Research progress of fluconazole derivatives

XU Kehan; HUANG Lei; WU Junqi; QI Lin; JIN Yongsheng; YU Shichong

doi:10.3969/j.issn.1006-0111.2016.02.004

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Volume 34 Issue 2

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2016 > 34(2): 110-113,128

XU Kehan, HUANG Lei, WU Junqi, QI Lin, JIN Yongsheng, YU Shichong. Research progress of fluconazole derivatives[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(2): 110-113,128. doi: 10.3969/j.issn.1006-0111.2016.02.004

Citation:

XU Kehan, HUANG Lei, WU Junqi, QI Lin, JIN Yongsheng, YU Shichong. Research progress of fluconazole derivatives[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(2): 110-113,128. doi: 10.3969/j.issn.1006-0111.2016.02.004

Research progress of fluconazole derivatives

doi: 10.3969/j.issn.1006-0111.2016.02.004

Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2015-01-04
Rev Recd Date: 2015-04-24

Abstract

Fluconazole, the third generation of triazole-antifungal drug, becomes the first choice in the treatment of fungal infection due to its broad antifungal spectrum, good water solubility and low toxicity. With an increasingly drug-resistant strain, developing new fluconazole derivatives is becoming an attractive topic. This review mainly indicates that people can get new fluconazole derivatives used by clinic through structural modification of fluconazole, which will give clues for advanced research.
- fluconazole,
- antifungal agents,
- structural modification,
- synthesis

References

[1]	Sobue S, Tan K, Haug-Pihale G. The effects of hepatic impairment on the pharmacokinetics of fosfluconazole and fluconazole following a single intravenous bolus injection of fosfluconazole[J]. Br J Clin Pharmacol, 2005,59(2):160-166.
[2]	Mora SJ, Cormick MP, Milanesio ME,et al. The photodynamic activity of a novel porphyrin derivative bearing a Fluconazole structure in different media and against Candida albicans[J]. Dyes Pigments, 2010, 87(3):234-240.
[3]	Zhou CH, Yu KG, Meng JP, et al. Dibenzimidazole and oniumcompound thereof, preparation method and medical use thereof:China, 101397276(A)[P].2009.
[4]	Francavilla C, Low E, Nair S, et al. Quaternary ammonium N,N-dichloroamines as topical antimicrobial agents[J]. Bioorg Med Chem Lett, 2009, 19(10):2731-2734.
[5]	Zhou CH, Mi JL, Wu J, et al. Triazole onium compound with antimicrobial activity, preparation method and medical use:China, 101391985(A)[P].2009.
[6]	Zhang YY, Mi JL, Zhou CH, et al. Synthesis of novel fluconazoliums and their evaluation for antibacterial and antifungal activities[J]. Eur J Med Chem, 2011, 46(9):4391-4402.
[7]	Sheng CQ, Zhang WN, Ji HT, et al. Structure-based optimization of azole antifungal agents by CoMFA, CoMSIA, and molecular docking[J]. J Med Chem, 2006, 49(8):2512-2525.
[8]	Chai XY, Zhang J, Yu S C, et al. Design,synthesis,and biological evaluation of novel 1-(1H-1,2,4-tri-Azole-1-yl)-2-(2,4-difluorophenyl)-3-substituted benzylamino-2-propanols[J]. Bioorg Med Chem Lett, 2009, 19(6):1811-1814.
[9]	Wang WY, Sheng CQ, Che XY, et al. Design, synthesis, and antifungal activity of novel conformationally restricted triazole derivatives[J]. Arch Pharm(Weinheim), 2009, 342(12):732-739.
[10]	Li WH, Zhao L, Tan GG, et al. Enantioseparation of the new antifungal drug iodiconazole and structually related triaditimenol analogues by CE with neutral cyclodextrin additives[J]. Chromatograp-Hia, 2011, 73(8):1009-1014.
