Nitrobenzofurazan derivatives of N’-hydroxyamidines as potent inhibitors of indoleamine-2,3-dioxygenase 1 was written by Paul, Saurav;Roy, Ashalata;Deka, Suman Jyoti;Panda, Subhankar;Trivedi, Vishal;Manna, Debasis. And the article was included in European Journal of Medicinal Chemistry in 2016.Synthetic Route of C8H9BrN2O The following contents are mentioned in the article:
Tryptophan metabolism through the kynurenine pathway is considered as a crucial mechanism in immune tolerance. Indoleamine 2,3-dioxygenase 1 (IDO1) plays a key role in tryptophan catabolism in the immune system and it is also considered as an important therapeutic target for the treatment of cancer and other diseases that are linked with kynurenine pathway. Nitrobenzofurazan derivatives of N’-hydroxybenzimidamides and N’-hydroxy-2-phenylacetimidamides were synthesized and their inhibitory activities against human IDO1 enzyme were tested using in-vitro and cellular enzyme activity assay. The optimization leads to the identification of three potent compounds (IC50 = 39-80 nM), which are either competitive or uncompetitive inhibitors of IDO1 enzyme. These compounds also showed IDO1 inhibition potencies in the nanomolar range (IC50 = 50-71 nM) in MDA-MB-231 cells with no/negligible amount of cytotoxicity. The stronger selectivity of the potent compounds for IDO1 enzyme over tryptophan 2,3-dioxygenase (TDO) enzyme (312-1593-fold) also makes them very attractive for further immunotherapeutic applications. This study involved multiple reactions and reactants, such as 2-(4-Bromophenyl)-N-hydroxyacetimidamide (cas: 422560-40-5Synthetic Route of C8H9BrN2O).
2-(4-Bromophenyl)-N-hydroxyacetimidamide (cas: 422560-40-5) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Synthetic Route of C8H9BrN2O
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary