76153-57-6

Upstream product

• 2740-81-0 2-chlorophenylisothiocyanate 
• 1208-86-2 N-(4-methoxyphenyl)phenylamine 
• 75-15-0 carbon disulfide 
• 104-94-9 4-methoxy-aniline 
• 95-51-2 o-chloroaniline 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 

Downstream Products

• 76153-63-4 3-(2-Chloro-phenyl)-6-hydroxy-1-(4-methoxy-phenyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 76153-46-3 3-(2-Chloro-phenyl)-6-hydroxy-1-(4-methoxy-phenyl)-5-(2-methoxy-phenylazo)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 76153-53-2 3-(2-Chloro-phenyl)-6-hydroxy-1-(4-methoxy-phenyl)-5-(4-methoxy-phenylazo)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 76153-19-0 3-(o-Chlorophenyl)-5-(o-chlorophenylazo)-1-(p-methoxyphenyl)-2-thiobarbituric acid 
• 76153-26-9 5-(4-Bromo-phenylazo)-3-(2-chloro-phenyl)-6-hydroxy-1-(4-methoxy-phenyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 76153-33-8 3-(2-Chloro-phenyl)-6-hydroxy-1-(4-methoxy-phenyl)-2-thioxo-5-o-tolylazo-2,3-dihydro-1H-pyrimidin-4-one 
• 76153-12-3 3-(2-Chloro-phenyl)-6-hydroxy-1-(4-methoxy-phenyl)-5-phenylazo-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 

Relevant academic research and scientific papers

Synthesis and erythroid induction activity of new thiourea derivatives

Background: The use of medicinal agents to augment the fetal hemoglobin (HbF) accretion is an important approach for the treatment of sickle-cell anemia and β-thalassemia. HbF inducers have the potential to reduce the clinical symptoms and blood transfusion dependence in the patients of β-hemoglobinopathies. Objective: The current study was aimed to examine the erythroid induction potential of newly synthesized thiourea derivatives. Methods: Thiourea derivatives 1-27 were synthesized by using environmentally friendly methods. Compounds 3, 10 and 22 were found to be new. The structures of synthesized derivatives were de-duced by using various spectroscopic techniques. These derivatives were then evaluated for their erythroid induction using the human erythroleukemic K562 cell line, as a model. The benzidine-H2 O2 assay was used to evaluate erythroid induction, while HbF expression was studied through immunocyto-chemistry using the Anti-HbF antibody. Cytotoxicity of compounds 1-27 was also evaluated on mouse fibroblast 3T3 cell line and cancer Hela cell line using MTT assay. Result: All the compounds (1-27) have not been reported for their erythroid induction activity previ-ously. Compounds 1, 2, and 3 were found to be the potent erythroid inducing agents with % induction of 45± 6.9, 44± 5.9, and 41± 6.1, at 1.56, 0.78, and 0.78 μM concentrations, respectively, as compared to untreated control (12 ± 1 % induction). Furthermore, compound 1, 2, and 3 significantly induced fetal hemoglobin the expression up to 4.2-fold, 4.06-fold, and 3.52-fold, respectively, as compared to untreated control. Moreover, the compounds 1-4, 6-9, 11, 12, 15, 17, 19, 22, 23, and 25 were found to be non-cytotoxic against the 3T3 cell line. Conclusion: This study signifies that the compounds reported here may serve as the starting point for the designing and development of new fetal hemoglobin inducers for the treatment of β-hemoglobinopathies.

Development of (4-methoxyphenyl)-1H-tetrazol-5-amine regioisomers as a new class of selective antitubercular agents

A series of halogenated (4-methoxyphenyl)-1H-tetrazol-5-amine regioisomers (1a-9a, 1b-9b) were synthesized from their corresponding thiourea analogues (1–9). The synthesis pathway was confirmed by an X-ray crystallographic studies of 1a, 1b and 5a. Title derivatives were tested for their in vitro antitubercular activity against standard, “wild-type” and atypical mycobacteria. The highest therapeutic potential was attributed to isomeric N-(bromophenyl)tetrazoles 8a and 9a. Their growth-inhibitory effect against multidrug-resistant Mycobacterium tuberculosis Spec. 210 was 8-16-fold stronger than that of the first-line tuberculostatics. Other new tetrazole-derived compounds were also more or equally effective towards that pathogen comparing to the established pharmaceuticals. Among non-tuberculous strains, Mycobacterium scrofulaceum was the most susceptible to the presence of the majority of tetrazole derivatives. The synergistic interaction was found between 9a and streptomycin, as well as the additivity of both 8a and 9a in pairs with isoniazid, rifampicin and ethambutol. None of the studied compounds displayed antibacterial or cytotoxic properties against normal and cancer cell lines, which indicated their highly selective antimycobacterial effects.

A simple and straightforward synthesis of phenyl isothiocyanates, symmetrical and unsymmetrical thioureas under ball milling

Promoted by KOH under ball milling, anilines were efficiently transformed into isothiocyanates (in presence of 5.0 equiv. CS2) or symmetrical thioureas (in presence of 1.0 equiv. CS2), without using any other harsh or toxic decomposition reagent. Some in situ generated isothiocyanates can directly "click" with other amines to afford unsymmetrical thioureas.