[11]	Yu S, Chai X, Hu N, et al. Synthesis and antifungal activity of the novel triazole compounds[J]. Medchemcomm, 2013, 4(4):704-708.
[12]	Yu S, Chai X, Hu H, et al. Synthesis and antifungal evaluation of the novel triazole derivatives as inhibitors of cytochrome P45014a-demethylase[J]. Eur J Med Chem, 2010, 45(3):4435-4445.
[13]	Chai XY, Zhang J, Yu SC, et al. Design,synthesis,and biological evaluation of novel 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted benzylamino-2-propanols[J]. Bioorg Med Chem Lett, 2009, 19(6):1811-1814.
[14]	Giraud F, Loge C, Pagniez F, et al. Design, synthesis, and evaluation of 1-(N-benzylamino)-2-phn-yl-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents[J]. Bioorg Med Chem Lett, 2008, 18(6):1820-1824.
[15]	Giraud F, Guillon R, Loge C, et al. Synthesis and structure-activity relationships of 2-phenyl-1-[(pyridinyl-and piperidinylmethyl)amino]-3-(1H-1,2,4-triazol-1-yl) propan-2-ols as antifungal agents[J]. Bioorg Med Chem Lett, 2009, 19(2):301-304.
[16]	Gan LL, Cai JL, Zhou CH. Advances in the research of piperazine compounds as receptor ligands[J]. Chin Pharma J, 2009, 44:1361-1368.
[17]	Gan LL, Lu YH, Zhou CH. Advances in the research of piperazine compounds as enzyme inhibitors[J]. Chin J Biochem Pharm, 2009, 30:127-131.
[18]	Cai JL, Lu YH, Gan LL, et al. Recent advance in the research of piperazine-containing compounds as antimicrobial agents[J]. Chin J Antibiot, 2009, 34:454-462.
[19]	Gan LL, Zhou CH. Synthesis of azole-containing piperazine derivatives and evaluation of their antibacterial, antifungal and cytotoxic activities[J].Bull Korean Chem Soc, 2010, 31(12):3684-3692.
[20]	Na YM. Synthesis and activity of novel 1-halogenobenzylindole linked triazole derivatives as antifungal agents[J]. Bull Korean Chem Soc, 2011, 32(1):307-310.
[21]	Zhao JX, Cao YY, Quan H, et al. In vitro and in vivo activities of HQQ-3, a new triazole antifungal agent[J]. Biol Pharm Bull, 2006, 29(10):2031-2034.
[22]	Xu JM, Cao YB, Zhang J, et al. Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives[J]. Eur J Med Chem, 2011, 46(7):3142-3148.
[23]	Jiang YW, Zhang J, Cao YB, et al. Synthesis, in vitro evaluation and molecular docking studies of new triazole derivatives as antifungal agents[J]. Bioorg Med Chem Lett, 2011, 21(15):4471-4475.
[24]	Tron GC, Pirali T, Billing RA, et al. Click chemistry reaction in medicinal chemistry:applications of the 1,3-dipolar cycloaddition between azides and alkynes[J].Med Res Rev, 2008, 28(2):278-308.
[25]	WeiJJ, Wang Y, Wang XL, et al. Recent advances of1,2,3-triazole compounds in medicinal chemistry[J]. Chin Pharm J, 2011, 46:481-485.
[26]	Wang BG, Yu SC, Chai XY, et al. Design synthesis and biological evaluation of 3-substituted triazole derivatives[J]. Chin Chem Lett, 2011, 22(5):519-522.
[27]	Fang B, Zhou CH, Rao XC. Synthesis and biological activities of novel amine-derived bis-azoles as potential antibacterial and antifungal agents[J]. Eur J Med Chem, 2010, 45(9):4388-4398.
[28]	Zhou CH, Fang B, Gan LL. Benzyl chloride tertiary amine double azole antimicrobial compounds, preparation and medical use thereof:China, 101323594(B)[P].2011.
[29]	Bendaha H, Yu L, Touzani R, et al. New azole antifungal agents with novel modes of action:synthesis and biological studies of new tridentate ligands based on pyrazole and triazole[J]. Eur J Med Chem, 2011, 46(9):4117-4124.

