Isoquinolinedione-urea hybrids: Synthesis, antibacterial evaluation, drug-likeness, molecular docking and DFT studies

Date

2022-03-01

Author

HAN, MUHAMMED İHSAN
Dengiz, Çağatay
Dogan, Sengul Diem
GÜNDÜZ, MİYASE GÖZDE
KÖPRÜ, SEMİHA
ÖZKUL KOÇAK, CEREN

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

264
views

0
downloads

In the present study, we applied the molecular hybridization approach to combine isoquinolinedione and urea pharmacophores in the same molecules. The hybrid compounds (IU1-IU14) were obtained by the reaction of 2-aminohomophthalimide and an equivalent amount of various isocyanate derivatives. After confirming the chemical structures and evaluating drug-likeness properties, the synthesized compounds were examined for their antibacterial activities against a wide range of bacteria. The compounds possessing lipophilic halogen substituents showed better activities against Gram-positive bacteria, particularly on Staphylococcus aureus strains. This activity trend was further supported by molecular docking studies in the ATP pocket of S. aureus DNA gyrase. Several important parameters such as, ionization potential (IP), electron affinity (EA), global chemical hardness (eta), global softness (sigma), and electronegativity (chi) were carried out to gain insights into the structural properties and stabilities of selected active compounds by means of density functional theory (DFT) at the B3LYP functional using basis set B3LYP/6-311G(d,p). Electrostatic potential maps (ESPs) and frontier orbital visualizations were further used to comment on molecular polarity and stability. (C) 2021 Elsevier B.V. All rights reserved.

Subject Keywords

Homophthalimide, Isoquinoline, Urea, Density functional theory, Molecular modeling, Molecular hybridization, DNA GYRASE, HOMO-LUMO, TD-DFT, INHIBITORS, DISCOVERY, DERIVATIVES, ANALOGS, NMR, NLO

URI

https://hdl.handle.net/11511/95289

Journal

JOURNAL OF MOLECULAR STRUCTURE

DOI

https://doi.org/10.1016/j.molstruc.2021.132007

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Comonomer effects on binding performances and morphology of acrylate-based imprinted polymers Tunc, Yeliz; Hasırcı, Nesrin; Yesilada, Akgul; Ulubayram, Kezban (2006-09-20) The objective of this study was to investigate the effect of different functional groups of molecularly imprinted polymers (MIPs) on the binding characteristics towards a specific template molecule by examining selectivity and recognition processes. Several non-covalent theophylline imprinted polymers (TIPs) were prepared by using only methacrylic acid (MAA), or MAA and 2-hydroxyethyl methacrylate (HEMA) comonomer, or MAA and acrylamide (ACM) comonomer. In all cases, a high amount of ethylene glycol dimetha...
Cyclization of RGD Peptides by Suzuki-Miyaura Cross-Coupling Kemker, Isabell; Schnepel, Christian; Schroeder, David C.; Marıon, Antoıne; Sewald, Norbert (American Chemical Society (ACS), 2019-08-22) Halogenated L- or D-tryptophan obtained by biocatalytic halogenation was incorporated into RGD peptides together with a variety of alkyl or aryl boronic acids. Suzuki-Miyaura cross-coupling either in solution or on-resin results in side chain-to-tail-cyclized RGD peptides, for example, with biaryl moieties, providing a new dimension of structure-activity relationships. An array of RGD peptides differing in macrocycle size, the presence of D-amino acid, N-methylation, or connectivity between the indole moiet...
Distyryl-boradiazaindacenes: facile synthesis of novel near IR emitting fluorophores Dost, Zeynep; Atilgan, Serdar; Akkaya, Engin U. (Elsevier BV, 2006-09-04) Boradiazaindacenes with methyl substituents at 3 and 5 positions were for the first time shown to undergo efficient double condensation reactions with an aromatic aldehyde yielding a series of extended conjugation dyes. These new fluorophores have absorption maxima in the range of 650-660 nm. The dyes reported here have large quantum yields with 20 nm Stokes' shifted emission peaks. The straightforward synthesis of such red shifted BODIPY derivatives is important in relation to the synthesis of novel and us...
Chemoselective Immobilization of Proteins by Microcontact Printing and Bio-orthogonal Click Reactions Tolstyka, Zachary P.; Richardson, Wade; Bat, Erhan; Stevens, Caitlin J.; Parra, Dayanara P.; Dozier, Jonathan K.; Distefano, Mark D.; Dunn, Bruce; Maynard, Heather D. (Wiley, 2013-12-16) Herein, a combination of microcontact printing of functionalized alkanethiols and site-specific modification of proteins is utilized to chemoselectively immobilize proteins onto gold surfaces, either by oxime- or copper-catalyzed alkyne-azide click chemistry. Two molecules capable of click reactions were synthesized, an aminooxy-functionalized alkanethiol and an azide-functionalized alkanethiol, and self-assembled monolayer (SAM) formation on gold was confirmed by IR spectroscopy. The alkanethiols were then...
Investigation of biologically important small molecules: quantum chemical and molecular dynamics calculations Tekin, Emine Deniz; Erkoç, Şakir; Department of Physics (2010) In this thesis, six small molecules (S-allylcysteine, S-allyl mercaptocysteine, allicin, methyl propyl disulfide, allyl methyl sulfide and dipropylsulfide) that are found in garlic and onion, and are known to be beneficial for human health were studied using molecular mechanics, semi-empirical methods, ab-initio (Restricted Hartree Fock), and density functional theory. Using the same methods, a synthetic pyrethroid pesticide molecule, called cyfluthrin, was also studied. Structural, vibrational and electron...

Citation Formats

M. İ. HAN, Ç. Dengiz, S. D. Dogan, M. G. GÜNDÜZ, S. KÖPRÜ, and C. ÖZKUL KOÇAK, “Isoquinolinedione-urea hybrids: Synthesis, antibacterial evaluation, drug-likeness, molecular docking and DFT studies,” JOURNAL OF MOLECULAR STRUCTURE, vol. 1252, pp. 0–0, 2022, Accessed: 00, 2022. [Online]. Available: https://hdl.handle.net/11511/95289.