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• 2284-20-0 4-Methoxyphenyl isothiocyanate 
• 371-40-4 4-fluoroaniline 
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• 1544-68-9 4-fluorophenyl isothiocyanate 
• 1208-86-2 N-(4-methoxyphenyl)phenylamine 

Relevant academic research and scientific papers

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.

Molecular modeling and synthesis of some new 2-imino-4-thiazolidinone derivatives with promising TNF-α inhibitory activity

A new series of thirty two 2-imino-4-thiazolidinone derivatives were synthesized, and the synthesized compounds were docked for in silico studies against the TNF-α target. The predicted results were confirmed through an in vitro TNF-α study which revealed that compounds 3f and 3g showed better TNF-α inhibition as compared to the standard drug indomethacin without causing any cytotoxicity. Fourteen compounds exhibiting significant in vitro TNF-α activity were further tested for in vivo anti-inflammatory activity by a carrageenan induced method. Compounds 3f and 3g showed better inhibition of inflammation in vivo as compared to the standard drug without causing any damage to the stomach. Furthermore, an immunohistochemical study showed that the compounds 3f and 3g exhibited better reduction in protein expression of TNF-α as compared to indomethacin. The in silico, in vitro and in vivo studies suggested that the compounds 3f and 3g might be considered as potent anti-inflammatory agents.

A model for a solvent-free synthetic organic research laboratory: Click-mechanosynthesis and structural characterization of thioureas without bulk solvents

The mechanochemical click coupling of isothiocyanates and amines has been used as a model reaction to demonstrate that the concept of a solvent-free research laboratory, which eliminates the use of bulk solvents for either chemical synthesis or structural characterization, is applicable to the synthesis of small organic molecules. Whereas the click coupling is achieved in high yields by simple manual grinding of reactants, the use of an electrical, digitally controllable laboratory mill provides a rapid, quantitative and general route to symmetrical and non-symmetrical aromatic or aromatic-aliphatic thioureas. The enhanced efficiency of electrical ball milling techniques, neat grinding or liquid-assisted grinding, over manual mortar-and-pestle synthesis is demonstrated in the synthesis of 49 different thiourea derivatives. Comparison of powder X-ray diffraction data of mechanochemical products with structural information found in the Cambridge Structural Database (CSD), or obtained herein through single crystal X-ray diffraction, indicates that the mechanochemically obtained thiourea derivatives are pure in a chemical sense, but can also demonstrate purity in a supramolecular sense, i.e. in all structurally explored cases the product consisted of a single polymorph. As an extension of our previous work on solvent-free synthesis of coordination polymers, it is now demonstrated that such polymorphic and chemical purity of selected thiourea derivatives, the latter being evidenced through quantitative reaction yields, can enable the direct solvent-free structural characterization of mechanochemical products through powder X-ray diffraction aided by solid-state NMR spectroscopy.