Bioactivity of semisynthetic eugenol derivatives against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae infesting maize in Colombia

The anti-acetylcholinesterase, larvicidal, antifeedant activities and general toxicity of 15 semisynthetic eugenol derivatives based on clove oil (including the own oil), were evaluated against the maize armyworm, Spodoptera frugiperda (J.E. Smith). Therefore, promising eugenol molecules were classified with larvicidal, anti-acetylcholinesterase and antifeedant activities for controlling this pest. During structure–activity relationship studies and physicochemical profile analysis, it was found that among tested molecules 1-15, eugenol 1, prenyl eugenol 4, isoeugenol 8 and isoeugenol acetate 11 exhibited lethal effects LD50 at concentrations < 1 mg/g of insect. On the other hand, eugenol 1, metallyl eugenol 3, isoeugenol 8 and isoeugenol acetate 11 showed a good antifeedant activity (CE50 =158-209 µg/mL) with a high antifeedant index (70-78 %) at concentration 1000 µg/mL, possessing a weak antiacetylcholinesterase activity (IC50 = 21-31 g/mL). According to their ecotoxicological profiles (LC50 = 2033.1-6303.8 µg/mL on Artemia salina larvae), isoeugenol 8 and its acetate derivative 11 could be potential used in control of the growth, feeding, or reproduction of S. frugiperda larvae, acting as moderate insecticidal acetylcholinesterase inhibitors and/or antifeedant molecules. Such structure–activity relationship studies could stimulate the identification of lead structures from natural sources for the development of larvicidal and deterrent products against S. frugiperda and related insect pests.Fil: Vargas Méndez, Leonor Y.. Universidad Santo Tomás; ColombiaFil: Sanabria Flórez, Pedro L.. Universidad Santo Tomás; ColombiaFil: Saavedra Reyes, Laura Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Santo Tomás; ColombiaFil: Merchan Arenas, Diego R.. Universidad Industrial Santander; ColombiaFil: Kouznetsov, Vladimir V.. Universidad Industrial Santander; Colombi

Chemical-Enhanced Oil Recovery Using N,N-Dimethylcyclohexylamine on a Colombian Crude Oil

Oil recovery was improved using the tertiary amine, N,N-dimethylcyclohexylamine (DMCHA), a powerful and promissory switchable solvent, in simulated conditions similar to the Colombian crude oil reserves. Firstly, the Colombian crude oil (CCO) and the soil were characterized completely. Afterwards, an aged crude-rock system was obtained to use DMCHA that gave an oil crude extraction of 80% in our preliminary studies. Thus, a sand-pack column (soil-kaolin, 95 : 5) frame saturated with CCO was used to simulate the conditions, in which DMCHA could recover the oil. After the secondary recovery process, 15.4–33.8% of original oil in place (OOIP) is obtained. Following the injection of DMCHA, the recovery yield rose to 87–97% of OOIP. Finally, 54–60% of DMCHA was recovered and reinjected without affecting its potential in the simulated conditions

Reacción de imino diels-alder de tres componentes con precursores de origen natural. generación de nuevas tetrahidroquinolinas 2,4- diaril disustituidas.

The efficient and diastereoselective synthesis of the new substituted 2,4-diaryl- 1,2,3,4,-tetrahydroquinoline (THQ) was realized via trans-anethole or cis/transisoeugenol, anilines and benzaldehydes condensation with acid catalysts. The BF3?OEt2 was the most efficient catalyst for this reaction. In addition, the essential oil of anise was employed for the direct synthesis of these compounds (THQ). Finally, the extract of the dry anise seeds was used after the extraction under supercritical fluid conditions (scCO2) and the THQ was obtained in good yield and solventless.Se realizó la eficiente y diaestereoselectiva síntesis de nuevas 2,4-diaril-1,2,3,4- tetrahidroquinolinas (THQ) sustituidas, bajo una condensación entre trans-anetol o cis/trans-isoeugenol, anilinas y benzaldehídos sustituidos, en presencia de catalizadores ácidos. Entre varios catalizadores estudiados el BF3?OEt2 fue el más eficiente para este tipo de condensación. También se utilizó el aceite esencial de anís estrellado para la síntesis directa de dichos compuestos y finalmente se empleó el extracto de la semilla seca de anís obtenido con la técnica de extracción con fluido supercrítico e in situ se obtienen las respectivas THQ con buenos rendimientos y libre de solvente

Selective activity of 2,4-diaryl-1,2,3,4-tetrahydroquinolines on Trypanosoma cruzi epimastigotes and amastigotes expressing β-galactosidase

The 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.Departamento Administrativo de Ciencia, Tecnología e Innovación [CO] Colciencias5507-543-31904Programa: Bioprospección y desarrollo de ingredientes naturales para las industrias cosmética, farmacéutica y de productos de aseo con base en la biodiversidad colombianan

Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline

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.Departamento Administrativo de Ciencia, Tecnología e Innovación [CO] Colciencias5507-543-31904Programa: Bioprospección y desarrollo de ingredientes naturales para las industrias cosmética, farmacéutica y de productos de aseo con base en la biodiversidad colombianan

Diastereoselective Synthesis of Dihydroisoindolo[2,1‑a]quinolin-11- ones by Solvent-Free AMCell-SO3H‑Catalyzed Imino Diels−Alder/Intramolecular Amide Cyclization Cascade Reactions

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.Departamento Administrativo de Ciencia, Tecnología e Innovación [CO] Colciencias5507-543-31904Programa: Bioprospección y desarrollo de ingredientes naturales para las industrias cosmética, farmacéutica y de productos de aseo con base en la biodiversidad colombianan