The synthesis of 7-N-acetyl-3'-demethyllavendamycin propyl ester (61 ), 7-N-butr-3'-demethyllavendamycin amide of N,N-dimethylethylenediamine (62), 7-N-acetyllavendamycin butyl amide (64), 7-N- acetyllavendamycin amide of ethanolamine (63) are described. Incorporation of the Pictet-Spengler condensation of 7acetamido-2-formylquinoline-5, 8-dione (32) or 7-butyramido-2-formylquinoline-5, 8dione (7) with tryptophan propyl ester (65), L-tryptophan amide of N, N dimethylethylenediamine (66), f3-methyltryptophan butyl amide (68), or methyltryptophan amide of ethanolamine (67) in xylene afforded four lavendamycin analogs.Aldehydes 32, 74 and 86 were prepared according to the following general procedure. Nitration of 8-hydroxy-2-methylquinoline (69) yielded 8-hydroxy-2-methyl - 5,7-dinitroquinoline (29). Compound 29 was then hydrogenated and acylated with acetic anhydride or butyric anhydride or 2-furoyl chloride followed by hydrolysis to yield 5,7diacetamido-8-hydroxy-2-methylquinoline (75) or 5,7- dibutyramido-8- hydroxy-2methylquinoline (73) or 5,7-difuroylamino-8-hydroxy-2- methylquinoline (84). Compounds 75 and 73 and 84 were oxidized by potassium dichromate to give the corresponding 5,8-diones 31 or 72 or 85. Treatment of 31 or 72 or 85 with selenium dioxide in refluxing 1,4-dioxane afforded compounds 32 and 74 and 86, respectively.Tryptophan propyl ester (65) was synthesized via a Fischer esterification of Ltryptophan with propyl alcohol saturated with hydrogen chloride. Compounds 66, 67, 68, 76, 77, 78, 79, and 80 were synthesized via the conversion of esters to amides with dimethylaluminum amides. Tryptophan methyl ester (23) and (3-methyltryptophan methylester (11) were treated with premixed trimethylaluminum and primary amines and refluxed to afford the desired tryptophan and (3-methyltryptophan amides.The structures of the novel compounds 61, 62, 63, 64, 66, 67, 68, 76, 77, 78, 79, 80, were confirmed through 1H NMR, IR, EIMS, and HRMS. Elemental analyses of Compounds 66, 68, 76, 77, 78 and 80 were also included. 1H NMR and IR for known compounds 29, 30, 31, 32, 71, 73, 74, 75, 84, 85, 86 were provided also. / Department of Chemistry
| Identifer | oai:union.ndltd.org:BSU/oai:cardinalscholar.bsu.edu:handle/186935 |
| Date | January 2001 |
| Creators | Mirzaei, Hamid |
| Contributors | Behforouz, Mohammad |
| Source Sets | Ball State University |
| Detected Language | English |
| Format | xix, 172 leaves : ill., charts ; 28 cm. |
| Source | Virtual Press |
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