The synthesis of 7-N-formyllavendamycin methyl ester (59), 7-N-formyldemethyl lavendamycin n-octyl ester (60), 7-N-formyldemethyllavendamycin ethyl ester (61), 7-Nformyldemethyllavendamycin amide (62), are described.The Pictet-Spengler condensation of 7-N-formamido-2-formylquinoline-5,8-dione (52) with (3-methyltryptophan methyl ester (4),L-tryptophan ethyl ester (54), DL-tryptophan n-octyl ester (56), DL-tryptophan amide (58) in dry distilled xylene or anisole directly afforded the four lavendamycin analogs 59 - 62.Aldehyde 52 was prepared according to the following general procedure: Nitration of 8-hydroxy-2-methylquinoline (43) with a 70 % mixture of HNO3 / H2SO4 yielded 8-hydroxy2-methyl-5,7-dinitroquinoline (44). Compound 44 was then reduced in the presence of 5 palladium on charcoal in a hydrochloric acid solution to yield 5,7-diamino-8-hydroxy-2 methylquinoline dihydrochloride salt (45). Treatment of the resulting 45 with trimethylacetic formic anhydride (49) at 25° C under an argon atmosphere afforded _5,7-diformamido-8hydroxy-2-methylquinoline (50). Compound 50 was oxidized by potassium dichromate to give the 7-formamido-2-methylqunoline-5,8-dione (51). Oxidation of 51 by selenium dioxide in refluxing dry and distilled 1,4-dioxane afforded 7-formamido-2-formylquinoline5,8-dione (52).Trimethylacetic formic anhydride (49) was prepared according to Fife's method29 by the treatment of sodium formate (47) with trimethylacetic chloride (46) in the presence of poly 4-vinylpyridine-N-oxide (48) as a catalyst in dry acetonitrile at room temperature under argon. Tryptophans 54, 56, and 58 were prepared through the neutralization of L-tryptophan ethyl ester hydrochloride, DL-tryptophan octyl ester hydrochloride and DL-tryptophan amide hydrochloride with a 14 % ammonium hydroxide solution followed by extraction.A sample of P-methyltryptophan methyl ester (4) was given to me by Wen Cai. Ester 4 has been prepared by the method reported by Behforouz et.al.23The structures of the novel compounds 52, 59, 60, 61, 62 were confirmed by iH NMR, IR, EIMS and HRMS.The structures of 44, 45, 49, 50, 51, 54, 56, 58, were also confirmed by 1H NMR and IR spectroscopy. / Department of Chemistry

The synthesis of 6-methoxylavendamycin methyl ester (39) and 6-methoxy detnethyllavendamycin methyl ester (40) is reported. Also the synthesis of 7-propionamido-2-methylquinoline-5,8-dione (33) and 7propionamido-3-methylquinoline-5,8-dione (34) via the Diels-Alder reaction is described.The Pictet-Spengler condensation of 7-amino-6-methoxy-2-formylquinoline-5,8-dione (37) with 8-methyltryptophan methyl ester (4) and tryptophan methyl ester (38), produced respectively the lavendamycin analogs 39 and 40.Aldehyde 37 was prepared by the oxidation of 7-amino-6-methoxy-2methylauinoline-5,8-dione (47) with selenium dioxide under reflux in dry 1,4-dioxane.Our original plan for the synthesis of aldehyde 37 via 7-bromo-6methoxy-2-methylquinoline-5,8-dione (36) was not successful. The DielsAlder reaction of 3-methoxy-2,6-dibromobenzoquinone (35) and N-(O-(t-butyldimethylsilyloxy)]-2-methyl-1-aza-1,3-butadiene (11) gave a very low yield of 36 and consequently this route was abandoned.An alternate known multistep route was chosen to produce the bromoquinolinedione 36. Reaction of 4-methoxy-2-nitroaniline (41) with crotonaldehyde (42) gave 6-methoxy-2-methyl-8-nitroquinoline-5,8-dione (43). Subsequent nitration, reduction, oxidation, and bromination of mononitroquinoline 43 yielded the desired bromoquinolinedione 36 with success. A change to Boger's procedure in the next reaction involving the azido intermediate 46 was done due to its effectiveness in producing a greater yield and purer product than that of Liao's procedure. The final preparation of 7-amino-6-methoxy-2-methylquinoline-5,8-dione (47) was accomplished by the hydrogenation of azidoquinolinedione 46 in the presence of platinum oxide in anhydrous methanol.Two other quinolinediones, 33 and 34, were earlier synthesized using the Diels-Alder reaction. Quinolinediones 33 and 34 were prepared by reacting 2-propionamido-6-bromobenzoquinone (32) with azadienes 11 and 19 to respectively yield 7-propionamido-2-methylquinoline-5,8-dione (33) and 7propionamido-3-methylquinoline-5,8-dione (34).Bromobenzoquinone 32 was prepared according to Kelly's method of preparation. 2,4-Dibromophenol (48) was nitrated, reduced, propionylated, hydrolyzed, and finally oxidized to produce 2-propionamido-6bromobenzoquinone (32). / Department of Chemistry

