Design, facile synthesis, and evaluation of novel spiro- and pyrazolo[1,5-c]quinazolines as cholinesterase inhibitors: Molecular docking and MM/GBSA studies

Gálvez, Jaime; Polo, Stivens; Insuasty, Braulio; Gutiérrez, Margarita; Cáceres, Daniela; Alzate‐Morales, Jans; De-la-Torre, Pedro; Quiroga, Jairo

doi:10.1016/j.compbiolchem.2018.03.001

Cited by 42 publications

(16 citation statements)

References 67 publications

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“…Some researchers try to find a new antimalarial drug base on the molecular docking study [7][8][9][10][11][12]. Binding free energy between ligand-receptor of the best pose (conformation) resulted from docking procedure are then calculated via Molecular Mechanics/Generalized Born Surface Area (MM/GBSA) approach [13][14]. The invention can be performed by testing compounds which are derived from previously mutated P. falciparum dihydrofolate reductase (pDHFR) resistance, e.g.…”

Section: ■ Introductionmentioning

confidence: 99%

Docking of New Designed Compounds Derived from 1,6-Dihydro-1,3,5-triazine-2,4-diamine Toward Quadruple Mutant Plasmodium Dihydrofolate Reductase

2019

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Resistance to the traditional antifolates is now widespread in Plasmodium falciparum and Plasmodium vivax. To find the interaction model of some compounds derived from 1,6-dihydro-1,3,5-triazine-2,4-diamine, molecular docking technique was carried out using these compounds ligand and pDHFR as the receptor. Complex ligand and the receptor from Protein Data Bank (PDB ID 1J3K) were chosen as an interaction model between a ligand and its receptor. Each compound was optimized using ab initio methods with 6-311G basis set. Partial charges of ligand were added using AM1-BCC methods. Each ligand was docked to the receptor utilizing Dock6 software. Theoretical prediction based on the binding energy between these compounds as the ligand with pDHFR as receptor resulted in 1 compound, namely 6,6-dimethyl-1-[3-(2-chloro-4,5-dibromophenoxy)propoxy]-1,6-dihydro-1,3,5-triazine-2,4-diamine possessing binding affinity better than that of WR99210 which was known to have good antimalarial activity.

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Section: ■ Introductionmentioning

confidence: 99%

Docking of New Designed Compounds Derived from 1,6-Dihydro-1,3,5-triazine-2,4-diamine Toward Quadruple Mutant Plasmodium Dihydrofolate Reductase

2019

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“…For example, the CYP1B1 inhibitors with heterocyclic chalcones were useful to treat glaucoma and ischemia [1]. The cholinesterase inhibitors including pyrazolo [1,5-c]quinazolines showed anti-inflammatory and analgesic activity [2]. A novel insecticide with pyridine group had a strong effect on imidacloprid (IMI)-resistant rice pests [3].…”

Section: Introductionmentioning

confidence: 99%

“…Recently, fluorescence properties of heterocyclic compounds have also received much more attention. For example, dibenzo[a,c] [1,2,5] tiadiazolo [3,4-i]phenazine [6], fluorimetric [7], hydroxyphenylquinazolinone [8], 3-hydroxyflavone derivative [9], carbazole schiff base [10], have been applied to fluorescence chemosensor or probe. Alkynylgold(III) complexes [11], pyrene-pyrazoline [12], piro-annulated benzimidazole host [13] have been used as organic light-emitting devices.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Fluorescence Properties of Two New Heterocyclic Compounds Containing 1,5-Dioxaspiro Group

Zeng

Jiang

et al. 2018

Crystals

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A precursor, C 21 H 29 NO 8 (A1) was prepared by reactions of 1,1-dimethoxy-N,Ndimethylmethanamine and 1,5-dioxaspiro[5.5]undecane-2,4-dione. The new N-containing heterocyclic compound, C 19 H 19 NO 4 (B1) was obtained by adding A1 into ethanol solution of o-toluidine. The crystal structure determination of two compounds were both found to belong to the triclinic P-1 space group. The precursor includes one (C 2 H 8 N) + cation and one (C 19 H 21 O 8 ) − anion, which constituted a chained structure by N-H···O intra-and intermolecular interactions. The title compound (B1) formed a 3D-network structure by weak C-H···O intermolecular interactions and π···π stacking interactions. The fluorescent behaviors of A1 and B1 in ethanol solution were discussed. The result shows that they exhibit blue and purplish blue emission, respectively.

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“…The Molecular Mechanics/Poisson-Boltzmann Surface Area (MM/PBSA) and Molecular Mechanics/Generalized Born Surface Area (MM/GBSA) method, 35,36 widely used in elucidating receptor-ligand binding mechanisms, [37][38][39][40][41][42][43][44][45][46][47][48] were employed to estimate the ERK2-inhibitor binding free energies in AMBER14. In MM/PB(GB)SA, the binding free energy can be decomposed into several terms and 200 snapshots were extracted from the last 3 ns MD trajectory for the free energy calculations.…”

Section: Mm/pb(gb)sa Binding Free Energy Calculations and Residue Decmentioning

confidence: 99%

Importance of protein flexibility in ranking ERK2 Type I^1/2inhibitor affinities: a computational study

Niu

Yao

2019

RSC Adv.

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Design, facile synthesis, and evaluation of novel spiro- and pyrazolo[1,5-c]quinazolines as cholinesterase inhibitors: Molecular docking and MM/GBSA studies

Cited by 42 publications

References 67 publications

Docking of New Designed Compounds Derived from 1,6-Dihydro-1,3,5-triazine-2,4-diamine Toward Quadruple Mutant Plasmodium Dihydrofolate Reductase

Docking of New Designed Compounds Derived from 1,6-Dihydro-1,3,5-triazine-2,4-diamine Toward Quadruple Mutant Plasmodium Dihydrofolate Reductase

Synthesis, Characterization, and Fluorescence Properties of Two New Heterocyclic Compounds Containing 1,5-Dioxaspiro Group

Importance of protein flexibility in ranking ERK2 Type I^1/2inhibitor affinities: a computational study

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Design, facile synthesis, and evaluation of novel spiro- and pyrazolo[1,5-c]quinazolines as cholinesterase inhibitors: Molecular docking and MM/GBSA studies

Cited by 42 publications

References 67 publications

Docking of New Designed Compounds Derived from 1,6-Dihydro-1,3,5-triazine-2,4-diamine Toward Quadruple Mutant Plasmodium Dihydrofolate Reductase

Docking of New Designed Compounds Derived from 1,6-Dihydro-1,3,5-triazine-2,4-diamine Toward Quadruple Mutant Plasmodium Dihydrofolate Reductase

Synthesis, Characterization, and Fluorescence Properties of Two New Heterocyclic Compounds Containing 1,5-Dioxaspiro Group

Importance of protein flexibility in ranking ERK2 Type I1/2inhibitor affinities: a computational study

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Importance of protein flexibility in ranking ERK2 Type I^1/2inhibitor affinities: a computational study