37014-08-7

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-Methoxyphenyl)-2-thiourea is used as a pharmaceutical intermediate for the synthesis of various therapeutic agents. Its unique structure allows it to be a key component in the development of drugs targeting specific biological pathways or receptors.
Used in Agricultural Industry:
In agriculture, 1-(3-Methoxyphenyl)-2-thiourea may be utilized as a chemical component in the formulation of agrochemicals, such as pesticides or herbicides, due to its potential to interact with specific plant or pest enzymes.
Used in Organic Synthesis:
1-(3-Methoxyphenyl)-2-thiourea serves as a reagent in organic synthesis, facilitating the creation of a range of organic compounds through its ability to participate in various chemical reactions, including condensation, substitution, and rearrangement processes.
Used in Research and Development:
1-(3-METHOXYPHENYL)-2-THIOUREA is employed in research and development settings to explore its chemical properties, reactivity, and potential applications in new material development or as a precursor to novel compounds with specific functions.

InChI:InChI=1/C8H10N2OS/c1-11-7-4-2-3-6(5-7)10-8(9)12/h2-5H,1H3,(H3,9,10,12)

Upstream product

• 3125-64-2 3-methoxyphenyl isothiocyanate 
• 1147550-11-5 ammonium thiocyanate 
• 536-90-3 m-Anisidine 
• 532-55-8 Benzoyl isothiocyanate 
• 75-15-0 carbon disulfide 
• 540-72-7 sodium thiocyanide 
• 27191-09-9 m-anisidine hydrochloride 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 22476-62-6 2-(3-methoxyphenylamino)thiazol-4-one 
• 54346-87-1 2-amino-5-methoxybenzothiazole 
• 54469-61-3 (4-benzothiazol-2-yl-thiazol-2-yl)-(3-methoxy-phenyl)-amine 
• 61108-57-4 [2'-(4-chloro-phenyl)-4'-methyl-[4,5']bithiazolyl-2-yl]-(3-methoxy-phenyl)-amine 
• 21352-54-5 2,7-bis-(3-methoxy-anilino)-1,6-dithia-3,8-diaza-spiro[4.4]nona-2,7-diene-4,9-dione 
• 95942-37-3 4-amino-3-(3-methoxy-phenyl)-5-phenyl-3H-thiazol-2-ylideneamine 
• 67241-33-2 [4-(2,5-dichloro-phenyl)-thiazol-2-yl]-(3-methoxy-phenyl)-amine 
• 61108-48-3 (3-methoxy-phenyl)-[2'-(4-methoxy-phenyl)-4'-methyl-[4,5']bithiazolyl-2-yl]-amine 
• 115541-02-1 2-(m-methoxyphenylamino)-4-(2'-pyrazinyl)thiazole 
• 79571-45-2 4-(5-Nitro-2-furyl)-2-(m-methoxyphenylamino)thiazole 
• 88352-18-5 2-S-Methyl-1-(3-methoxyphenyl)-5-(2-pyridyl)isodithiobiuret 
• 82636-19-9 1-(3-Methoxy-phenyl)-2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 88352-31-2 2-S-Methyl-1-(3-methoxyphenyl)-5-(2-furfuryl)isodithiobiuret 
• 82635-92-5 2-[3-(3-Methoxy-phenyl)-2-methyl-isothioureidomethylene]-malonic acid diethyl ester 

Relevant academic research and scientific papers

SMALL MOLECULE PROSTAGLADIN TRANSPORT INHIBITORS

The disclosure provides compounds of Formula 1, and the pharmaceutically acceptable salts thereof. The variables in Formula 1, e.g. X1-X5, A1, A2, and R1-R4 are described herein. Such compounds are useful as prostaglandin transport (PGT) inhibitors. The disclosure further includes pharmaceutical compositions comprising a compound of Formula 1 or salt thereof and methods of using compounds of Formula 1 and salts thereof to treat diseases and disorders mediated, at least in part, by prostaglandin levels or cyclooxygenase activity. Such diseases and disorders include painful and inflammatory conditions.

