51146-74-8

Usage

Uses

Used in Pharmaceutical Research:
[(3-methoxyphenyl)methylideneamino]thiourea is used as a compound in pharmaceutical research for its potential biological activities. [(3-methoxyphenyl)methylideneamino]thiourea's unique structure allows it to be a candidate for the development of new therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, [(3-methoxyphenyl)methylideneamino]thiourea is used as a building block for the creation of more complex molecules. Its versatile structure makes it a valuable component in the synthesis of various organic compounds.
Used in Antifungal Applications:
[(3-methoxyphenyl)methylideneamino]thiourea is used as an antifungal agent, leveraging its reported antifungal properties to combat fungal infections. It serves as a potential alternative or addition to existing antifungal treatments.
Used in Antibacterial Applications:
[(3-methoxyphenyl)methylideneamino]thiourea is also used as an antibacterial agent, taking advantage of its reported antibacterial properties to fight bacterial infections. It may be employed in the development of new antibiotics or as a supplement to current treatments.
Used in Antituberculosis Applications:
[(3-methoxyphenyl)methylideneamino]thiourea is used as an antituberculosis agent, capitalizing on its potential to combat tuberculosis. It is being studied for its effectiveness in treating this specific disease, possibly leading to the development of novel antituberculosis drugs.

InChI:InChI=1/C9H11N3OS/c1-13-8-4-2-3-7(5-8)6-11-12-9(10)14/h2-6H,1H3,(H3,10,12,14)/b11-6+

Upstream product

• 79-19-6 thiosemicarbazide 
• 591-31-1 3-methoxy-benzaldehyde 
• 1005043-75-3 2,4-bis(3-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one 

Downstream Products

• 1408315-95-6 (E)?3?(2?(2?(3?methoxybenzylidene)hydrazinyl)thiazol?4?yl)?2H?chromen?2?one 
• 324066-99-1 2-(2-(3-methoxybenzylidene)hydrazinyl)thiazol-4(5H)-one 
• 247109-15-5 5-(3-methoxyphenyl)-1,3,4-thiadiazol-2-amine 
• 113111-43-6 2-Chloro-5-(3-methoxy-phenyl)-[1,3,4]thiadiazole 
• 112764-40-6 [5-(3-Methoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-hydrazine; hydrochloride 

Relevant academic research and scientific papers

DFT calculations, Hirshfeld surface analysis and docking studies of 3-anisaldehyde thiosemicarbazone

Abstract: We report herein the synthesis, quantum chemical electronic structure, Hirshfeld surface and molecular docking studies of 3-anisaldehyde thiosemicarbazone (I). The compound has been characterized by NMR (1H, 13C) and IR spectroscopy. Hirshfeld surface analysis has been performed to understand the intermolecular interactions. The quantum chemical calculations show good consistency between the predicted and experimental parameters. Molecular docking studies of I with two different cancer target enzymes exhibit higher binding energy than its ortho substituted analogue. Graphic abstract: Synthesis, spectroscopic characterization, quantum chemical calculations, Hirshfeld surface analysis and molecular docking studies have been investigated for the compound 3-anisaldehyde thiosemicarbazone (I). The theoretical results gave a better understanding of the molecular interactions and the docking results suggest I can be used for in vitro anticancer study.[Figure not available: see fulltext.].

The design, synthesis, and: In vitro trypanocidal and leishmanicidal activities of 1,3-thiazole and 4-thiazolidinone ester derivatives

Chagas and leishmaniasis are both neglected tropical diseases, whose inefficient therapies have made them remain the cause for millions of deaths worldwide. Given this, we synthesized 27 novel 1,3-thiazoles and 4-thiazolidinones using bioisosteric and est

Aryl hydrazones linked thiazolyl coumarin hybrids as potential urease inhibitors

Aryl hydrazones bearing thiazolyl coumarin hybrids 1–32 were prepared by following 'one-pot' two-steps reaction scheme. Various arylaldehydes were reacted to thiosemicarbazide under acidic condition to form aryl thiosemicarbazone intermediates which in turn treated with 3-bromoacetyl coumarin under basic condition to afford thiazolyl coumarin hybrids 1–32. All hybrids were recognized by EI- and HREI-MS and 1H- and 13C-NMR spectroscopic techniques. Compounds 1–32 were screened for in vitro inhibitory activity against urease enzyme and displayed good to moderate inhibitory potential in the ranges of IC50 = 16.29 ± 1.1–256.30 ± 1.4?μM. Worth stating that compound 21 (IC50 = 16.29 ± 1.1?μM) was identified as more potent urease inhibitor than the standard acetohydroxamic acid (IC50 = 27.0 ± 0.5?μM). Derivatives 19 (IC50 = 77.67 ± 1.5?μM) and 30 (IC50 = 71.21 ± 1.6?μM) were found to be moderately active. Structure–activity relationship revealed that -F, -Cl, -OH, and -OMe groups and their respective positions on aryl ring are playing important role in urease enzyme inhibition. Molecular docking studies identified important interaction between the ligand (active hybrids) and urease active site.

