36070-75-4Relevant articles and documents
Benzoxaborole Antimalarial Agents. Part 4. Discovery of Potent 6-(2-(Alkoxycarbonyl)pyrazinyl-5-oxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles
Zhang, Yong-Kang,Plattner, Jacob J.,Easom, Eric E.,Jacobs, Robert T.,Guo, Denghui,Sanders, Virginia,Freund, Yvonne R.,Campo, Brice,Rosenthal, Philip J.,Bu, Wei,Gamo, Francisco-Javier,Sanz, Laura M.,Ge, Min,Li, Liang,Ding, Jie,Yang, Yin
, p. 5344 - 5354 (2015/08/03)
A series of 6-hetaryloxy benzoxaborole compounds was designed and synthesized for a structure-activity relationship (SAR) investigation to assess the changes in antimalarial activity which result from 6-aryloxy structural variation, substituent modification on the pyrazine ring, and optimization of the side chain ester group. This SAR study discovered highly potent 6-(2-(alkoxycarbonyl)pyrazinyl-5-oxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles (9, 27-34) with IC50s = 0.2-22 nM against cultured Plasmodium falciparum W2 and 3D7 strains. Compound 9 also demonstrated excellent in vivo efficacy against P. berghei in infected mice (ED90 = 7.0 mg/kg).
Synthesis and antimycobacterial evaluation of N-substituted 3-aminopyrazine-2,5-dicarbonitriles
Zitko, Jan,Jampilek, Josef,Dobrovolny, Luka?,Svobodova, Michaela,Kune?, Ji?i,Dole?al, Martin
body text, p. 1598 - 1601 (2012/04/04)
A series of 14 new compounds related to pyrazinamide were synthesized, characterized with analytical data and screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and two types of Mycobacterium avium. The series comprised of N-substituted 3-aminopyrazine- 2,5-dicarbonitriles derived from 3-chloropyrazine-2,5- dicarbonitrile by nucleophilic substitution of chlorine by various non-aromatic amines (alkylamines, cycloalkylamines and heterocyclic amines). Noteworthy antimycobacterial activity against M. tuberculosis was found among the alkylamino derivatives, for example, 3-(heptylamino)pyrazine-2,5-dicarbonitrile inhibited M. tuberculosis at MIC = 51 lmol/L. 3-(Hexylamino)pyrazine-2,5- dicarbonitrile inhibited M. kansasii at MIC = 218 lmol/L. Basic structure-activity relationships are discussed. A comparison between calculated and experimentally determined lipophilicity parameters within the series is included.
Studies on Pyrazines. Part 10. Substitution Effect on Reaction of Pyrazine N-Oxides with Phosphoryl chloride
Sato, Nobuhiro
, p. 2860 - 2875 (2007/10/02)
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