The synthesis of 7-amino-2-methylquinoline-5-8-dione (17) and 7-amino-3-methylquinoline-5,8-dione (157) are described.7-Amino-3-methylquinoline-5,8-dione (157) was prepared via alkaline hydrolysis of 7-acetamido-3-methylquinoline5,8-dione (149). 7-Acetamido-3-methylquinoline-5,8-dione (149) was prepared via the Diels-Alder reaction of 2-acetamido-6-bromo-1,4-benzoquinone (6) and 2-methyl-2propenal dimethylhydrazone (110).7-Amino-2-methylquinoline-5,8-dione (17) was prepared by the acid hydrolysis of 7-(triphenylphosphineimino)-2methylquinoline-5,8-dione (16). 7-(Triphenylphosphineimino)2-methylquinoline-5,8-dione (16) was prepared by tie treatment of 7-azido-2-methylquinoline-5,3-dione (15) with triphenylphosphine. 7-Azido-2-methylquinoline-5,8-dione (15) was prepared by treating 7-bromo-2-methylquinoline-5,8-dione (14) with sodium azide. The structures of the new compounds 15, 16, 17,149 and 157 were confirmed using MP, NMR, IR, MS and HRMS data. NMR, IR and MS data for known compounds 10, 11, 12, 13 and 14 are included for future reference.Ball State UniversityMuncie, IN 47306

The purpose of the study was to determine if perceived severity of the consequences of physical inactivity is an important component for exercise motivation in college students. The participants of the study were 581 college students who had enrolled in HSC 160, Fundamentals of Human Health, at Ball State University during the spring semester of 2001. Using a cross-sectional data collection process, participants completed a survey instrument consisting of the stages of change for exercise scale, the perceived severity of the consequences of physical inactivity scale, and demographic questions.The data were analyzed using both univariate and bivariate analyses. Specific descriptive and inferential statistic analyses were used to: 1) determine the degree of association between the participants' perceived severity and their identified stages of change for exercise, 2) examine the relationship between the stages of change for exercise and the participants' demographic characteristics, and 3) determine the difference between perceived severity of consequences of physical inactivity and the Participants' demographic characteristics.The results indicated that those who perceived the threat of a health condition as a result of not being physically active to be high were more likely to exercise regularly. Males and females differed in their exercise stage of change with males being more likely in the maintenance stage whereas females were more likely to be in the preparation stage. Also, perceived severity of the consequences from the lack of physical activity was greater in females than males, suggesting that those men who exercise regularly do so, but not exclusively for preventing negative health conditions.The results of this study should be useful to health and physical education instructors to assist them with organizing and tailoring appropriate physical activity lecture topics and emphasizing the severity of the consequences to those who are not physically active.Finally, additional research should be conducted in order to determine what factors affect perceived severity of a health threat as it relates to physical inactivity such as demographics, sociopsychological, and structural variables, to help identify all the possible factors that could impact future program planning efforts. / Department of Biology