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Synthesis and Screening of Anilides Having Olefinic and Alkyl Moiety in the Side Chain as Chemical Hybridizing Agents for Wheat ( Triticum aestivum L.)

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Relation http://eprints.cmfri.org.in/9955/
 
Title Synthesis and Screening of Anilides Having Olefinic and Alkyl
Moiety in the Side Chain as Chemical Hybridizing Agents for
Wheat ( Triticum aestivum L.)
 
Creator Chakraborty, Kajal
Devakumar, C
 
Subject Bioactive compound
 
Description Induction of male sterility by deployment of chemical hybridizing agents (CHAs) holds immense
potential in heterosis breeding of wheat. A total of 21 anilides having different aromatic substitutions
and side-chain variation were synthesized and screened as CHAs on three genotypes of wheat viz.,
PBW 343, HW 2046, and HD 2733, at winter season. Various anilides having vinyl moiety in the acyl
side chain were synthesized by condensation between substituted anilines with different esters or
acid chlorides. Another lead in the form of N-alkyl anilines also became evident. The percent male
sterility data caused by CHAs revealed the significant contribution of anilides containing vinyl double
bond incorporated in the form of closed ring structure viz., furyl moiety as the side chain. 4¢-Fluorofuryl
anilide (1) and 4¢-bromo-furyl anilide (2) are found to be promising lead CHAs for the design of
highly active molecules. QSAR analysis revealed a direct relationship of field effect exemplified by
the Swain-Lupton constant Fp for the aromatic substitution but an inverse relationship of molar
refractivity MR for the side chain. The negative influences of parachor for the acyl domain have been
underlined. The real guiding principle for selectivity of CHA action was found to be the ð value. The
CHAs act by mimicking UDP-glucose, the key substrate in the synthesis of callose, or lead to an
imbalance in acid-base equilibrium in pollen mother cells resulting in dissolution of callose wall by
premature callase secretion.
 
Publisher American Chemical Society
 
Date 2005
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/9955/1/10.pdf
Chakraborty, Kajal and Devakumar, C (2005) Synthesis and Screening of Anilides Having Olefinic and Alkyl Moiety in the Side Chain as Chemical Hybridizing Agents for Wheat ( Triticum aestivum L.). Journal of Agricultural and Food Chemistry, 53. pp. 5959-5968.