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A new series of halogenated 4-thiazolidinone derivatives bearing the sulfonamide moiety was synthesized and characterized via FT-IR, 1H NMR, 13C NMR, HRMS and single crystal X-ray analysis. The newly synthesized target compounds were screened for their in vitro cytotoxicity on the HepG2 and MDA-MB-231 cell lines, and antimicrobial and antitubercular activity. The compounds showed promising anticancer activity towards the MDA-MB-231 cell line, and the trichloro derivatives with p-chloro substitution (6i) and p-hydroxy substitution (7e) exhibited excellent anticancer activity. Compounds 6b and 7c were observed to be moderate antimicrobial agents. The seven most potent anticancer agents were further studied for their antitubercular activity against an M. tuberculosis strain and it was found that compound 7e showed significant antitubercular activity. The potent candidates were also tested for hemolysis activity against human RBC cells and were found to be non-toxic. The mode of action for the observed anticancer activity was further supported by molecular docking studies of the potent compounds against the enzyme Aurora kinase (PDB ID: URL URL="HTTP://XLINK.RSC.ORG/?PDB=4ZTR"4ZTR/URL). Molecular dynamics (MD) simulations were further performed to study the stability of the ligand–protein complex. [ABSTRACT FROM AUTHOR]

Three quinazolin-4-ylamino derivatives containing phenylbenzenesulfonamides (7a-7c) were synthesized by reacting (E)- N '-(2-cyanophenyl)- N,N -dimethyl formamidine (6) with different 4-amino- N -(phenyl)benzenesulfonamides (4a-4c) and characterized by different techniques such as HRMS, IR, 1H NMR and 13C NMR spectroscopy. The structural properties were further examined by single crystal X-ray diffraction method. The X-ray data shows that compounds 7a and 7c contain two molecules and 7b contains one molecule in the asymmetric unit. Comparison of conformation of two distinct molecules, "A" and "B", in the asymmetric unit of 7a and 7c were studied with the aid of reported literature. The in vitro antiproliferative activity of the compounds was tested against two breast cancer cell lines (MDA-MB-231 and MCF7). Compound 7b observed as a highest potent candidate against MDA-MB-231with IC 50 of 5.44 μg/mL. Antimicrobial activity was also screened against bacterial and fungal strains. Compound 7a with chloro substitution was observed as the most potent candidate against the Gram-negative bacterial strains, whereas the compounds showed no significant activity against the fungal strain. Image 1 • Three quinazolin-4-ylamino derivatives containing phenylbenzenesulfonamides (7a-7c) were synthesized. • Structural properties were examined by single crystal X-ray diffraction. • Two different types (A and B) of molecular conformations of crystals were studied. • In vitro antiproliferative and antimicrobial activity studies were performed. [ABSTRACT FROM AUTHOR]