Terminal Double Bond Research Articles

Highly tough and elastic microspheric gel for transarterial catheter embolization in treatment of liver metastasis tumor.

Transarterial embolization is a widely recognized clinical treatment method for liver tumors. Given that the soft and easily damaged features of embolic particles may limit tumor embolization efficiency, the present study carries out an attempt of fabricating tough and elastic microspheric gel for promoting embolization efficiency. To promote the toughness of hydrogel, poly(ethylene glycol)-co-poly(ε-caprolactone)-co-poly(ethylene glycol) (PPP) and PPP with two terminal double bonds (PPPDA) are co-assembled into nano-micelles, which are connected with methacrylated chitosan (CSMA) to fabricate microspheric gels via microfluidic technology. Lowering double bond density of micelles promotes the freedom degree of micelles, significantly enhancing hydrogel toughness. To compensate for the strength loss caused by the decrease of double bond density of micelles, phytic acid (PA) are employed to interact with CS to form a physical network, further improving hydrogel strength and toughness. The CS-PPPDA&PPP-PA microspheric gels exhibit higher blocking effect in vitro. A rabbit VX2 liver metastasis tumor model is prepared to verify the embolization efficacy of CS-PPPDA&PPP-PA microspheric gels. Compared with clinical used microspheres, fewer CS-PPPDA&PPP-PA microspheric gels can achieve enough embolization efficiency. After embolization for 14 days, CS-PPPDA&PPP-PA microspheric gels exhibit improved tumor necrosis rate and promoted tumor cells apoptosis with reduced inflammation in surrounding tissues, confirming advanced embolic efficiency of tough microgels.

Chemodivergent, Regio- and Enantioselective Cycloaddition Reactions between 1,3-Dienes and Alkynes.

Alkynes and 1,3-dienes are among the most readily available precursors for organic synthesis. We report two distinctly different, catalyst-dependent, modes of regio- and enantioselective cycloaddition reactions between these classes of compounds providing rapid access to highly functionalized 1,4-cyclohexadienes or cyclobutenes from the same precursors. Complexes of an earth abundant metal, cobalt, with several commercially available chiral bisphosphine ligands with narrow bite angles catalyze [4+2]-cycloadditions between a 1,3-diene and an alkyne giving a cyclohexa-1,4-diene in excellent chemo-, regio- and enantioselectivities. In sharp contrast, complex of a finely tuned phosphino-oxazoline ligand promotes unique [2+2]-cycloaddition between the alkyne and the terminal double bond of the diene giving a highly functionalized cyclobutene in excellent regio- and enantioselectivities.

Chemodivergent, Regio‐ and Enantioselective Cycloaddition Reactions between 1,3‐Dienes and Alkynes

AbstractAlkynes and 1,3‐dienes are among the most readily available precursors for organic synthesis. We report two distinctly different, catalyst‐dependent, modes of regio‐ and enantioselective cycloaddition reactions between these classes of compounds providing rapid access to highly functionalized 1,4‐cyclohexadienes or cyclobutenes from the same precursors. Complexes of an earth abundant metal, cobalt, with several commercially available chiral bisphosphine ligands with narrow bite angles catalyze [4+2]‐cycloadditions between a 1,3‐diene and an alkyne giving a cyclohexa‐1,4‐diene in excellent chemo‐, regio‐ and enantioselectivities. In sharp contrast, complex of a finely tuned phosphino‐oxazoline ligand promotes unique [2+2]‐cycloaddition between the alkyne and the terminal double bond of the diene giving a highly functionalized cyclobutene in excellent regio‐ and enantioselectivities.

A computational investigation towards substitution effects on 8π electrocyclisation of conjugated 1,3,5,7-octatetraenes.

