César Solorio

• University of Guanajuato

Maleimide core is a broadly used chemical‐based scaffold for natural and new compounds synthesis. Several of them show anticancer and multidrug resistance (MDR) reversal activity. A new family of twelve 3,4‐substituted N‐benzyl and N‐methyl maleimides were synthesized in a two‐step sequence consisting of bromination and Suzuki cross‐coupling or bro...

Iodine(III) reagents have become a highly relevant tool in organic synthesis due to their great versatility as strong but green oxidants. Several transformations involving cyclizations as well as functionalization of different organic cores have been broadly described and reviewed. Herein, the participation of these reagents in photochemical transf...

Iodine(III) reagents became a highly relevant tool in organic synthesis due to the great versatility as strong but green oxidants. Several transformations involving the cyclizations as well as functionalization of different organic cores have been broadly described and reviewed. Herein a new facet which involves the participation of these reagents...

Multidrug Resistance (MDR) can be considered one of the most frightening adaptation types in bacteria, fungi, protozoa, and eukaryotic cells. It allows the organisms to survive the attack of many drugs used in the daily basis. This forces the development of new and more complex, highly specific drugs to fight diseases. Given the high usage of medic...

The reaction mechanism for the chlorination and bromination of 2-naphthol with PIDA or PIFA and AlX3 (X = Cl, Br), previously reported by our group, was elucidated via quantum chemical calculations using density functional theory. The chlorination mechanism using PIFA and AlCl3 demonstrated a better experimental and theoretical yield compared to us...

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...

The chlorination and bromination reaction mechanisms of 2-naphthol under the previously reported PIDA- or PIFA-AlX 3 (X= Cl, Br) systems by our research group, was elucidated via quantum chemical calculations within the density functional theory. The studied chlorination mechanism using PIFA and AlCl 3 demonstrated better experimental and theoretic...

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...

Multi‐Drug Resistance (MDR) is one of the most frequent problems observed in the course of cancer chemotherapy. Cells under treatment, tend to develop survival mechanisms to drug‐action thus generating drug‐resistance. One of the most important mechanism to get it is the over expression of P‐gp glycoprotein, which acts as an efflux‐pump releasing t...

Metformin is a versatile, biocompatible, and cheap bis‐guanidine used as first response line in the type II diabetes treatment. Since its first human trials (1956) several structural modifications were carried out to increase its activity. However, with this augmented activity, the biological compatibility diminishes, generating serious side effect...

Metformin is the most widely known anti-hyperglycemic, officially acquired by the USA government in 1995 and in 2001 it became the most prescribed treatment for type II diabetes. But how did it become the must-use drug for this disease in such a short period of time? it all started with traditional medicine, by using a plant known as "goat's rue" f...

Dimorphic species of Mucor, which are cosmopolitan fungi belonging to subphylum Mucoromycotina, are metabolically versatile. Some species of Mucor are sources of biotechnological products, such as biodiesel from Mucor circinelloides and expression of heterologous proteins from Mucor lusitanicus. Furthermore, Mucor lusitanicus has been described as...

An efficient iodine(III)‐based protocol for the chlorination and catalytic nitration of N‐tosyl anilines as well as the proposed reaction mechanism is described. The synergistic combination of the commercially available [bis(trifluoroacetoxy)iodo]benzene (PIFA) with AlCl3, or (PhIO)n with Al(NO3)3, allowed the electrophilic introduction of chlorine...

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...

One of the most important (NSAID) non‐steroidal anti‐inflammatory drug‐containing the indol core is represented by the indomethacin. This highly relevant compound has been used for the last 50 years with excellent pharmacological results. Due to its relevant efficacy as an anti‐inflammatory treatment, several syntheses have been developed during th...

Iodine(III) reagents represent nowadays a class of highly relevant oxidants in organic synthesis which possess important properties such as safer, non-toxic, green and easy to handle compounds. These characteristics in several cases, make them important alternatives to the procedures which use hazardous and strong reaction conditions. Based upon th...

