3-Keto-11,12-carbazate derivatives of 6-O-methylerythromycin A synthesis and in vitro activity.
作者： GEORGE GRIESGRABER , YAT SUN OR , DANIEL T. W. CHU , ANGELA M. NILIUS , PAULINE M. JOHNSON
DOI: 10.7164/ANTIBIOTICS.49.465
关键词: Acylation 、 Combinatorial chemistry 、 Stereochemistry 、 Structure–activity relationship 、 Antibacterial activity 、 In vitro 、 Alkylation 、 Bacteria 、 Erythromycin 、 Biology 、 Antibacterial agent
摘要: The 11,12-cyclic carbazate of 3-keto-6-O-methylerythromycin A (4) was prepared. This compound shows in vitro antibacterial activity comparable to erythromycin (1) against erythromycin-susceptible organisms and increased some erythromycin-resistant organisms. Using 4 as a lead, series analogues prepared by acylation or alkylation the nitrogen. Several N-alkylated derivatives showed dramatically improved both susceptible resistant compared A.
sci-hub.se 参考文章(10)
William R. Baker, Jerry D. Clark, Richard L. Stephens, Ki H. Kim, Modification of macrolide antibiotics. Synthesis of 11-deoxy-11-(carboxyamino)-6-O-methylerythromycin A 11,12-(cyclic esters) via an intramolecular Michael reaction of O-carbamates with an α,β-unsaturated ketone Journal of Organic Chemistry. ,vol. 53, pp. 2340- 2345 ,(1988) , 10.1021/JO00245A038
P B Fernandes, W R Baker, L A Freiberg, D J Hardy, E J McDonald, New macrolides active against Streptococcus pyogenes with inducible or constitutive type of macrolide-lincosamide-streptogramin B resistance. Antimicrobial Agents and Chemotherapy. ,vol. 33, pp. 78- 81 ,(1989) , 10.1128/AAC.33.1.78
G. MICHAEL BRIGHT, ARTHUR A. NAGEL, JON BORDNER, KISHOR A. DESAI, JOSEPH N. DIBRINO, JOLANTA NOWAKOWSKA, LAWRENCE VINCENT, RICHARD M. WATROUS, FRANK C. SCIAVOLINO, ARTHUR R. ENGLISH, JAMES A. RETSEMA, MARGARET R. ANDERSON, LORI A. BRENNAN, ROBERTA J. BOROVOY, CAROLINE R. CIMOCHOWSKI, JAMES A. FAIELLA, ARTHUR E. GIRARD, DENNIS GIRARD, CAROL HERBERT, MARY MANOUSOS, RACHEL MASON, Synthesis, in vitro and in vivo activity of novel 9-deoxo-9a-AZA-9a-homoerythromycin A derivatives; a new class of macrolide antibiotics, the azalides. The Journal of Antibiotics. ,vol. 41, pp. 1029- 1047 ,(1988) , 10.7164/ANTIBIOTICS.41.1029
P. Kurath, P. H. Jones, R. S. Egan, T. J. Perun, Acid degradation of erythromycin A and erythromycin B Cellular and Molecular Life Sciences. ,vol. 27, pp. 362- 362 ,(1971) , 10.1007/BF02137246
Daniel TW Chu, Section Review Anti-infectives: Recent developments in 14- and 15-membered macrolides Expert Opinion on Investigational Drugs. ,vol. 4, pp. 65- 94 ,(1995) , 10.1517/13543784.4.2.65
Z. Itoh, M. Nakaya, T. Suzuki, H. Arai, K. Wakabayashi, Erythromycin mimics exogenous motilin in gastrointestinal contractile activity in the dog. American Journal of Physiology-gastrointestinal and Liver Physiology. ,vol. 247, ,(1984) , 10.1152/AJPGI.1984.247.6.G688
N. E. Allen, Macrolide Resistance in Staphylococcus aureus: Inducers of Macrolide Resistance Antimicrobial Agents and Chemotherapy. ,vol. 11, pp. 669- 674 ,(1977) , 10.1128/AAC.11.4.669
SLOBODAN DJOKIC, GABRIJELA KOBREHEL, GORJANA LAZAREVSKI, Erythromycin series. XII. Antibacterial in vitro evaluation of 10-dihydro-10-deoxo-11-azaerythromycin A: synthesis and structure-activity relationship of its acyl derivatives. The Journal of Antibiotics. ,vol. 40, pp. 1006- 1015 ,(1987) , 10.7164/ANTIBIOTICS.40.1006
SHIGEO MORIMOTO, YOKO MISAWA, TAKASHI ADACHI, TAKATOSHI NAGATE, YOSHIAKI WATANABE, SADAFUMI OMURA, CHEMICAL MODIFICATION OF ERYTHROMYCINS II. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF O -ALKYL DERIVATIVES OF ERYTHROMYCIN A The Journal of Antibiotics. ,vol. 43, pp. 286- 294 ,(1990) , 10.7164/ANTIBIOTICS.43.286
Constantin Agouridas, Jean Francois Chantot, Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. ,(1995)