93733-07-4Relevant academic research and scientific papers
Synthesis and biological activity of imidazole based 1,4-naphthoquinones
Chakravarty, Debamitra,Choudhari, Dinkar,Gejji, Shridhar P.,Gonnade, Rajesh,Lande, Dipali N.,Puranik, Vedavati G.,Rao, Pradeep Kumar,Salunke-Gawali, Sunita,Satpute, Surekha,Shaikh, Samir R.
, p. 6889 - 6901 (2020/05/16)
Design and development of drugs in multi-drug resistant (MDR) infections have been of growing interest. We report the syntheses, and antibacterial and antifungal activities of imidazole-based 1,4-naphthoquinones (I-1toI-4; 1-alkyl-2-methyl-1H-naphtho[2,3-d]imidazole-4,9-dione (alkyl = methyl to butyl)) and their precursors (B-3;N-(3-chloro-1,-dioxo-1,4-dihydronaphthalen-2-yl)acetamide) andA-1toA-4;N-(3-(alkylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide (alkyl = methyl to butyl). Crystal structures ofB-3A-1toA-3andI-2toI-4were obtained through single crystal X-ray diffraction experiments. Electronic structure and charge distribution have further been characterized with the use of Density Functional Theory. Seven of these derivatives display a broad spectrum of antibacterial activity against few selected bacterial strains (Gram-positive and Gram-negative). As demonstrated MIC values withB-2andB-3against bacterial isolates were 8-64 μg ml?1and those against pathogenic yeast,C. albicans, were observed in the range of 128-256 μg ml?1. MIC data of these derivatives suggest them to be promising against pathogens.
Antimalarial N1, N3-Dialkyldioxonaphthoimidazoliums: Synthesis, Biological Activity, and Structure-activity Relationships
Ahenkorah, Stephen,Birkholtz, Lyn-Marie,Coertzen, Dina,Fridianto, Kevin,Go, Mei-Lin,Haynes, Richard K.,Lam, Yulin,Tan, Kevin S. W.,Tong, Jie Xin,Wittlin, Sergio
, p. 49 - 55 (2020/02/06)
Here we report the nanomolar potencies of N1,N3-dialkyldioxonaphthoimidazoliums against asexual forms of sensitive and resistant Plasmodium falciparum. Activity was dependent on the presence of the fused quinone-imidazolium entity and lipophilicity imparted by the N1/N3 alkyl residues on the scaffold. Gametocytocidal activity was also detected, with most members active at IC50 1 μM. A representative analog with good solubility, limited PAMPA permeability, and microsomal stability demonstrated oral efficacy on a humanized mouse model of P. falciparum.
