The reaction of 1-adamantyl isothiocyanate 4 with the various cyclic secondary amines yielded the corresponding N-(1-adamantyl)carbothioamides 5a–e, 6, 7, 8a–c and 9. Similarly, the reaction of 4 with piperazine and trans-2,5-dimethylpiperazine in 2:1
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The reaction of 1-adamantyl isothiocyanate 4
with the various cyclic secondary amines yielded the corresponding N
. Similarly, the reaction of 4
with piperazine and trans
-2,5-dimethylpiperazine in 2:1 molar ratio yielded the corresponding N
, respectively. The reaction of N
with excess hydrazine hydrate yielded the target carbohydrazide 11
, in addition to 4-(1-adamantyl)thiosemicarbazide 12
as a minor product. The reaction of the carbohydrazide 11
with methyl or phenyl isothiocyanate followed by heating in aqueous sodium hydroxide yielded the 1,2,4-triazole analogues 14a
. The reaction of the carbohydrazide 11
with various aromatic aldehydes yielded the corresponding N'
-arylideneamino derivatives 15a
. The compounds 5a
were tested for in vitro
antimicrobial activity against certain strains of pathogenic Gram-positive and Gram-negative bacteria and the yeast-like fungus Candida albicans
. The compounds 5c
showed potent antibacterial activity against one or more of the tested microorganisms. The oral hypoglycemic activity of compounds 5c
was determined in streptozotocin (STZ)-induced diabetic rats. Compound 5c
produced significant reduction of serum glucose levels, compared to gliclazide.