153255-91-5

Upstream product

• 653-37-2 perfluorobenzaldehyde 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 120651-13-0 1,2,3,4-tetrafluoro-7-methoxy-acridine 
• 730992-56-0 meso-N,N'-bis(4-methoxyphenyl)-1,2-bis(pentafluorophenyl)ethane-1,2-diamine 

Relevant academic research and scientific papers

Synthesis and biological evaluation of new fluconazole β-lactam conjugates linked via 1,2,3-triazole

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.

Palladium-catalyzed coupling of polyfluorinated arenes with heteroarenes via C-F/C-H activation

The first palladium-catalyzed coupling of 2-pyridyl-polyfluoroarenes and benzoxazole, thiazole, benzothiazole, benzoimidazole, oxazole or oxadiazole via a concurrent C-F/C-H activation is described. Initial mechanistic studies showed that C-F activation o

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

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

Asymmetric synthesis of α-arylglycinols via additions of lithium methyl p-tolyl sulfoxide to N-(PMP)arylaldimines followed by 'non oxidative' Pummerer reaction

The results presented in this paper demonstrate that the stereochemical outcome of the reversible additions of lithium (R)-methyl p-tolyl sulfoxide to N-arylidene-p-anisidines (N-PMP imines) is a function of a) the reaction conditions used and b) the electronic properties of the arylidene moiety on the starting imine. High kinetically controlled (2S,R(S)) diastereoselectivity (-70 °C) was achieved for additions of imines bearing relatively electron-rich N-arylidene groups, while an electron-deficient nature of this group was found to favor the opposite stereochemical outcome. On the other hand, the reactions run under thermodynamically controlled conditions (0 °C) afforded equimolar mixtures of the diastereomeric products regardless of the pattern of substitution on the starting imines. Enantiopure α-arylglycinols were readily synthesized by 'non-oxidative' Pummerer rearrangement of diastereomerically pure β-aryl-β-N-(acyl)aminoalkyl sulfoxides, prepared from the corresponding N-PMP derivatives.

One-pot synthesis of 1,2,3,4-tetrafluoroacridines from pentafluorobenzaldehyde

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

A new one-pot synthesis of 1,2,3,4-tetrafluoroacridines and some 7-substituted derivatives

1,2,3,4-Tetrafluoroacridine (1a) and a range of 7-substituted analogues can be synthesised by heating pre-formed Schiff bases (E)-C6F5CH=NC6H4R-p (3) (from C6F5CHO + H2NC6H4R-p) with the parent aniline H2NC6H4R-p (1:1 molar ratio) or by heating a mixture of the aldehyde C6F5CHO and the aniline H2NC6H4R-p (R=H, OMe, Me, But, F, Cl and Br) (1:2 molar ratio) in toluene or 1,2-dichlorobenzene under reflux.The mechanism has been deduced through the isolation in certain reactions of ortho-substituted Schiff bases 2-(p-RC6H4NH)C6F4CH=NC6H4R-p (6) (R=Cl or Br), which on acid catalysis (by p-RC6H4NH3(+)F(-)) undergo ring-closure with elimination of the aniline p-RC6H4NH2.Except where R=F, Cl or Br, substantial amounts of the corresponding 3-anilino-1,2,4-trifluoroacridines 5 are also formed; these arise via sequential para- and ortho-substitution of fluorine in the pentafluorophenyl moiety of the Schiff bases.The synthesis is capable of extension to other fluorinated aromatic aldehydes, e.g. the formation of 1-fluoro-7-methoxyacridine (9) from 2,6-difluorobenzaldehyde and p-anisidine.