Luis Chacón-García

• Doctor of Pharmacy
• Universidad Michoacana de San Nicolás de Hidalgo

A series of 1,5-disubstituted tetrazole-indole hybrids were synthesized via a high-order multicomponent reaction consisting of an Ugi-azide/Pd/Cu-catalyzed hetero-annulation cascade sequence. This operationally simple one-pot protocol allowed high bond-forming efficiency and creating six new bonds (two CC , three C-N, and one N-N). Additionally, th...

A rapid and efficient protocol for synthesizing two series of benzofuran-based hybrid polyheterocycles is presented: benzofuran-isatin and benzofuran N-acylhydrazones, and evaluation of their antibacterial activity both in vitro and in silico against two strains of Pseudomonas aeruginosa, PAO1 and PA14 were determined. Six of the tested compounds w...

A molecular switch based on the metastable radical anion derived from a substituted heteroaryl quinone is described. Pyrrolyl quinone thiocyanate (PQ 9) showed an interaction with the fluoride anion that was visible to the naked eye and quantified by UV/vis and 1H and 13 C NMR. The metastable quinoid species formed by the interaction with F⁻ (“ON”...

A synthetic strategy for obtaining a new series of 1,5-disubstituted tetrazole-benzofuran hybrid systems via a one-pot five-component reaction is described. This process involves a Ugi-azide multicomponent reaction coupled to an...

Background A family of 4H-benzo[d][1,3]oxazines were obtained from a group of N-(2-alkynyl)aryl benzamides precursors via gold(I) catalysed chemoselective 6-exo-dig C-O cyclization. Method The precursors and oxazines obtained were studied in breast cancer cell lines MCF-7, CAMA-1, HCC1954 and SKBR-3 with differential biological activity showing va...

Nitrogen‐containing drugs represent one of the worldwide most extensive sources of treatments for different diseases. Indomethacin as example, is one of the most important non‐steroidal anti‐inflammatories (NSAID) indol‐containing drug. Its relevance has been demonstrated the last 50 years with excellent pharmacological results. Its efficacy as an...

Strategies for introducing halogens and other inorganic groups in aromatic systems, usually involve non‐general and strong oxidative protocols which resulted in poor functional group compatibility. Iodine(III) reagents have emerged as an excellent alternative for the aromatic inorganic functionalization due to their low toxicity and strong oxidativ...

The anticarcinogenic potential of a series of 1,5-disubstituted tetrazole-1,2,3-triazole hybrids (T-THs) was evaluated in the breast cancer (BC)-derived cell lines MCF-7 (ER+, PR+, and HER2−), CAMA-1 (ER+, PR+/−, and HER2−), SKBR-3 (ER+, PR+, and HER2+), and HCC1954 (ER+, PR+, and HER2+). The T-THs 7f, 7l, and 7g inhibited the proliferation of MCF-...

An almost underexplored field within the natural products area is the synthesis of pseudo‐natural product libraries by employing isocyanide‐based multicomponent reactions as powerful synthetic tools and natural products or their functionalized derivatives as starting reagents. In this work, a novel synthetic strategy behind the late‐stage functiona...

The high population growth worldwide causes a high demand for food with an increase in the use of different agrochemicals, with pesticides and herbicides being the primary pollutants of anthropogenic origin in the environment. One of the critical aims of ecotoxicology is the evaluation of toxic effects of mixtures of chemical substances that can ha...

A facile and rapid synthesis of a family of new hybrid system 1,5-disusbtituted 1H-tetrazol-5yl 4,5-dihydro [1,2,3]triazolo[1,5-a]pyrazin-6-ones in moderate yields is described. Compounds were synthetized by a high-order multicomponent reaction (MCR) to give N-acylated 1,5-disubstituted tetrazoles followed, without chromatographic purification, by...

The first iodine(III)‐mediated para‐selective iodination protocol for free anilines as well as the mechanistic elucidation of the reaction pathway is described. The developed method proceeded under clean, non‐toxic, efficient, and in general mild reaction conditions. To the best of our knowledge this report describes for the first time a procedure...

