Novel 3-deoxy-3-descladinosyl-6-O-methyl erythromycin a analogues. Synthesis and in vitro activity

Elliott, Richard L.; Pireh, Daisy; Nilius, Angela M.; Johnson, Pauline M.; Flamm, Robert K.; Chu, Daniel T. W.; Plattner, Jacob J.; Or, Yat Sun

doi:10.1016/s0960-894x(97)00078-4

Cited by 28 publications

(16 citation statements)

References 14 publications

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“…The direct conversion of des-cladinose clarithromycin (206) to the C-3 xanthate 207 was accomplished in 56% yield by treatment with 3 equiv. sodium hydride followed by sequential addition of carbon sulfide (CS 2 ) and methyl iodide (Scheme 42) [73]. Under these conditions, only a small amount of the 2', 3-O-bis xanthate macrolide was formed.…”

Section: -Hydroxylmentioning

confidence: 99%

Highlights of Semi-synthetic Developments from Erythromycin A

Wu¹

2000

CPD

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Earlier semi-synthetic studies of erythromycin A culminated in the discovery of two successful second generation macrolide antibiotics, azithromycin and clarithromycin, for the treatment of community-acquired bacterial infections. More recent structural modifications of erythromycin A have resulted in the discovery of novel ketolide antibiotics and new motilide prokinetic agents. This review is an account of the semi-synthetic developments from erythromycin A by chemical transformations.

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Section: -Hydroxylmentioning

confidence: 99%

Highlights of Semi-synthetic Developments from Erythromycin A

Wu¹

2000

CPD

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“…In addition to ketolides, other macrolides with various substituents at C-3 instead of cladinose have also been designed and investigated over the past decade, such as acylide, 6 3, 6-bicyclolide (Figure 2), 7 2, 3-anhydrolide, 8 2, 3-enol ether, 9 3-deoxy, 10 3-O-phenyl ether, 11 3, 6-ketal 12 and 3, 6-ether. 13 In our search for novel erythromycin derivatives, we previously reported some alkylides (Figure 2) with improved activity against erythromycin-resistant pathogens.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial activity of 2, 3-dehydro-3-O-(3-aryl-E-prop-2-enyl)-10, 11-anhydroclarithromycin derivatives

et al. 2011

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An allyl group was attached to 3-keto function of ketolides in the presence of allyl bromide and KOtBu. Consequently, the Heck reaction of the resulting 2, 3-dehydro-3-O-allyl-10, 11-anhydroclarithromycin derivatives, in the presence of palladium (II) acetate and tri(o-tolyl)phosphine, afforded a 3-O-(3-aryl-E-prop-2-enyl) sidechain, not the previously reported 3-O-(3-aryl-Z-prop-1-enyl) sidechain. The results suggested that some steric factors in b-hydrogen elimination might regulate the isomerization. The activity of 2, 3-dehydro-3-O-(3-aryl-E-prop-2-enyl)-10, 11-anhydroclarithromycin derivatives was low.

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“…As a result, modification at 3-OH led to the emergence of ketolide, [3][4][5][6] acylide, 7 bicyclolide, 8 anhydrolide, 9 2,3-enol-ether, 10 3-deoxy, 11 3-ether, 12 3,6-ketal 13 and 3,6-ether. 14 Second, an aryl side chain tethered to the erythronolide core is believed to be very important for the improvement of activities against erythromycin-resistant bacteria, due to the interaction with a secondary ribosomal binding site.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and antibacterial activity of a novel alkylide: 3-O-(3-aryl-propenyl)clarithromycin derivatives

et al. 2009

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A series of novel 3-O-(3-aryl-propenyl)clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. Regioselective allylation at 3-OH was efficiently achieved in the presence of 9-oxime ether, compared with 9-keto. Most of the side chains were identified as the 3-O-(3-aryl-Z-prop-1-enyl) group, not the expected 3-O-(3-aryl-E-prop-2-enyl) group. Some derivatives of this series showed improved activities against erythromycin-resistant Staphylococcus aureus and Staphylococcus pneumoniae compared with the reference compound, clarithromycin, but weaker activities against susceptible strains.

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Novel 3-deoxy-3-descladinosyl-6-O-methyl erythromycin a analogues. Synthesis and in vitro activity

Cited by 28 publications

References 14 publications

Highlights of Semi-synthetic Developments from Erythromycin A

Highlights of Semi-synthetic Developments from Erythromycin A

Synthesis and antibacterial activity of 2, 3-dehydro-3-O-(3-aryl-E-prop-2-enyl)-10, 11-anhydroclarithromycin derivatives

Design, synthesis and antibacterial activity of a novel alkylide: 3-O-(3-aryl-propenyl)clarithromycin derivatives

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