2003
DOI: 10.1021/jo030047d
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Versatile and Facile Synthesis of Diverse Semisynthetic Tetracycline Derivatives via Pd-Catalyzed Reactions

Abstract: A diverse collection of tetracycline derivatives has been synthesized utilizing Heck, Suzuki, and other palladium-coupling reactions via tetracycline arenediazonium and iodoarene salts. Large numbers of tetracyclines are now possible via these reactions, including numerous upper periphery derivatives of doxycycline, minocycline, sancycline, and methacycline modified at positions C7, C9, and C6-C13 on the tetracycline naphthacene ring. Application of palladium-coupling reactions to the tetracyclines has yielded… Show more

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Cited by 50 publications
(20 citation statements)
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“…The results with aclarubicin were particularly interesting because this compound has been reported to increase the proportion of transcripts including exon 7 relative to those lacking exon 7 in cells (17), yet it had no effect on exon 7 splicing in our cell-free assay. Because aclarubicin is structurally similar to tetracycline, we also screened a number of tetracycline derivatives from Paratek Pharmaceuticals' chemical library (26). One of these derivatives, PTK-SMA1, increased the amount of full-length SMN2 transcripts relative to the exon 7–skipped form (Fig.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…The results with aclarubicin were particularly interesting because this compound has been reported to increase the proportion of transcripts including exon 7 relative to those lacking exon 7 in cells (17), yet it had no effect on exon 7 splicing in our cell-free assay. Because aclarubicin is structurally similar to tetracycline, we also screened a number of tetracycline derivatives from Paratek Pharmaceuticals' chemical library (26). One of these derivatives, PTK-SMA1, increased the amount of full-length SMN2 transcripts relative to the exon 7–skipped form (Fig.…”
Section: Resultsmentioning
confidence: 99%
“…PTK-SMA1 is a novel compound generated by derivatization of the tetracycline scaffold at the C7 position of the naphthacene ring (26) (Fig. 2A).…”
Section: Resultsmentioning
confidence: 99%
“…Chemistries for the synthesis of novel tetracyclines have been previously described (5). Briefly, reagents and catalysts were used without further purification.…”
Section: Methodsmentioning
confidence: 99%
“…To generate such second-generation drugs, the chemical modification of tetracyclines [286,287] is a plausible and costeffective means by which structure-function relationships can be generated and the biological properties of tetracyclines optimized. Such modifications would aim to reduce antibacterial activity to eliminate potential adverse effects and the development of bacterial resistance which can occur from long-term use.…”
Section: Discussionmentioning
confidence: 99%