153255-91-5Relevant articles and documents
Synthesis and biological evaluation of new fluconazole β-lactam conjugates linked via 1,2,3-triazole
Divse, Jaisingh M.,Mhaske, Santosh B.,Charolkar, Chaitanya R.,Sant, Duhita G.,Tupe, Santosh G.,Deshpande, Mukund V.,Khedkar, Vijay M.,Nawale, Laxman U.,Sarkar, Dhiman,Pore, Vandana S.
, p. 470 - 479 (2017)
Novel 1,2,3-triazole-linked β-lactam-fluconazole conjugates 12(a-l) were designed and synthesized. The compounds showed potent antifungal activity against two pathogenic Candida strains; Candida albicans ATCC 24433 and Candida albicans ATCC 10231 with MIC values in the range of 0.0625-2 μg mL-1. Compounds 12h, 12j and 12k showed promising antifungal activity against all the tested fungal pathogens except C. neoformans ATCC 34554 compared to fluconazole. Compound 12j in which the β-lactam ring was formed using para-anisidine and benzaldehyde was found to be more potent than fluconazole against all the fungal strains with an IC50 value of -1 for Candida albicans (ATCC 24433). Mechanistic studies for active compounds revealed that the antifungal action was due to ergosterol inhibition. Compounds 12h and 12j at a concentration of 0.125 μg mL-1 caused 91.5 and 96.8% ergosterol depletion, respectively, compared to fluconazole which at the same concentration caused 49% ergosterol depletion. The molecular docking study revealed that all the fluconazole β-lactam conjugates 12(a-l) could snugly fit into the active site of lanosterol 14α-demethylase (CYP51) with varying degrees of affinities. As anticipated, the binding energy for compound 12j (-58.961 kcal mol-1) was much smaller than that for fluconazole (-52.92 kcal mol-1). The synthesized compounds have therapeutic potential for the control of candidemia.
Synthesis of enantiomerically pure (R,R)- and (S,S)-1,2-Bis(pentafluorophenyl)ethane-1,2-diamine and evaluation of the pK a value by ab initio calculations
Sakai, Takashi,Korenaga, Toshinobu,Washio, Noriyuki,Nishio, Yuji,Minami, Shinichi,Ema, Tadashi
, p. 1001 - 1008 (2007/10/03)
1,2-Bis(pentafluorophenyl)ethane-1,2-diamine (1) was synthesized by the imino pinacol coupling of 4-methoxy-N-(pentafluorobenzylidene)benzylamine using a Zn-Cu couple and p-TsOH·H2O. The optical resolution of (±)-1 by means of chiral HPLC gave
One-pot synthesis of 1,2,3,4-tetrafluoroacridines from pentafluorobenzaldehyde
Adamson, Adrian J.,Banks, R. Eric,Fields, Roy,Tipping, Anthony E.
, p. 530 - 555 (2007/10/03)
Treatment of pentafluorobenzaldehyde with a two-molar equivalence of aniline in o-dichlorobenzene at ca. 180 yields a complex mixture of products from which 1,2,3,4-tetrafluoroacridine (1a) and its 3-anilino derivative (7a) can be isolated in at least 48
