Synthesis and Bioactivity of Thiosemicarbazones Containing Adamantane Skeletons

Abstract

Reaction of 4-(1-adamantyl)-3-thiosemicarbazide (1) with numerous substituted acetophenones and benzaldehydes yielded the corresponding thiosemicarbazones containing adamantane skeletons. The synthesized compounds were evaluated for their in vitro activities against some Gram-positive and Gram-negative bacteria, and the fungus Candida albicans, and cytotoxicity against four cancer cell lines (Hep3B, HeLa, A549, and MCF-7). All of them showed good antifungal activity against Candida albicans. Compounds 2c, 2d, 2g, 2j and 3a, 3e, 3g displayed significant inhibitory activity against Enterococcus faecalis. Compounds 2a, 2e, 2h, 2k and 3j had moderate inhibitory potency against Staphylococcus aureus. Compounds 2a, 2e and 2g found so good inhibitory effect on Bacillus cereus. Compounds 2d and 2h, which contain (ortho) hydroxyl groups on the phenyl ring, were shown to be good candidates as potential agents for killing the tested cancer cell lines, i.e., Hep3B, A549, and MCF-7. Compounds 2a–c, 2f, 2g, 2j, 2k, 3g, and 3i were moderate inhibitors against MCF-7.

Enhanced Efficacy of Thiosemicarbazone Derivative-Encapsulated Fibrin Liposomes against Candidiasis in Murine Model

“…In recent years, thiosemicarbazones have mostly been exploited for their antimicrobial and anticancer activities in the development of new drugs. Various studies have reported the antifungal activity of a series of thiosemicarbazone derivatives against Candida species [ 21 , 22 , 23 ]. Additionally, compounds bearing ligand recognition ability have been screened against Candida species.…”

Novel Steroidal 5α,8α-Endoperoxide Derivatives with Semicarbazone/Thiosemicarbazone Side-chain as Apoptotic Inducers through an Intrinsic Apoptosis Pathway: Design, Synthesis and Biological Studies

“…[30][31][32][33]. In addition, thiosemicarbazones (TSCs) have a wide clinical antitumor spectrum with efficacy in various tumor types such as bladder cancer, pancreatic cancer, cervical cancer, non-small cell lung cancer, breast cancer, prostate cancer and leukemia [34][35][36][37]. Figure 3 shows some representative compounds with thiosemicarbazones structure in the clinical trial.…”

Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles

“…1) reduces the reproducibility of vaccinia virus, and also exhibits activity in vitro against some Gram-positive and Gramnegative bacteria and fungi. 2,3 Substituted aminoacetyladamantylamines B exhibit inhibitory activity against vaccinia virus (Fig. 1).…”

“…1). 3 1-Adamantanecarboxylic acid amide containing the (-)-10-amino-2-pinene fragment (structure C) 4 and N-(1-adamantyl)-2,2-diphenylacetamide D proved to be effective inhibitors of smallpox virus. 5 In addition, compounds containing the adamantyl fragment such as memantine E (Fig.…”