105262-70-2Relevant articles and documents
Synthesis and structural characterization of two nostoclide analogues
Teixeira,Barbosa,Santana,Veloso,Ellena,Doriguetto,Drew,Ismail
, p. 197 - 205 (2007)
The vinylogous aldol reaction between appropriate aldehydes and furan-based silyloxy diene synthon generated from 3-benzyl-5H-furan-2-one (3) afforded two truncated lactone analogues [compounds (4) and (5)] of nostoclides (2). The compounds were fully cha
Tailoring nostoclide structure to target the chloroplastic electron transport chain
Barbosa, Luiz C. A.,Varejao, Jodieh O. S.,Petrollino, Davide,Pinheiro, Patricia F.,Demuner, Antonio J.,Maltha, Celia R. A.,Forlani, Giuseppe
scheme or table, p. 15 - 32 (2012/03/10)
Aiming to improve their effectiveness, three modifications were introduced into the structure of the natural phytotoxins nostoclides, leading to the synthesis of novel 3-benzyl-4-isopropyl-5- (arylmethylene)furan-2(5H)-ones, 3-benzyl-5-(furan-2-ylmethylene)furan-2(5H)-ones, and 3,4 dihalo-5- arylidenefuran-2(5H)-ones. All compounds were characterized by IR, 1H and 13C NMR, NOEDIF, COSY, HETCOR and MS spectrometry. Increasing the length of the molecule was found to reduce the ability to interfere with ferricyanide reduction by isolated chloroplasts. The addition of an isopropyl moiety into the heterocyclic ring, as in naturally-occurring nostoclides, did not influence the inhibitory potential. Also the replacement of the electron-drawing phenyl substituent with two halogen residues did not improve the resulting activity. However, both latter modifications influenced the interaction with the photosynthetic machinery. These analogues could therefore represent novel leads to be explored toward the development of new herbicides targeting the chloroplastic electron transport chain. ARKAT-USA, Inc.
Phytogrowth activity of 3-(3-Chlorobenzyl)-5-arylidenefuran-2(5H)-ones
Barbosa, Luiz C. A.,Demuner, Antonio J.,Maltha, Celia R. A.,Teixeira, Robson R.,Souza, Kamilla A. P.,Bicalho, Keylla U.
scheme or table, p. 245 - 251 (2009/06/17)
Nine new 3-(3-chlorobenzyl)-5-arylidenefuran-2(5H)-ones were prepared in 20-87% yields by reaction of 3-(3-chlorobenzyl)furan-2(5H)-one with pertinent aldehydes. All compounds were fully characterized by IR and NMR spectroscopy as well as MS spectrometry. The phytotoxic properties of the synthesized lactones were evaluated as the ability to interfere with the growth of Sorghum bicolor and Cucumis sativus seedlings at 10 ppm and 100 ppm. Lactone 12, at 10 ppm, was the most active and selective, inhibiting the S. bicolor and C. sativus root growth by 70.7 % and 10.7 %, respectively. At 10 ppm, lactone 14 caused the larger effect on the inhibition (41.9 %) of C. sativus. In general, the results indicate the influence of the benzylidene ring substitution on the phytotoxic activity.
