28004-63-9

Usage

Uses

Used in Medicinal Chemistry:
2-Amino-5-(2,4-dichlorophenyl)-1,3,4-thiadiazole is used as a key component in the synthesis of various drugs targeted towards curing different diseases. Its bioactive properties make it a valuable compound in the development of new pharmaceuticals.
Used in Antibacterial Applications:
2-AMINO-5-(2,4-DICHLOROPHENYL)-1,3,4-THIADIAZOLE is used as an antibacterial agent, contributing to the development of effective medicinal drugs. Its ability to combat bacterial infections makes it a crucial component in the formulation of antibiotics.
Used in Antifungal Applications:
2-Amino-5-(2,4-dichlorophenyl)-1,3,4-thiadiazole is used as an antifungal agent, playing a significant role in the creation of drugs that can treat fungal infections.
Used in Anti-inflammatory Applications:
2-AMINO-5-(2,4-DICHLOROPHENYL)-1,3,4-THIADIAZOLE is used as an anti-inflammatory agent, helping in the development of drugs that can alleviate inflammation and related symptoms.
Used in Drug Design and Modification:
2-Amino-5-(2,4-dichlorophenyl)-1,3,4-thiadiazole is used in the design and modification of pharmaceutical compounds. Modifications in the phenyl ring or substitutions at the amino group can lead to compounds with improved pharmacological activities, enhancing the effectiveness of the drugs.

InChI:InChI=1/C8H5Cl2N3S/c9-4-1-2-5(6(10)3-4)7-12-13-8(11)14-7/h1-3H,(H2,11,13)

Upstream product

• 6957-92-2 (2,4-dichlorobenzylidenehydrazinyl)thiocarboxamide 
• 26036-09-9 1-(2,4-dichlorobenzoyl)-3-thiosemicarbazide 
• 50-84-0 2,4 dichlorobenzoic acid 
• 79-19-6 thiosemicarbazide 
• 874-42-0 2,4-dichlorobenzaldeyhde 

Downstream Products

• 139172-25-1 2-(2,4-dichlorophenyl)-7-methyl-5H-1,3,4-thiadiazolo(3,2-a)pyrimidin-5-one 
• 139172-20-6 (Z)-3-[5-(2,4-Dichloro-phenyl)-[1,3,4]thiadiazol-2-ylamino]-but-2-enoic acid ethyl ester 
• 139172-30-8 5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-iminobenzylidene 
• 147054-27-1 [5-(2,4-Dichloro-phenyl)-[1,3,4]thiadiazol-2-yl]-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amine 
• 132407-84-2 1-(2,4-Dichloro-benzoyl)-3-[5-(2,4-dichloro-phenyl)-[1,3,4]thiadiazol-2-yl]-thiourea 
• 139172-28-4 6-ethoxycarbonyl-2-(2,4-dichlorophenyl)-5H-1,3,4-thiadiazolo(3,2-a)pyrimidin-5-one 

Relevant academic research and scientific papers

Synthesis, in vitro thymidine phosphorylase activity and molecular docking study of thiadiazole bearing isatin analogs

A series of seventeen analogs (1─17) were synthesized and characterized through different spectroscopic techniques such as 1H, 13CNMR, HR-EI-MS and were evaluated for in vitro thymidine phosphorylase inhibition. All compounds showed excellent to good thymidine phosphorylase activity having IC50 value ranging between 4.10 ± 0.20 and 54.60 ± 1.40?μM when compared with standard drug 7-deazaxanthine (IC50 = 38.68 ± 1.12?μM). Among the series, compounds 1 (IC50 = 8.30 ± 0.30?μM), 6 (IC50 = 6.30 ± 0.10?μM), 11 (IC50 = 8.40 ± 0.30?μM) and 16 (IC50 = 4.10 ± 0.20?μM) were found more potent. Potent compounds were further subjected to molecular docking study to identify their interactions with the active site of amino acid. Structure activity relationship was done for all analogs mostly based on substitution pattern on phenyl and isatin rings. Graphic abstract: [Figure not available: see fulltext.]

