Browsing by Author "Merchan Arenas, Diego Rolando"
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Publication Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline(2013) Merchan Arenas, Diego Rolando; Martínez Bonilla, Carlos A.; Kouznetsov, Vladimir V.New green protocol for the efficient synthesis of pharmacologically relevant 4-amidyl-2-methyl-1,2,3,4-tetrahydroquinolines (THQs) through the domino type ABB’ imino Diels–Alder reaction in acidified water in the presence of sodium dodecyl sulphate (SDS) surfactant was developed for the first time. The influence of the SDS micelles and their different concentrations (5.0, 8.2 and 12.0 mM) on reactivity of the imino Diels–Alder reaction was studied. It was found that the best THQ yields (70–99%) are achieved above the critical micellar concentration (12 mM) using pH 1.0–2.5. This procedure resulted in a general and clean environmentally benign protocol to obtain the privileged diastereospecific cis 2,4-disubstituted THQ molecules of highest biological interest.Publication Diastereoselective Synthesis of Dihydroisoindolo[2,1‑a]quinolin-11- ones by Solvent-Free AMCell-SO3H‑Catalyzed Imino Diels−Alder/Intramolecular Amide Cyclization Cascade Reactions(2014-04-30) Merchan Arenas, Diego Rolando; Kouznetsov, Vladimir V.Nineteen bioactive highly functionalized 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-one derivatives were easily prepared in good yield without solvent using catalytic amorphous milled cellulose sulfonic acid (AMCell-SO3H), substituted anilines, propenyl-phenols, and phthaldehydic acid. The cascade reaction gave high regioselectivity and diastereoselectivity.Publication Modificación química del aceite esencial de Eugenia caryophyllus y del eugenol en la búsqueda de nuevos antioxidantes para la industria(2014) Rincón Ramírez, John Jairo; Vargas Méndez, Leonor Yamile; Merchan Arenas, Diego RolandoPublication Selective activity of 2,4-diaryl-1,2,3,4-tetrahydroquinolines on Trypanosoma cruzi epimastigotes and amastigotes expressing β-galactosidase(2013-07) Fonseca Berzal, Cristina; Merchan Arenas, Diego Rolando; Romero Bohórquez, Arnold R.; Escario, José A.; Kouznetsov, Vladimir V.; Gómez Barrio, AliciaThe growth inhibitory effect on Trypanosoma cruzi epimastigotes and the unspecific cytotoxicity over NCTC-929 fibroblasts of two series of previously synthesized 2,4-diaryl-1,2,3,4-tetrahydroquinolines (THQ), have been studied in vitro and compared with those of benznidazole (BZ). Derivatives AR39, AR40, AR41, AR91 and DM15 achieved outstanding selectivity indexes (SI) on the extracellular form (SITHQ > SIBZ > 9.44) and thus, were tested in a more specific in vitro assay against amastigotes, showing less effectiveness than the reference drug (SIBZ > 320) but also accomplishing great selectivity on the intracellular stage (SITHQ > 25). These promising results, supported by the in-silico prediction of high bioavailability and less potential risk than benznidazole, reveal several tetrahydroquinolines as prototypes of potential antichagasic drugs.