16502-08-2

Usage

Uses

Used in Pharmaceutical Industry:
5-Benzyl-[1,3,4]thiadiazol-2-ylamine is used as a lead compound for the development of new drugs due to its potential antimicrobial, antiviral, and anti-inflammatory properties. Its unique chemical structure allows for the possibility of being modified to enhance its therapeutic effects and target specific diseases.
Used in Antimicrobial Applications:
In the field of antimicrobial research, 5-benzyl-[1,3,4]thiadiazol-2-ylamine is utilized as an antimicrobial agent to combat various types of bacteria. Its ability to inhibit bacterial growth makes it a valuable asset in the development of new antibiotics to address the growing issue of antibiotic resistance.
Used in Antiviral Applications:
5-Benzyl-[1,3,4]thiadiazol-2-ylamine is also being studied for its potential as an antiviral agent, with the aim of developing treatments for viral infections. Its antiviral properties could be harnessed to create new therapeutics that can help manage and treat a range of viral diseases.
Used in Anti-inflammatory Applications:
5-BENZYL-[1,3,4]THIADIAZOL-2-YLAMINE is used as an anti-inflammatory agent, which can be beneficial in the treatment of various inflammatory conditions. Its potential to reduce inflammation may lead to the development of new medications for chronic inflammatory diseases, such as arthritis and autoimmune disorders.
Used in Medicinal Chemistry Research:
5-Benzyl-[1,3,4]thiadiazol-2-ylamine serves as a subject of interest in medicinal chemistry research, where its unique structure and potential biological activities are further investigated. This research aims to understand its mechanisms of action and to optimize its properties for specific therapeutic applications, ultimately contributing to the advancement of drug discovery and development.

InChI:InChI=1/C9H9N3S/c10-9-12-11-8(13-9)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,10,12)

Upstream product

• 79-19-6 thiosemicarbazide 
• 103-80-0 phenylacetyl chloride 
• 122-78-1 phenylacetaldehyde 
• 7420-49-7 1-(2-phenylethylidene)thiosemicarbazide 
• 140-29-4 phenylacetonitrile 
• 101-41-7 benzeneacetic acid methyl ester 
• 937-39-3 2-phenylacetylhydrazine 
• 5442-34-2 ethyl 2-phenylacetimidate hydrochloride 
• 103-82-2 phenylacetic acid 
• 5351-69-9 4-Phenyl-3-thiosemicarbazide 
• 96133-98-1 C₁₁H₁₅N₃OS 
• 29313-28-8 1-phenylacetyl-thiosemicarbazide 

Downstream Products

• 388631-27-4 2-[1-([5-benzyl-[1,3,4]thiadiazol-2-yl]aminocarbonyl)cyclopentylmethyl]-4-methoxybutyric acid tert-butyl ester 
• 1239310-67-8 tert-butyl [4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]-carbamate 
• 1239310-80-5 tert-butyl trans-(E)-3-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)-phenyl]cyclohexyl}acrylate 
• 1622955-62-7 C₁₉H₁₅N₅O₂S 
• 906069-87-2 2-[1-(5-benzyl-[1,3,4]thiadiazol-2-ylcarbamoyl)-cyclopentylmethyl]-pentanoic acid tert-butyl ester 
• 93606-28-1 5-benzyl-3-methyl-3H-[1,3,4]thiadiazol-2-ylideneamine 
• 22926-54-1 N-(5-benzyl-[1,3,4]thiadiazol-2-yl)-2,2,2-trifluoro-acetamide 
• 31737-05-0 N-(5-benzyl-[1,3,4]thiadiazol-2-yl)-3-oxo-butyramide 
• 1175882-77-5 2-benzyl-6-(4-fluorophenyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde 

Relevant academic research and scientific papers

Synthesis of 5-alkyl-2-amino-1,3,4-thiadiazoles and α,ω-bis(2- amino-1,3,4-thiadiazol-5-yl)alkanes in ionic liquids

Reaction of thiosemicarbazide with carboxylic acids, including N-substituted amino acids, in ionic liquids with H2SO4 as a catalyst affords 5-R-2-amino-1,3,4-thiadiazoles. On using alkanedicarboxylic acids, α,ω-bis(2-amino-1,3,4,-thiadiazol-5-yl)alkanes were obtained.

