An ebselen like catalyst with enhanced GPx activity via a selenol intermediate.
The reaction of KSeO(t)Bu with 2-iodo-arylbenzamides gave benzamide ring-substituted, quinine-derived isoselenazolones 1b–1d. The reaction of PhSH with ortho-methyl-substituted isoselenazolone 1b gave selenol 3b, which is oxidized by H2O2 to regenerate 1b. Isoselenazolone 1b shows a high rate (0.33 × 103 μM min(−1)) of oxidation of PhSH with H2O2, which is ∼103-fold more active than ebselen (1a) and ≥30-fold more active than the other isoselenazolones of this study. Compound 1b shows less inhibition of the growth of yeast cells than 1a.
Department of Chemistry, Indian Institute of Science Education and Research Bhopal (IISER), Indore bypass Road, Bhopal, MP 462 066, India. sangitkumar@iiserb.ac.in.
Shah Jaimin
SJ
Balkrishna
Shailesh
S
Kumar
Gajendra Kumar
GK
Azad
Bhagat Singh
BS
Bhakuni
Piyush
P
Panini
Navjeet
N
Ahalawat
Raghuvir Singh
RS
Tomar
Michael R
MR
Detty
Sangit
S
Kumar
D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology; D001393:Azoles / Q000737:chemistry* / Q000494:pharmacology; D001549:Benzamides / Q000737:chemistry; D002384:Catalysis; D005979:Glutathione Peroxidase / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry; D054833:Isoindoles; D008958:Models, Molecular; D016566:Organoselenium Compounds / Q000737:chemistry* / Q000494:pharmacology; D010084:Oxidation-Reduction; D018036:Selenium Compounds / Q000737:chemistry* / Q000494:pharmacology; D015003:Yeasts / Q000187:drug effects / Q000254:growth & development
D000975:Antioxidants; D001393:Azoles; D001549:Benzamides; D054833:Isoindoles; D016566:Organoselenium Compounds; D018036:Selenium Compounds; C442270:selenol; C042986:ebselen; C037689:benzamide; D006861:Hydrogen Peroxide; D005979:Glutathione Peroxidase