Synthesis and evaluation of the molluscicidal activity of the 5,6-dimethyl-dihydro-pyran-2,4-dione and 6-substituted analogous

Five dihydro-piran-2,4-diones, including 5,6-dimethyl-dihydro-piran-2,4-dione one of the intermediates of the synthesis of caloverticilic acid, were synthesized and submitted to molluscicidal bioassay. The compound's yields varied from moderate to good (42%- 80%) and were achieved through the p...

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Published in:Bioorganic & medicinal chemistry 2004-03, Vol.12 (5), p.865-869
Main Authors: DE SOUZA, Laura Cristiane, FEITOSA DOS SANTOS, Aldenir, GOULART SANT'ANA, Antonio Euzébio, DE OLIVEIRA IMBROISI, Dennis
Format: Article
Language:English
Subjects:
Animals
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiparasitic agents
Biological and medical sciences
Biomphalaria - drug effects
Biomphalaria - parasitology
Medical sciences
Mollusca - drug effects
Mollusca - parasitology
Ovum - drug effects
Pharmacology. Drug treatments
Pyrones - chemical synthesis
Pyrones - pharmacology
Schistosoma mansoni
Schistosomiasis - prevention & control
Schistosomiasis - transmission
Structure-Activity Relationship
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Summary:Five dihydro-piran-2,4-diones, including 5,6-dimethyl-dihydro-piran-2,4-dione one of the intermediates of the synthesis of caloverticilic acid, were synthesized and submitted to molluscicidal bioassay. The compound's yields varied from moderate to good (42%- 80%) and were achieved through the preparation of the dianion of ethyl acetoacetate, reaction with and aldehyde followed by hydrolysis of the ester (NaOH, H(2)O, 2 h, T.A.) and lactonization in acidic medium (HCl, 0 degrees C). The 5,6-dimethyl-dihydro-piran-2,4-dione and three analogous dihydro-piran-2,4-diones 6-substituted,-phenyl, (4-methoxy-phenyl), and -propenyl, showed significant activities against the Biomphalaria glabrata egg masses, while the analogous 6-(3,4-dimethoxy-phenyl) was inactive as molluscicide. This activity is reported for the first time, extending the range of biological activities of this group.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2004.01.001