Abstract
A large and structurally diverse group of macrocyclic substances exhibit useful anti-infective properties. These compounds are non-peptidic in composition and can be differentiated by general structure and antimicrobial profile. Some substances are principally active against bacteria while others mainly target fungi. The most important antibacterial members contain a characteristic macrocyclic lactone nucleus and are referred to as ‘macrolides’. The macrolides are usually 14-membered or 16-membered lactones adorned with small alkyl groups and oxygen-based functionality (hydroxyl, alkyloxy and ketone groups); all antibacterially active congeners have sugar unit(s) extending from the macrocycle. The macrolides are constructed by soil microorganisms and many of these natural products are valuable chemotherapeutic agents. In addition, a number of semi-synthetic derivatives have also reached the market. The antifungal agents are inherently different from the macrolides and other macrocyclic antibacterials, and will only be mentioned for structural comparison with the antibacterial classes.
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Further reading,Rifamycin antibacterial agents
A.J. Bryskier, J.-P. Butzler, H.C. Neu and P.M. Tulkens (Eds) (1993)Macrolides: chemistry, pharmacology and clinical uses Arnette Blackwell, Paris.
S. Omura, (Ed.) (1984)Macrolide Antibiotics: Chemistry, Biology and Practice Academic Press, Orlando, FL.
H.A. Kirst, J.P. Leeds, J.W. Paschal and J. Martynow (1993) ‘Stereospecific modifications of erythromycin derivatives’, inRecent Advances in the Chemistry of Anti-infective Agents P.H. Bentley and R. Ponsford (Eds), Royal Society of Chemistry, Cambridge, UK, pp. 67–78.
H. Kirst(1993) ‘Semi-synthetic derivatives of erythromycin’, inProgress in Medicinal Chemistry Vol. 30, CP. Ellis and D.K. Luscombe (Eds), Elsevier Science, pp. 57–88.
H. Kirst(1993) ‘Semi-synthetic derivatives of erythromycin’, inProgress in Medicinal Chemistry Vol. 30, CP. Ellis and D.K. Luscombe (Eds),Elsevier Science, pp. 57–88.
H. Kirst and G.D. Sides (1989) ‘New directions for macrolide antibiotics: structural modifications and in vitro activity’,Antimicrob. Agents Chemother. 33, 1413.
H. Kirst and G.D. Sides (1989) ‘New directions for macrolide antibiotics: pharmacokinetics and clinical efficacy’,Antimicrob. Agents Chemother. 33, 1419.
R. Leclercq and P. Courvalin (1991) ‘Bacterial resistance to macrolide, lincosamide and streptogramin antibiotics by target modification’,Antimicrob. Agents Chemother. 35, 1267.
F.J. Antosz (1992) ‘Macrolides’ (Antibiotics), inKirk-Othmer Encyclopedia of Chemical Technology 4th edn, John Wiley, New York, pp. 926–961.
D. Vazquez (1975) ‘The macrolide antibiotics’, inAntibiotics III, Mechanism of Action of Antimicrobial and Antitumor Agents J.W. Corcoran and F.E. Hahn (Eds), Springer-Verlag, New York, pp. 459–479.
D. Vazquez (1967) ‘Macrolide antibiotics-spiramycin, carbomycin, angolamycin, methymycin and lancamycin’, inAntibiotics I, Mechanism of Action D. Gottlieb and P.D. Shaw (Eds), Springer-Verlag, New York, pp. 366–377.
F.E. Hahn (1967) ‘Erythromycin and oleandomycin’, inAntibiotics I, Mechanism of Action D. Gottlieb and P.D. Shaw (Eds), Springer-Verlag, New York, pp. 378–386.
N.L. Oleinick (1967) ‘The erythromycins’, inAntibiotics I, Mechanism of ActionD. Gottlieb and P.D. Shaw (Eds), Springer-Verlag, New York, pp. 396–419.
E.E. Schmid(1971) ‘The macrolide group of antibiotics’, inAntibiotics and Chemotherapy Vol. 17, Karger, Basel, pp. 52–66.
R.K. Boeckman, Jr. and S.W. Goldstein (1988) ‘The total synthesis of macrocyclic lactones’, inThe Total Synthesis of Natural Products Vol. 7, J. ApSimon (Ed.), John Wiley, New York, pp. 1–140.
S. Masamune (1978) ‘Recent progress in macrolide synthesis’,Aldrichimica Acta 11, 23.
S. Masamune, G.S. Bates and J.W. Corcoran (1977) ‘Macrolides. Recent progress in chemistry and biochemistry’,Angew. Chem. Int. Ed. Engl. 16, 585.
T.G. Back,(1977) ‘The synthesis of macrocyclic lactones, approaches to complex macrolide antibiotics’,Tetrahedron(Report 46), 33, 3041.
K.C. Nicolaou(1977) ‘Synthesis of macrolides’,Tetrahedron(Report 27), 33, 683.
R.R. Wilkening, R.W. Ratcliffe, G.A. Doss, K.F. Bartizal, A.C. Graham and CM. Herbert (1993) ‘The synthesis of novel 8a—Aza—8a—homoerythromycin derivatives via the Beekman rearrangement of (9Z)-erythromycin A oxime’,Bioorg. Med. Chem. Lett. 3, 1287.
W.D. Celmer(1971) ‘Stereochemical problems in macrolide antibiotics’, inSymposium on Antibiotics S. Rakhit (Ed.), Organic Chemistry Division Section on Medicinal Chemistry in conjunction with The Medicinal Chemistry Division of the Chemical Institute of Canada and the Canadian Society for Microbiologists, pp. 413–453.
Rifamycin antibacterial agents
P. Sensi (1983) ‘History of the development of rifampin’,Rev. Infectious Diseases5, Suppl. 3, S402.
G. Lancini and W. Zanichelli (1977) ‘Structure-activity relationships in rifamycins’, inStructure-Activity Relationships among the Semisynthetic AntibioticsD. Perlman (Ed.), Academic Press, New York, pp. 531–600.
W. Wehrli and M. Staehelin (1974) ‘Rifamycins and other ansamycins’, inAntibiotics III, Mechanism of Action of Antimicrobial and Antitumor Agents J.W. Corcoran and F.E. Hahn (Eds), Springer-Verlag, Berlin, pp. 252–268.
W. Wehrli and M. Staehelin (1971) ‘Actions of the rifamycins’,Bacteriol. Rev.35, 290.
W. Wehrli, F. Knusel, K. Schmid and M. Staehelin (1968) ‘Interaction of rifamycin with bacterial RNA polymerase’,Proc. Nat. Acad. Sei. Biochem.61, 667.
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Dax, S.L. (1997). The non-peptidic macrocyclic antibacterials. In: Antibacterial Chemotherapeutic Agents. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0097-4_6
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DOI: https://doi.org/10.1007/978-94-009-0097-4_6
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