Synthesis, in vitro α-glucosidase inhibitory potential and molecular docking study of thiadiazole analogs

α-Glucosidase is a catabolic enzyme that regulates the body's plasma glucose levels by providing energy sources to maintain healthy functioning. 2-Amino-thiadiazole (1–13) and 2-amino-thiadiazole based Schiff bases (14–22) were synthesized, characterized by 1H NMR and HREI-MS and screened for α-glucosidase inhibitory activity. All twenty-two (22) analogs exhibit varied degree of α-glucosidase inhibitory potential with IC50 values ranging between 2.30 ± 0.1 to 38.30 ± 0.7 μM, when compare with standard drug acarbose having IC50 value of 39.60 ± 0.70 μM. Among the series eight derivatives 1, 2, 6, 7, 14, 17, 19 and 20 showed outstanding α-glucosidase inhibitory potential with IC50 values of 3.30 ± 0.1, 5.80 ± 0.2, 2.30 ± 0.1, 2.70 ± 0.1, 2.30 ± 0.1, 5.50 ± 0.1, 4.70 ± 0.2, and 5.50 ± 0.2 μM respectively, which is many fold better than the standard drug acarbose. The remaining analogs showed good to excellent α-glucosidase inhibition. Structure activity relationship has been established for all compounds. The binding interactions of these compounds were confirmed through molecular docking.

Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents

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 correspondin

Synthesis of 2-amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via sequential condensation and I2-mediated oxidative C-O/C-S bond formation

2-Amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were synthesized via condensation of semicarbazide/thiosemicarbazide and the corresponding aldehydes followed by I2-mediated oxidative C-O/C-S bond formation. This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.

Novel 4-thiazolidinones as non-nucleoside inhibitors of hepatitis C virus NS5B RNA-dependent RNA polymerase

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 most active compound in this series with an IC50 value of 25.3 μM. Molecular docking studies were performed on the thumb pocket-II of NS5B to postulate the binding mode for these compounds.

Design, synthesis and evaluation of small molecule imidazo[2,1-b][1,3,4]thiadiazoles as inhibitors of transforming growth factor-β type-I receptor kinase (ALK5)

A new series of imidazo[2,1-b][1,3,4]thiadiazoles 5(a-g), 6(a-g), 9(a-i) and 12(a-h) were synthesized as transforming growth factor-β (TGF-β) type I receptor (also known as activin receptor-like kinase 5 or ALK5) inhibitors. These compounds were evaluated

Synthesis and anti-inflammatory activity of some new thiadiazole linked pyrazole benzene sulphonamides as cyclooxygenase inhibitors

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 invitro COX-II inhibition assay. The compounds 6b and 6m showed most significant in-vivo antiinflammatory with 72.33 &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 Cyclooxygenase (COX-II) enzyme (PDB Id: 3PGH), therefore the compounds 6b and 6m are used as promising lead candidates for the support of drug development.

FeCl3-promoted synthesis of 1,3,4-thiadiazoles under combined microwave and ultrasound irradiation in water

An 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.

Synthesis of 2-amino-5-aryl-1,3,4-thiadiazolopeptides as potent antitubercular agents

A novel series of 2-amino-5-aryl-thiadiazole analogs of amino acids and dipeptides were synthesized using 1-ethyl-3-(3- dimethylaminopropyl)carbodiimide as coupling agent and N-methyl morpholine (NMM) as base. Structure of all the newly synthesized compounds was confirmed by IR, 1H NMR, 13C NMR and mass spectral data. All the synthesized compounds were screened for their antitubercular, antibacterial and antifungal activity.

Thiadiazole derivatives as potential anticonvulsant agents

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,1HNMR,13C NMR and mass spectral data confir