Iodine(III) reagents have attracted chemical relvance in organic synthesis by their use as safe, non-toxic, green and easy to handle reagents in different transformations. These characteristics make them important alternatives to procedures involving hazardous and harsh reaction conditions. Their versatility as oxidants has been exploited in the fu...

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...

Since the 1950s, diaryliodonium(III) salts have been demonstrated to participate in various arylation reactions, forming aryl-heteroatom and aryl-carbon bonds. Incorporating the arylation step into sequential transformations would provide access to complex molecules in short steps. This focus review summarizes the double functionalization of carbon...

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...

This study evaluated the inhibitory effect of myristic acid (MA) on models of inflammation and nociception. The in vitro anti-inflammatory activities of MA were assessed on LPS-stimulated macrophages, membrane stabilization assay, and inhibition of protein denaturation, whereas the inhibitory activity of MA on in vivo inflammation was assessed on T...

The initial results on a novel procedure for the synthesis of benzo [b] carbazols via gold (I)-catalyzed tandem cyclization/Migration/cyclization is described. The procedure allowed the access to a highly functionalized benzo [b] carbazols in a one-pot process starting from tertiary anilines. The mechanism of this reaction by using gold (I) catalys...

A series of ten 1,5-disubstituted-1H-tetrazoles (1,5-DS-T) were synthesized via Ugi-azide isocyanide-based multicomponent reactions (IMCR) in low to good yields (30–85%), using propargyl amine or 2-azidobenzaldehyde as a component, and using ultrasound irradiation (USI) as an alternative energy source. 1,5-DS-T are useful heterocyclic moieties, pre...

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...

Ethnopharmacological relevance Asclepias curassavica L. (Apocynaceae) is a perennial shrub used in the folk treatment of parasitism, pain, and inflammation. Aim of the study This work assessed the antiparasitic, anti-inflammatory, antinociceptive, and sedative effects of an ethanol extract from the aerial parts of Asclepias curassavica (ACE). Mat...

Objective This study aims to assess the prevalence of herbal medicine (HM) use and factors influencing HM usage including the identification of the main plants consumed by patients with type 2 diabetes mellitus (T2DM) in central-western Mexico. Design A total of 1862 patients with diabetes were surveyed in public and private hospitals in four stat...

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...

The initial results on a novel procedure for the synthesis of pyrrolo[1,2-a]indoles via gold(I)-catalyzed tandem cyclization/C-H activation/cyclization is described. The procedure allowed access to a highly functionalized pyrrolo[1,2-a]indoles in a one-pot process starting from anilinodiynes. The mechanism of this reaction by using gold(I) catalysi...

The initial results on a novel procedure for the synthesis of benzo[b]carbazols via gold(I)- catalyzed tandem cyclization/Migration/cyclization is described. The procedure allowed the access to a highly functionalized benzo[b]carbazols in a one-pot process starting from tertiary anilines. The mechanism of this reaction by using gold(I) catalysis, i...

A series of three 2,5-Diketopiperazine (DKPs) were synthesized via one-pot process through the post- isocyanide-based multicomponent reactions (IMCR)-transformation strategy. This strategy emphasizes the role of orthogonal bifunctional reagents in the IMCR process to increase their synthetic potential, allowing us accessing a synthetic platform fro...

The chemoselective reaction of the C- followed by the O-centered naphthyl radicals with the more electron-deficient hypervalent bond of the diaryliodonium(III) salts is described. This discovered reactivity constitutes a new activation mode of the diaryliodonium(III) salts which enabled a one-pot doubly arylation of naphthols through the sequential...

Introduction Bidens odorata Cav (Asteraceae) is a medicinal plant employed for the treatment of pain, anxiety, and depression. This study aimed to evaluate some neuropharmacological effects of an ethanol extract of B. odorata (BOE) and assess its antinociceptive interaction with naproxen and paracetamol. Materials and methods The following neuroph...