A computational investigation using M06-2X/6-31+G(d) method is reported for the substitution effects on 8π electrocyclisation of conjugated octatetraene. This systematic study describes the mono- and di-substitution effect across the 1,3,5,7-octatetraene skeleton. A general preference of the outward substitution over the inward, at C1 position of the monosubstituted system is observed. However, mesomerically electron donating group (-NH2 and -OH) display an opposite effect with respect to secondary orbital interaction (SOI) between the lone pair on the substituent and the orbital. A comparative evaluation on the computed activation energies for the 1-, 2-, 3-, and 4-monosubstituted system showed an insignificant impact on the rate of the reaction, in contrast to the electrocyclic ring closure of the unsubstituted compound. Computations of disubstituted system are more pronounced, where a remarkable acceleration is observed for 2-NO2-7-NO2 substituted octatetraene at 4.9 kcal mol-1, and a noticeable deceleration for 4-CH3-5-CH3 substituted octatetraene at 25.4 kcal mol-1 from the parent molecule, 17.0 kcal mol-1. A visible accelerated effects are commonly exhibited by the substitution on the terminal double bonds (C1, C2, C7, and C8), that are 1,2-, 1,7-, 1,8-, and 2,7-patterns, in regard to the greater orbital interaction for the new σ-bond formation. Despite the unfavourable steric clashes of the substituents in the 1,8-system, an apparent reduction in the energy barrier up to 7.4 kcal mol-1 is computed for 1-NH2-8-NO2 system from 17.0 kcal mol-1. This is due to the synergistic effect of the electron donor and electron acceptor, enhancing the stability of the transition structure. The electrocyclic ring closure involving vicinal substitution patterns, such as 1,2-, 2,3-, 3,4-, and 4,5-systems are critically dominated by steric crowding between the adjacent functional groups. In certain cases of the 1,2-substituted system, a noticeable accelerated effects are found for 1-NH2-2-NH2-substituted compound (9.7 kcal mol-1) due to an increased in electronic density on the substituted terminal double bond (C1-C2), hence favouring the formation of the new σ-bond.

Rhenium(I) Block Copolymers Based on Polyvinylpyrrolidone: A Successful Strategy to Water-Solubility and Biocompatibility

A series of diphosphine Re(I) complexes Re1-Re4 have been designed via decoration of the archetypal core {Re(CO)2(N^N)} through the installations of the phosphines P0 and P1 bearing the terminal double bond, where N^N = 2,2'-bipyridine (N^N1), 4,4'-di-tert-butyl-2,2'-bipyridine (N^N2) or 2,9-dimethyl-1,10-phenanthroline (N^N3) and P0 = diphenylvinylphosphine, and P1 = 4-(diphenylphosphino)styrene. These complexes were copolymerized with the corresponding N-vinylpyrrolidone-based Macro-RAFT agents of different polymer chain lengths to give water-soluble copolymers of low-molecular p(VP-l-Re) and high-molecular p(VP-h-Re) block-copolymers containing rhenium complexes. Compounds Re1-Re4, as well as the copolymers p(VP-l-Re) and p(VP-h-Re), demonstrate phosphorescence from a 3MLCT excited state typical for this type of chromophores. The copolymers p(VP-l-Re#) and p(VP-h-Re#) display weak sensitivity to molecular oxygen in aqueous and buffered media, which becomes almost negligible in the model physiological media. In cell experiments with CHO-K1 cell line, p(VP-l-Re2) and p(VP-h-Re2) displayed significantly reduced toxicity compared to the initial Re2 complex and internalized into cells presumably by endocytic pathways, being eventually accumulated in endosomes. The sensitivity of the copolymers to oxygen examined in CHO-K1 cells via phosphorescence lifetime imaging microscopy (PLIM) proved to be inessential.

Ultrasound-assisted facile synthesis of Boron-Heck-coupled sclareol analogues as potential antibacterial agents against Staphylococcus aureus.

To evaluate the antimicrobial capability of sclareol and its derivatives against Staphylococcus aureus and its Methicillin-resistant strain (MRSA). A new series of Boron-Heck-coupled sclareol analogues were prepared by structural modifications at the C-15 terminal double bond of sclareol using ultrasonication. The structural modifications were designed to keep the stereochemistry of all the five chiral centres of sclareol intact. A two-step reaction scheme consisting of Boron-Heck coupling of sclareol followed by Wittig reaction was carried out to produce novel sclareol congeners for antimicrobial evaluation. Three compounds SAJ-1, SAJ-2 and SB-11 exhibited strong antibacterial activity against S. aureus and Methicillin-resistant strain (MRSA) with MIC values between 3 and 11 μM. Among all the screened compounds, SAJ-1 and SAJ-2 showed the best antibiofilm profiles against both strains. Moreover, SAJ-1 and SAJ-2 acted synergistically with streptomycin against S. aureus while creating varying outcomes in combination with ciprofloxacin, penicillin and ampicillin. SAJ-1 also acted synergistically with ampicillin against S. aureus, while SB-11 showed synergism with ciprofloxacin against both pathogens. Moreover, SAJ-1 and SAJ-2 also inhibited staphyloxanthin production in S. aureus and MRSA and induced postantibiotic effects against both pathogens. It can be inferred that SAJ-1, SAJ-2 and SB-11 may act as potential chemical entities for the development of antibacterial substances. The study revealed that SAJ-1 and SAJ-2 are the most suitable sclareol analogues for further studies towards the development of antibacterial substances. SAJ-1, SAJ-2 and SB-11 show promising antibacterial properties against Staphylococcus aureus. Efforts should be made and more research should be done utilizing in vivo models to determine their efficacy as antibiotics.