A semisynthesis of 6β-acetoxyvouacapane-1,5-disusbtituted tetrazoles derivatives from the leaves of Caesalpinia platyloba by using the Ugi-azide multicomponent reaction as a key step reaction is described. To our knowledge, this is the first report where a non-natural product such as 1,5-disusbtituted tetrazole has been linked to a natural product...

A novel bis‐heterocyclic system encompassing the 1,2‐dihydro‐3H‐pyrrolo[3,4‐b]indolizin‐3‐one and 1,5‐disubstituted tetrazole moieties was designed, synthesized, and evaluated as a Copper (II) recognizing agent. This was achieved by exploiting the optical characteristics of indolizine and the copper recognizing activity of tetrazoles. For the prepa...

The metals present in freshwater have a toxic profile with bioaccumulation and are biomagnified along the aquatic food chain. The metals induce high sensitivity in most aquatic organisms, while others, such as some microalgae species, evolve towards resistance. Therefore, this research predicted through the Combination Index method the binary inter...

Zygomycetes are ubiquitous saprophytes in natural environments which transform organic matter. Some zygomycetes of gender Mucor have attracted interest in health sector. Due to its ability as opportunistic microorganisms infecting immuno-compromised people and to the few available pharmacological treatments, the mucormycosis is receiving worldwide...

The first gold(I)-catalyzed cycloisomerization procedure applied to the synthesis of substituted 4H-benzo[d][1,3]oxazines has been developed starting from N-(2-alkynyl)aryl benzamides. The chemoselective oxygen cyclization via the 6-exo-dig pathway yielded the observed heterocycles in modest to good chemical yields under very mild reaction conditio...

Background Tuberculosis is an infectious disease caused by the bacillus Mycobacterium tuberculosis. Compounds including a sulfur-containing scaffold have been shown to be key scaffolds in various antituberculosis agents. Interestingly, the 3-hydroxy-3-phenyl-prop-2-enedithioic acids 11a-j have, to the best of our knowledge, not been previously desc...

A high-order multicomponent reaction involving a six-component reaction to obtain the novel linked 1,5-disubstituted tetrazole-1,2,3-triazole hybrids in low to moderate yield is described. This one-pot reaction is carried out under a cascade process consisting of three sequential reactions: Ugi-azide, bimolecular nucleophilic substitution (SN2), an...

A synthetic novel strategy involving a pseudo three component reaction to obtain 1,6-dihydroazaazulenes derivates via cyclization of pyrrolyl-enones by a novel pseudo three-component reaction was developed. This reaction is carried out under mild conditions from simple starting materials and catalyzed with ionic liquid. Notably, 3 new C-C bonds are...

Perezone is a naturally occurring hydroxyquinone that has been deeply studied from different chemical aspects, such as therapeutics, electrochemistry, physical–chemical properties, or synthetic approaches that turn it an attractive template for new semisynthetic derivatives with a wide range of purposes. Herein, we describe a facile synthetic pathw...

Deep eutectic solvents (DESs) have been considered “the organic reaction medium of the century” because they can be used as solvents and active catalysts in chemical reactions. However, experimental and theoretical studies are still needed to provide information on the structures of DESs, the kinetics and thermodynamics properties, the interactions...

A docking study of a set of several 1,5-disubstituted tetrazoles compounds has been performed to predict the poses of some potential inhibitors of the Abelson tyrosine-protein kinase and the mutated Abelson tyrosine-protein kinase T315I. The study was conducted through Lamarckian genetic algorithms in Autodock4 package. Bayesian calculations were p...

A novel synthetic strategy to obtain acylhydrazone-oxazole hybrids in three-step reactions in moderate to good yields is reported. The key step reaction consists in a Van Leusen reaction using a bifunctional component of both an aldehyde and a functional group. The target molecules were evaluated via in-silico by molecular docking with the main pro...

