New hypotheses for the binding mode of 4- and 7-substituted indazoles in the active site of neuronal nitric oxide synthase

Iodoindazoles with Selective Magnesiation at Position 3: A Route to Highly Functionalized Indazoles

“…Indazole is found in many synthetic derivatives, particularly in the field of medicinal chemistry, in which it is generally used as an isostere of indole . Therefore, this scaffold was successfully used in drug development programs to afford anti‐HIV or anti‐tumor agents, cannabinoid, 5‐HT 2 , 5‐HT 3 or 5‐HT 4 receptors ligands, kinase or NO‐synthase inhibitors . Several indazole derivatives are now available as marketed drugs: granisetron, bendazac, benzydamine, or axitinib.…”

“…[5] Therefore, this scaffold was successfully used in drug development programs to afford anti-HIV [6] or anti-tumor agents, [7,8,9] cannabinoid, [10] 5-HT 2 , [11] 5-HT 3 [12] or 5-HT 4 [13,14] receptors ligands,k inase [15][16][17][18] or NO-synthase inhibitors. [19,20] Several indazole derivatives are now available as marketed drugs: granisetron,b endazac, benzydamine, or axitinib.…”

Ethyl 3-[7-(N-acetyl-4-methoxybenzenesulfonamido)-3-chloro-2H-indazol-2-yl]propionate

“…The indazole ring system is recognized to be a highly effective pharmacophore in medicinal chemistry as well as being the core of important nitrogen-containing heterocycles that show a broad range of biological activities, such as nitric oxide syntheses and HIV protease inhibitors, anti-inflammatory and anti-cancer agents, and serotonin 5-HT3 receptor antagonists (Lohou et al, 2012;Salerno et al, 2012;Kaltenbach et al, 2003;Thangadurai et al, 2012;Abbassi et al, 2012). The present work is a continuation of the investigation of the sulfonamide derivatives published recently by our team (Abbassi, et al, 2013;Chicha, et al, 2013).…”

A regioselective C7 bromination and C7 palladium-catalyzed Suzuki–Miyaura cross-coupling arylation of 4-substituted NH-free indazoles

“…The regioselective C7 bromination of N-(1H-indazol-4-yl)-4methylbenzenesulfonamide 3a, used as model substrate, was attempted with N-bromosuccinimide (NBS) 57,58 as depicted in Table 1. Compared to room temperature conditions ( Table 1, entry 1), we were pleased to nd that the treatment of N-(1H-Scheme 1 Reagents and conditions for the synthesis of 3a-c and 4ac.…”