57235-50-4

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-CYCLOPROPYL-1,3,4-THIADIAZOLE is used as an antibacterial agent for its ability to combat bacterial infections. Its chemical properties contribute to its effectiveness in this application, making it a valuable compound in the development of new drugs and treatments for bacterial-related illnesses.
Used in Chemical Industry:
In the chemical industry, 2-AMINO-5-CYCLOPROPYL-1,3,4-THIADIAZOLE can be utilized as a building block or intermediate in the synthesis of various compounds. Its unique structure and properties allow it to be a versatile component in the creation of new materials and products.

InChI:InChI=1/C5H7N3S/c6-5-8-7-4(9-5)3-1-2-3/h3H,1-2H2,(H2,6,8)

Upstream product

• 4023-34-1 cyclopropanecarboxylic acid chloride 
• 79-19-6 thiosemicarbazide 
• 1759-53-1 cyclopropanecarboxylic acid 
• 5500-21-0 cyclopropropanecarbonitrile 

Relevant academic research and scientific papers

Synthesis and Antimicrobial Activity Evaluation of Imidazole-Fused Imidazo[2,1-b][1,3,4]thiadiazole Analogues

Three series of new imidazole-fused imidazo[2,1-b][1,3,4]thiadiazole analogues (compounds 20 a–g, 21 a–g, and 22 a–g) have been synthesized, and their antibacterial and antifungal activities have been evaluated. All the target compounds showed strong anti

Discovery of novel nonpeptide small-molecule NRP1 antagonists: Virtual screening, molecular simulation and structural modification

Multifaceted roles of vascular endothelial growth factor (VEGF)-neuropilin-1 (NRP1) interaction have been implicated in cancer, but reports on small-molecule inhibitors of VEGF-NRP1 interaction are scarce. Herein, we describe the identification of 1, a novel nonpeptide small-molecule NRP1 antagonist with moderate activity via structure-based virtual screening. Ensemble docking and molecular dynamics (MD) simulations of 1 were carried out and an interesting binding model was obtained. We found that the “aromatic box” enclosed by Tyr297, Trp301 and Tyr353 of NRP1 is critical for NRP1-1 binding. Further structure modification of 1 based on the binding model derived from MD simulations resulted in the identification of 12a with significantly improved activity.

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.

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 biological activity of acylthiourea derivatives contain 1,2,3-thiadiazole and 1,3,4-thiadiazole

In order to investigate the biological activity of novel thiourea compounds, some novel 1,2,3-thiadiazole derivatives containing 1,3,4-thiadiazole were synthesized under phase transfer catalyzed condition(PEG-600)by multi-step reactions. The chemical structures of all compounds were established by 1H NMR, FTIR, MS, and elemental analysis, and some of these compounds were investigated for fungicidal activity and plant growth regulatory activity. The bioassay results indicated that some of these compound exhibited moderate activities.

Synthesis and anticancer evaluation of novel 2-cyclopropylimidazo[2,1-b][1, 3,4]-thiadiazole derivatives

A series of 2,5,6-trisubstituted imidazo[2,1-b][1,3,4]-thiadiazole derivatives 4(a-k) have been prepared by reaction of 2-amino-5-cyclopropyl-1,3, 4-thiadiazole and an appropriate phenacyl bromide. Further 5-bromo 5(a-k) and 5-thiocyanato 6(a-k) derivativ

Synthesis, antifungal activities and 3D-QSAR study of N-(5-substituted-1,3,4-thiadiazol-2-yl)cyclopropanecarboxamides

A series of cyclopropanecarboxamide were prepared and tested for antifungal activity in vivo. The preliminary bioassays indicated that some compounds are comparable to the commercial fungicides. To further explore the comprehensive structure-activity relationship on the basis of fungicidal activity data, comparative molecular field analysis (CoMFA) was performed, and a statistically reliable model with good predictive power (r2 = 0.8, q2 = 0.516) was achieved. Based on the CoMFA, compound 7p was designed and synthesized, which was found to display a good antifungal activity (79.38%) as 7g and 7h.

Phase transfer catalysts promoting the one-pot synthesis under ultrasonic irradiation and biological activity of n-(5-substituted-1,3,4-thiadiazole-2-yl)- N'-(5-methylisoxazoyl)-thiourea derivatives

Reaction of 2-amino-5-substitute-1,3,4-thiadiazoles with 5-methylisoxazoyl chloride and ammonium thiocyanate under the condition of solid-liquid phase-transfer catalysis using polyethylene glycol-600 (PEG-600) as the catalyst under ultrasonic irradiation yielded N-(5-substituted-1,3,4-thiadiazole-2-yl)- N'-(5-methylisoxazoyl)-thiourea derivatives 3a-1 in good-to-excellent yield. The chemical structure of all compounds was established by 1H NMR, FTIR, MS, and elemental analysis studies. Some of the compounds were investigated for fungicidal activity. The bioassay results indicated that some of these compounds exhibit moderate fungicidal activities.

SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS

The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed