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 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.
LaSO, Laboratório de Síntese Orgânica, Departamento de Química, CCEN, Universidade Federal de Alagoas, 57.072-970, Maceió, AL, Brazil.
Laura Cristiane
LC
de Souza
Aldenir Feitosa
AF
dos Santos
Antônio Euzébio Goulart
AE
Sant'Ana
Dennis
D
de Oliveira Imbroisi
D000818:Animals; D001700:Biomphalaria / Q000187:drug effects / Q000469:parasitology; D008974:Mollusca / Q000187:drug effects* / Q000469:parasitology; D010063:Ovum / Q000187:drug effects; D011753:Pyrones / Q000138:chemical synthesis* / Q000494:pharmacology; D012550:Schistosoma mansoni; D012552:Schistosomiasis / Q000517:prevention & control* / Q000635:transmission; D013329:Structure-Activity Relationship
D011753:Pyrones