Synthesis, modelling, and biological evaluation of substituted pyrazole derivatives as potential anti-skin cancer, anti-tyrosinase, and antioxidant agents.

Twenty-five azole compounds (-) were synthesised using regioselective base-metal catalysed and microwave-assisted approaches, fully characterised by high-resolution mass spectrometry (HRMS), nuclear magnetic resonance (NMR), and infrared spectra (IR) analyses, and evaluated for anticancer, anti-tyrosinase, and anti-oxidant activities and . exhibited potent anticancer activity against cells of four skin cancer (SC) lines, with selectivity for melanoma (A375, SK-Mel-28) or non-melanoma (A431, SCC-12) SC cells over non-cancerous HaCaT-keratinocytes. Clonogenic, scratch-wound, and immunoblotting assay data were consistent with anti-proliferative results, expression profiling therewith implicating intrinsic and extrinsic apoptosis activation.

1,3-diarylpyrazolones as potential anticancer agents for non-small cell lung cancer: Synthesis and antiproliferative activity evaluation.

A series of pyrazolone compounds with different substitution patterns have been synthesized using microwave-assisted methods and evaluated their in vitro antiproliferative activity against human lung adenocarcinoma cell lines (A549 and NCI-H522). Among the tested compounds, the pyrazolone P7 exhibited high antiproliferative activity against both A549 and NCIH522 cancer cell lines while being 10 times less cytotoxic to non-cancerous cells. Moreover, our compounds P7 and P11 exhibited higher antiproliferative activity and selectivity against A549 and NCIH522 cells compared with the clinically approved drugs Afatinib and Gefitinib.

Identification of new fisetin analogs as kinase inhibitors: Data on synthesis and anti-skin cancer activities evaluation.

This article contains supplemental datasets of the recently published related research article by Roy et al., [1]. It provides in-depth data not included in the original co-submission on the biophysical, molecular docking, and biological characterization of newly synthesized flavonol-based analogs of fisetin, a natural dietary small molecule with anticancer and anti-inflammatory properties.

Synthesis, inverse docking-assisted identification and in vitro biological characterization of Flavonol-based analogs of fisetin as c-Kit, CDK2 and mTOR inhibitors against melanoma and non-melanoma skin cancers.

Due to hurdles, including resistance, adverse effects, and poor bioavailability, among others linked with existing therapies, there is an urgent unmet need to devise new, safe, and more effective treatment modalities for skin cancers. Herein, a series of flavonol-based derivatives of fisetin, a plant-based flavonoid identified as an anti-tumorigenic agent targeting the mammalian targets of rapamycin (mTOR)-regulated pathways, were synthesized and fully characterized. New potential inhibitors of receptor tyrosine kinases (c-KITs), cyclin-dependent kinase-2 (CDK2), and mTOR, representing attractive therapeutic targets for melanoma and non-melanoma skin cancers (NMSCs) treatment, were identified using inverse-docking, in vitro kinase activity and various cell-based anticancer screening assays.

Statistical modelling and simulation of nanohybrid shish-kebab architecture of PE-b-PEG copolymers and carbon nanotubes.

Carbon nanotubes have been known to develop hierarchically ordered polymer nanocomposites by virtue of epitaxial crystallization. A unique product of CNT induced crystallization is generation of nanohybrid shish-kebab (NHSK) structure, which has gained tremendous attention owing to its unique applications. However, research faces major challenges in terms of producing tunable patterns on CNTs, which are largely governed by precise control of the crystallization parameters.

Fe-catalyzed synthesis of substituted N-aryl oxazolidines.

A novel iron-catalyzed synthesis of substituted N-aryl oxazolidines was developed via C-N bond formation and methylenation. The reaction of aryl hydroxylamines with allyl alcohols, in the presence of formaldehyde or its equivalents, afforded variety of oxazolidine heterocycles in very good yields. This catalytic method is most effective for para-substituted aryl hydroxylamines and 3-methyl allyl alcohols.

Fe-Catalyzed Direct α C-H Amination of Carbonyl Compounds.

A direct Fe-catalyzed α-amination of 1,3-dicarbonyl compounds has been accomplished using arylhydroxylamines as aminating agents. This novel protocol allows convenient access to α-amino carbonyl derivatives without the need for any postreaction manipulations. This is an operationally simple procedure that works at low temperatures in shorter reaction times and produces high yields with excellent N-selectivity.

