抗真菌和抗结核活性均采用标准的生物学方法进行了评估。被退电子的氟和硝基取代的化合物 2m 和 2l 对金黄色葡萄球菌、黑曲霉和热带念珠菌具有极佳的抑制活性，其 MIC 值为 8 µg/mL，而含有释放电子的二甲基氨基的 2i 则对普通变形杆菌具有很强的活性。此外，2m 以及 2j、2k 和 2l 也显示出比标准吡嗪酰胺更强的抗霉菌活性。这些化合物的活性数据为开发新的抗菌和抗结核药物铺平了道路。
• Synthesis of novel thiadiazole derivatives as selective COX-2 inhibitors
  作者：Fatma A. Ragab、Helmi I. Heiba、Marwa G. El-Gazzar、Sahar M. Abou-Seri、Walaa A. El-Sabbagh、Reham M. El-Hazek

  DOI：10.1039/c6md00367b

  日期：——

  A novel series of thiadiazole derivatives were designed and synthesized for evaluation as selective COX-2 inhibitors in vitro and were investigated in vivo as anti-inflammatory and analgesic agents against carrageenan-induced rat paw oedema model in irradiated rats, since it is well-known that ionizing radiation plays an important role in exaggerating the inflammatory responses in experimental animals

  设计并合成了一系列新的噻二唑衍生物，以评价其在体外的选择性COX-2抑制剂的活性，并在体内作为抗角叉菜胶诱导的大鼠爪水肿模型的抗炎和镇痛药进行了体内研究，因为它是众所周知的电离辐射在夸大实验动物的炎症反应中起着重要作用。评估了最有效的化合物的致溃疡活性和急性毒性。为了了解合成的化合物与COX-2酶活性位点的结合方式，进行了对接研究。大多数测试化合物显示出对COX-2的高抑制能力。其中，带有磺酰胺基团的噻二唑衍生物7b，Ç和13c中，ê，是最有效的COX-2抑制剂，相比于塞来昔布极高的选择性指数（SI）; 它们在胃黏膜上显示出很高的安全范围，没有溃疡作用，并且在实验大鼠中被发现是无毒的。对接研究表明，这些化合物的取向与塞来昔布在COX-2酶的活性位点内的取向相似，并且具有深入浸入其他口袋并与Arg513和His90（负责选择性的关键氨基酸）结合的相似能力。
• An Interactive Human Carbonic Anhydrase-II (hCA-II) Receptor - Pharmacophore Molecular Model & Anti-Convulsant Activity of the Designed and Synthesized 5-Amino-1,3,4-Thiadiazole-2-Thiol Conjugated Imine Derivatives
  作者：Mohammad Yusuf、Riaz A. Khan、Maria Khan、Bahar Ahmed

  DOI：10.1111/cbdd.12113

  日期：2013.5

  New imines, derived from aromatic aldehyde, chalcones and 5‐amino‐1,3,4‐thiadiazole‐2‐thiol exhibited promising anti‐convulsant activity which is explained through chemo‐biological interactions at receptor site producing the inhibition of human Carbonic Anhydrase‐II enzyme (hCA‐II) through the proposed pharmacophore model at molecular levels as basis for pharmacological activity. The compounds 5‐1‐(4‐Chlorophenyl)‐3‐[4‐(methoxy‐phenyl)‐prop‐2‐en‐1‐ylidene]amino}‐1,3,4‐thiadiazole‐2‐thiol (2b), 5‐[1‐(4‐chloro‐phenyl)]‐3‐[4‐(dimethyl‐amino‐phenyl)‐prop‐2‐en‐1‐ylidene]amino}‐1,3,4‐thiadiazole‐2‐thiol (2c) and 5‐[1‐(4‐chloro‐phenyl)]‐3‐[(4‐amino‐phenyl)‐prop‐2‐en‐1‐ylidene]amino}‐1,3,4‐thiadiazole‐2‐thiol (2f) showed 100% activity in comparison with standard Acetazolamide, a known anti‐convulsant drug. The compounds 2c, 2f also passed the Rotarod and Ethanol Potentiation tests which further confirmed them to be safe in motor coordination activity and safe from generating neurological toxicity.
• Ahmed, Bahar; Yusuf, Md., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 2, p. 241 - 246
  作者：Ahmed, Bahar、Yusuf, Md.

  DOI：——

  日期：——
• SYNTHESIS OF SOME NOVEL AND BIOLOGICALLY ACTIVE SCHIFF BASES BEARING A 1,3,4-THIADIAZOLE MOIETY UNDER ACIDIC AND PTC CONDITIONS
  作者：A MOBINIKHALEDI、M JABBARPOUR、A HAMTA

  DOI：10.4067/s0717-97072011000300020

  日期：——

  The synthesis of some new Schiff bases bearing a 1,3,4-thiadiazole moiety, 3a-1, by reaction of 2-amino-5-mercapto-1,3,4-thiadiazole with aromatic aldehydes under acidic and phase transfer catalyst (PTC) conditions was studied. The structure of all the Schiff bases was characterized using FT-IR and NMR spectroscopy, and elemental analyses. The antibacterial activity of these compounds was investigated against Staphylococcus aureus (RTCC, 1885), and Escherichia coli (ATCC, 35922).