Influence of elongation and desaturation on chemosensory properties in acrylates and their corresponding 1-alken-3-ones

Acrylates as well as 1-alken-3-ones are both known to be odour active substances but are generally identified in different materials. Nonetheless, butyl acrylate and 1-octen-3-one were both found to elicit a similar mushroom-like odour in previous studies. This led to the question of whether acrylates and enones with the same overall chain length generally elicited similar odours and whether they had similar odour thresholds. Overall, most of the investigated substances showed a mushroom-like, geranium-like or fruity odour. In contrast, short chained substances elicited garlic-like, lighter gas-like or glue-like, odour qualities, suggesting a correlation between the odour quality and the overall chain length. The results showed that only between the analogue structures butyl acrylate and 1-octen-3-one as well as hexyl acrylate and 1-decen-3-one could similar odour qualities be observed. All investigated substances showed low odour threshold values in air between 0.0032 ng/lair (1-hexen-3-one) and 55 ng/lair (1-dodecen-3-one). Overall, 1-alken-3-ones revealed a higher dependency on the chain length when compared to their respective acrylates. The introduction of a second terminal double bond led to a decrease of OT values in case of the acrylates and to an increase in case of the ketones that neither contained a second terminal double bond nor a double bond located close to the carbonyl group. Despite their structural similarities, the results suggest that both substance classes are perceived in a different manner and are therefore likely to be recognized by different types of receptors or are related to different activation patterns in multi-receptor stimulation processes.Graphical abstract

Iodine-Mediated Alkoxyselenylation of Alkenes and Dienes with Elemental Selenium

A one-pot synthesis of linear and cyclic β-alkoxyselenides is developed through the iodine-mediated three-component reaction of elemental selenium with alkenes (dienes) and alcohols. Selenylation of 1,5-hexadiene gives 2,5-di(methoxymethyl)tetrahydroselenophene and 2-methoxy-6-(methoxymethyl)tetrahydro-2H-selenopyran via the 5-exo-trig and 6-endo-trig cyclization. 1,7-Octadiene affords only linear 1:2 adduct with two terminal double bonds. 1,5-Cyclooctadiene results in one diastereomer of 2,6-dialkoxy-9-selenabicyclo [3.3.1]nonanes via 6-exo-trig cyclization. With 1,3-diethenyl-1,1,3,3-tetramethyldisiloxane, the first ring-substituted representative of a very rare class of heterocycles, 1,4,2,6-oxaselenadisilinanes, was obtained at a high yield.

Photocatalytic Approaches for Sustainable Olefin Transfer Hydrogenation and Semihydrogenation of Alkynes Using Natural Sunlight

A sustainable, solar energy-driven method for olefin hydrogenation and semihydrogenation of alkynes is presented. The approach uses a Pd nanoparticle-decorated semiconductor heterojunction photocatalyst that drives hydrogenation using renewable ethanol and sunlight for energy. The catalyst hydrogenates both terminal and internal double bonds, including activated and unactivated species, and preferentially hydrogenates alkynes over alkenes. This system represents a platform for transitioning critical catalytic processes toward sustainable approaches.

Photoredox Hydroxy-arylation of the Terminal Double Bond of N-Substituted 3-Methyleneisoindolin-1-ones in Visible Light.

Mild and efficient ruthenium-catalyzed hydroxy-arylation of the terminal double bond of N-substituted 3-methyleneisoindolin-1-ones is described. The reaction takes place with aryl diazonium salt as the arylating reagent and water as the hydroxyl source in visible light at ambient temperature. The strategy entails vicinal difunctionalization of alkene and enables construction of 3-benzyl-3-hydroxyisoindolin-1-one heterocyclic scaffolds in moderate to good yields. C-C and C-O bonds are formed in one pot without any external additive and oxidant through an in situ generation of a carbocation intermediate in green light.

