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

Abstract

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.

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

“…(3) and 6,8-dibromoquinoline (4) treated with NaOMe or CuCN were synthesized according to our reported procedures. [14,39] Furthermore, the synthesis of 5,7-dibromo-8-hydroxyquinoline (17) and 5,7-dibromo-8-methoxyquinoline (19) via bromination of 8hydroxyquinoline (15) and 8-methoxyquinoline (16), respectively, was reported in our recent works. [40,55] The isolated compounds, 2-10, 12-14, and 17-19, were fully characterized by melting point, HRMS analysis, infrared, 1 H, 13 C, HMBC (heteronuclear multiple bond correlation), and HETCOR spectroscopy in these papers.…”

“…[13][14][15] Many studies about pharmacological features of aryl or nitro/ amino-substituted quinolines have been interested due to that they have been starting materials for bioactive polycyclic systems. [16,17] Nitrated derivatives, which exhibit biological potency, that is, antileishmanial [18] or potent mutagenic activities, [19] are important key compounds for the preparation of amino derivatives for pharmacological use. [16,20] The aryl-substituted quinolines displayed a high antipesticide activity against the nematode Haemonchus contortus, [21] agricultural predatory activity, significant antibacterial activity, [22] anti-inflammatory, analgesic, antipyretic activities, and efficient inhibition of the COX-2 enzyme.…”

“…[16,17] Nitrated derivatives, which exhibit biological potency, that is, antileishmanial [18] or potent mutagenic activities, [19] are important key compounds for the preparation of amino derivatives for pharmacological use. [16,20] The aryl-substituted quinolines displayed a high antipesticide activity against the nematode Haemonchus contortus, [21] agricultural predatory activity, significant antibacterial activity, [22] anti-inflammatory, analgesic, antipyretic activities, and efficient inhibition of the COX-2 enzyme. [23] Moreover, a series of substituted 2-phenylquinolines exhibited a superior ERβ affinity in a cell-based transcriptional assay, [24] potent antiplatelet activities, [25] antimitotic activity, [26] and antiproliferative activity against (colon cancer), MCF7 (breast cancer), and MDA-MB-435 (breast cancer) with low GI 50 values.…”

Arylated Quinoline and Tetrahydroquinolines: Synthesis, Characterization and Their Metabolic Enzyme Inhibitory and Antimicrobial Activities

“…[30,31] In our current studies, the synthesis of polyfunctional quinoline derivatives of 1,2,3,4-tetrahydroquinoline [11,15,32] with molecular bromine and then their corresponding derivatives has been provided via different reaction methods. [11,13,[33][34] In this context, new functional derivatives were obtained by further bromination of the prepared quinoline derivatives. Then, the bioactivities of substituted quinolines against various cancer cells, some metabolic enzymes and bacteria strains were investigated.…”