Iodine(III)-based reagents has been broadly used in oxidative reactions for the structural functionalization with several functional groups. Among the more relevant and useful synthetic transformations using these hypervalent γ ³ -reagents, it can be found the fluorination, chlorination, bromination as well as the iodination protocols. Herein, we p...

The first iodine(III)-based procedure for the benzylic oxidation of different arenes is described by using the (PhIO)n/Al(NO3)3 system under catalytic conditions leading to the formation of the corresponding carbonyl derivatives. The method proceeds under mild, operationally simple, room temperature, short reaction times, and open flask conditions....

Multidrug resistance (MDR) is a great concern worldwide. There is a great need to develop new drugs with the potential to attack target cells that show MDR phenotype. The purpose of this study was to assess the reversing effect of new N-alkyl-3,4-diarylmaleimides on Bacillus subtilis resistant to rhodamine 6G as an indicator of its activity as modu...

An efficient chlorination and bromination of arenes mediated by in situ-formed PhI(X)OAlX 2 (X = -Cl, -Br), which is proposed as a plausible halogenating species, is described. The proposed dual role displayed by AlX 3 , enables the Iodosylbenzene [(PhIO) n ]depolymerization while also acting as the halogen source by transferring the chlorine or br...

Ethnopharmacological relevance: Mexico ranks second in the world for obesity prevalence. In Mexico, obese and overweight subjects commonly seek alternative treatments for weight-loss, including the use of herbal products. Aim of the study: The main objective of this study was to evaluate the prevalence of self-medication with herbal products for we...

A straightforward, concise, and building block-scalable, seven-step total synthesis of the unnatural 3-methylated regioisomer analog of the marine alkaloid kealiiquinone is described. The construction by a regioselective way of the 4-anisyl-3-methylbenzimidazolone core of this analog, as well as the homologation of the aromatic π-system through a 4...

An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a non-toxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled mono-iodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild...

A catalytic, practical and high-yielding procedure for the synthesis of indenes by direct Csp3-H activation under gold(I) catalysis was developed. The scope of the protocol was determined by synthesizing some electron-neutral, electron-poor as well as electron-rich derivatives including the dibenzofurane and carbazole heterocycles. The mechanism of...

A practical, concise and straightforward total synthesis of kealiiquinone 1, a naphtho[2,3-d]imidazole alkaloid obtained from the Micronesian marine sponge Leucetta sp. was accomplished. The squaric acid chemistry to construct the 1,4-quinoid ring and the regioselective N-methylation through a benzo[c][1,2,5]selenadiazolium heterocycle are the key...

The modular protecting-group-free total synthesis of 3-methylkealiiquinone, an analogue of the marine alkaloid kealiiquinone, was accomplished in seven steps. A regioselectively-constructed functionalized arylbenzimidazolone moiety and dimethyl squarate were used as the only two building blocks. A thermal ring expansion via 6π-conrotatory ring clos...

A practical electrophilic bromination procedure for phenols and phenol–ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(III)-based brominating reagent PhIOAcBr is operation...

Self-medication during pregnancy represents a serious threat for mother and child health. The objective of this study was to evaluate the prevalence and the factors associated with self-medication among Mexican women living in the central region of Mexico. This is a descriptive interview-study of 1798 pregnant women or women who were pregnant no mo...

A new and in situ formed reagent generated by mixing PIFA/AlCl3 was introduced in the organic synthesis for the direct and highly regioselective ortho-chlorination of phenols and phenol-ethers. An efficient electrophilic chlorination for these electron rich arenes as well as the starting scope of the reaction herein are described. An easy, practica...

A series of new 3,4-diarylmaleimides were synthesized in an optimized and efficient lineal sequence of three steps, starting from commercial maleimide. The biological evaluation of these compounds as enhancers (activity modulators) in the co-administration with doxorubicin treatment in breast cancer cells directly obtained from a patient, were essa...

Resumen La formación del enlace Csp2-O vía oxidación directa del enlace Csp2-H de compuestos ricos en electrones como los naftoles, es un proceso que generalmente necesita condiciones drásticas de reacción como temperatura y presiones elevadas. Además oxidantes fuertes como H2O2, reactivos de yodo hipervalente (λ3 o λ5), metales de transición costo...