A two-step synthesis of the novel 5,8-dimethyl-7,8-dihydro-5,8-ethanoindolizine-6,9(5H)-dione from 2,3-dimethyl-1,4-benzoquinone is described. The key step of the synthesis of this unusual fused tricyclic system is the intramolecular regiospecific aza-Michael addition of a pyrrole to an activated double bond by reaction with tetrabutylammonium fluo...

In regard to the actual public health global emergency and, based on the state of the art about the ways to inhibit the SARS-CoV-2 treating the COVID19, a family of 1,5-disubstituted tetrazole-1,2,3-triazoles, previously synthesized, have been evaluated through in silico assays against the main protease of the mentioned virus (CoV-2-M Pro ). The re...

Six 1,3-oxazoles were synthetized in moderate to good yields by Van Leusen reaction in a pressure reactor. The methodology allowed to decrease the reaction times reported in the literature from hours to 20 min. In addition, preliminary qualitative recognition of cations with some synthetized oxazoles such as Hg2+, Ni2+, Zn2+, Ag+, Cu2+, Pb2+ was do...

An eco-friendly methodology for the synthesis of novel Schiff base analogs of Raltegravir, an Integrase inhibitor drug is described. Pertinence of these imine derivatives is related to Medicinal Chemistry to develop new anti-VIH compounds. To our knowledge, this is the first report of the synthesis of Schiff base using a Raltegravir drug fragment a...

Environmental factors such as temperature and light are the most determinants in the photosynthetic productivity in microalgae. However, under extreme of these conditions, certain resistant microalgae strains possess additional abilities such as growth in the presence of high concentrations of metals and some can improve in combinations of more tha...

An efficient transition-metal-based heterogeneous catalyst free procedure for obtaining the oxidative amidation of benzaldehyde using quinones as oxidizing agents in low molar proportions is described here. Pyrrolylquinones (PQ) proved to be more suitable than DDQ and 2,5-dimethylbenzoquinone to conduct the oxidation process. Although the solvent i...

A new synthetic strategy to obtain new linked 1,5-disubstituted tetrazole-1,2,3-triazoles via the Ugi-azide reaction followed by a copper -catalyzed alkyne-azide reaction (CuAAC) was developed. This strategy used solvent-free conditions for the Ugi-azide reaction. This two-step strategy affords the products in moderate to good yields. To the best o...

Quinolones are a family of antimicrobial agents that have been used in antibacterial and anticancer chemotherapy. Fluoroquinolone targets DNA gyrase and topoisomerase IV enzymes affecting several cellular processes, like cell death and proliferation; the best way to act is in the form of carboxylic acid or, recently, as quinolone-metal complex. In...

Molecular modeling applies several computational chemistry tools as molecular docking; this later has been useful in medicinal chemistry for prediction of interactions between small ligands and biological targets measuring angles, enthalpy and other physical-chemical properties involved in the supramolecular entities. In this chapter, we present mo...

A docking studies of a set of several 1,5-disubstituted tetrazoles (1,5-DS-T) compounds to find potential inhibitors of the Abelson tyrosine-protein kinase (ABL kinase) and the mutated ABL kinase T315I were conducted by using Lamarckian genetic algorithms as search algorithms in Autodock4. Bayesian calculations were performed, and specificity (Sp)...

DNA nanotechnology has recently emerged as a powerful discipline with diverse applications. However, studies focused on the combination of DNA and metal nanoparticles for catalyst design are scanty. We have prepared a catalyst composed of palladium nanoparticles supported on DNA which has been characterised by TEM, SEM, EDX, UV, FTIR and XPS. The c...

Most of the quinolone antibacterial research has been focused on the functionality at C-7 position where the nature of substituents is responsible for antibacterial spectrum, potency, bioavailability, and side effects of the quinolones. Then, a 7-amino-fluoroquinolone could be the starting point of a wide variety of potentially useful compounds lik...

A one-step synthesis of symmetric biaryls is reported under very mild conditions via the homocoupling reaction of substituted arylboronic acids using an air- and moisture-stable 4-aminoantipyrine-Pd(II) complex as catalyst. The reaction is conducted at a low catalyst loading of 0.1 mol% at room temperature in methanol in the presence of K2CO3 as th...

