摘要
目的 综述近年来国内外在NFDE6唑烷酮类抗菌剂构效关系领域内的研究进展,为正在从事或将要从事NFDE6唑烷酮抗菌剂研究的研究人员提供参考。方法 查阅整理国内外相关文献,从NFDE6唑烷酮的新结构及其抗菌活性,新的NFDE6唑烷酮抗菌剂设计思想,定量构效关系这几个方面,综述近年来国内外NFDE6唑烷酮抗菌剂的研究进展。结果与结论 以利奈唑胺为参照,NFDE6唑烷酮类抗菌剂的结构修饰主要集中在吗啉基、乙酰胺基甲基、NFDE6唑烷酮环的替换、苯环取代基修饰,以及与其他经典抗菌剂的拼合方面,对NFDE6唑烷酮抗菌剂的定量构效关系研究也有所开展,说明近年来NFDE6唑烷酮抗菌剂的构效关系研究仍然较为活跃,基于目前已开展的研究工作,NFDE6唑烷酮抗菌剂的结构修饰仍为一个研究热点。
关键词
NFDE6唑烷酮抗菌剂 /
构效关系 /
定量构效关系
{{custom_keyword}} /
秦文灵 肖尚友 夏之宁.
NFDE6唑烷酮抗菌剂构效关系研究进展[J]. 中国药学杂志, 2010, 45(13): 961-965
{{custom_sec.title}}
{{custom_sec.title}}
{{custom_sec.content}}
参考文献
[1] PATRICIA K, LI Q X, DEAN L, et al. Resistance mutations in 23S rRNA identify the site of action of the protein synthesis inhibitor linezolid in the ribosomal peptidyl transferase center[J].J Mol Biol, 1999, 294(1):93-101.
[2] JIN H. Novel Synthetic Antibacterial Agents-Linezolid[J].Chin Pharm J(中国药学杂志), 2001, 36(8):571-572.
[3] WILLEMS R J, TOP J, SMITH D J, et al. Mutations in the DNA Mismatch Repair Proteins MutS and MutL of Oxazolidinone- Resistant or-Susceptible Enterococcus faecium[J].Antimicrob Agents Chemother, 2003, 47(1):3061-3066.
[4] BOZDOGAN B, APPELBAUM P C. Oxazolidinones: activity, mode of action, and mechanism of resistance[J].Int J Antimicrob Agents, 2004, 23(2):113-119.
[5] FUKUDA, Y. New approaches to overcoming bacterial resistance[J].Drugs Fut, 2009, 34(2):127-136.
[6] YAMANE K, ARAKAWA Y. Recent trend and research issues related to antimicrobial-resistant bacteria[J]. Masui, 2010, 59(1):4-16.
[7] ADAM R, RENSLO A, ANDY A, et al. A distal methyl substituent attenuates mitochondrial protein synthesis inhibition in oxazolidinone antibacterials[J].Bioorg Med Chem Let, 2007, 17(18):5036-5040.
[8] YANG Y, XU G, JI R, et al. Novel oxazolidone derivatives have powerful antibacterial activity, especially activity of resisting drug tolerant bacteria: China, 2006/1749256-A2[P]. 2006-03-22.
[9] LI R P, ZHOU W C, ZHOU W L. Synthesis and antibacterial activity of (S)-5-acetylaminomethyl-3-[(4-substituted-aminomethyl) phenyl]-2-oxazolindinone derivatives[J].Acta Pharm Sin (药学学报), 2006, 41(5):418-425.
[10] BISWAJIT D, SONALI R, AJAY Y, et al. Synthesis and SAR of novel oxazolidinones:Discovery of ranbezolid[J].Bioorg Med Chem Let, 2005, 15(19):4261-4267.
[11] BRIJESH K S, MUKUL R, et al. Synthesis and in vitro antibacterial activities of novel oxazolidinones[J].Eur J Med Chem, 2008, 43(4):683-693.
[12] RUDRA S, YADAV A, Rao A, et al. Synthesis and antibacterial activity of potent heterocyclico -xazolidinones and the identification of RBx 8700[J].Bioorg Med Chem Let, 2007, 17(24):6714-6719.
[13] TAKHI M, SINGH G, MURUGAN, C, et al. Novel and potent oxazolidinone antibacterials featuring 3-indoly-lglyoxamide substitute -nts[J].Bioorg Med Chem Let, 2008, 18(18):5150-5155.
