Structure–cytotoxic activity relationship of 3-arylideneflavanone and chromanone (E,Z isomers) and 3-arylflavones

Identification of structural requirements of estrogen receptor modulators using pharmacoinformatics techniques for application to estrogen therapy

“…This descriptor reflects electrophilic reactivity and plays a important role in reductive processes in which an electron from a molecular donor anion or metallic surface is assumed to transfer into this orbital on an acceptor molecule (Burrow and Modelli 2013). The orbital energy has been successfully used in the development of QSAR models (Kupcewicz et al 2013;Levet et al 2013;Nandy et al 2013;Nantasenamat et al 2013). The negative coefficient of this descriptor in the model suggested that highly nucleophile compounds resulted in high binding affinity and might influence binding at the ERα subtype.…”

The relationship between Hirshfeld potential and cytotoxic activity: a study along a series of flavonoid and chromanone derivatives

“…A comparison of the logP value (theoretical) with the contribution of various contacts to the Hirshfeld surface found that theoretical lipophilicity (logP) is also inversely proportional to the percentage contribution of the CÁ Á ÁC contacts to the Hirshfeld surface. This analysis has been extended by similar flavonoid compounds and benzylidenochromanone derivatives available from our previous research (Kupcewicz et al, 2013;Adamus-Grabicka et al, 2018;Suchojad et al, The cytotoxic activity (expressed as log 1 IC 50 ) against the HL-60, NALM-6, WM-115 and COLO-205 cancer cell lines.…”

RM1 Semiempirical Model: Chemistry, Pharmaceutical Research, Molecular Biology and Materials Science

“…In addition, the RM1 method has also been employed by organic chemists to calculate the energy of the lowest unoccupied molecular orbital (LUMO), and of the highest unoccupied molecular orbital (HOMO), that are associated with the reactivity of organic compounds. 70,77,100,[104][105][106]117,125 Organic compounds, that had their orbital energies (LUMO, and HOMO) calculated by RM1, include: 3-arylideneflavanone; 70 E,Z isomers of chromanone; 70 3-arylflavones; 70 polymethine cyanine dyes in solutions of β-cyclodextrin; 106 trans-1-acetyl-4,5-di-tert-butyl-2-imidazolidinone; 104 a set of (E)-4-aryl-4-oxo-2-butenoic acids; 105 a set of nitroaromatic compounds; 117 species involved in a revised mechanism of Boyland-Sims oxidation; 125 2,6-dibromo-4-[(E)-2-(1-methylquinolinium-4 -y l ) e t h e ny l ] -p h e n o l a t e ; 100 a n d 2 100 In this sense, a QSPR study reported by Hu et al 77 employed the RM1 method to calculate geometry optimizations, energy, and electronic properties of a set of fourteen polybrominated diphenyl ether congeners, as such 2-mono-BDE (BDE-1), and 3-mono-BDE (BDE-2). The descriptors calculated by RM1 were used in statistical analyses based on artificial neural network models.…”

“…Several articles employed the RM1 method in medicinal chemistry research. 70,84, In general, usage of the RM1 method in such research includes: (i) geometry optimizations, and (ii) calculations of energy, and electronic properties of compounds that exhibited biological activities; as well as (iii) in studies based on the quantitative structureactivity relationships (QSAR), and quantitative structuretoxicity relationships (QSTR). Now let us explore the main uses of RM1 in medicinal chemistry.…”

“…Other medicinal chemistry studies employed the RM1 method to optimize the geometries of the following compounds of biological interest: a potent thiazolylhydrazone-based antitrypanosomal; 84 alkaloids obtained from Hippeastrum morelianum Lem. (Amaryllidaceae); 173 C-glucosidic ellagitannins, prepared by a biomimetic synthesis of compound 5-O-desgalloylepipunicacortein A; 187 (5Z)-5-[(5-bromo-1H-indol-3-yl)methylene]-3-(4-chlorobenzyl)-thiazolidine-2,4-dione, which is effective as pan peroxisome proliferatoractivated receptor agonist and cyclooxygenase inhibitor; 189 1,7-bis(aminoalkyl)diazachrysene derivatives, that are capable of inhibiting three unrelated pathogens: the botulinum neurotoxin serotype A light chain; Plasmodium falciparum malaria and Ebola filovirus; 190 derivatives of thiazolidinones with anti-Trypanosoma cruzi activity; 192 derivatives of the E,Z-isomers of 3-arylidene substituted flavanone, chromanone and 3-aryl substituted flavone, that exhibited biological activities for the treatment of the following types of cancer: cell lines (HL-60, NALM-6, WM-115) and normal cell line (HUVEC); 70 2-pyridyl thiazoles, that are anti-Trypanosoma cruzi agents; 193 surfactants of the type bispyridinium diexadecyl cationic gemini, which are nonviral gene-deliveries; 196 phthalimides with antiproliferative and immunomodulatory activities; 202 Aedes aegypti larvicidal based on thiosemicarbazones; 209 inhibitors of chikungunya virus (CHIKV; genus Alphavirus) protease; 210 peroxisome proliferator-activated receptor gamma (PPARγ), which is capable of regulating pathways involved in the pathogenesis of obesity and atherosclerosis; 215 a series of 4-amino-7-chloroquinoline (4,7-ACQ) compounds, that exhibited higher antimalarial activities; 216 usnic acid enamines that enhance the cytotoxic effect of camptothecin, and, therefore, are inhibitors of the tyrosyl-DNA phosphodiesterase; 218 cyclic urea and carbamate derivatives that are α-glucosidase inhibitors; 166 4-aminoquinolines as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa; 222 and a set of 77 Leishmania donovani inhibitors of N-myristoyltransferase. 224 Optimized geometries calculated by RM1 were also used as strategy to obtain initial structure for the target systems, to subsequently employ DFT and/or ab initio methods.…”