Valorization of palm oil via cross-metathesis reaction using 1-octene

The use of palm oil-derived polyol in polyurethane manufacturing is restricted owing to its poor hydroxyl value, which results in a suboptimal polyurethane network. Palm oil could be first chemically modified by cross metathesis (CM) into olefin and ester products with terminal double bonds prior to converting it to the polyols with optimum hydroxyl value. Due to the catalyst degradation and the unwanted self-metathesis reaction, the plant oil CM employing ethylene has been limited by its poor selectivity and low yield. The goal of present research is to investigate the palm oil CM using 1-octene from the aspects of parametric and kinetic analysis. The use of 1-octene was hypothesized to prevent the formation of undesired catalytic intermediates and hence allowing the ruthenium-based Hoveyda Grubbs second generation catalyst (2nd HGC) to maintain its activity and stability. Adopting one factorial at time (OFAT) in a batch system, the effect of different parameters on cross-metathesis of palm oil was examined. The variation in reaction time, temperature, reactant molar ratio of 1-octene to triolein (MOC/TR), and catalyst loadings were correlated to triolein conversion, yield, and selectivity of 1-decene. The products such as 1-decene and glyceryl tri-9-decenoate were quantified using Gas Chromatography-Mass Spectrometry (GC-MS). The maximum triolein conversion and 1-decene yield, 97.78% and 293.36% respectively, were obtained when the cross metathesis of palm oil using 1-octene occurred at 343 K for 2 h with MOC/TR of 8 and catalyst loading of 5 ppm. After three consecutive catalytic tests carried out at best operating condition, the insignificant decline in the reaction performance evidenced that the 2nd HGC catalyst remained active and stable. It was also found that the power-law model well predicted the concentration profile of the cross-metathesis of palm oil using 1-octene, estimating activation energy of 22583 J/mol. This study developed a new technically feasible process for adding value to palm oil, by enabling the use of palm oil as a feedstock for the production of polyol.

PH/Redox/Lysozyme-Sensitive Hybrid Nanocarriers With Transformable Size for Multistage Drug Delivery.

The majority of current nanocarriers in cancer treatment fail to deliver encapsulated cargos to their final targets at therapeutic levels, which decreases the ultimate efficacy. In this work, a novel core–shell nanocarrier with a biodegradable property was synthesized for efficient drug release and subcellular organelle delivery. Initially, silver nanoparticles (AgNPs) were grafted with terminal double bonds originating from N, N′-bisacrylamide cystamine (BAC). Then, the outer coatings consisting of chitosan (CTS) and polyvinyl alcohol (PVA) were deposited on the surface of modified AgNPs using an emulsion method. To improve the stability, disulfide-containing BAC was simultaneously reintroduced to cross-link CTS. The as-prepared nanoparticles (CAB) possessed the desired colloidal stability and exhibited a high drug loading efficiency of cationic anticancer agent doxorubicin (DOX). Furthermore, CAB was tailored to transform their size into ultrasmall nanovehicles responding to weak acidity, high glutathione (GSH) levels, and overexpressed enzymes. The process of transformation was accompanied by sufficient DOX release from CAB. Due to the triple sensitivity, CAB enabled DOX to accumulate in the nucleus, leading to a great effect against malignant cells. In vivo assays demonstrated CAB loading DOX held excellent biosafety and superior antitumor capacity. Incorporating all the benefits, this proposed nanoplatform may provide valuable strategies for efficient drug delivery.

Improved melt strength and processability of impact copolymer polypropylene by introducing long‐chain branching via reactive extrusion with “ene” functionalized dendrimer

AbstractA generation two dendrimer (G2) having eight terminal double bonds has been prepared via esterification reaction from a dendritic precursor having eight hydroxyl end groups (G1). The reactive extrusion of impact co‐polymer polypropylene (ICP) with G1 resulted in improved processability while leading to enhanced melt strength in the case of linear low‐density polyethylene (LLDPE). G2 being an extension of G1, was melt grafted on ICP using a radical initiator to introduce long‐chain branching in the polymer backbone. The prepared samples were analyzed for their molecular weight distribution, thermal, rheological properties, and mechanical properties. Thermogravimetric analysis (TGA) and differential scanning calorimetric (DSC) analysis showed higher thermal stability and slightly higher crystallization temperature with grafting of G2 on ICP. The rheological analysis through melt flow index measurements and parallel plate rheometer indicated higher processability, melt strength, complex viscosity, and zero‐shear viscosity for ICP grafted with an optimized amount of G2. The presence of long‐chain branching was confirmed with an increase in activation energy for ICP modified with G2 as compared to neat ICP. Modified ICP samples retained their bulk mechanical properties as neat ICP.