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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

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Research progress of fluconazole derivatives

Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2015-01-04

Rev Recd Date: 2015-04-24

Key words:

Abstract: Fluconazole, the third generation of triazole-antifungal drug, becomes the first choice in the treatment of fungal infection due to its broad antifungal spectrum, good water solubility and low toxicity. With an increasingly drug-resistant strain, developing new fluconazole derivatives is becoming an attractive topic. This review mainly indicates that people can get new fluconazole derivatives used by clinic through structural modification of fluconazole, which will give clues for advanced research.

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Reference (29)

[1]	Sobue S, Tan K, Haug-Pihale G. The effects of hepatic impairment on the pharmacokinetics of fosfluconazole and fluconazole following a single intravenous bolus injection of fosfluconazole[J]. Br J Clin Pharmacol, 2005,59(2):160-166.
[2]	Mora SJ, Cormick MP, Milanesio ME,et al. The photodynamic activity of a novel porphyrin derivative bearing a Fluconazole structure in different media and against Candida albicans[J]. Dyes Pigments, 2010, 87(3):234-240.
[3]	Zhou CH, Yu KG, Meng JP, et al. Dibenzimidazole and oniumcompound thereof, preparation method and medical use thereof:China, 101397276(A)[P].2009.
[4]	Francavilla C, Low E, Nair S, et al. Quaternary ammonium N,N-dichloroamines as topical antimicrobial agents[J]. Bioorg Med Chem Lett, 2009, 19(10):2731-2734.
[5]	Zhou CH, Mi JL, Wu J, et al. Triazole onium compound with antimicrobial activity, preparation method and medical use:China, 101391985(A)[P].2009.
[6]	Zhang YY, Mi JL, Zhou CH, et al. Synthesis of novel fluconazoliums and their evaluation for antibacterial and antifungal activities[J]. Eur J Med Chem, 2011, 46(9):4391-4402.
[7]	Sheng CQ, Zhang WN, Ji HT, et al. Structure-based optimization of azole antifungal agents by CoMFA, CoMSIA, and molecular docking[J]. J Med Chem, 2006, 49(8):2512-2525.
[8]	Chai XY, Zhang J, Yu S C, et al. Design,synthesis,and biological evaluation of novel 1-(1H-1,2,4-tri-Azole-1-yl)-2-(2,4-difluorophenyl)-3-substituted benzylamino-2-propanols[J]. Bioorg Med Chem Lett, 2009, 19(6):1811-1814.
[9]	Wang WY, Sheng CQ, Che XY, et al. Design, synthesis, and antifungal activity of novel conformationally restricted triazole derivatives[J]. Arch Pharm(Weinheim), 2009, 342(12):732-739.
[10]	Li WH, Zhao L, Tan GG, et al. Enantioseparation of the new antifungal drug iodiconazole and structually related triaditimenol analogues by CE with neutral cyclodextrin additives[J]. Chromatograp-Hia, 2011, 73(8):1009-1014.
[11]	Yu S, Chai X, Hu N, et al. Synthesis and antifungal activity of the novel triazole compounds[J]. Medchemcomm, 2013, 4(4):704-708.
[12]	Yu S, Chai X, Hu H, et al. Synthesis and antifungal evaluation of the novel triazole derivatives as inhibitors of cytochrome P45014a-demethylase[J]. Eur J Med Chem, 2010, 45(3):4435-4445.
[13]	Chai XY, Zhang J, Yu SC, et al. Design,synthesis,and biological evaluation of novel 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted benzylamino-2-propanols[J]. Bioorg Med Chem Lett, 2009, 19(6):1811-1814.
[14]	Giraud F, Loge C, Pagniez F, et al. Design, synthesis, and evaluation of 1-(N-benzylamino)-2-phn-yl-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents[J]. Bioorg Med Chem Lett, 2008, 18(6):1820-1824.
[15]	Giraud F, Guillon R, Loge C, et al. Synthesis and structure-activity relationships of 2-phenyl-1-[(pyridinyl-and piperidinylmethyl)amino]-3-(1H-1,2,4-triazol-1-yl) propan-2-ols as antifungal agents[J]. Bioorg Med Chem Lett, 2009, 19(2):301-304.
[16]	Gan LL, Cai JL, Zhou CH. Advances in the research of piperazine compounds as receptor ligands[J]. Chin Pharma J, 2009, 44:1361-1368.
[17]	Gan LL, Lu YH, Zhou CH. Advances in the research of piperazine compounds as enzyme inhibitors[J]. Chin J Biochem Pharm, 2009, 30:127-131.
[18]	Cai JL, Lu YH, Gan LL, et al. Recent advance in the research of piperazine-containing compounds as antimicrobial agents[J]. Chin J Antibiot, 2009, 34:454-462.
[19]	Gan LL, Zhou CH. Synthesis of azole-containing piperazine derivatives and evaluation of their antibacterial, antifungal and cytotoxic activities[J].Bull Korean Chem Soc, 2010, 31(12):3684-3692.
[20]	Na YM. Synthesis and activity of novel 1-halogenobenzylindole linked triazole derivatives as antifungal agents[J]. Bull Korean Chem Soc, 2011, 32(1):307-310.
[21]	Zhao JX, Cao YY, Quan H, et al. In vitro and in vivo activities of HQQ-3, a new triazole antifungal agent[J]. Biol Pharm Bull, 2006, 29(10):2031-2034.
[22]	Xu JM, Cao YB, Zhang J, et al. Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives[J]. Eur J Med Chem, 2011, 46(7):3142-3148.
[23]	Jiang YW, Zhang J, Cao YB, et al. Synthesis, in vitro evaluation and molecular docking studies of new triazole derivatives as antifungal agents[J]. Bioorg Med Chem Lett, 2011, 21(15):4471-4475.
[24]	Tron GC, Pirali T, Billing RA, et al. Click chemistry reaction in medicinal chemistry:applications of the 1,3-dipolar cycloaddition between azides and alkynes[J].Med Res Rev, 2008, 28(2):278-308.
[25]	WeiJJ, Wang Y, Wang XL, et al. Recent advances of1,2,3-triazole compounds in medicinal chemistry[J]. Chin Pharm J, 2011, 46:481-485.
[26]	Wang BG, Yu SC, Chai XY, et al. Design synthesis and biological evaluation of 3-substituted triazole derivatives[J]. Chin Chem Lett, 2011, 22(5):519-522.
[27]	Fang B, Zhou CH, Rao XC. Synthesis and biological activities of novel amine-derived bis-azoles as potential antibacterial and antifungal agents[J]. Eur J Med Chem, 2010, 45(9):4388-4398.
[28]	Zhou CH, Fang B, Gan LL. Benzyl chloride tertiary amine double azole antimicrobial compounds, preparation and medical use thereof:China, 101323594(B)[P].2011.
[29]	Bendaha H, Yu L, Touzani R, et al. New azole antifungal agents with novel modes of action:synthesis and biological studies of new tridentate ligands based on pyrazole and triazole[J]. Eur J Med Chem, 2011, 46(9):4117-4124.

Message Board

Research progress of fluconazole derivatives

doi: 10.3969/j.issn.1006-0111.2016.02.004

Abstract

References

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通讯作者: 陈斌, bchen63@163.com

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