A simple and efficient catalytic system based on a Pd complex of 4-aminoantipyrine, 4-AAP–Pd(II), was found to be highly active for Suzuki–Miyaura cross-coupling of aryl iodides and bromides with phenylboronic acids under mild reaction conditions. Good to excellent product yields from the cross-coupling reaction can be achieved when the reaction is...

The synthesis of the novel 1-adamantyl-(N-meso-dipyrrolylmethylene)-carboxamide is described, providing a three-step, two-pot reaction. Docking studies with 11-b-HSD1 revealed favorable binding interactions with the enzyme.

The aim of this work was to characterize the mucilage extracted from six species of O puntia . The species studied were as follows: O . atropes , O . tomentosa , O . hyptiacantha , O . streptacantha y O . joconostle and O . ficus‐indica . The first step was to find the best extraction conditions to obtain an unaltered chemical structure of mucilage...

The aim of this work was to characterize the mucilage extracted from six species of O puntia . The species studied were as follows: O . atropes , O . tomentosa , O . hyptiacantha , O . streptacantha y O . joconostle and O . ficus‐indica . The first step was to find the best extraction conditions to obtain an unaltered chemical structure of mucilage...

A mild and efficient method for the ipso-hydroxylation of arylboronic acids to the corresponding phenols was developed using (NH4)2S2O8 as an oxidizing agent.The reactions were performed under metal-, ligand-, and base-free conditions.

A mild and efficient method for the ipso-hydroxylation of arylboronic acids to the corresponding phenols was developed using (NH4)2S2O8 as an oxidizing agent. The reactions were performed under metal-, ligand-, and base-free conditions.1. IntroductionPhenol and its derivatives are present in numerous natural products (e.g., aromatic steroids, canna...

The synthesis of a novel 2-dipyrrolyl-2,5-dimethyl-p-benzoquinone is described, and its interactions with fluoride were characterized. An unprecedented interaction between fluoride anions and the quinone ring was observed.

The condensation of a pyrrole and acetone or cyclohexanone that gives the corresponding tetrameric calix[4]pyrrole, catalyzed by HAuCl 4 or Bi(NO 3) 3 , was tuned to yield the pentameric macrocycle calix[5]pyrrole as the major product in the presence of the biomolecule DNA obtained from salmon sperm in the reaction mixture. The DNA affected the rat...

We describe the synthesis of the novel 2-(1,5-dimethyl-4-oxo-hexyl)-3-hydroxy-5-methyl-6-pyrrolyl-1,4-benzoquinone 2 from the natural product perezone 1. The anion-guest properties of the new compound were evaluated in the presence of fluoride, chloride, bromide and iodide tetrabutylammonium salts using 1H NMR titration techniques in deuterated dic...

Supplementary material is available on the publishers Web site along with the published article.

One of the more elusive classes of macrocycles includes the calix[5]pyrroles, which can be obtained from pyrrole and acetone in the presence of low concentrations of Bi(NO3)(3)-5H(2)O. An isotopic labeling experiment aided the proposal of a mechanism to explain the formation of calix[5]pyrrole at low acid concentrations and the exclusive formation...

One of the more elusive classes of macrocycles includes the calix[5]pyrroles, which can be obtained from pyrrole and acetone in the presence of low concentrations of Bi(NO 3) 3-5H 2 O. An isotopic labeling experiment aided the proposal of a mechanism to explain the formation of calix[5]pyrrole at low acid concentrations and the exclusive formation...

We describe the first synthesis of the novel meso-pentaspirocyclohexyl calix[5]pyrrole 2b. Anion–guest properties of the new compound were evaluated with respect to fluoride, chloride, and bromide tetrabutylammonium salts by 1H NMR titration techniques in deuterated dichloromethane at 22°C by following the induced shifts in the NH resonances upon c...

In this chapter thermal relaxation properties of chitosan neutralized and nonneutralized films will be reported as a function of water content using dynamical mechanical analysis and dielectric spectroscopy in the temperature range from 20 to 250°C. Three relaxation processes have been observed in different temperature and frequencies ranges. For t...