Design, synthesis, and structure–Activity relationships of thiazole analogs as anticholinesterase agents for alzheimer’s disease

Dementia is a neurological condition commonly correlated with Alzheimer’s disease (AD), and it is seen with many other central nervous system (CNS) disorders. The restricted number of medications is not appropriate to offer enough relief to enhance the quality of life of patients suffering from this symptom; thus, all therapeutic choices should be carefully assessed. In this study, new thiazolylhydrazone derivatives (2a–2l) were designed and synthesized based on the cholinergic hypothesis. Their chemical structures were confirmed by 1H NMR, 13C NMR, and HRMS spectrometric techniques. The ADME (absorption, distribution, metabolism, elimination) parameters of the synthesized compounds were predicted by using QikProp 4.8 software. It was concluded that all compounds presented satisfactory drug-like characteristics. Furthermore, their inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) in vitro were also tested by modified the Ellman spectrophotometric method. According to the results, all compounds showed a weak inhibitory effect on BChE. On the other hand, most of the compounds (2a, 2b, 2d, 2e, 2g, 2i, and 2j) had a certain AChE inhibitory activity, and the IC50 values of them were calculated as 0.063 ± 0.003, 0.056 ± 0.002, 0.147 ± 0.006, 0.040 ± 0.001, 0.031 ± 0.001, 0.028 ± 0.001, and 0.138 ± 0.005 μM, respectively. Among these derivatives, compound 2i was found to be the most active agent in the series with an IC50 value of 0.028 ± 0.001 μM, which indicated an inhibition profile at a similar rate as the reference drug, donepezil. The potential binding modes of compounds 2a, 2b, 2e, 2g, and 2i with AChE were investigated and compared with each other by the molecular docking studies. The results showed that these compounds were strongly bound up with the AChE enzyme active site with the optimal conformations.

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.

Synthesis and antimicrobial evaluation of novel 3-(arylideneamino)-3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-diones and their 2-thioxo analogues

The preparation of some novel 3-(arylideneamino)-3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-diones 8(i–xiv) and 3-(arylideneamino)-3a,8a-dihydroxy-2-thioxo-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(2H)-ones 9(i–xiv) have been reported through one-pot catalyst-free reaction of aldehydes, semicarbazide hydrochloride/thiosemicarbazide with ninhydrin. All the synthesized compounds have been screened for antimicrobial activity and some of them were observed to possess broad spectrum antibacterial potential as well as significant antagonistic potential against fungal pathogens.

Design, Synthesis, and Evaluation of 3-((4-(t-Butyl)-2-(2-benzylidenehydrazinyl)thiazol-5-yl)methyl)quinolin-2(1H)-ones as Neuraminidase Inhibitors

A series of novel 3-((4-(t-butyl)-2-(2-benzylidenehydrazinyl)thiazol-5-yl)methyl)quinolin-2(1H)-ones (7a-7z) were designed, synthesized and evaluated for their ability of inhibiting neuraminidase (NA) of in?uenza H1N1 virus. Some compounds displayed moder

Synthesis and Biological Evaluation of 3-thiazolocoumarinyl Schiff-base Derivatives as Cholinesterase Inhibitors

On the basis of the observed biological activity of the coumarins, a new set of 3-thiazolocoumarinyl Schiff-base derivatives with chlorine, hydroxy and methoxy functional group substitutions were designed and synthesized. These compounds were tested against acetylcholinesterase from Electrophorus electricus and butyrylcholinesterase from horse serum and their structure-activity relationship was established. Studies revealed them as the potential inhibitors of cholinesterase (acetylcholinesterase and butyrylcholinesterase). The 3f was found to be most potent against acetylcholinesterase with Ki value of 1.05±0.3μm and 3l showed excellent inhibitory action against butyrylcholinesterase with Ki value of 0.041±0.002μm. The synthesized compounds were also docked into the active sites of the homology models of acetylcholinesterase and butyrylcholinesterase to predict the binding modes of these compounds. It was predicted that most of the compounds have similar binding modes with reasonable binding affinities. Our docking studies have also shown that these synthesized compounds have better interaction patterns with butyrylcholinesterase over acetylcholinesterase. The main objective of the study was to develop new potent and selective compounds, which might be further optimized to prevent the progression of the Alzheimer's disease and could provide symptomatic treatment.

Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors

A series of new and novel Schiff base derivatives were synthesized and investigated as potential new inhibitors of Jack bean urease. The most potent compounds were 3f with (Ki = 0.09 μM) and 3k (Ki = 0.122 μM). A pure competitive mec

Design, synthesis and biological evaluation of thiazolidinone derivatives as potential EGFR and HER-2 kinase inhibitors

Two series of thiazolidinone derivatives designing for potential EGFR and HER-2 kinase inhibitors have been discovered. Some of them exhibited significant EGFR and HER-2 inhibitory activity. Compound 2-(2-(5-bromo-2-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one (12) displayed the most potent inhibitory activity (IC50 = 0.09 μM for EGFR and IC50 = 0.42 μM for HER-2), comparable to the positive control erlotinib. Docking simulation was performed to position compound 12 into the EGFR active site to determine the probable binding model. Antiproliferative assay results indicating that some of the thiazolidinone derivatives own high antiproliferative activity against MCF-7. Compound 12 with potent inhibitory activity in tumor growth inhibition would be a potential anticancer agent.