Kumar, H. V. and Gnanendra, C. R. and Chenne Gowda, D. and Naik, N. (2009) Synthesis of amino acid analogues of 10-methoxy dibenzb,f]azepine and evaluation of their radical scavenging activity. Bulgarian Chemical Communications, 41 (1). pp. 72-79. ISSN 0324-1130
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A method for the synthesis of L-aminoacid (L-tyrosine, L-phenylalanine, L-hydroxyproline and L-threonine) analogues of 10-methoxy-dibenzb,f]azepine is proposed. 10-Methoxy-dibenzb,f]azepine, as a basic molecule was prepared by a known method. The key intermediate 3-chloro-1-(10-methoxy-5H-dibenzb,f]azepine-5-yl)propan-1-one, was obtained by N-acylation of 10-methoxy-dibenzb,f]azepine with 3-chloro-propionylchloride. Further coupling of the respective L-aminoacids was accomplished to produce 3-(4-hydroxyphenyl)-2-(3-(10-methoxy-5H-dibenzb,f]azepin-5-yl)-3-oxop ropylamino)propanoic acid, 2-(3-(10-methoxy-5H-dibenzb,f]azepin-5-yl)-3-oxopropylamino)-3-phenyl -propanoic acid, 3-hydroxy-1-(3-(10-methoxy-5H-dibenzb,f]azepin-5-yl)-3-oxopropyl)pyrr olidine-2-carboxylic acid, and 3-hydroxy-2-(3-(10-methoxy-5H-dibenzb,f]azepin-5-yl)-3-oxopropylamino )butanoic acid, respectively. The synthesized compounds were evaluated in regard to their potential over the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Butylhydroxy anisole (BHA) and ascorbic acid (AA) were used as reference antioxidant compounds and also a comparative study with the newly synthesized compounds was done. Under the present experimental conditions, the analogues containing L-tyrosine, L-hydroxyproline and L-threonine, possess a direct scavenging effect by trapping the stable DPPH free radical. L-Hydroxyproline analogues showed a significant radical scavenging activity among the synthesized analogues. DPPH activity of the pure L-aminoacids was also determined and a comparative study with the newly synthesized products was done. The DPPH activity of products was found to be greater than that of the L-aminoacids.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | 10-methoxy-5H-dibenzb,f]azepine; 3-chloro-1-(10-methoxy-5H-dibenzb,f]azepine-5-yl)propan-1-one; L-aminoacids; radical scavenging activity |
| Subjects: | C Chemical Science > Chemistry |
| Divisions: | Department of > Chemistry |
| Depositing User: | Users 19 not found. |
| Date Deposited: | 29 Aug 2019 06:25 |
| Last Modified: | 02 Jul 2022 06:15 |
| URI: | http://eprints.uni-mysore.ac.in/id/eprint/7303 |
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