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(9S)-12-亚甲基红霉素衍生物的合成及体外抗菌活性 被引量：3

Synthesis of derivatives of (9S)-12-methylene erythromycin and their antibacterial activity in vitro
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摘要 目的　合成新的具有抗菌活性的红霉素衍生物。方法　以红霉素为原料,合成中间体2′O, 4″O 二苯甲酰基-(9S)-9-O, 11-O-异丙基-12-亚甲基红霉素与6, 7 去氢-2′-O,-4″-O-二苯甲酰基-(9S)-9-O, 11-O 异丙基12-亚甲基红霉素,进而合成相应(9S) 9 O, 11-O-亚乙基-12-亚甲基衍生物。产物结构经13CNMR,FAB MS确证。对所得化合物进行体外抗菌活性测定。结果　制备11个红霉素衍生物,其中5个未见文献报道。化合物9和12进行了体外抗菌活性测定。结论　化合物9和12表现出较弱的抗菌活性。 Aim To synthesizs of derivatives of (9S)-12-methylene erythromycin possessed potent antibacterial activity. Methods Using erythromycin A as a starting material,via two intermediate compounds protected 12,21-dehydroerythromycin A and 6,7∶12,21-didehydro erythromycin A, several 9-O,11-O-ethylidene compounds were obtained. During this process, benzyl and isopropyl have been selected as the protecting group. The structures of compounds obtained were confirmed with ^(13)C NMR and MS-FAB. Their antibacterial activity in vitro was tested. Results Eleven derivatives of erythromycin were synthesized. Five of them were unknown compounds. Conclusion The preliminary biological test showed that two target compounds exhibited less potent antibacterial activity in vitro.
作者 刘露 杨瑶 施阳 许蓬 雷平生
机构地区 中国医学科学院
出处 《药学学报》 CAS CSCD 北大核心 2005年第5期423-427,共5页 Acta Pharmaceutica Sinica
关键词 (9S)-9-O 11-O-亚乙基-12-亚甲基红霉素衍生物 合成 抗菌活性 (9S)-9-O,11-O-ethylene-12-methylene erythromycin derivatives synthesis antibacterial activity
分类号 R915.11 [医药卫生—微生物与生化药学]
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参考文献13

  • 1.抗菌药物与细菌耐药性[M].Shanghai: Huadongligong press,2001.131-135.
  • 2Zhanel G, Walters M, Noreddin A, et al. The ketolides A critical review [ J ]. Drug, 2002,62 ( 12 ): 1771 -1804.
  • 3Tanikawa T, Asaka T, Kashimura M, et al. Synthesis and antibacterial activity of a novel series of acylides: 3-O-(3-pyridyl) acetylerythromycin A derivatives [ J ]. J Med Chem, 2003,46( 13 ) :2706 - 2715.
  • 4Henninger T, Macielag M, Tennakoon M, et al. 6-O-acyl ketolide derivatives of erythromycin useful as antibacterials [ P]. WO Pat: 03050132 A1, 2003-06-19.
  • 5Guerry P, Kellenberger J. Macrolides with antibacterial activity [ P]. US Pat: 20030212011 A1, 2003-11-13.
  • 6Yong H, Gu K, Ma Z. Tricyclic macrolide antibacterial compounds [P]. WO Pat: 03093289 A1, 2003-11-13.
  • 7Phan L, Or S, Ma Z. Preparation of 6-O-alky1-2-nor-2-substituted erythromycin ketolide derivatives as antibacterial agents [P]. US Pat: 6569836, 2003-05-27.
  • 8Agouridas C, Bretin F, Denis A. Preparation of macrolide erythromycins as antibacterial agents [ P ]. Fr Pat: 2784682, 2002-03-05.
  • 9Ashley G, Li Y, Shaw S. Amido macrolides [ P]. WO Pat: 03061671 A1, 2003-07-31.
  • 10Kellenberger J, Guerry P. Macrolides with antibacreial activity [P]. WO Pat: 03072588 A1, 2003-09-04.

同被引文献84

  • 1雷平生,许蓬,刘露.红霉素酮基内酯衍生物合成进展[J].中国医学科学院学报,2004,26(4):467-473. 被引量：1
  • 2AGOURIDAS C, DENIS A, AUGER J M, et al. Synthesis and antibacterial activity of ketolides (6-O-Methyl-3-oxoerythromycin derivatives): a new class of antibacterials highly potent against macrolide-resistant and susceptible respiratory pathogens [J ]. J Med Chem, 1998,41 (21 ) : 4080 -- 4100.
  • 3DENIS A, AGOURIDAS C, AUGER J M, et al. Synthesis and antibacterial activity of HMR3647-a new ketolide highly potent against erythromycin-resistant and susceptible pathogens [ J ]. Bioorg Med Chem Lett, 1999,9(21 ) :3075 - 3080.
  • 4NILIUS A M, MA Z K. Ketolides: the future of the macrolides [J]. Curr Opin Pharmacol,2002,2(5) :493 - 500.
  • 5WANG Y T, HU L, CHEN W M, et al. Synthesis and antibacterial activities of ( 9S )-3-O-descladinose-6-O-methyl-3-oxc-12-( △-pyrazolinyl)- 12-dehydroxy-21-demethyl-9-dihydroerythrmaycin A[ J ]. Lett in Org Chem,2009,6(4) :306 - 310.
  • 6CHEN W M. Synthetic studies of erythromycin derivatives: the reactivity of the C12-21 alkene[J]. Molecules,2006,11 (1) : 121 - 129.
  • 7BURGER M T, LIN X D, CHU D T, et al. Synthesis and antibacterial activity of novel C12 vinyl ketolides[J 1. J Med Chem, 2006,49(5) : 1730 - 1743.
  • 8BROWN D S, ELLIOTF M C, MOODY C J, et al. Ligand effects in the rhodium ( Ⅱ )-catalyzed reactions of α-diazoamides, oxindole formation is promoted by the use of rhodium( Ⅱ ) perfluorocarboxarnide catalysts[J]. J Org Chem, 1994, 59(9): 2447 - 2455.
  • 9VEBREL J, TONNARD F, CARRIE R. Study on the diastereospecificity of diazomethane cycloadditions to substituted 1,2-dihydronaphthalenes[J ]. Bulletin dela Societe Chimique de France, 1987(6) : 1056 - 1064.
  • 10HUISGEN R, KOSZINOWSKI J, OHTA A, et al. Cycloadditions of diazoalkanes to 1-alkenes [ J ]. Angewandte Chemie, 1980, 92: 198- 199.

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药学学报
2005年 第5期

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