Synthesis and β-Adrenergic Properties of (Z)-N-[3-(Alkylamino)-2-hydroxypropylidene](aryl-methyloxy)amines: Effects of the Configuration Around the Methyloxyiminomethyl (MOIM) Double Bond on the Biopharmacological Properties of MOIM-type β-Blocking Agents

Balsamo, Aldo; Breschi, Maria Cristina; Chiellini, Grazia; Lapucci, Annalina; Lazzeri, Nicola; Macchia, Marco; Martinelli, Adriano; Micali, E.; Nencetti, Susanna; Rossello, Armando

doi:10.1016/s0968-0896(98)00172-2

Cited by 5 publications

(1 citation statement)

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“…To a solution of the commercially available polyhydroxybenzaldehyde 17-21 (0.264 mmol) in MeOH (4 mL), an aqueous solution (1 mL) of the opportune hydroxylamine hydrochloride 16a-e (0.264 mmol) [17][18][19] was added. The reaction mixture was stirred for 1 h at room temperature until the disappearance of the starting material (TLC analysis).…”

Section: Chemistrymentioning

confidence: 99%

Nature-Inspired O-Benzyl Oxime-Based Derivatives as New Dual-Acting Agents Targeting Aldose Reductase and Oxidative Stress

et al. 2022

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Aldose reductase (ALR2) is the enzyme in charge of developing cellular toxicity caused by diabetic hyperglycemia, which in turn leads to the generation of reactive oxygen species triggering oxidative stress. Therefore, inhibiting ALR2 while pursuing a concomitant anti-oxidant activity through dual-acting agents is now recognized as the gold standard treatment for preventing or at least delaying the progression of diabetic complications. Herein we describe a novel series of (E)-benzaldehyde O-benzyl oximes 6a–e, 7a–e, 8a–e, and 9–11 as ALR2 inhibitors endowed with anti-oxidant properties. Inspired by the natural products, the synthesized derivatives are characterized by a different polyhydroxy substitution pattern on their benzaldehyde fragment, which proved crucial for both the enzyme inhibitory activity and the anti-oxidant capacity. Derivatives (E)-2,3,4-trihydroxybenzaldehyde O-(3-methoxybenzyl) oxime (7b) and (E)-2,3,4-trihydroxybenzaldehyde O-(4-methoxybenzyl) oxime (8b) turned out to be the most effective dual-acting products, proving to combine the best ALR2 inhibitory properties with significant anti-oxidant efficacy.

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Section: Chemistrymentioning

confidence: 99%