Synthesis and Biological Activity of Modified Steroids

Abstract

Steroids are biologically active organic compounds present in most of the living forms and have two principal biological functions, an important cell membrane component that alter membrane fluidity; and as signaling molecules. Any deficiency or malfunctioning of the natural form results in disruption of normal body functioning and sometimes it becomes fatal too. Numerous research is going on like addition and modification of functional groups to produce wide variety of steroidal medications with improved efficiencies. These modifications are performed using conventional organic synthesis and/or biotransformation techniques. In line with the ongoing research around the globe, the present work comprises of designing and synthesis of modified steroids. Four different groups of steroidal derivatives namely steroidal Schiff bases, steroidal hydrazones, steroidal carbonhydrazide and steroidal arylidenes are efficiently prepared, structurally evaluated and biologically screened for various activities. For steroidal Schiff bases, the initial regent estrone and 4 -bromomethyl-2-cyanobiphenyl reacted in presence of potassium carbonate and potassium iodode in anhydrous acetone leads ether 4 -(-3-yloxymethyl)-estrone-biphenyl-2-carbonitrile formation, which on sequential condensation with hydrazine hydrate and aromatic aldehydes give steroidal Schiff bases in significant yield. Their structures were confirmed by Elemental analysis (C, H, and N), Mass spectra, IR spectra and 1H, 13C NMR spectroscopy. The newly synthesized Schiff bases showed high cytotoxicity against the MCF-7 breast cancer cell line. In search of new antimicrobial agents, series of new steroidal hydrazones were designed and synthesized and their structure were confirmed by IR, 1H, 13C NMR amd Mass spectra. newline