[14] BRAJ B L, VIDYA B L, BRIJESH K S, et al. Novel tetrahydro-thieno pyridyl oxazolidinone: an antibacterial agent[J].Bioorg Med Chem, 2004, 12(17):4557-4564.
[15] SHEILA I, HAUCK, CHRISTER C, et al. New carbon-linked azole oxazolidinones with improved potency and pharmacokinetics[J].Bioorg Med Chem Let, 2007, 17(2):337-340.
[16] BRIJESH K S, RINA S, JAYENDRA Z P, et al. Synthesis and in vitro antibacterial activity of novel methyl amino piperidinyl oxazolidinones[J].Bioorg Med Chem Let, 2007, 17:5227-5232.
[17] SELVAKUMAR N, RAJULU G G, REDDY K C S, et al. Synthesis, SAR, and antibacterial activity of novel oxazolidinone analogues possessing urea functionality[J].Bioorg Med Chem Let, 2008, 18(2):856-860.
[18] KIM S J, MYUNG H, KYUNG H, et al. Synthesis and antibacterial activities of novel oxazolidinones having cyclicsulfonamide moieties[J].Bioorg Med Chem Let, 2008, 18(21):5815-5818.
[19] KIM J Y, BOYER F E, CHOY A L, et al. Synthesis and structure-activity studies of novel homomorpholine oxazolidinone antibacterial agents[J].Bioorg Med Chem Let, 2009, 19(2):550-553.
[20] CISKE F L, BARBACHYN M R, GENIN M J, et al. The effect of remote chirality on the antibacterial activity of indolinyl, tetrahydroquinolyl and dihydrobenzoxazinyl oxazolidinone[J]. Bioorg Med Chem Let, 2003, 13(23):4235-4239.
[21] CHOY A L, PRASAD J V, BOYER F E, et al. Synthesis and SAR of novel conformationally restricted oxazolidinones possessing Gram-positive and fastidious Gram-negative antibacterial activity. Part 2: Amino substitutions on heterocyclic D-ring system[J]. Bioorg Med Chem Let, 2007, 17(16):4699-4702.
[22] FREDERICK E, BOYER J V N, VARA P, et al. Synthesis and SAR of novel conformationally-restricted oxazolidinones possessing Gram-positive and fastidious Gram-negative antibacterial activity. Part 1: Substituted pyrazoles[J].Bioorg Med Chem Let, 2007, 17(16):4694-4698.
[23] EBNER D C, CULHANE J C, WINKELMAN T N, et al. Synthesis of novel oxazolidinone antimicrobial agents[J].Bioorg Med Chem, 2008, 16(5):2651-2656.
[24] TOKUYAMA R, TAKAHASHI Y, TOMITA Y, et al. Structure-Activity Relationship (SAR) Studies on Oxazolidinone Antibacterial Agents: Conversion of 5-Substituent on Oxazolidinone[J]. Chem Pharm Bull, 2001, 49(4):347-352.
[25] HLASTA D.New amidinomethyl and guanidinomethyl-oxazolidone compounds useful as antibacterial agents active against drug resistant bacteria: American, 2001/42229 A1[P]. 2001-06-14.
[26] PHILLIPS O A, UDO E E, SAMUEL S M, et al. Synthesis and structure antibacterial activity of triazolyl oxazolidinones containing long chain acyl moiety[J].Eur J Med Chem, 2008, 43(5):1095-1104.
[27] FAN H X, CHEN Y L, JIANG Z T, et al. Synthesis and biological evaluation of new N-linked 5-triazolyl methyl oxazolidinones[J].Eur J Med Chem, 2008, 43(8):1706-1714.
[28] DEMARAY J A, THUENER J E, DAWSON M N, et al. Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity [J].Bioorg Med Chem Let, 2008, 18(17):4868-4871.
[29] ZHAI X, WANG Y M, GONG P. Recent progress in the research of novel oxazolidinone antibacterial agents[J].J Shenyang Pharm Univ(沈阳药科大学学报), 2006, 23(11): 739-744.
[30] RUDRA S, SANGITA F, GUJRATI A, et al. Synthesis and antibacterial activity of novel oxazolidinones with methyllene oxygen- and methylene sulfur-linked substituents at C5-position[J]. Bioorg Med Chem Let, 2007, 17(17):4778-4783.