Design, synthesis and biological evaluation of novel semicarbazone-selenochroman-4-ones hybrids as potent antifungal agents

A series of novel 2,3-dihydro-4H-1-benzoselenin-4-one (thio)semicarbazone derivatives were designed and synthesized by using molecular hybridization approach. All the target compounds were characterized by HRMS and NMR and evaluated in vitro antifungal activity against five pathogenic strains. In comparison with precursor selenochroman-4-ones, the hybrid molecules in this study showed significant improvement in antifungal activities. Notably, compound B8 showed significant antifungal activity against other strains excluding Aspergillus fumigatus (0.25 μg/mL on Candida albicans, 2 μg/mL on Cryptococcus neoformans, 8 μg/mL on Candida zeylanoides and 2 μg/mL on fluconazole-sensitive strains of Candida albicans). Moreover, compounds B8, B9 and C2 also displayed most potent activities against four fluconazole-resistance strains. Especially the MIC values of the hybrid molecule B8 against fluconazole-resistant strains were in the range of 0.5–2 μg/mL. Therefore, the molecular hybridization approach in this study provided new ideas for the development of antifungal drug.

Discovery of Multitarget Agents Active as Broad-Spectrum Antivirals and Correctors of Cystic Fibrosis Transmembrane Conductance Regulator for Associated Pulmonary Diseases

Enteroviruses (EVs) are among the most frequent infectious agents in humans worldwide and represent the leading cause of upper respiratory tract infections. No drugs for the treatment of EV infections are currently available. Recent studies have also linked EV infection with pulmonary exacerbations, especially in cystic fibrosis (CF) patients, and the importance of this link is probably underestimated. The aim of this work was to develop a new class of multitarget agents active both as broad-spectrum antivirals and as correctors of the F508del-cystic fibrosis transmembrane conductance regulator (CFTR) folding defect responsible for >90% of CF cases. We report herein the discovery of the first small molecules able to simultaneously act as correctors of the F508del-CFTR folding defect and as broad-spectrum antivirals against a panel of EVs representative of all major species.

Neurodegenerative Therapies

The present invention provides a compound of formula (I) wherein: Y represents a C or N atom which may be substituted or form a cyclic group with R′″ but may not be a quaternary C atom; R′ is —OR1, —CONH2, —CF3, F, —OH, —NO2, —CN or —OCOR1 in which R1, is C1-3 alkyl and each may be in the beta or gamma position; R″ is C1-3 alkyl or H; and R′″ is H or a group consisting of 1-12 non-hydrogen atoms and may be linear, branched and/or incorporate one or more cyclic groups, cyclic groups may be aromatic and/or heterocyclic and 2 or more cyclic groups may be linked or fused and each may be substituted; or a salt, hydrate or solvate of a compound of formula (I) for use in the treatment or prevention of a neurodegenerative disorder by inhibiting formation of neurofibrillary (tau) tangles and/or by inhibiting Dyrk 1A. The invention further relates to non-therapeutic uses of these compounds.

Probing the ATP-Binding Pocket of Protein Kinase DYRK1A with Benzothiazole Fragment Molecules

DYRK1A has emerged as a potential target for therapies of Alzheimer's disease using small molecules. On the basis of the observation of selective DYRK1A inhibition by firefly d-luciferin, we have explored static and dynamic structural properties of fragment sized variants of the benzothiazole scaffold with respect to DYRK1A using X-ray crystallography and NMR techniques. The compounds have excellent ligand efficiencies and show a remarkable diversity of binding modes in dynamic equilibrium. Binding geometries are determined in part by interactions often considered "weak", including "orthogonal multipolar" types represented by, for example, F-CO, sulfur-aromatic, and halogen-aromatic interactions, together with hydrogen bonds that are modulated by variation of electron withdrawing groups. These studies show how the benzothiazole scaffold is highly promising for the development of therapeutic DYRK1A inhibitors. In addition, the subtleties of the binding interactions, including dynamics, show how full structural studies are required to fully interpret the essential physical determinants of binding.

