Gorman

Robert S. Gordee and Marvin Gorman Eli Lilly and Company, Indianapolis, Indiana 

Tolnaftate - A series of antifungal compounds called naphthi-omates were described by Noguchi et al. in 1962.29 These compounds exhibit a narrow but extremely potent antifungal spectrum. Two of the substances, naphthiomate T (l) and N (ll), have received detailed evaluation.The former, known as tolnaftate, is available as a 1 Polyethyleneglycol solution (TlNACTIlf ) for topical treatment of dermatophytoses l 35 

Detailed analyses of the change in antifungal activity with chemical modification have appeared.3° 39 Naphthlomate-N is very active, but the other three naphthalene isomer combinations are inert. Various substituted phenols may be used in place of the p-naphthol moiety. Of the N-methyl (essential for activity) anilines tried, hydrogen, methyl, methoxyl, and halogen containing compounds were active whereas nltro, di-methylamino, carboxyl, etc., derivatives were inactive. The carbamates still retained some activity but other variations of the thiocarbamate system, such as the dithiocarbamate derivatives, were devoid of antifungal action. 

Pyrrolnitrin - A unique, substituted 3 Phenyl pyrrole derivative was reported by Arima and co-workers in 19614-. This compound, produced in Jhe fermentation of several species of the genus Pseudomonas,42 found to have structure III. 

The biosynthetic origin of pyrrolnitrin has been studied.5 Since the yield of this antifungal agent is increased when D-tryptophan is added to pyrrolnitrin-producing cultures, this amino acid appears to be a specific precursor. Incorporation of i4C-labeled tryptophan yielded pyrrolnitrin containing iSjt of the radioactivity,As the level of added tryptophan Increases, 3-chloroindole and 3-(2 -amino-3 -chlorophenyl)-i -chloropyrrole were observed. This latter compound, when reintroduced into a fresh culture, is rapidly converted to pyrrolnitrin. Excess 3-chloroindole added to the culture inhibits production of the antifungal substance. 

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Folkers J P, Gorman C B, Laibinis P E, Buchholz S and Whitesides G M 1995 Self-assembled monolayers of long-chain hydroxamic acids on the native oxides of metals Langmuir 813-24... 

Food Products Maga ne, Neir Products Annual, Gorman Publishing Co., Chicago, 1991. 

Gorman s Food Conference, Sth A.nnual Conference on Neiv Products Neiv Foods, New Keality, Fessonsfrom the Past Decade, Gorman Publishing, Chicago, 1990. 

R. W. Ratcliffe and G. Albers-Schitnberg, "The Chemistry of Tbienamycin and Other Carbapenem Antibitotics" and 1. Ernest, "The Penems" ia R. B. Moria and M. Gorman, eds.. Chemist andBio/ogy of fd-Ractam A.ntibiotics, Academic Press, New York, 1982, Chapts. 4 and 5. 

Product Hterature on activated carbon cloth. Charcoal Cloth Ltd., UK, 1985, and on C-tex products, Siebe Gorman Co., Ltd., UK, 1985. 

Has been purified by co-distillation with ethylene glycol (boils at 197.5°), from which it can be recovered by additn of water, followed by crysm from 95% EtOH, benzene, toluene, a mixture of benzene/xylene (4 1), or EtjO. It has also been chromatographed on alumina with pet ether in a dark room (to avoid photo-oxidation of adsorbed anthracene to anthraquinone). Other purification methods include sublimation in a N2 atmosphere (in some cases after refluxing with sodium), and recrystd from toluene [Gorman et al. J Am Chem Soc 107 4404 1985]. 

Benzopbenone [119-61-9] M 182.2, m 48.5-49°, pK -6.0 (aq H2SO4). Crystd from MeOH, EtOH, cyclohexane, benzene or pet ether, then dried in a current of warm air and stored over BaO or P2O5. Also purified by zone melting and by sublimation [Itoh J Phys Chem 89 3949 1985 Naguib et al. J Am Chem Soc 108 128 1986 Gorman and Rodgers J Am Chem Soc 108 5074 1986 Ohamoto and Teranishi J Am Chem Soc 108 6378 1986 Naguib et al. J Phys Chem 91 3033 1987],... 

Fluoranthene (ben2o[/,A ]fluorene) [206-44-0] M 202.3, m 110-111°. Purified by chromatography of CCI4 solns on alumina, with benzene as eluent. Crystd from EtOH, MeOH or benzene. Purified by zone melting. [Gorman et al. J Am Chem Soc 107 4404 1985.]... 

Perylene [198-55-0] M 252.3, m 173-214°. Purified by silica-gel chromatography of its recrystd picrate. [Ware J Am Chem Soc 83 4374 1961.] Crystd from benzene, toluene or EtOH and sublimed in a flow of oxygen-free nitrogen. [Gorman et al. J Am Chem Soc 107 4404 1985 Johansson et al. J Am Chem Soc 109 7374 1987.]... 

Acknowledgement—This research is partially supported by the NSF (ASC-9217368) and by the Materials and Molecular Simulation Center. We thank J. Vazquez for help with the SEM imaging of nanotubes, G. Gorman and R. Savoy for X-ray analysis, and M. 3. dc Vries for mass spectrometry. 

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