Ethnopharmacological relevance: Bidens odorata Cav (Asteraceae)is used for the empirical treatment of inflammation and pain. Aim of the study: This work evaluatedthein vitro and in vivo toxicity, antioxidant activity, as well as the anti-inflammatory and antinociceptive effects of an ethanol extract from Bidens odorata leaves (BOE). Materials a...

La halogenación de arilfenoles describe una síntesis para obtener compuestos bromados en una reacción de un solo paso rápida, fácil y práctica. Los ejemplos de compuestos bromados se obtuvieron gracias a la optimización de la reacción con acetonitrilo como disolvente. El sistema PIDA / AlBr3 como nuestra mezcla de compuestos dieron como producto la...

Ethnopharmacological relevance: The use of medicinal plants in Mexico has been documented since pre-Hispanic times. Nevertheless, the level of use of medicinal plants by health professionals in Mexico remains to be explored. Aim of the study: To evaluate the use, acceptance and prescription of medicinal plants by health professionals in 9 of the...

A practical, concise and scalable synthesis of a key intermediate in the preparation of the alkaloid ningalin C was developed over four steps in 29% overall yield. The procedure involves three commercially available starting materials and uses the chemistry of squaric esters. In view of the relevance of scalability in recent times, herein is highli...

By design: The site-selective oxidation of unactivated secondary C sp 3H bonds was accomplished with hypervalent iodine(III) reagents and tert-butyl hydroperoxide. The preparation and derivatization of the hypervalent iodine(III) reagent are simple, thus allowing the rational design of these reagents to optimize the site selectivity of the oxidati...

Fluxional molecules which rapidly pass back and forth between a large number of constitutional isomers through low-energy rearrangements have fascinated chemists owing to their role in the study of fundamental theoretical concepts[ 2] and their potential to adapt their chemical structures in response to their environment or to act as prototypical m...

Cationic gold(I) promotes the retro-Buchner reaction of 7-substituted 1,3,5-cycloheptatrienes, leading to gold(I) carbenes that cyclopropanate alkenes.

The gold(I)-catalyzed cyclization of 1-(prop-2-yn-1-yl)-2-alkenylbenzenes substituted at the benzylic position with OR groups gives 1,3-disubstituted naphthalenes with concomitant fragmentation of the alkene. One of these annulations proceeds by a retro-cyclopropanation that leads to free gold(I) carbenes.

The synthesis of nine 2-hydroxynaphthoquinones was achieved starting from squaric acid esters. The electrochemical and biological evaluations of these compounds were tested using the sea urchin ovules as a model. An interesting correlation between structure and activity was observed, as well as the possibility to predict the substitution patterns o...

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Shifty moves: 1,n-Enynes with propargyl alcohol, ether, or silyl ether units undergo gold(I)-catalyzed intramolecular 1, (n-1)-migration via allylgold cations (see scheme). These intermediates have been trapped by olefins, indole, and by a formal intramolecular C-H insertion. In the case of aryl-substituted 1,7-enynes, a cascade process involving a...

The synthesis of nine 2-hydroxynaphthoquinones was achieved starting from squaric acid esters. The electrochemical and biological evaluations of these compounds were tested using the sea urchin ovules as a model. An interesting correlation between structure and activity was observed, as well as the possibility to predict the substitution patterns o...

The synthesis of two analogues of parvaquone was accomplished starting form diisopropyl squarate. In addition to the classical conditions for ring expansion-cyclization process, a microwave-assisted reaction was introduced.

Parvaquone 1, a hydroxylated naphthoquinone with antiviral properties, was prepared in 26% overall yield in a straightforward manner starting from diisopropylsquarate 3. The key features of the synthesis include addition of commercial cyclohexylmagnesium chloride to 3, followed by acid-catalyzed rearrangement to furnish the cyclohexyl-substituted i...