The 6-Deoxytetracyclines. VIII. Acylaminomethylamides

Martell, Michael J.; Ross, Adma S.; Boothe, James H.

doi:10.1021/jm00315a043

Cited by 9 publications

(3 citation statements)

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“…Treatment of tetracycline nitriles with, for instance, hydroxymethylenephthalimide in strong acids (Einhorn reaction) produces a condensation product similar to the Mannich products, e.g., compound (27), this being without any antibacterial activity (MARTELL 1967b). Compound (27) treated with boiling methanol in the presence of n-butylamine gives the amine (28), which is highly unstable and is degraded to 6-demethyl-6-deoxytetracycline.…”

Section: Amentioning

confidence: 99%

Chemical Modification of the Tetracyclines

Rogalski¹

1985

The Tetracyclines

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Section: Amentioning

confidence: 99%

Chemical Modification of the Tetracyclines

Rogalski¹

1985

The Tetracyclines

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“…X-ray crystallographic studies of several tetracyclines have revealed that subtle changes in molecular structure can lead to dramatic changes in the overall conformation of the tetracycline (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16). For example, X-ray diffraction results have indicated that the "A" ring of anhydrous oxytetracycline exists in a neutral "enol" form, 2, whereas the dihydrate of oxytetracycline exists exclusively in the "keto" form, 3 (6).…”

Section: Introductionmentioning

confidence: 99%

A nitrogen-15 nuclear magnetic resonance study of the tetracycline antibiotics

Curtis¹,

Wasylishen²

1991

Can. J. Chem.

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. Can. J. Chem. 69, 834 (1991).Natural abundance I5N NMR has been used to study several tetracycline antibiotics in the solid state and in solution. In the solid state, the I5N chemical shifts of the tetracycline free bases are sensitive to the site of protonation in the "A" ring. A high frequency shift of 14ppm is observed for the keto form of oxytetracycline (N protonated) relative to the en01 form of oxytetracycline (0 protonated). Comparison of I5N chemical shifts in the solid and solution states indicates for the first time that the structural integrity (site of protonation and hence conformation) of the tetracyclines is maintained in (CD,)'SO solutions. In addition, the solid state 15N CP/MAS NMR spectra are sensitive to subtle conformational changes of the "A" ring amide substituent.Key words: antibiotics, tetracyclines, "N NMR, molecular structure RONALD D. CURTIS et RODERICK E. WASYLISHEN. Can. J. Chem. 69, 834 (1991).On a ufilist a RMN du "N en abondance naturelle pour Ctudier plusieurs tCtracycline antibiotiques, a 1'Ctat solid6 et en solution. A I'Ctat solide, les dkplacernents chimiques du "N des tCtracyclines sous laformede bases libres sont sensibles aux sites de protonation dans le cycle a A )). On observe un dCplacement de 14 ppm vers les hautes frCquences pour le forme cCtonique de I'oxytCtracycline (N protonee) par rapport a la forme Cnolique de 1'oxytCtracycline ( 0 protonCe). Une comparaison des dCplacements chirniques du 15N i I'etat solid6 et en solution indique pour la premikre fois que 1'intCgritC structurale (site de protonation ainsi que conformation) des tetracyclines est maintenue en solutions dans le (CD3)?SO. De plus, les spectres RMN du "N CP/MAS sont sensibles a des changements subtils de conformation du substituent amide du cycle x A n.

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“…This compound has the highest biological activity among the tetracyclines and still occupies a unique position in broad spectrum chemotherapy (6). In addition, because the uptake mechanism of minocycline in bacteria is different from that of other tetracyclines (7), it remains active against tetracycline-resistant pathogens, including staphylococci (3,6,8).…”

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confidence: 99%