2-(benzylideneamino)-5-mercapto-1,3,4-thiadiazole | 137996-43-1

• 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: 2-(benzylideneamino)-5-mercapto-1,3,4-thiadiazole
• 英文别名: 5-(benzylideneamino)-1,3,4-thiadiazole-2-thiol；5-(benzylideneamino)-3H-1,3,4-thiadiazole-2-thione
• CAS: 137996-43-1
• 化学式: C₉H₇N₃S₂
• 分子量: 221.307
• InChiKey: NQTMKHUWXOYDOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 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：

  2-(benzylideneamino)-5-mercapto-1,3,4-thiadiazole 在 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 7.0h， 生成 2-Ethylsulfanyl-6,7-diphenyl-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：

  苯甲醛 、 2-氨基-5-巯基-1,3,4-噻二唑 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到2-(benzylideneamino)-5-mercapto-1,3,4-thiadiazole
  参考文献：
  名称：

  Antimicrobial and antitubercular evaluation of some new 5-amino-1,3,4-thiadiazole-2-thiol derived Schiff bases

  摘要：

  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。

  DOI：

  10.33224/rrch.2020.65.9.01

文献信息

• Molecular docking studies and biological evaluation of 1,3,4-thiadiazole derivatives bearing Schiff base moieties as tyrosinase inhibitors
  作者：Junyuan Tang、Jinbing Liu、Fengyan Wu

  DOI：10.1016/j.bioorg.2016.09.007

  日期：2016.12

  1,3,4-Thiadiazole derivatives bearing Schiff base moieties were designed, synthesized, and their tyrosinase inhibitory activities were evaluated. Some compounds displayed potent tyrosinase inhibitory activities, especially, 4-(((5-mercapto-1,3,4-thiadiazol-2-yl)-imino)methyl)-2-methoxy-phenol (14) exhibited superior inhibitory effect to the other compounds with an IC50 value of 0.036 μM. The structure–activity

  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。
• 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).
• US11939326B1
  申请人：——

  公开号：——

  公开（公告）日：——
• 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。
• Hetero Diels-Alder Synthesis and Fungitoxicity of New 1,3,4-Thiadiazolo[3,2-a]-s-triazine-5(H)-thiones
  作者：Lal Dhar S. Yadav、Sangeeta Sharma、Anjum Vaish

  DOI：10.1021/jf00042a020

  日期：1994.6

  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.