Modeling of the Branching Point Distribution During the Polymerization of N‐Vinylpyrrolidone

AbstractTo gain insights into the microstructure of polyvinylpyrrolidone (PVP), a detailed reaction mechanism is developed, which characterizes the polymer along the property coordinate chain length, terminal double bonds (TDB), and branching points. For practical purposes, calculations with three property coordinates are unfeasible, and model reduction is needed. Here, a reduced model with only one single property coordinate without significant loss of accuracy is derived. In the first step, the coordinate TDBs are reduced by a linear relationship between TDBs and chain length. As the parameters of this relation are state dependent, they are dynamically adjusted from a parallel calculated 0D model. In a second step, the pseudodistribution approach is used to reduce the 2D distribution to chain length as the only property coordinate and calculate moments of branching points as a function of chain length. A 2D class model is set up for validation. To demonstrate the benefits of the model, the chain length distribution and moments of branching points are calculated for different average residence times and monomer concentrations in a stirred tank reactor. In a future publication, the model will be validated by experimental data in terms of chain length distribution and branching points.

Transition-Metal-Free Regioselective Intermolecular Hydroamination of Conjugated 1,3-Dienes with Heterocyclic Amines.

The unique property of hexafluoroisopropanol (HFIP) enables the regioselective hydroamination of 1,3-dienes with nitrogen heterocycles in a Markovnikov manner in the presence of catalytic Brønsted acid. This transition-metal-free intermolecular hydroamination protocol is achieved under mild reaction conditions. The aggregation by HFIP and Brønsted acid helps to activate the terminal double bond regioselectively. Following the protonation of diene, the C-N bond formation is accomplished upon the involvement of heterocyclic amines.

Tunable Protein Adsorption by Zwitterionic Spherical Poly(CBAA) Brushes Prepared via Photoemulsion Polymerization

Zwitterionic polymer brushes are well-known as excellent hydrophilic and antifouling materials. However, they demonstrate a certain degree of adsorption for proteins and other substances in practical application, and little research has been conducted into this area. Herein, a facile and efficient approach was employed to prepare zwitterionic spherical polymer brushes, polystyrene-poly(2-carboxy-N,N-dimethyl-N-(3′-acrylamidopropyl) ethanaminium inner salt) brushes (PS–PCBAA brushes). Specifically, the preparation process consists of three steps. First, polystyrene (PS) nanospheres were synthesized via conventional emulsion polymerization, and then photoinitiator with terminal double bond was immobilized on the surface of the PS core by copolymerizing with styrene (PS@HMEM). Finally, zwitterionic polymer chains (PCBAA) were grafted onto the surface of PS@HMEM via photoemulsion polymerization. The hydrodynamic diameter and size distribution, morphology, and chemical composition of PS–PCBAA brushes were characterized. The interaction between PS–PCBAA brushes and proteins was investigated by turbidity and size change. The interaction between brushes and proteins was mainly affected by two factors: the electrostatic interaction between polymer chains and proteins, and the transition of zwitterionic polymers from a fouling polymer to a nonfouling polymer. This work provided a simple and environmentally friendly method for constructing zwitterionic materials that showed potential application in the controllable adsorption and desorption of proteins.

Elongation and branching of α-olefins by two ethylene molecules.

α-Olefins are important starting materials for the production of plastics, pharmaceuticals, and fine and bulk chemicals. However, the selective synthesis of α-olefins from ethylene, a highly abundant and inexpensive feedstock, is restricted, and thus a broadly applicable selective α-olefin synthesis using ethylene is highly desirable. Here, we report the catalytic reaction of an α-olefin with two ethylene molecules. The first ethylene molecule forms a 4-ethyl branch and the second a new terminal carbon-carbon double bond (C2 elongation). The key to this reaction is the development of a highly active and stable molecular titanium catalyst that undergoes extremely fast β-hydride elimination and transfer.

