Efficient microwave enhanced regioselective synthesis of a series of benzimidazolyl/triazolyl spiro [indole-thiazolidinones] as potent antifungal agents and crystal structure of spiro[3H-indole-3,2'-thiazolidine]-3'(1,2,4-triazol-3-yl)-2,4'(1H)-dione.
A microwave-assisted three-component, regioselective one-pot cyclocondensation method has been developed for the synthesis of a series of novel spiro[indole-thiazolidinones] (6a-l) using an environmentally benign procedure at atmospheric pressure in open vessel. This rapid method produces pure products in high yields within few minutes in comparison to a conventional two-step procedure. The crystal structure of one representative compound has been determined by X-ray diffraction. The synthesized compounds have been screened 'in vitro' for antifungal activity against Rhizoctonia solani, Fusarium oxysporum and Collectotrichum capsici. All compounds have shown good activity against these pathogens.
Dandia
Anshu
A
Department of Chemistry, University of Rajasthan, Jaipur, India. dranshudandia@eth.net
Singh
Ruby
R
Khaturia
Sarita
S
Mérienne
Claude
C
Morgant
Georges
G
Loupy
André
A
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001562:Benzimidazoles / Q000737:chemistry* / Q000528:radiation effects; D020231:Colletotrichum / Q000145:classification / Q000187:drug effects; D003460:Crystallization; D005670:Fusarium / Q000145:classification / Q000187:drug effects; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000528:radiation effects; D008872:Microwaves; D008958:Models, Molecular; D015394:Molecular Structure; D012232:Rhizoctonia / Q000145:classification / Q000187:drug effects; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000737:chemistry / Q000528:radiation effects; D053778:Thiazolidines; D014230:Triazoles / Q000737:chemistry* / Q000528:radiation effects; D014961:X-Ray Diffraction
D000935:Antifungal Agents; D001562:Benzimidazoles; D007211:Indoles; D013141:Spiro Compounds; D013844:Thiazoles; D053778:Thiazolidines; D014230:Triazoles; C511149:spiro(3H-indole-3,2'-thiazolidine)-3'(1,2,4-triazol-3-yl)-2,4'(1H)-dione