Synthesis of novel five-membered nitrogen-containing heterocyclic compounds from derivatives of arylsulfonyl- and arylthioacetic and -propionic acids

A series of novel substituted 1,3,4-oxa(thia)diazoles and triazoline-3-thiones has been synthesized from thiosemicarbazides and nitriles of arylthio-, arylsulfonylacetic and -propionic acids. A mechanism is proposed for the preparation of 2-amino-5-substi

Synthesis of (1,3,4-thiadiazol-2-yl)-acrylamide derivatives as potential antitumor agents against acute leukemia cells

A lead compound with the (1,3,4-thiadiazol-2-yl)-acrylamide scaffold was discovered to have significant cytotoxicity on several tumor cell lines in an in-house cell-based screening. A total of 60 derivative compounds were then synthesized and tested in a CCK-8 cell viability assay. Some of them exhibited improved cytotoxic activities. The most potent compounds had IC50 values of 1–5 μM on two acute leukemia tumor cell lines, i.e. RS4;11 and HL-60. Flow cytometry analysis of several active compounds and detection of caspase activation indicated that they induced caspase-dependent apoptosis. It was also encouraging to observe that these compounds did not have obvious cytotoxicity on normal cells, i.e. IC50 > 50 μM on HEK-293T cells. Although the molecular targets of this class of compound are yet to be revealed, our current results suggest that this class of compound represents a new possibility for developing drug candidates against acute leukemia.

Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies

A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole am

PhI-Catalyzed Intramolecular Oxidative Coupling Toward Synthesis of 2-Amino-1,3,4-Thiadizoles

A highly efficient method for the synthesis of thiadiazole derivatives via intramolecular oxidative coupling of thiosemicarbazide, using the in situ generated hypervalent iodine(III) reagents is developed. The protocol can be carried out smoothly and provides a variety of thiadiazole derivatives in moderate to excellent yields. Graphical Abstract: A highly efficient method for the synthesis of thiadiazole derivatives via PhI-catalyzed intramolecular oxidative coupling of thiosemicarbazide has been developed.

Gamma-glutamyl transpeptidase inhibitors and methods of use

Compositions that are effective in inhibiting gamma-glutamyl transpeptidase are disclosed. Methods of producing and using these compositions are also disclosed.

Synthesis and antiinflammatory activity of some imidazo[2,1-b][1,3,4]thiadiazole derivatives

A number of imidazo[2,1-b][1,3,4]thiadiazole derivatives having alkyl and aryl moieties attached to positions 2 and 6 of imidazo[2,1-b][1,3,4]thiadiazole nucleus, respectively, were prepared and characterized by IR, NMR and mass spectroscopy. Antiinflamma

Synthesis and antiproliferative assay of norcantharidin derivatives in cancer cells

Diels-Alder reaction between furan and maleic anhydride resulted in 5,6-dehydro norcantharidin, then norcantharidin was obtained by reduction. The substituted-carboxylic acid was condensed with N-aminothiourea in presence of phosphorus oxychloride, yielding 2-amino-1,3,4-thiadiazole derivatives. Novel norcantharidin derivatives were synthesized with acylation, then intramolecular condensation using norcantharidin (or 5,6-dehydro norcantharidin) and 2-amino-1,3,4-thiadiazole derivatives. All the target compounds were confirmed by IR, 1HNMR, ESI-MS and were reported for the first time. Norcantharidin derivatives antiproliferative assay was tested by MTT method against A549 and PC-3 cell lines. The results showed that all the norcantharidin derivatives displayed moderate inhibitory activities.

One-pot synthesis of 5H-1,3,4-thiadiazolo[3,2-a] pyrimidin-5-one derivatives

A novel and efficient one-pot method has been developed for the synthesis of 2-substituted-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5- one derivative by the combination of [3 + 3] cycloaddition, reduction, deamination reactions. The fused heterocyclic compoun

Design, synthesis and preliminary bioactivity studies of 1,3,4-thiadiazole hydroxamic acid derivatives as novel histone deacetylase inhibitors

Histone deacetylase (HDAC) inhibitors have emerged as a new class of anticancer agents, targeting the biological processes including cell cycle, apoptosis and differentiation. In the present study, a series of 1,3,4-thiadiazole based hydroxamic acids were developed as potent HDAC inhibitors. Some of them showed good inhibitory activity in HDAC enzyme assay and potent growth inhibition in some tumor cell lines. Among them, compound 6i (IC50 = 0.089 μM), exhibited better inhibitory effect compared with SAHA (IC50 = 0.15 μM).