[31] YING J, CUI A B, YA X, et al. Syntheses and antibacterial activity of a series of 3-(pyridine-3-yl)-2-oxazolidinone[J].Eur J Med Chem, 2005, 40(2):209-214.
[32] RENSLO A R, LUEHR G W, GORDEEV M F, et al. Developments in the identification of novel oxazolidinone antibacterial agents[J].Bioorg Med Chem, 2006, 14(12):4227-4240.
[33] SNYDER L B, MENG Z X, MATE R, et al. Discovery of isoxazolinone antibacterial agents. Nitrogen as a replacement for the stereogenic center found in oxazolidinone antibacterials[J].Bioorg Med Chem Let, 2004, 14(18): 4735-4739.
[34] DU G J, CHEN D L, LU R J, et al. Synthesis and antibacterial activity of 3-(morpholinopyridyl)-5-substituted isoxazole derivatives[J].Chin J Org Chem(有机化学), 2009, 29(10):1575-1581.
[35] GORDEEV M F, PATEL D V, BARBACHYN M R, et al. Antimicrobial quinolone derivatives and use of the same totreat bacterial infections: American, 2004/6689769 B2[P]. 2004-02-10.
[36] CHRISTIAN H, JEAN L S, CHRISTINE S, et al. Design,synthesis and biological evaluation of oxazolidinone-quinolone hybrids[J].Bioorg Med Chem, 2003, 11(10):2313-2319.
[37] ZHOU W, YU H, LI R. Fluoroquinolone-oxazolidone derivative, its preparation method and application: China, CN1948306-A[P]. 2007-04-18.
[38] HUBSCHWERLEN C, SPECKLIN J L, BAESCHLIN D K, et al. Structure-activity relationship in the oxazolidinone-quinolone hybrid series:influence of the central spacer on the antibacterial activity and the mode of action Christian Hubschwerlen[J].Bioorg Med Chem Let, 2003, 13(23):4229-4233.
[39] YU H J, ZHOU W C. Synthesis and antibacterial activities of 7-{4-[2-[2-substituted-4-((5S)-5-acetylaminomethyl-2-oxo-oxazolidin- 3-yl)-phenyl]-ethyl]-piperazin-1-yl}-fluoroquinolones[J]. Acta Pharm Sin (药学学报), 2006, 41(10): 990-999.
[40] MA L, ZHOU W C, ZHOU W L. Synthesis and in vitro antibacterial activities of some bis-oxazolidinones[J].Chin J Pharm(中国医药工业杂志), 2006, 37(10):649-652.
[41] SELVAKUMAR N, SUNIL K G, MALAR A A, et al. Synthesis, SAR and antibacterial studies on novel chalcone oxazolidinone hybrids[J].Eur J Med Chem, 2007, 42(4):538-543.
[42] WANG J W, HUANG J, WU Y, et al. Design and synthesis of novel thioether-linked carbapenem-oxazolidinone hybrids as potential antimicrobial agents[J].Lett Org Chem, 2008, 5(5):336-341.
[43] ZHOU J C, ASHOKE B, CHEN S L, et al. Design at the atomic level: Design of biaryloxazolidinones as potent orally active antibiotics[J].Bioorg Med Chem Let, 2008, 18(23):6175-6183.
[44] JI R Y, RONG S B, CHEN K X. Computer-Aided Drug Design[J].Chin Pharm J(中国药学杂志), 1997, 32(11):571-572.
[45] LI Z C, L Q Z. Quantitative structure-activity relationship study on oxazolidinone antibiotics[J].Comp Appl Chem(计算机与应用化学), 2006, 23(7):663-667.
[46] ZOU C, ZHOU L. Quantitative structure-activity relationship of oxazolidinone compounds[J].West Chin J Pharm Sci (华西药学杂志), 2007, 22 (3):255-258.
[47] LOHRAY B B, NEHA G, BRIJESH K S, et al. 3D QSAR studies of N-4-arylacryloylpiperazin-1-yl-phenyl-oxazolidinones: A novel class of antibacterial agents[J].Bioorg Med Chem Let, 2006, 16(14):3817-3823.
{{custom_fnGroup.title_cn}}
脚注
{{custom_fn.content}}