Synthesis of substituted quinolines via allylic amination and intramolecular Heck-coupling.

A new catalytic approach for the synthesis of substituted quinolines via C-N and C-C bond formation using 2-haloaryl hydroxylamines and allylic C-H substrates is described. Fe-catalyzed allylic C-H amination followed by Pd-catalyzed intramolecular Heck-coupling and aerobic dehydrogenation deliver the valuable quinoline and naphthyridine heterocycles in good to excellent overall yields. In this process, Pd(OAc)2 plays a dual role in catalyzing Heck coupling as well as aerobic dehydrogenation of dihydroquinolines.

Direct synthesis of β-alkyl N-aryl aza Baylis-Hillman adducts via nitroso-ene reaction.

A new approach for the direct Fe-catalyzed synthesis of β-alkyl N-aryl aza Baylis-Hillman (ABH) adducts is reported. This approach involves the formation of a C-N bond via a nitroso-ene reaction. This is a simple, fast, and best alternate method to overcome the substrate scope limitations of the ABH reaction, which converts allyl esters and carbonyl compounds to novel ABH adducts.

Arylthioureas with bromine or its equivalents gives no 'Hugerschoff' reaction product.

The in situ generated aryl-alkyl unsymmetrical thiourea obtained by the reaction of an aryl isothiocyanate with an aliphatic secondary amine on treatment with bromine or its equivalent gave exclusively a product having a thioamido guanidino moiety and not the expected Hugerschoff product 2-aminobenzothiazole. A plausible reaction mechanism has been proposed for this unprecedented transformation and the scope has been extended to various substrates.

A comprehensive decomposition analysis of stabilization energy (CDASE) and its application in locating the rate-determining step of multi-step reactions.

Stabilization energy, as proposed by Parr and Pearson (J. Am. Chem.

Intra- and intermolecular C-S bond formation using a single catalytic system: first direct access to arylthiobenzothiazoles.

We have for the first time developed two ligand-assisted Cu(I)-catalyzed sequential intra- and intermolecular S-arylations leading to the direct synthesis of arylthiobenzothiazoles in one pot without an inert atmosphere. Low catalyst loading, inexpensive metal catalyst and ligand, lower reaction temperature, and shorter reaction times make this method superior to all reported methods for the synthesis of arylthiobenzothiazole.

Acyl-isothiocyanates as efficient thiocyanate transfer reagents.

An unprecedented transfer of a thiocyanate (-SCN) group from aroyl/acyl isothiocyanate to alkyl or benzylic bromide is observed in the presence of a tertiary amine. This process is most effective when the bromomethyl proton is less acidic, while the presence of a more acidic proton gives 1,3-oxathiol-2-ylidine and other related products.

Copper(I)-catalyzed synthesis of substituted 2-mercapto benzimidazoles.

An efficient method for the preparation of various substituted 2-mercapto benzimidazoles from their corresponding thioureas has been developed. S-alkylation of thioureas followed by Cu-catalyzed intramolecular N-arylation furnished substituted 2-mercapto benzimidazoles in high yields and short reaction times. Furthermore, 2-mercapto benzimidazoles substituted with a p-methoxybenzyl group allowed access to benzimidazole thiones.

Hypervalent iodine(III)-mediated regioselective N-acylation of 1,3-disubstituted thioureas.

Reaction of asymmetrical 1,3-disubstituted thioureas with diacetoxyiodobenzene (DIB) produces regioselectively N-acetylurea in shorter time. Regioselectivity is dependent on the pKa's of the amine attached to the thiourea moiety with acylation taking place toward the amine having a lower pKa. This is the first example of DIB being employed as an N-acetylating agent.

It is "thiazolidene-2-imine" and not imidazole-2-thione as the reaction product of 1-benzoyl-3-phenylthiourea with Br(2)/enolizable ketone.

[Structure: see text] The products obtained by the reaction of benzoyl-3-phenylthioureas with bromine and enolizable ketones in the presence of triethylamine are not imidazole-2-thione derivatives as reported (Org. Lett. 2003, 5, 1657-1659) rather they are thiazolidene-2-imine derivatives.