- Peptide derivatives of tylosin-related macrolides
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Approaches to the synthesis of model compounds based on the tylosin-related macrolides desmycosin and O-mycaminosyltylonolide were developed to study the conformation and topography of the nascent peptide chain in the ribosome tunnel using specially designed peptide derivatives of macrolide antibiotics. A method for selective bromoacetylation of desmycosin at the hydroxyl group of mycinose was developed, which involves preliminary acetylation of mycaminose. The reaction of the 4″-bromoacetyl derivative of the antibiotic with cesium salts of the dipeptide Boc-Ala-Ala-OH and the hexapeptide MeOTr-Gly-Pro-Gly-Pro- Gly-Pro-OH led to the corresponding peptide derivatives of desmycosin. The protected peptides Boc-Ala-Ala-OH, Boc-Ala-Ala-Phe-OH, and Boc-Gly-Pro-Gly-Pro- Gly-Pro-OH were condensed with the C23-hydroxyl group of O- mycaminosyltylonolide.
- Korshunova,Sumbatyan,Fedorova,Kuznetsova,Shishkina,Bogdanov
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- New dihydro and tetrahydro derivatives of desmycosin. III. The opening of oxirane ring of 12,13-epoxydesmycosin
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Opening the oxirane ring of 12,13-epoxydesmycosin dimethylacetal (1) by catalytic hydrogenation gave the 10,11-dihydro-12,13-epoxy derivative (3) as the main product. Reductive oxirane cleavage was accomplished with dissolved metal (Zn) giving the 10,13-dihydro-13-hydroxy compound (6). Mild acid hydrolysis of 6 gave expected 10,13-dihydro-13-hydroxydesmycosin (8), but hydrolysis of 3, under the same conditions, gave three tautomeric desepoxy products.
- Naranda, Amalia,Lopotar, Nevenka,Kelneric, Zeljko
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- Method for using tylosin D as raw material to prepare tilmicosin
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The invention relates to a method for using tylosin D as a raw material to prepare tilmicosin. The method comprises the steps of using tylosin D as the raw material, oxidizing a C[20]position primary dydroxide radical into a formyl group through a selective oxidant to obtain a first midbody, then conducting hydrolysis and decarbonization on mycarose to obtain a second midbody, and making formic acid and 3,5 dimethyl piperidine subjected to a reductive ammonolysis reaction to obtain the product tilmcosin. According to the method for using tylosin D as the raw material to prepare tilmicosin, tylosin D is adopted as the raw material, through the specific selective oxidant, tylosin D is converted into an effective component in compound tilmicosin and is prevented from being converted into impurities, thus a new path is opened up for the preparation of tilmicosin, and the problems that the impurities are high in residual rate and the yield rate is low when tylosin is adopted as an original raw material to prepare tilmicosin are solved.
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- TYLOSIN DERIVATIVES AND METHOD FOR PREPARATION THEREOF
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The present invention relates to new macrolide derivatives, in particular new tylosin derivatives of the formula (Ila), a pharmaceutical or veterinary composition comprising the derivatives; a method for preparation thereof; a method for treating and/or preventing bacterial infections in an animal, wherein the method comprises administering the derivatives or the composition; and a use of the derivatives for the manufacture of medicaments for treating and/or preventing bacterial infections in an animal.
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Page/Page column 51
(2014/12/12)
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- ANTIBACTERIAL TYLOSIN DERIVATIVES AND METHODS FOR THEIR PREPARATION
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The present invention relates to new macrolide derivatives, in particular new tylosin derivatives of the formula (I); a pharmaceutical or veterinary composition comprising the derivatives; a method for preparation thereof; a method for treating and/or preventing bacterial infections in an animal, wherein the method comprises administering the derivatives or the composition; and a use of the derivatives for the manufacture of medicaments for treating and/or preventing bacterial infections in an animal.
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Paragraph 0071
(2013/06/06)
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- 3,6-BRIDGED TYLOSIN DERIVATIVES
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The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.
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Page/Page column 33
(2008/06/13)
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- New amidino-benzimidazolyl derivatives of tylosin and desmycosin
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New amidino-benzimidazolyl derivatives of antibiotics tylosin and desmycosin are prepared in the reaction of corresponding amidino-substituted o-phenylendiamine with tylosin respectively desmyicosin on the 20-C aldehyde group. The reaction was carried out in absolute ethanol in the presence of p-benzoquinone. On this way are prepared: 20-[5-(N-isopropylamidino)-2-benzimidazolyl]tylosin hydrochloride 9, 20-[5-(2-imidazolinyl)-2-benzimidazolyl]tylosin hydrochloride 10, 20-[5-(N-morpholinylamidino)-2-benzimidazolyl]tylosin hydrochloride 11, 20-[5-(N-isopropylamidino)-2-benzimidazolyl]desmycosin hydrochloride 12, 20-[5-(2-imidazolinyl)-2-benzimidazolyl]desmycosin hydrochloride 13, 20-[5-(N-morpholinylamidino)-2-benzimidazolyl]desmycosin hydrochloride 14. Their antimicrobial activity was tested on a series of microorganisms.
- Hranjec, Marijana,Starcevic, Kristina,Zamola, Branimir,Mutak, Stjepan,Derek, Marko,Karminski-Zamola, Grace
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p. 308 - 314
(2007/10/03)
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