Theoretical Study on the Conformations of 3 Tigloyl Azadirachtol and Azadirachtin Derivatives

H.BALDONI; ENRIZ R.D.; E JAUREGUI; I. CSIZMADIA

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 1997 vol. 391 p. 27 - 38

0166-1280

Conformational and electronic studies of 3-tigloyl-azadiractol and other azadirachtin derivatives were carried out using molecular mechanics and AM1 calculations. A comparative analysis of the conformational characteristics of 3-tigloyl-azadirachtol, azadirachtin and its structurally related derivatives was also performed. Our results indicate that the lack of antifeedant activity of 7-ketoazadirachtin and other inactive compounds can be explained on the basis of their different conformational behaviour. The conformationally restricted azadirachtin analogues provide us with crucial information about the optimal conformational requirement necessary to stimulate an antifeedant response.