Effect of Atmospheric Pressure Plasma in Inert Gases on Orthopedic Ultra-High Molecular Weight Polyethylene

In this work, studies have been conducted on the treatment of ultrahigh molecular weight polyethylene (UHMWPE), which is one of the structural materials used in the endoprostheses, with atmospheric pressure plasma in high-purity argon and helium. For this purpose, an installation consisting of a high-voltage pulsed generator, voltage and current measuring devices and a reaction quartz chamber with electrodes, in which UHMWPE samples were placed, was developed and constructed. It is shown that processing under certain conditions in Ar plasma and He at atmospheric pressure leads to the appearance of terminal double bonds in the structure of the processed polyethylene, as evidenced by the appearance of a peak of 880 cm-1, in the attenuated total reflection IR spectrum. This peak is observed both for samples treated in helium and argon plasma. The formation of such bonds is a consequence of the generation of active radicals in the UHMWPE surface layer under plasma treatment, which, during recombination, also form intermolecular crosslinking, thereby increasing the strength characteristics of the material as a whole. The modification of the surface of the treated samples begins within the first minute of processing and reaches its peak values 10-20 minutes after treatment in plasma.

Synthesis of (±)-Baclofen using Wittig Olefination–Claisen Rearrangement

Baclofen, a lipophilic derivative of GABA (gamma-Aminobutyric acid), which acts as an inhibitory neurotransmitter in CNS (central nervous system) was synthesized by Witting olefination-Claisen rearrangement protocol. 4-Chlorobenzaldehyde was subjected to Wittig reaction with ((allyloxy)methylene)triphenyl-phosphane to give 1-(2-(allyloxy)vinyl)-4-chlorobenzene which on heating under reflux condition in toluene underwent Claisen rearrangement to give 2-(4-chlorophenyl)pent-4-enal. Aldehyde was reduced to corresponding alcohol 2-(4-chlorophenyl)pent-4-en-1-ol as an important precursor which can be used for the synthesis of Baclofen and different GABA derivatives. Further tosylation, formation-reduction of azide group and oxidative ozonolysis of terminal double bond yields 4-amino-3-(4-chlorophenyl)butanoic acid in excellent yield. Therefore, an efficient method was developed for the synthesis of (±)-Baclofen in a simple seven step procedure.

Antileishmanial Effects of Acetylene Acetogenins from Seeds of Porcelia macrocarpa (Warm.) R.E. Fries (Annonaceae) and Semisynthetic Derivatives.

As part of our continuous studies involving the prospection of natural products from Brazilian flora aiming at the discovery of prototypes for the development of new antiparasitic drugs, the present study describes the isolation of two natural acetylene acetogenins, (2S,3R,4R)-3-hydroxy-4-methyl-2-(n-eicos-11′-yn-19′-enyl)butanolide (1) and (2S,3R,4R)-3-hydroxy-4-methyl-2-(n-eicos-11′-ynyl)butanolide (2), from the seeds of Porcelia macrocarpa (Warm.) R.E. Fries (Annonaceae). Using an ex-vivo assay, compound 1 showed an IC50 value of 29.9 μM against the intracellular amastigote forms of Leishmania (L.) infantum, whereas compound 2 was inactive. These results suggested that the terminal double bond plays an important role in the activity. This effect was also observed for the semisynthetic acetylated (1a and 2a) and eliminated (1b and 2b) derivatives, since only compounds containing a double bond at C-19 displayed activity, resulting in IC50 values of 43.3 μM (1a) and 23.1 μM (1b). In order to evaluate the effect of the triple bond in the antileishmanial potential, the mixture of compounds 1 + 2 was subjected to catalytic hydrogenation to afford a compound 3 containing a saturated side chain. The antiparasitic assays performed with compound 3, acetylated (3a), and eliminated (3b) derivatives confirmed the lack of activity. Furthermore, an in-silico study using the SwissADME online platform was performed to bioactive compounds 1, 1a, and 1b in order to investigate their physicochemical parameters, pharmacokinetics, and drug-likeness. Despite the reduced effect against amastigote forms of the parasite to the purified compounds, different mixtures of compounds 1 + 2, 1a + 2a, and 1b + 2b were prepared and exhibited IC50 values ranging from 7.9 to 38.4 μM, with no toxicity for NCTC mammalian cells (CC50 > 200 μM). Selectivity indexes to these mixtures ranged from >5.2 to >25.3. The obtained results indicate that seeds of Porcelia macrocarpa are a promising source of interesting prototypes for further modifications aiming at the discovery of new antileishmanial drugs.