New amidino-benzimidazolyl derivatives of tylosin and desmycosin

J Antibiot (Tokyo). 2002 Mar;55(3):308-14. doi: 10.7164/antibiotics.55.308.

Abstract

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 ofp-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.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Bacteria / drug effects
  • Macrolides*
  • Microbial Sensitivity Tests
  • Tylosin / analogs & derivatives*
  • Tylosin / chemical synthesis*
  • Tylosin / chemistry*
  • Tylosin / pharmacology

Substances

  • 20-(5-(2-imidazolinyl)-2-benzimidazolyl)tylosin
  • 20-(5-(N-isopropylamidino)-2-benzimidazolyl)desmycosin
  • 20-(5-(N-isopropylamidino)-2-benzimidazolyl)tylosin
  • 20-(5-(N-morpholinylamidino)-2-benzimidazolyl)tylosin
  • 20-(5-(imidazolinyl)-2-benzimidazolyl)desmycosin
  • Anti-Bacterial Agents
  • Macrolides
  • tylosin B
  • Tylosin