This book presents data on thermal relaxation properties of chitosan neutralized and non-neutralized films as a function of water content using dynamical mechanical analysis and dielectric spectroscopy in the temperature range from 20 to 250°C. Three relaxation processes have been observed in different temperature and frequency ranges. For the firs...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The first direct synthesis of beta-unsubstituted meso-decamethylcalix[5]pyrrole from pyrrole and acetone, with moderate yield, is described. The results showed that a bismuth salt was necessary to obtain calix[5]pyrrole, with the best results obtained using Bi(NO(3))(3).

The first synthesis of 4´-X-phenylverbenene (X = F and Cl) via reaction of myrtenal with 4-X phenylmagne-sium bromide and Bi(NO 3) 3 is described. Verbenene is formed due to the electron-withdrawing effect of the 4-electronegative group, either fluorine or a Cl–Bi complex.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

An efficient synthesis of calix[4]pyrroles that uses soft conditions and bismuth salts, which are relatively nontoxic, readily available and inexpensive, is described.

The discovery of new compounds with antitumoral activity has become one of the most important goals in medicinal chemistry. One interesting group of chemotherapeutic agents used in cancer therapy comprises molecules that interact with DNA. Research in this area has revealed a range of DNA recognizing molecules that act as antitumoral agents, includ...

Treatment of hydroxythiol 4 with α,α-diethoxyacetophenone at room temperature yielded a mixture of epimeric S,O-acetals 6 and 7 (1:4, 92% yield), which were efficiently separated by flash chromatography. The OTBS derivatives 8 and 9 were treated with several Grignard reagents to afford carbinols 10 and 13 respectively (85–99% yield, >95% dr). After...

For Abstract see ChemInform Abstract in Full Text.

The enantioselective synthesis of several 1-phenyl-1,2-ethanodiol derivatives using 2-benzoyl-1,3-oxathiane 1 as a chiral auxiliary is described. Nucleophilic additions of Grignard reagents, methyl lithium and LS-Selectride on benzoyloxathiane 1 proceeded in >95% diastereomeric ratio (dr) affording the corresponding tertiary carbinols, which were s...

A series of bisalkanoic anilides and bisbenzoyl diamines were synthesized with the aim of elucidating the relationship between molecular structure and cytotoxic activity. Twenty-one derivatives were synthesized and tested on three tumoral cell lines. No apparent relationship was observed between electronic effects and cytotoxic activity, but it was...

Se describe el análisis conformacional del compuesto nombrado en el título. Los resultados muestran que la conformación preferida no es la esperada a partir de consideraciones estéricas. El cambio de disolvente de CDCl3 a benceno-d6 no tuvo efecto significativo en el equilibrio.

The synthesis of pyrrolo[2,3-e]indole derivatives with the structural characteristics of DNA bis- and mono-intercalators are described. A dihydro benzoindol analogue was also synthesised to elucidate the major structural requirements for cytotoxic activity. A biological evaluation of the test compounds was carried out in six different tumoral cell...

The synthesis of novel oxathiane 3 and its acetyl derivative 12, from commercially available (−)-myrtenal 4, is described. The addition of several nucleophilic reagents to 12 furnished the corresponding tertiary carbinols in highly diastereomeric excess. The hydrolysis of 11a, b yielded the expected α-hydroxycarbonyl compounds in excellent enantiom...

The one- and two-step syntheses of N,N'-(dinitrophenyl)alkanediamides and N,N'-(diaminophenyl)alkanediamides from 4-nitroaniline were carried out. These compounds were subjected to cytotoxic evaluation against different tumoural cell lines. A QSAR analysis for the aminated series, introducing a QSAR descriptor (DCL) designed herein for groove binde...

A conformational analysis of the title compound in sol u - tion is described. Results show that the preferred conformation is no t the one expected from steric considerations. Change of the solven t from CDC l 3 to benzene- d 6had no significant effect on the equilibr i - um .