Analysis and DNA interaction of the profluralin herbicide

Morawska, Kamila; Jedlińska, Katarzyna; Smarzewska, Sylwia; Metelka, Radovan; Ciesielski, Witold; Guziejewski, Dariusz

doi:10.1007/s10311-019-00865-1

Cited by 10 publications

(3 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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%

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

et al. 2023

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

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

et al. 2023

View full text Add to dashboard Cite

show abstract

“…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

View full text Add to dashboard Cite

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.

show abstract

“…The effect of a nitro group on the biological properties of a given pharmaceutical compound is very varied; it has been seen that it can have effects ranging from antibacterial, antiparasitic, antihypertensive, antineoplastic, and tranquilizer. As a consequence, there is a great interest in the investigation of methodologies to introduce this functional group [28][29][30][31][32][33][34].…”

mentioning

confidence: 99%

Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives

Leyva,

Loredo-Carrillo,

Aguilar

2023

Reactions

View full text Add to dashboard Cite

Nitrated products are important since they are intermediates in the synthesis of other compounds, such as explosives, perfumes, dyes and plastics, among others, and they have an easy capacity to convert into other functional groups. The synthesis of compounds with biological activity that have a nitro group in their structure is relevant to improving and/or enhancing their effect. In this work, different methodologies for the nitration of naphthoquinone derivative compounds are presented. The nitration of 3-R-2-(phenylamino)-1,4-naphthoquinone derivatives was carried out with nitric acid and sulfuric acid; milder reaction conditions were also established by diluting the acids or performing the reaction with weaker acids. Other methodologies were tested using nitrate salts for mononitrate product synthesis. We used a solvent-free reaction with oxalic acid using 3-R-2-(phenylamino)-1,4-naphthoquinones (R=H, Br or Cl), noting that the electronegativity of the chlorine group is decisive for achieving nitration with good yields. Finally, a Michael addition was performed with some nitrated anilines. To obtain denitrated compounds in the ortho and para positions, the reaction with strong acids is feasible; however, for the formation of mononitrated products, the Michael-type addition is more convenient.

show abstract

Analysis and DNA interaction of the profluralin herbicide

Cited by 10 publications

References 46 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

The Diverse Biological Activity of Recently Synthesized Nitro Compounds

Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives

Contact Info

Product

Resources

About