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-(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 molar ratio yielded the corresponding
N,
N'-bis(1-adamantyl)piperazine-1,4-dicarbothioamides
10a and
10b, respectively. The reaction of
N-(1-adamantyl)-4-ethoxycarbonylpiperidine-1-carbothioamide
8c 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 and
14b. The reaction of the carbohydrazide
11 with various aromatic aldehydes yielded the corresponding
N'-arylideneamino derivatives
15a–
g. The compounds
5a–
e,
6,
7,
8a–
c,
9,
10a,
10b,
14a,
14b and
15a–
g 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,
5d,
5e,
6,
7,
10a,
10b,
15a,
15f and
15g showed potent antibacterial activity against one or more of the tested microorganisms. The oral hypoglycemic activity of compounds
5c,
6,
8b,
9,
14a and
15b was determined in streptozotocin (STZ)-induced diabetic rats. Compound
5c produced significant reduction of serum glucose levels, compared to gliclazide.
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