Novel cytotoxic amphiphilic nitro-compounds derived from a synthetic route for paraconic acids

Ribeiro, Talita A.; Machado-Ferreira, Erik; Guimarães, Lohaine F.; Cavaleiro, Jéssica; Britto, Alan Messala de Aguiar; Redua, Nataly; Souza, Lucas Miguel Pereira; Pimentel, André Silva; Picciani, Paulo H. S.; Oliveira, Osvaldo N.; Barreto, Cleber B.; Soares, Carlos A. G.

doi:10.1016/j.colsurfa.2021.126984

Cited by 8 publications

(8 citation statements)

References 150 publications

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“…The 1 H NMR and 13 C NMR spectra were obtained using a Bruker high-resolution NMR spectrometer of frequency 400-100 MHz with CDCl3 as a solvent. Fourier transform infrared (FT-IR) spectra were recorded in the range of 400-4000 cm −1 on a Bruker IR spectrophotometer.…”

Section: Instrumentationmentioning

confidence: 99%

“…Some functional groups, viz. -NO2 is an efficient scaffold for bioactive molecules that have a wide spectrum of activities [10][11][12][13][14][15][16]. The tert-butyl group is a common group present in many drugs across different therapeutic classes.…”

Section: Introductionmentioning

confidence: 99%

“…The 4-(tert-butyl)-4-nitro-1,1-biphenyl (4-TBNB) compound has been synthesized and its structure has been characterized using FT-IR, 1 H NMR and 13 C NMR techniques. The chemical structure was validated by the single-crystal Xray diffraction method, and an optimized structure was obtained using DFT and Hartree-Fock (HF) approaches.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl

et al. 2023

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4-(tert-Butyl)-4-nitro-1,1-biphenyl has been synthesized, and its structure has been characterized by using some spectroscopic and single-crystal X-ray diffraction techniques. It crystallizes in a monoclinic crystal system with space group P21/n and unit cell parameters: a = 6.4478(3) Å, b = 9.2477(4) Å, c = 23.4572(9) Å, β = 95.114(4)°, V = 1393.11(10) Å3, Z = 4. The molecular structure has been solved by using the intrinsic phasing method. The crystal structure is stabilized by C-H···O interactions. Computational studies were performed using density functional theory (DFT) and Hartree-Fock (HF) methods. The optimized geometry obtained from DFT and HF in the gas phase was compared with solid-phase experimental data retrieved from single-crystal X-ray diffraction results. Frontier molecular orbitals, such as the HOMO/LUMO energy gap, the molecular electrostatic potential, and Mulliken atomic charges, have been investigated. The HOMO LUMO energy gap of 3.97 eV indicates that the molecule is soft and highly reactive. The Hirshfeld surface analysis and their associated fingerprint plots have been used to quantitatively validate the interactions. Further insilico molecular docking studies have been performed with the molecular target Type-II topoisomerase (PDB ID: 1JIJ) and their results suggest that 4-(tert-butyl)-4-nitro-1,1-biphenyl could be considered an anticancer drug.

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Section: Instrumentationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl

et al. 2023

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“…Among the compounds with significant pharmacological activities, compounds containing a nitro group are highlighted because they have an important pharmacophoric functionality in their molecules, which facilitates their use in medicinal and therapeutic applications. Nitro-derivatives are associated with several biological activities including anti-inflammatory, [39] antitumor, [40] antimicrobial, [41] and antileishmanial [42] activities. To ascertain the effect of the nitro group at position 3, we planned to synthesize nitro product 3 by nitration of compound 2 with a mixture of fuming nitric acid and sulfuric acid in acetic acid (Scheme 3).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, anticancer evaluation, and molecular docking study of novel 4‐hydroxybenzo[h][1,6]naphthyridine‐2,5‐dione derivatives

