Semisynthetic derivatives of purpuromycin as potential topical agents for vaginal infections

Journal of Medicinal Chemistry

Volumn 40, Issue 6, 1997, Pages 967-971

  Trani, Aldo ^a   Dallanoce, Clelia ^a   Panzone, Gianbattista ^a   Ripamonti, Franca ^a   Goldstein, Beth P ^a,b   Ciabatti, Romeo ^a  

^a Biosearch Italia   (Italy)

^b Applied Microbiology Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PUROMYCIN; PUROMYCIN DERIVATIVE; PURPUROMYCIN; PURPUROMYCIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CANDIDA; DRUG FORMULATION; DRUG PROTEIN BINDING; DRUG SOLUBILITY; DRUG SYNTHESIS; GARDNERELLA VAGINALIS; TRICHOMONAS VAGINALIS; VAGINITIS;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTI-INFECTIVE AGENTS, LOCAL; CANDIDA; FEMALE; GARDNERELLA VAGINALIS; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; NAPHTHOQUINONES; TRICHOMONAS VAGINALIS; VAGINA;

EID: 0030946322     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960672t     Document Type: Article

References (15)

1. Lossick, J. G.; Kent, H. L. Trichomoniasis: Trends in Diagnosis and Management. Am. J. Obstet. Gynecol. 1991, 165, 1217-1222.
2. Adamson, G. D. Three-day Treatment of Vulvovaginal Candidiasis. Am. J. Obstet. Gynecol. 1988, 158, 1002-1005.
3. Tobin, J. M.; Loo, P.; Granger, S. E. Treatment of Vaginal Candidosis: A Comparative Study of the Efficacy and Acceptability of Itraconazole and Clotrimazole. Genitourin. Med. 1992, 68, 36-38.
4. Coronelli, C.; Pagani, H.; Bardone, M. R.; Lancini, G. C. Purpuromycin, a New Antibiotic Isolated from Actinoplanes ianthinogenes n. sp. J. Antibiot. 1974, 27, 161-168.
5. Parenti, F.; Goldstein, B.; Simioni, L. (Gruppo Lepetit S.p.A) Use of Purpuromycin in the Treatment of Vaginal Infections and Pharmaceutical Composition Containing Purpuromycin. European Patent 389924.
6. Pitkin, D. H.; Mico, B. A.; Sitrin, R. D.; Nisbet, L. J. Charge and Lipophilicity Govern the Pharmacokinetics of Glycopeptide Antibiotics. Antimicrob. Agents Chemother. 1986, 29, 440-444.
7. Trani, A.; Kettenring, J.; Ripamonti, F.; Goldstein, B.; Ciabatti, R. Chemical Modifications of the Antibiotic Purpuromycin. Il Farmaco 1993, 48 (5), 637-651.
8. Trani, A.; Dallanoce, C.; Ferrari, P.; Goldstein, B.; Ripamonti, F.; Ciabatti, R. Syntheses and Antimicrobial Activities of 4-purpuromycin Derivatives. Accepted for publication in Il Farmaco.
9. Fieser, L. F.; Turner, R. B. The Addition of Sulfhydryl Derivatives to 2-Methyl-1,4-naphthoquinone. J. Am. Chem. Soc. 1947, 69, 2335-2338.
10. The Chemistry of the Quinonoid Compounds. Part II. Patai 1974, 1079.
11. Huisman, H. O. Investigations on Quinones and Quinone-derivatives. Recl. Trav. Chim. Pays-Bas 1950, 69, 1133-1156.
12. Moore, R. E.; Scheuer, P. J. Nuclear Magnetic Resonance Spectra of Substituted Naphthoquinones. Influence of Substituents on Tautomerism, Anisotropy, and Stereochemistry in the Naphthazarin System. J. Org. Chem. 1966, 31, 3272-3283.
13. Goldstein, B. P.; King, A.; Ripamonti, F.; Trani, A.; Phillips, I. In-vitro Activity of Purpuromycin and MDL 63,604 against Microorganisms that Cause Vaginitis and Vaginosis. J. Antimicrob. Chemother. 1995, 36, 1061-1065.
14. Bardone, M. R.; Martinelli, E.; Zerilli, L.; Coronelli, C. Structure Determination of Purpuromycin, a new Antibiotic. Tetrahedron 1974, 30, 2747-2754.
15. National Committeee for Clinical Laboratory Standards. Approved Standart M7-A2. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, 2nd ed.; National Committee for Clinical Laboratory Standards: Villanova, (PA), Italy, 1990.