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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.

Reaction of 1-adamantyl carbohydrazide ( 1 ) with various substituted benzaldehydes and acetophenones yielded the corresponding hydrazide-hydrazones with a 1-adamantane carbonyl moiety. The new synthesized compounds were tested for activities against some Gram-negative and Gram-positive bacteria, and the fungus Candida albicans . Compounds 4a , 4b , 5a , and 5c displayed potential antibacterial activity against tested Gram-positive bacteria and C. albicans , while compounds 4e and 5e possessed cytotoxicity against tested human cancer cell lines.