4683-00-5

Usage

Uses

Used in Organic Chemistry Research:
2-AMINO-5-(2-THIENYL)-1,3,4-THIADIAZOLE is used as a research compound for the synthesis of more complex organic compounds. Its unique structure and properties make it a valuable component in the development of novel organic molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-AMINO-5-(2-THIENYL)-1,3,4-THIADIAZOLE is used as a building block for the development of new drugs. Its heterocyclic structure allows for the creation of diverse chemical entities with potential therapeutic properties, making it a valuable asset in drug discovery and design.
Used in Chemical Synthesis:
2-AMINO-5-(2-THIENYL)-1,3,4-THIADIAZOLE is used as a synthetic intermediate for the production of various chemical compounds. Its reactivity and stability make it suitable for use in a wide range of chemical reactions, facilitating the synthesis of target molecules with specific properties and applications.
Used in Material Science:
In the field of material science, 2-AMINO-5-(2-THIENYL)-1,3,4-THIADIAZOLE is used as a component in the development of new materials with unique properties. Its aromatic nature and heterocyclic structure can contribute to the creation of materials with enhanced stability, conductivity, or other desirable characteristics.
Used in Agrochemical Industry:
2-AMINO-5-(2-THIENYL)-1,3,4-THIADIAZOLE is used as a starting material for the synthesis of agrochemicals, such as pesticides and herbicides. Its chemical properties allow for the development of effective compounds that can protect crops from pests and diseases, contributing to increased agricultural productivity.

InChI:InChI=1/C6H5N3S2/c7-6-9-8-5(11-6)4-2-1-3-10-4/h1-3H,(H2,7,9)

Upstream product

• 1003-31-2 thiophene-2-carbonitrile 
• 79-19-6 thiosemicarbazide 

Downstream Products

• 73653-61-9 6-phenyl-2-(thiophen-2-yl)imidazo[2,1-b][1,3,4]thiadiazole 
• 1000383-25-4 6-(4-methoxyphenyl)-2-(thiophen-2-yl)imidazo[2,1-b][1,3,4]thiadiazole 
• 1000383-24-3 6-(4-methylphenyl)-2-(thiophen-2-yl)imidazo[2,1-b][1,3,4]thiadiazole 

Relevant academic research and scientific papers

N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings as novel antibacterial agents: Design, synthesis, biological evaluation and target identification

Due to the occurrence of antibiotic resistance, bacterial infectious diseases have become a serious threat to public health. To overcome antibiotic resistance, novel antibiotics are urgently needed. N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides are a potential new class of antibacterial agents, as one of its derivatives was identified as an antibacterial agent against S. aureus. However, no potency-directed structural optimization has been performed. In this study, we designed and synthesized 37 derivatives, and evaluated their antibacterial activity against S. aureus ATCC29213, which led to the identification of ten potent antibacterial agents with minimum inhibitory concentration (MIC) values below 1 μg/mL. Next, we performed bacterial growth inhibition assays against a panel of drug-resistant clinical isolates, including methicillin-resistant S. aureus, and cytotoxicity assays with HepG2 and HUVEC cells. One of the tested compounds named 1-ethyl-4-hydroxy-2-oxo-N-(5-(thiazol-2-yl)-1,3,4-thiadiazol-2-yl)-1,2-dihydroquinoline-3-carboxamide (g37) showed 2 to 128-times improvement compared with vancomycin in term of antibacterial potency against the tested strains (MICs: 0.25–1 μg/mL vs. 1–64 μg/mL) and an optimal selective toxicity (HepG2/MRSA, 110.6 to 221.2; HUVEC/MRSA, 77.6–155.2). Further, comprehensive evaluation indicated that g37 did not induce resistance development of MRSA over 20 passages, and it has been confirmed as a bactericidal, metabolically stable, orally active antibacterial agent. More importantly, we have identified the S. aureus DNA gyrase B as its potential target and proposed a potential binding mode by molecular docking. Taken together, the present work reports the most potent derivative of this chemical series (g37) and uncovers its potential target, which lays a solid foundation for further lead optimization facilitated by the structure-based drug design technique.

Natural product-inspired rational design, synthesis and biological evaluation of 2,3-dihydropyrano[2,3-f]chromen-4(8H)-one based hybrids as potential mitochondrial apoptosis inducers

Synthesis of novel pyranochromanone amide hybrids, by combining pyranochromanone pharmacophore and privileged scaffolds such as 2-amino-1,3,4-thiadiaole/2-aminothiazole/aminopyridine/aminonaphthalene and anti-cancer evaluation of a series led us to discover a series of new chemical entities (NCEs) showing broad spectrum of anti-cancer activity against three different human cancer cell lines (MCF-7, A549 and HeLa), at IC50values ranging from 14.3 to 97.8?μM. Among them, some compounds such as 15b, 15d, 20a and 20b displayed excellent activity against breast cancer cell line MCF-7. Detailed biological studies such as AO/EB dual staining, Hoechst 33342 staining, FACS analysis of mitochondrial membrane potential (Δψm) using JC-1 dye and DNA fragmentation confirmed the apoptosis induced by the hybrids. Gene expression studies by Real time RT-PCR has shown that these compounds are efficient regulator of anti-apoptotic gene Bcl-2. Western blot analysis also revealed that these compounds persuade apoptosis through intrinsic pathway by up-regulating the pro-apoptotic protein Bax and down-regulating the anti-apoptotic protein Bcl-2. Molecular docking studies reveal that compounds 15b and 20b binds efficiently with Bcl-2 promoter G-quadruplex.