Rifamycins, Antibacterial Antibiotics and Their New Applications

Selva, Enrico; Lancini, Giancarlo

doi:10.1002/9783527630035.ch7

Cited by 2 publications

(1 citation statement)

References 33 publications

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“…They inhibit bacterial DNA-dependent RNA polymerase [109][110][111]. Rifamycin S (4) and several analogues showing promising activities have been prepared [112][113][114][115].…”

Section: Expeditious Asymmetric Synthesis Of the Stereoheptad C19-c27...mentioning

confidence: 99%

Expeditious Asymmetric Synthesis of Polypropionates Relying on Sulfur Dioxide-Induced C–C Bond Forming Reactions

Vogel

Gonzalo

2021

Catalysts

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For a long time, the organic chemistry of sulfur dioxide (SO2) consisted of sulfinates that react with carbon electrophiles to generate sulfones. With alkenes and other unsaturated compounds, SO2 generates polymeric materials such as polysulfones. More recently, H-ene, sila-ene and hetero-Diels–Alder reactions of SO2 have been realized under conditions that avoid polymer formation. Sultines resulting from the hetero-Diels–Alder reactions of conjugated dienes and SO2 are formed more rapidly than the corresponding more stable sulfolenes resulting from the cheletropic additions. In the presence of a protic or Lewis acid catalyst, the sultines derived from 1-alkoxydienes are ionized into zwitterionic intermediates bearing 1-alkoxyallylic cation moieties which react with electro-rich alkenes such as enol silyl ethers and allylsilanes with high stereoselectivity. (C–C-bond formation through Umpolung induced by SO2). This produces silyl sulfinates that react with carbon electrophiles to give sulfones (one-pot four component asymmetric synthesis of sulfones), or with Cl2, generating the corresponding sulfonamides that can be reacted in situ with primary and secondary amines (one-pot four component asymmetric synthesis of sulfonamides). Alternatively, Pd-catalyzed desulfinylation generates enantiomerically pure polypropionate stereotriads in one-pot operations. The chirons so obtained are flanked by an ethyl ketone moiety on one side and by a prop-1-en-1-yl carboxylate group on the other. They are ready for two-directional chain elongations, realizing expeditious synthesis of long-chain polypropionates and polyketides. The stereotriads have also been converted into simpler polypropionates such as the cyclohexanone moiety of baconipyrone A and B, Kishi’s stereoheptad unit of rifamycin S, Nicolaou’s C1–C11-fragment and Koert’s C16–CI fragment of apoptolidin A. This has also permitted the first total synthesis of (-)-dolabriferol.

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“…They inhibit bacterial DNA-dependent RNA polymerase [109][110][111]. Rifamycin S (4) and several analogues showing promising activities have been prepared [112][113][114][115].…”

Section: Expeditious Asymmetric Synthesis Of the Stereoheptad C19-c27...mentioning

confidence: 99%

Expeditious Asymmetric Synthesis of Polypropionates Relying on Sulfur Dioxide-Induced C–C Bond Forming Reactions

Vogel

Gonzalo

2021

Catalysts

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New Antibacterial Agents: Patent Applications Published in 2010

Stokes

Morningstar

Kocis

et al. 2012

Pharm. Pat. Analyst

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This review summarizes patent applications from 2010 for small molecules for which there is a claim of antibacterial activity. The primary criterion for inclusion in this analysis was reporting of cellular antibacterial activity data (MICs) for at least one compound. Patent applications are reviewed according to their biological target and antibacterial class. Protein synthesis inhibitors disclosed in this period include inhibitors of the 50S ribosome subunit (oxazolidinones, macrolides/ketolides and pleuromutilins), 30S ribosome subunit (aminoglycosides and tetracyclines) and nonribosomal targets (PDF inhibitors). DNA synthesis inhibitors include inhibitors of GyrA/ParC and GyrB/ParE. Cell envelope disruptors disclosed in 2010 cover both inhibitors of cell-envelope synthesis (LpxC inhibitors, β-lactams and glycopeptides), as well as membrane disruptors (lipopeptides and polymyxins). Other antibacterial classes covered in this review include rifamycins and antibacterial peptides. Patent applications for compounds aimed at overcoming resistance mechanisms (efflux inhibitors and β-lactamase inhibitors) are also described.

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Rifamycins, Antibacterial Antibiotics and Their New Applications

Cited by 2 publications

References 33 publications

Expeditious Asymmetric Synthesis of Polypropionates Relying on Sulfur Dioxide-Induced C–C Bond Forming Reactions

Expeditious Asymmetric Synthesis of Polypropionates Relying on Sulfur Dioxide-Induced C–C Bond Forming Reactions

New Antibacterial Agents: Patent Applications Published in 2010

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