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Volumn 13, Issue 19, 2003, Pages 3345-3350

Muraymycins, novel peptidoglycan biosynthesis inhibitors: Synthesis and SAR of their analogues

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; ARGININE; DRUG ANALOG; GLYCOSYLTRANSFERASE; LIPID; MURAYMYCIN; PEPTIDOGLYCAN; RIBOSE; UNCLASSIFIED DRUG;

EID: 0041330368     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00671-1     Document Type: Article
Times cited : (70)

References (17)
  • 13
    • 85031079273 scopus 로고    scopus 로고
    • note
    • 2/MeOH/ether=50/50/1/1), to give 6 (990 mg, 14%) and 5 (2.14 g, 31%). Further elution gave a mixture of two other diastereomers (710 mg, 10%) and the recovered 4 (1.6 g, 36%). Compounds 5 and 6 were separately hydrogenated using 10% Pd/C in MeOH, to give 7 and 8, respectively. A solution of 7 and para-nitrophenylisocyanate (1.2 mol equiv) in THF was stirred at room temperature under nitrogen for 24 h. The solution was concentrated in vacuo, and the residue was chromatographed (flash column, silica gel, EtOAc/hexenes) to give the corresponding urea. Crystals suitable for X-ray diffraction were obtained from methanol. The para-nitrophenyl urea of 8 was prepared in a similar manner, and crystals for X-ray were obtained from acetonitrile. The crystallographic data for the para-nitrophenyl urea derivatives of 7 and 8 have been deposited with the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EW, UK, as supplementary publication nos CCDC 199820 and 199821, respectively.
  • 14
    • 0001756474 scopus 로고    scopus 로고
    • (2S,3S)-3-Hydroxyleucine was prepared by using the literature procedure:
    • (2S,3S)-3-Hydroxyleucine was prepared by using the literature procedure: Panek J.S., Masse C.E. J. Org. Chem. 63:1998;2382.
    • (1998) J. Org. Chem. , vol.63 , pp. 2382
    • Panek, J.S.1    Masse, C.E.2
  • 15
    • 85031085330 scopus 로고    scopus 로고
    • note
    • 2), to give 20a as a white solid (84 mg, 58%).
  • 16
    • 85031070859 scopus 로고    scopus 로고
    • note
    • 2 for a-h in compounds 18a-h, 19a-h, 20a-c, 21a, 22a, and 23c-32c is same as those in 11a-h (Scheme 2).
  • 17
    • 85031071457 scopus 로고    scopus 로고
    • note
    • NCCLS4. Methods for Dilution Antimicrobial Susceptibility Test for Bacteria That Grow Aerobically; Approved Standards: M7-A5, Vol. 20. National Committee for Clinical Laboratory Standards, Wayne, PA, USA, 2000.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.