Synthesis and biological evaluation of 2-phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-ones as IKK2 inhibitors

In a search for novel molecules to treat inflammatory disorders, we identified several compounds with inhibitory action against the IKK2 enzyme using in silico methods. Based on the virtual hit of compounds 1 and 2, a novel series of 2-phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-one derivatives was designed, synthesized, and evaluated for IKK2 inhibitory activity. Among the synthesized derivatives, compounds 17f and 19f showed good IKK2 inhibitory potency, which have 4-carboxaminophenyl on the 2-furan ring and a methoxy group on the phenylimino moiety at the 2-position of the core structure. The most potent compound was 2-(2,4-dimethoxyphenyl)imino-5((5(4-carboxaminophenyl)furan-2-yl)methylene)thiazolidin-4-one (19f, IC50 = 0.94 μM), which represents a synergic effect of the two virtual hit compounds against IKK2. We also identified compounds showing inhibitory activities against interleukin (IL)-17, CCK-8, and tumor necrosis factor-alpha (TNF-α), which are NF-κB-dependent pro-inflammatory cytokine mediators.

QSAR modeling of synthesized 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potent antibacterial agents

Present communication elicits the designing and synthesis of 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potential antibacterial agents. A number of substituted 2-amino benzothiazoles, 2-amino-5-[(E)-phenyl diazenyl] benzoic acid, and 2-phenyl-4H benzo[d] [1,3] oxazin-4-one were synthesized as the precursor substrates. The compounds were synthesized in excellent yields and the structures were corroborated on the basis of IR, 1H NMR, Mass, and elemental analysis data. These compounds were screened in vitro for their antibacterial activity against a representative panel of Gram positive and Gram negative bacteria and models were generated through quantitative structure-activity relationship (QSAR).The activity contributions due to structural and substituent effects were determined using sequential regression procedure. The antimicrobial assay data show that the synthesized compounds are found to manifest profound antimicrobial activity. Springer Science+Business Media, LLC 2011.

4-Pyridylanilinothiazoles that selectively target von Hippel - Lindau deficient renal cell carcinoma cells by inducing autophagic cell death

Renal cell carcinomas (RCC) are refractory to standard therapy with advanced RCC having a poor prognosis; consequently treatment of advanced RCC represents an unmet clinical need. The von Hippel-Lindau (VHL) tumor suppressor gene is mutated or inactivated in a majority of RCCs. We recently identified a 4-pyridyl-2-anilinothiazole (PAT) with selective cytotoxicity against VHL-deficient renal cells mediated by induction of autophagy and increased acidification of autolysosomes. We report exploration of structure-activity relationships (SAR) around this PAT lead. Analogues with substituents on each of the three rings, and various linkers between rings, were synthesized and tested in vitro using paired RCC4 cell lines. A contour map describing the relative spatial contributions of different chemical features to potency illustrates a region, adjacent to the pyridyl ring, with potential for further development. Examples probing this domain validated this approach and may provide the opportunity to develop this novel chemotype as a targeted approach to the treatment of RCC. 2009 American Chemical Society.

HETEROARYL COMPOUNDS, COMPOSITIONS, AND METHODS OF USE IN CANCER TREATMENT

Provided herein are novel heteroaryl compounds, compositions comprising the compounds, and methods of treatment or prevention comprising administration of the compounds. The compounds are effective in the targeting of cells defective in the von Hippel-Lindau gene and in inducing autophagic cell death. The methods are directed to treating or preventing diseases such as cancer, and in particular cancers resulting from von Hippel-Lindau disease. The compounds of the invention may be administered in combination with another therapeutic agent.

4′-Methyl-4,5′-bithiazole-based correctors of defective ΔF508-CFTR cellular processing

The synthesis and ΔF508-CFTR corrector activity of a 148-member methylbithiazole-based library are reported. Synthetic routes were devised and optimized to generate methylbithiazole analogs in four steps. Corrector potency and efficacy were assayed using epithelial cells expressing human ΔF508-CFTR. These structure-activity data establish that the bithiazole substructure plays a critical function; eight novel methylbithiazole correctors were identified with low micromolar potencies.