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Volume 31 Issue 6
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Article Navigation >  Journal of Pharmaceutical Practice and Service  > 2013  >  31(6): 442-445

CHEN Hai, YAO Jian-zhong, SHENG Chun-quan, MIAO Zhen-yuan, ZHANG Wan-nian. Synthesis of 4-[1-alkyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl] benzoic acids[J]. Journal of Pharmaceutical Practice and Service, 2013, 31(6): 442-445. doi: 10.3969/j.issn.1006-0111.2013.06.012
Citation: CHEN Hai, YAO Jian-zhong, SHENG Chun-quan, MIAO Zhen-yuan, ZHANG Wan-nian. Synthesis of 4-[1-alkyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl] benzoic acids[J]. Journal of Pharmaceutical Practice and Service, 2013, 31(6): 442-445. doi: 10.3969/j.issn.1006-0111.2013.06.012
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Synthesis of 4-[1-alkyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl] benzoic acids

doi: 10.3969/j.issn.1006-0111.2013.06.012

  • School of Pharmacy, Second Military Medical University, Shanghai 200433, China

  • Received Date: 2013-01-25
  • Rev Recd Date: 2013-04-08
  • Objective To prepare 4-[1-alkyl-5-oxo-1H-1,2,4-triazol-4 (5H)-yl] benzoic acids (5), which was the key fatty acid chain pharmaceutical intermediates for the total synthesis of novel caspofungin-like cyclohexa lipopeptide antifungal agents. Methods Starting from 4-aminobenzoic acid (1), the target compounds 5a~5n were prepared via amino phenoxy-carbonyl acylation, hydrazinolysis, formamidine cyclization, and the N-alkylation reaction, respectively. Results Target compounds 5a~5n had been successfully synthesized with the overall yield ranged from 42.9% to 46.2%. Their structures were confirmed by ESI-MS and 1H-NMR spectra. All target compounds were reported for the first time. Conclusion The process developed had several advantages such as convenient workup and high yield, which was suitable to industrial production.
  • [1] Georgopapakou NH.Update on antifungals targeted to the cellwall focus on beta-1, 3-glucan synthase inhibitors[J].Expert Opin Invest Drugs, 2001,10 (2):269.
    [2] Petrikkos G,Skiada A.Recent advances in antifungal chemotherapy[J].Intl J Antimicrob Agents,2007,30:108.
    [3] Kathiravan MK,Salake AB,Chothe AS,et al.The biology and chemistry of antifungal agents:a review[J].Bioorg Med Chem,2012,20:5678.
    [4] Sheng CQ,Che XY,Wang WY,et al.Design and synthesis of novel triazole antifungal derivatives by structure-based bioisosterism[J].Eur J Med Chem,2011,46,5276.
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Synthesis of 4-[1-alkyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl] benzoic acids

doi: 10.3969/j.issn.1006-0111.2013.06.012
  • School of Pharmacy, Second Military Medical University, Shanghai 200433, China
  • Received Date: 2013-01-25
  • Rev Recd Date: 2013-04-08

Abstract: Objective To prepare 4-[1-alkyl-5-oxo-1H-1,2,4-triazol-4 (5H)-yl] benzoic acids (5), which was the key fatty acid chain pharmaceutical intermediates for the total synthesis of novel caspofungin-like cyclohexa lipopeptide antifungal agents. Methods Starting from 4-aminobenzoic acid (1), the target compounds 5a~5n were prepared via amino phenoxy-carbonyl acylation, hydrazinolysis, formamidine cyclization, and the N-alkylation reaction, respectively. Results Target compounds 5a~5n had been successfully synthesized with the overall yield ranged from 42.9% to 46.2%. Their structures were confirmed by ESI-MS and 1H-NMR spectra. All target compounds were reported for the first time. Conclusion The process developed had several advantages such as convenient workup and high yield, which was suitable to industrial production.

CHEN Hai, YAO Jian-zhong, SHENG Chun-quan, MIAO Zhen-yuan, ZHANG Wan-nian. Synthesis of 4-[1-alkyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl] benzoic acids[J]. Journal of Pharmaceutical Practice and Service, 2013, 31(6): 442-445. doi: 10.3969/j.issn.1006-0111.2013.06.012
Citation: CHEN Hai, YAO Jian-zhong, SHENG Chun-quan, MIAO Zhen-yuan, ZHANG Wan-nian. Synthesis of 4-[1-alkyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl] benzoic acids[J]. Journal of Pharmaceutical Practice and Service, 2013, 31(6): 442-445. doi: 10.3969/j.issn.1006-0111.2013.06.012
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