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Novel Synthetic Antibacterial Agents

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Heterocyclic Antitumor Antibiotics

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 2))

Abstract

Classical (fermentation-based) and nonclassical (nonfermentation-based) antibacterials are conventionally used for the treatment of bacterial infections. This chapter describes the syntheses of different classes of nonfermentation-based antibacterial agents that have been reported during the past decade (1995–2005). The general trends in chemotherapy of infectious diseases and general classes of mechanism-based antibacterials are described in Sect. 1. The syntheses of novel quinolones including gemifloxacin, DQ-113, and garenoxacin, as well as of fused quinolones, is discussed in Sect. 2. In Sect. 3, the syntheses of novel oxazolidinone antibacterials, including eperezolid, linezolid, and PNU-10048, as well as that of fused oxazolidinones is described. The syntheses of antibacterial agents that inhibit bacterial peptide deformylase (PDF) including N-alkyl urea hydroxamic acid derivatives, proline-3-alkylsuccinyl hydroxamates, 5-arylidene-2-thioxothiazolidin-4-one-3-hexanoic acid derivatives, macrocyclic peptidomimetic PDF inhibitors, and isoxazole-3-hydroxamic acid derivatives is discussed in Sect. 4. Sect. 5 describes the syntheses of the inhibitors of bacterial fatty acid biosynthesis (LpxC) including oxazoline hydroxamates (such as L-159,692), its isoxazolone analogues, and carbohydrate-derived hydroxamic acid derivatives. The mechanism of action and rationale for the synthesis of each class of antibacterial agents is described in the corresponding section.

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Abbreviations

BOC:

t-Butoxycarbonyl

BPO:

Benzoyl peroxide

n-BuLi:

n-Butyllithium

CbzCl:

Benzyloxycarbonyl chloride

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCM:

Dichloromethane

DPPA:

Diphenylphosphoryl azide

DIBALH:

Diisobutylaluminum hydride

DMS:

Dimethyl sulfide

DIEA:

Diisopropylethylamine

DMF:

Dimethylformamide

EDAC:

Ethylenediamine carbonate

EDC:

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide

EDDA:

Ethylenediamine N,N′-diacetate

FDA:

Food and Drug Administration

HATU:

2-(1H-9-azobenzyltriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

HTS:

High-throughput screening

LAH:

Lithium aluminum hydride

LDA:

Lithium diisopropylamide

LHMDS:

Lithium hexamethyldisilazide

LPS:

Lipopolysaccharide

LpxC:

UDP-[3-O-(R-3-hydroxymyristoyl)]-N-acetylglucosamine deacetylase

MMP:

Matrix metalloprotease

MRSA:

Methicillin-resistant Staphylococcus aureus

NaH:

Sodium hydride

NaBH4 :

Sodium borohydride

NBS:

N-Bromosuccinimide

NCS:

N-Chlorosuccinimide

NDA:

New Drug Application

NaOEt:

Sodium ethoxide

PDF:

Peptide deformylase

PEG:

Polyethylene glycol

PRSP:

Penicillin-resistant Streptococcus pneumoniae

PyBop:

Benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate

SAR:

Structure–activity relationships

TBDMSCl:

(tert-Butyldimethyl)silyl chloride

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

TMSA:

Trimethylsilyl azide

VRE:

Vancomycin-resistant enterococci

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Acknowledgments

The author wishes to thank Ms. Margaret Connors for her editorial contribution and Dr. Chaomei Ma for checking the schemes and figures.

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  1. School of Pharmacy, Memorial University of Newfoundland, NL A1B 3V6, St. John's, Canada

    Mohsen Daneshtalab

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Correspondence to Mohsen Daneshtalab .

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Moses Lee

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Daneshtalab, M. Novel Synthetic Antibacterial Agents. In: Lee, M. (eds) Heterocyclic Antitumor Antibiotics. Topics in Heterocyclic Chemistry, vol 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_010

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