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Original Articles

Synthesis and antibacterial activity of two spiro [indole] thiadiazole derivatives

, &
Pages 941-946 | Received 08 Nov 2008, Accepted 17 Apr 2009, Published online: 23 Sep 2010
 

Abstract

Isatin reacts with thiosemicarbazide in 50% aqueous alcohol under reflux to give isatin-3-thiosemicarbazone (1′). Compound 1′ cyclizes on treatment with acetic anhydride and pyridine to yield 1,3′-diacetyl-5′-acetamido-3(1H)-spiro[indole-3,2′-[1,3,4]-thiadiazol]-2(1H)-one, 2′. Subsequent reaction of the diacetyl spiro compound, 2′, with hydrazine hydrate at room temperature furnished a white product, which was characterized by spectroscopic means to be 1,3′-diacetyl-5′-amino-3(1H)-spiro[indole-3,2′-[1,3,4]-thiadiazol]-2(1H)-one, 3′. All three compounds (1′, 2′, 3) were tested for antibacterial activity against six Gram-positive and four Gram-negative bacteria. 1′ showed activity against five Gram-positive and one Gram-negative bacterial strains, while 2′ showed activity against three Gram-positive and two Gram-negative bacterial strains. Compound 3′ showed activity against four Gram-positive and three Gram-negative bacterial strains (better activity than streptomycin, the reference standard).

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