Novel azalides derived from sixteen-membered macrolides. I. Isolation of the mobile dialdehyde and its one-pot macrocyclization with an amine

Journal of Antibiotics

Volumn 60, Issue 7, 2007, Pages 407-435

  Miura, Tomoaki ^a   Natsume, Satomi ^a   Kanemoto, Kenichi ^a   Atsumi, Kunio ^a   Fushimi, Hideki ^a   Sasai, Hiroaki ^b   Arai, Takayoshi ^b   Yoshida, Takuji ^a   Ajito, Keiichi ^a  

^a MEIJI SEIKA KAISHA LTD   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

16 membered macrolide; Azalide; Dialdehyde; Leucomycin; One pot macrocyclization

Indexed keywords

5 (3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY) 6 FORMYLMETHYL 9 HYDROXY 4 METHOXY 8 METHYL 11 (4 PHENYLBUTYL) 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 5 [4 O (2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 6 (2,2 DIMETHOXYETHYL) 9 HYDROXY 4 METHOXY 8 METHYL 11 (4 PHENYLBUTYL) 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 5 [4 O (2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 6 FORMYLMETHYL 9 HYDROXY 4 METHOXY 8 METHYL 11 (4 PHENYLBUTYL) 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 5 [4 O (3 O ACETYL 2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 6 (2,2 DIMETHOXYETHYL) 9 HDYROXY 4 METHOXY 8 METHYL 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 5 [4 O (3 O ACETYL 2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 6 (2,2 DIMETHOXYETHYL) 9 HYDROXY 4 METHOXY 8,11 DIMETHYL 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 5 [4 O (3 O ACETYL 2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 6 FORMYLMETHYL 9 HYDROXY 4 METHOXY 8 METHYL 11 (4 PHENYLBUTYL) 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 5 [4 O (3 O ACETYL 2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 6 FORMYLMETHYL 9 HYDROXY 4 METHOXY 8,11 DIMETHYL 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 5 [4 O (3 O ACETYL 2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 9 O,11 CARBONYL 6 (2,2 DIMETHOXYETHYL) 4 METHOXY 8 METHYL 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 5 [4 O (3 O ACETYL 2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 9 O,11 CARBONYL 6 FORMYLMETHYL 4 METHOXY 8 METHYL 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 5 [4 O (4 O BUTYRYL 2,6 DIDEOXY 3 C METHYL 3 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 6 FORMYLMETHYL 3,9 DIHYDROXY 4 METHOXY 8 METHYL 11 (4 PHENYLBUTYL) 11 AZA PENTADECAN 14 OLIDE; 5 [4O (3 O ACETYL 2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 6 FORMYLMETHYL 9 HYDROXY 4 METHOXY 8 METHYL 11 (2 PHENYLETHYL) 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 5 [4O (3 O ACETYL 2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 6 FORMYLMETHYL 9 HYDROXY 4 METHOXY 8 METHYL 11 (3 PHENYLPROPYL) 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 9 ACETOXY 5 [4 O (3 O ACETYL 2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 11 BENZYL 6 (2,2 DIMETHOXYETHYL) 4 METHOXY 8 METHYL 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 9 ACETOXY 5 [4 O (3 O ACETYL 2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 11 BENZYL 6 FORMYLMETHYL 4 METHOXY 8 METHYL 3 PROPIONYLOXY 11 AZA PENTADECAN 14 OLIDE; 9 ACETOXY 5 [4 O (3 O ACETYL 2,6 DIDEOXY 3 C METHYL 4 O PROPIONYL ALPHA LEVO RIBOHEXOPYRANOSYL) 3,6 DIDEOXY 3 DIMETHYLAMINO BETA DEXTRO GLUCOPYRANOSYLOXY] 6 FORMYLMETHYL 4 METHOXY 8,11,12 TRIMETHYL 3 PROPIONYLOXY 11,12 DIAZA HEXADECAN 15 OLIDE; ALDEHYDE; ALKADIENE; ANTIBIOTIC AGENT; DIAMINE; MACROLIDE; OSMIUM; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; AZITHROMYCIN; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; KITASAMYCIN; MACROCYCLIC COMPOUND; UMP DIALDEHYDE; URIDINE PHOSPHATE;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ISOLATION; ENZYME METABOLISM; MACROCYCLIZATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; BACTERIUM; CHEMISTRY; DRUG EFFECT; HUMAN; MICROBIOLOGICAL EXAMINATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; AZA COMPOUNDS; AZITHROMYCIN; BACTERIA; HUMANS; KITASAMYCIN; MACROCYCLIC COMPOUNDS; MACROLIDES; MICROBIAL SENSITIVITY TESTS; URIDINE MONOPHOSPHATE;

EID: 38449091444     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2007.55     Document Type: Article

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