Activation of 6-bromoquinoline by nitration: synthesis of morpholinyl and piperazinyl quinolines

Cumhuriyet Science Journal

Ersanlı

Çakmak

2018

The chemical properties of recently synthesized 6-bromo-5-nitroquinoline-1-oxide under a mild reaction condition by regioselective nitration of 6-bromoquinoline-1-oxide at C5 on going our research were investigated as theoretical. The crystal structure of 6-bromo-5-nitroquinoline-1-oxide, C 9 H 5 BrN 2 O 3 , was determined by X-ray analysis. Crystallized in Pmc2 1 in the orthorhombic space group with a = 13.6694 (13) Å, b = 9.6036 (10) Å, c = 14.1177 (16) Å, Z = 8, D x = 1.929 mg/m 3. In this study, theoretical calculations were performed using the GaussView 4.1 molecular imaging program and the Gaussian03W packet program. In the ground state, stable structures of the wholes molecule in the gaseous phase are investigated based on Density Functional Theory (DFT). Molecularly optimized geometries, dipole moments, charge density, thermodynamic properties (heat capacity, enthalpy, entropy), chemical shift values (1 H NMR and 13 C NMR), energies, molecular electrostatic potentials and frontier orbitals (HOMO and LUMO) B3LYP/6-311G(d,p) base set. Thus, the results obtained by the X-ray diffraction method are supported by theoretical foundations. Finally, the distribution of interactions between molecules in the crystal structure of 6-bromo-5-nitroquinoline-1-oxide (3) was investigated by analysis using Hirshfeld surface production and two-dimensional fingerprinting.

Section: Introductionmentioning

confidence: 93%

Section: H and 13 C Nmr Spectramentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Structural Characterization of 6-Bromo-5-nitroquinoline-1-oxide: A Quantum Chemical Study and XRD Investigations

Cumhuriyet Science Journal

Ersanlı

Çakmak

2018

“…[3,4,[28][29][30]33] In brief, the synthesis of 6-bromo-5-nitroquinoline (11) via direct nitration of 6-bromoquinoline was reported recently in our previous publication. [33] The brominated 8-hydroxyquinolines (2, 3) starting from 8-hydroxyquinoline treatment of molecular bromine were synthesized according to our reported procedure. [29] Cyano substituted 8-hydroxyquinolines were synthesized by metal-assisted substitution reaction according to our reported procedures.…”

Section: Synthesis Of the Substituted Quinoline Compoundsmentioning

confidence: 99%

Decision making for promising quinoline‐based anticancer agents through combined methodology

Özcan

J Biochem & Molecular Tox

Eren

2020

During the development of effective drugs for the treatment of cancer, one of the most important tasks is to identify effective drug candidates having maximum antiproliferation and minimum side effects. This paper considers the problem of selecting the most promising anticancer agents, showing inhibition at low IC50 concentration and low releasing lactate dehydrogenase percentage (cytotoxicity). Recently, we prepared quinoline analogs bearing different functional groups and determined their anticancer potential against the HeLa, C6, and HT29 cancer cell lines using different anticancer assays. Experimentally, seven quinoline derivatives consisting of different substituents were determined as promising anticancer agents. We propose a multicriteria recommendation method to identify the most promising anticancer agents against all tested cell lines with an accurate prediction algorithm according to the available input data. A multicriteria decision‐making methodology (MCDM) was used for the solution of the relevant problem in this study. Both the experimental results and MCDM method indicated that 5,7‐dibromo‐8‐hydroxyquinoline (2) and 6,8‐dibromo‐1,2,3,4‐tetrahydroquinoline (6) are the most promising anticancer agents against the HeLa, HT29, and C6 cell lines.

Quinoline‐based promising anticancer and antibacterial agents, and some metabolic enzyme inhibitors

Aydın

Koçyiğit

et al. 2020

Archiv der Pharmazie

A series of substituted quinolines was screened for their antiproliferative, cytotoxic, antibacterial activities, DNA/protein binding affinity, and anticholinergic properties by using the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide cell proliferation, lactate dehydrogenase cytotoxicity, and microdilution assays, the Wolfe–Shimmer equality method, the Ellman method, and the esterase assay, respectively. The results of the cytotoxic and anticancer activities of the compounds displayed that 6‐bromotetrahydroquinoline (2), 6,8‐dibromotetrahydroquinoline (3), 8‐bromo‐6‐cyanoquinoline (10), 5‐bromo‐6,8‐dimethoxyquinoline (12), the novel N‐nitrated 6,8‐dimethoxyquinoline (13), and 5,7‐dibromo‐8‐hydroxyquinoline (17) showed a significant antiproliferative potency against the A549, HeLa, HT29, Hep3B, and MCF7 cancer cell lines (IC50 = 2–50 μg/ml) and low cytotoxicity (∼7–35%) as the controls, 5‐fluorouracil and cisplatin. The compound–DNA linkages are hyperchromic or hypochromic, causing variations in their spectra. This situation shows that they can be bound to DNA with the groove‐binding mode, with Kb value in the range of 2.0 × 103–2.2 × 105 M–1. Studies on human Gram(+) and Gram(−) pathogenic bacteria showed that the substituted quinolines exhibited selective antimicrobial activities with MIC values of 62.50–250 μg/ml. All tested quinoline derivatives were found to be effective inhibitors of acetylcholinesterase (AChE) and the human carbonic anhydrase I and II isoforms (hCA I and II), with Ki values of 46.04–956.82 nM for hCA I, 54.95–976.93 nM for hCA II, and 5.51–155.22 nM for AChE. As a result, the preliminary data showed that substituted quinolines displayed effective pharmacological features. Molecular docking studies were performed to investigate the binding modes and interaction energies for compounds 2–17 with AChE (PDB ID: 4EY6), hCA I (PDB ID: 1BMZ), and hCA II (PDB ID: 2ABE).