Mostafa

2022

J of Physical Organic Chem

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An operationally efficient and affordable lactone-to-lactam transformation was designed from pyrano [3,2-c]quinolinone 1 to obtain 4-hydroxybenzo [h][1,6] naphthyridine-2,5-dione 2 utilizing ammonium acetate. The newly synthesized compound 2 was subjected to different electrophilic substitution reactions such as nitration, chlorination, bromination, and N-acylation to obtain novel benzo [h][1,6]naphthyridine derivatives with different substituents at C-3, C-4, and NH. Structures of novel products were achieved by elemental analyses and spectroscopic techniques. The benzonapthyridine derivatives were screened for their antitumor activities against some cancer cell lines including HepG-2, HCT-116, and MCF-7. All the examined compounds revealed strong, good, moderate to weak anticancer activity compared with 5-fluorouracil as a reference standard. Compound (3, -3NO 2 ) was the most cytotoxic one and exhibited a higher inhibitory activity than the standard drug against HCT-116 and MCF-7 with IC 50 values of 20.7 ± 1.9 and 22.5 ± 2.1 μg/ml, respectively, and strong activity against HepG-2 with IC 50 = 15.3 ± 0.7 μg/ml. Moreover, a molecular docking study was carried out for the tested compounds against the crystallographic structure of the Topo II enzyme as a potential target to investigate their binding modes. Docking results showed that compound 6b fitted well into the active site of topoisomerase II (PDB ID: 1ZXM) with hydrogen bond interactions.

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“…After absorption, pharmaceuticals may undergo some structural changes with the consecutive change in activity, which can increase, decrease or even change. Since the discovery of chloramphenicol in 1947, nitro containing cycles and heterocycles have been extensively investigated due to their antibacterial activity; however, nitro containing molecules exhibit a wide variety of biological activities that are attractive to medicinal chemists, for example, some are antineoplastic, antibiotic, antihypertensive, antiparasitic agents, tranquilizers and even herbicides, among many others [1][2][3][4][5][6][7]. The nitro group (NO 2 ) is a functional group formed by one nitrogen atom linked to two oxygens, it is a particularly electron-withdrawing moiety since the N has no lone pair, hence it bears a positive charge (Figure 1) [8].…”

Section: Introductionmentioning

confidence: 99%

The Diverse Biological Activity of Recently Synthesized Nitro Compounds

et al. 2022

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The search for new and efficient pharmaceuticals is a constant struggle for medicinal chemists. New substances are needed in order to treat different pathologies affecting the health of humans and animals, and these new compounds should be safe, effective and have the fewest side effects possible. Some functional groups are known for having biological activity; in this matter, the nitro group (NO2) is an efficient scaffold when synthesizing new bioactive molecules. Nitro compounds display a wide spectrum of activities that include antineoplastic, antibiotic, antihypertensive, antiparasitic, tranquilizers and even herbicides, among many others. Most nitro molecules exhibit antimicrobial activity, and several of the compounds mentioned in this review may be further studied as lead compounds for the treatment of H. pylori, P. aeruginosa, M. tuberculosis and S. mutans infections, among others. The NO2 moiety triggers redox reactions within cells causing toxicity and the posterior death of microorganisms, not only bacteria but also multicellular organisms such as parasites. The same effect may be present in humans as well, so the nitro groups can be considered both a pharmacophore and a toxicophore at the same time. The role of the nitro group itself also has a deep effect on the polarity and electronic properties of the resulting molecules, and hence favors interactions with some amino acids in proteins. For these reasons, it is fundamental to analyze the recently synthesized nitro molecules that show any potential activity in order to develop new pharmacological treatments that enhance human health.

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Novel cytotoxic amphiphilic nitro-compounds derived from a synthetic route for paraconic acids

Cited by 8 publications

References 150 publications

Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl

Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl

Synthesis, anticancer evaluation, and molecular docking study of novel 4‐hydroxybenzo[h][1,6]naphthyridine‐2,5‐dione derivatives

The Diverse Biological Activity of Recently Synthesized Nitro Compounds

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