Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry, Pharmaceutical Sciences and Computational Chemistry


Design, synthesis and docking studies of C2-symmetric 1,4-bis sulphonamido diamino 2, 3- diolderivatives and hydrogen bond interactions with hydrolase

Author(s): N. Bramhananda Reddy, Venkataramudu Burra, L. K. Ravindranath, S. A. Aleem and N. S. Narendra

The syntheses of new C2Symmetric N,N'-((2R,3R)-2,3-dihydroxybutane-1,4-diyl)bis(N-(2-chloro-3-(trifluoromethyl) benzyl) benzenesulfonamide) from N,N'-((4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)bis(N-(2- chloro-3 (trifluorom ethyl )benz yl)benzenesulfonamide)derivatives aredescribedC2 Symmetric N,N'-((4R,5R)-2,2- dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)bis(N-(2-chloro-3 (trifluo romethyl)benzyl)benzene sulfonamide) derivatives fromN,N'-((4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl) bis (meth ylene)bis(benzenesulfonamide) derivatives are described. C2-symmetrical diamines were prepared via direct ((4R,5R)-2,2-dimethyl-1,3-dioxolane- 4,5-diyl)dimethanamine sinthesized by using(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxamide this is followed from the (4S,5S)-dimethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate molecule. For C2-symmetrical compounds, for the above targeted molecule reaction used to form the key intermediate, is a corboxamide from corboxilate. Some of the new chiral compounds, produced in good to high yields, potentially useful as asymmetric sterio chemical chemotherapeutic HIV agents. Thus, a bisulphonamido diamino 1, 3- dioxolane derivatives, used in substoichiometric amounts, was found to their broad spectrum of antibacterial activity. A series of novel sulfonamide derivatives were screened in hydrogen bond interactions with hydrolase. The results showed that the derivatives exhibited moderate hydrogen bond interactions against human hydrolase activity. The structure— activity relationships were also briefly discussed.