Browsing by Author "Pessoa Mahana, David"

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    Microwave-assisted synthesis and regioisomeric structural elucidation of novel benzimidazo[1,2d][1,4]benzodiazepinone derivatives
    (ARKAT USA INC, 2009) Pessoa Mahana, David; Espinosa Bustos, Christian; Mella Raipan, Jaime; Canales Pacheco, Jorge; Pessoa Mahana, Hernan
    The synthesis of 5H-benzimidazo [1,2-d] [1,4] benzodiazepin -6(7H)-ones 3a-e from readily available 2-(2-aminophenyl)-1H-benzo[d]imidazole derivatives 2a-e and 2-bromoacetyl bromide under microwave conditions is described. Unambiguous structural elucidation of the obtained regioisomers was finally established by means of 2D-NOESY experiment.
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    New Pyridone-Based Derivatives as Cannabinoid Receptor Type 2 Agonists
    (MDPI, 2021) Faundez Parraguez, Manuel; Alarcon Miranda, Carlos; Cho, Young Hwa; Pessoa Mahana, Hernan; Gallardo Garrido, Carlos; Chung, Hery; Faundez, Mario; Pessoa Mahana, David
    The activation of the human cannabinoid receptor type II (CB2R) is known to mediate analgesic and anti-inflammatory processes without the central adverse effects related to cannabinoid receptor type I (CB1R). In this work we describe the synthesis and evaluation of a novel series of N-aryl-2-pyridone-3-carboxamide derivatives tested as human cannabinoid receptor type II (CB2R) agonists. Different cycloalkanes linked to the N-aryl pyridone by an amide group displayed CB2R agonist activity as determined by intracellular [cAMP] levels. The most promising compound 8d exhibited a non-toxic profile and similar potency (EC50 = 112 nM) to endogenous agonists Anandamide (AEA) and 2-Arachidonoylglycerol (2-AG) providing new information for the development of small molecules activating CB2R. Molecular docking studies showed a binding pose consistent with two structurally different agonists WIN-55212-2 and AM12033 and suggested structural requirements on the pyridone substituents that can satisfy the orthosteric pocket and induce an agonist response. Our results provide additional evidence to support the 2-pyridone ring as a suitable scaffold for the design of CB2R agonists and represent a starting point for further optimization and development of novel compounds for the treatment of pain and inflammation.
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    Solvent-free microwave synthesis of 3-(4-benzo[b]thiophene-2-carbonyl)-1-piperazinyl-1-benzo[b]thiophen-2-yl-1-propanones. New hetero bis-ligands with potential 5-HT1A serotonergic activity
    (PERGAMON-ELSEVIER SCIENCE LTD, 2008) Pessoa Mahana, Hernan; Kosche, Johann; Ron, Nadia; Recabarren Gajardo, Gonzalo; Saitz, Claudio; Araya Maturana, Rarniro; Pessoa Mahana, David
    A novel series of 2-benzothiophenealkylpiperazine derivatives 11 (a-d) with potential affinity at 5-HT1A serotonin receptors have been synthesized via solvent-free, microwave-promoted Michael addition of benzo[b]thiophene piperazine derivatives 6(a-c) to substituted benzo[b]thiophen-2-yl propenones 10(b,c).