Synthesis and In vitro cytotoxic activity evaluation of (E)-16-(substituted benzylidene) derivatives of dehydroepiandrosterone

Abstract

Background and the purpose of the studyModified androsterone derivatives are class of steroidal compounds with potential anticancer properties. Various steroidal derivatives containing substitution at position 16 have shown diversified pharmacological activities. In the present study, a new series of cytotoxic 16-(substituted benzylidene) derivatives of dehydroepiandrosterone (DHEA) were synthesized and evaluated against three different cancer cell lines.MethodsThe cytotoxic 16-(substituted benzylidene) derivatives of DHEA were synthesized via aldol condensation of DHEA with corresponding benzaldehyde derivatives. The cytotoxic activity of synthesized derivatives was evaluated against three different cancer cells including KB, T47D and SK-N-MC cell lines by MTT reduction colorimetric assay.ResultsThe results indicated that 16-(substituted benzylidene) derivatives of DHEA could be served as a potent anti-cancer agent. The 3-cholro benzylidene derivatives of DHEA was the most potent synthesized derivative especially against KB and T47D cell lines (IC50 values were 0.6 and 1.7 μM; respectively).ConclusionThe cytotoxic potential of novel benzylidene derivatives of DHEA is mainly attributed to the position and nature of the substituted group on the benzylidene pendant.

The Use of Switchable Polarity Solvents for the Synthesis of 16‐Arylidene Steroids via Claisen–Schmidt Condensation

“…Benzylidene derivatives obtained by the Claisen–Schmidt condensation of steroidal ketones may serve as starting materials for the synthesis of compounds of pharmacological importance or may show favourable biological activity themselves . The 16‐arylidene group was found to be a good pharmacophore for cytotoxic activity.…”

“…The 16‐arylidene group was found to be a good pharmacophore for cytotoxic activity. Derivatives of androst‐5‐en‐3β‐ol‐17‐one showed significant activity against MCF‐7 (breast), NCl‐H460 (lung) and SF‐268 (central nervous system) cell lines, as well as against KB (human nasopharyngeal epidermoid carcinoma), T47D (human breast cancer) and SK‐N‐MC (human neuroblastoma) cells . The cytotoxic potential of these compounds was greatly influenced by the position and nature of the substituent on the benzylidene pendant.…”

Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities

“…1,3-Bis(4-(tert-butyl)benzyl)-1H-benzo [d] 34.67 (C8 0 ;8 00 ), 51.27 (C1 0 ;1 00 ), 113.78 (C4;7), 126.34 (C4 0 ;6 0 ;4 00 ;6 00 ), 127.09 (C5,6), 128.17 (C3 0 ;7 0 ;3 00 ;7 00 ), 129.56 (C8;9), 131.41 (C2 0 ;2 00 ), 143.0 (C2), 152.46 (C5 0 ;5 00 ).…”

“…Thus, the use of N-heterocyclic carbenes associated to palladium has been reported as efficient catalysts for the carbonyl coupling under mild and varied conditions. [30][31][32][33][34][35] Herein, we report the use of the two families of benzimidazolium salts already synthesized [36][37][38] as a ligand in the carbonylative cross coupling of 2-bromopyridine with different boronic acids under inert condition to form unsymmetrical arylpyridine ketones (Scheme 2). In addition, the cytotoxic activities against the cancer human cell lines such us MDA-MB-231, MCF-7 and T47D of the compounds 2 and 4 were also determined.…”

Design, synthesis, cytotoxicity evaluation and docking studies of 1,2,4-triazine derivatives bearing different arylidene-hydrazinyl moieties as potential mTOR inhibitors

“…Cancer is the main cause of death worldwide and it is estimated that the number of annual cancer deaths will increase to 11.4 million in 2030 ( 1 ). Despite various therapeutic approaches, treatment of cancer is still a significant obstacle and attempts to find new, effective and less toxic agents are being continued ( 2 3 4 5 ).…”