149764-68-1Relevant articles and documents
Chemoenzymatic synthesis, nanotization, and anti-Aspergillus activity of optically enriched fluconazole analogues
Malhotra, Shashwat,Singh, Seema,Rana, Neha,Tomar, Shilpi,Bhatnagar, Priyanka,Gupta, Mohit,Singh, Suraj K.,Singh, Brajendra K.,Chhillar, Anil K.,Prasad, Ashok K.,Len, Christophe,Kumar, Pradeep,Gupta, Kailash C.,Varma, Anjani J.,Kuhad, Ramesh C.,Sharma, Gainda L.,Parmar, Virinder S.,Richards, Nigel G. J.
, (2017)
Despite recent advances in diagnostic and therapeutic methods in antifungal research, aspergillosis still remains a leading cause of morbidity and mortality. One strategy to address this problem is to enhance the activity spectrum of known antifungals, and we now report the first successful application of Candida antarctica lipase (CAL) for the preparation of optically enriched fluconazole analogues. Anti-Aspergillus activity was observed for an optically enriched derivative, ()-S-2-(2=,4=difluorophenyl)-1-hexyl-amino-3-(1,2,4)triazol-1-yl-propan-2-ol, which exhibits MIC values of 15.6 g/ml and 7.8 g/disc in broth microdilution and disc diffusion assays, respectively. This compound is tolerated by mammalian erythrocytes and cell lines (A549 and U87) at concentrations of up to 1,000 g/ml. When incorporated into dextran nanoparticles, the novel, optically enriched fluconazole analogue exhibited improved antifungal activity against Aspergillus fumigatus (MIC, 1.63 g/ml). These results not only demonstrate the ability of biocatalytic approaches to yield novel, optically enriched fluconazole derivatives but also suggest that enantiomeri-cally pure fluconazole derivatives, and their nanotized counterparts, exhibiting anti-Aspergillus activity may have reduced toxicity.
Synthesis and Biological Activities of Diosgenin-Triazole Conjugates with a 1,3-Dipolar Cycloaddition Reaction
Liao, Jun,Liao, Guochao,Gao, Yun,Chai, Xiaoyun,Wu, Qiuye,Zhao, Qingjie
, p. 1074 - 1080 (2021/11/26)
A novel series of diosgenin-triazole conjugates (10a–d, 11a–c, 12a–c, 13a–c) was designed and synthesized as antifungal agents by using a 1,3-dipolar cycloaddition reaction in the presence of a Cu(I) catalyst. All the title compounds were characterized by 1H NMR, 13C NMR, and Q-TOF-MS. Results of preliminary antifungal tests against seven human pathogenic fungi in vitro revealed that half of the target compounds exhibited moderate or even better antifungal activities against Y0109 and C. albicans SC5314 species. Compound 10d showed excellent antifungal activities toward C. albicans Y0109 and C. albicans SC5314 than itraconazole, with MIC80 value of 1 μg/mL, respectively.
Synthesis, antifungal activity, and molecular docking studies of novel triazole derivatives
Wang, Nan,Chai, Xiaoyun,Chen, Ying,Zhang, Lei,Li, Wenjuan,Gao, Yijun,Bi, Yi,Yu, Shichong,Meng, Qingguo
, p. 384 - 388 (2013/07/28)
In order to meet the urgent need for novel antifungal agents with improved activity and broader spectrum, a series of 3/4-[[N-alkyl-2-(2,4-difluorophenyl)- 2-hydroxy-3-(1H-1, 2, 4-triazole)] propylamino] benzylethyl carbonate were designed, synthesized and evaluated as antifungal agents. The MIC80 values indicate that all the compounds showed only moderate or even no antifungal activities against nearly all the tested fungal pathogens. Moreover, the interactions of the most active compounds in the drug binding site of CACYP51 were also explored with the help of docking studies.
Design synthesis and biological evaluation of 3-substituted triazole derivatives
Wang, Bao Gang,Yu, Shi Chong,Chai, Xiao Yun,Yan, Yong Zheng,Hu, Hong Gang,Wu, Qiu Ye
, p. 519 - 522 (2012/01/05)
Based on the active site of lanosterol 14α-demethylase of azole antifungal agents, sixteen 1-(1H-1,2,4-triazole-1-yl)- 2-(2,4-difluorophenyl)-3- (N-n-butyl-N-1-substitutedbenzyl-4-methylene-1H-1,2,3-triazole)-2-propanols have been designed, synthesized and evaluated as antifungal agents. Results of preliminary antifungal tests against eight human pathogenic fungi in vitro showed that some of the compounds exhibited excellent activities with broad spectrum.
Design, synthesis, and biological evaluation of novel 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted benzylamino-2-propanols
Chai, Xiaoyun,Zhang, Jun,Yu, Shichong,Hu, Honggang,Zou, Yan,Zhao, Qingjie,Dan, Zhigang,Zhang, Dazhi,Wu, Qiuye
supporting information; experimental part, p. 1811 - 1814 (2009/11/30)
Based on the results of computational docking to the active site of the cytochrome P450 14α-demethylase (CYP51), a series of 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted benzylamino-2-propanols as analogs of fluconazole were designed, synthesized, and evaluated as antifungal agents. Results of preliminary antifungal tests against eight human pathogenic fungi in vitro showed that all the title compounds exhibited excellent activities with broad spectrum.
