Synthesis and biological evaluation of indole containing derivatives of thiosemicarbazide and their cyclic 1,2,4-triazole and 1,3,4-thiadiazole analogs
A. Varvaresou et al., Synthesis and biological evaluation of indole containing derivatives of thiosemicarbazide and their cyclic 1,2,4-triazole and 1,3,4-thiadiazole analogs, ARZNEI-FOR, 50(1), 2000, pp. 48-54
New indolic derivatives of thiosemicarbazides and some cyclic 1,2,4-triazol
-5-thione analogs were synthesized. The newly synthesized compounds as well
as some indole containing thiosemicarbazides. 1,2,4-triazoles and 1,3,4- t
hiadiazoles, which have been reported previously, were investigated for ant
imicrobial, antifungal and antiphage activity. Certain thiosemicarbazide de
rivatives and the corresponding cyclic 1,2,4-triazole analogs showed select
ive antimicrobial or antifungal activity, while they lack any antiphage act
ivity. Antiphage activity was detected for one compound, bearing the 1,3,3-
thiadiazole nucleus. The selectively active compounds cover a wide range li
pophilicity. Structure-activity relations show a remarkably similarity in t
he antimicrobial and antifungal behav lour of the thiosemicarbazides and th
eir cyclic triazo-thien-5-yl analogs, while alpha-naphtyl substitution in t
he non indolic portion of the molecule is favorable. C5 substitution on the
indolic nucleus may also be critical for selective activity.