Browse > Article
http://dx.doi.org/10.5012/jkcs.2021.65.2.113

Synthesis of Asymmetric Pyrazoline Derivatives from Phenylthiophenechalcones; DFT Mechanistic Study  

Aboelnaga, Asmaa (Department of Chemistry, Faculty of Women for Arts, Science and Education, Egypt, Ain Shams University)
Mansour, Eman (Department of Chemistry, Faculty of Women for Arts, Science and Education, Egypt, Ain Shams University)
Ahmed, Hoda. A. (Faculty of Science, Department of Chemistry, Cairo University)
Hagar, Mohamed (Faculty of Science, Chemistry Department, Alexandria University)
Publication Information
Journal of the Korean Chemical Society / v.65, no.2, 2021 , pp. 113-120 More about this Journal
Abstract
New phenylthiophenechalcones,1-(biphenyl-4-yl)-3-(5-phenylthiophen-2-yl)prop-2-en-1-one (3a) and 3-(5-phenylthiophen-2-yl)-1-(4-(piperidin-1-yl) phenyl) prop-2-en-1-one (3b) were synthesized, next, their treatment with thiosemicarbazide in ethanol afforded their pyrazoline derivatives (4a) and (4b), respectively. The molecular structures of the synthesized compounds were confirmed via elemental analysis, FT-IR, 1H, 13C NMR and mass spectroscopy. The geometrical elucidation of four suggested conformers has been studied for these compounds. DFT calculations have been performed to study the stability and the structural parameters of the predicted conformers and revealed that orientation of the biphenyl and the phenylthiophene moieties affect the stability of the estimated conformers of the synthesized chalcones and pyrazoline. Moreover, two reaction mechanisms have been proposed to illustrate the reaction products and the DFT calculations have been used to confirm the reaction mechanism of the pyrazoline compounds.
Keywords
Phenylthiophenechalcone; Conformers; Carbothioamide; Pyrazole; DFT; Mechanistic study;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Konieczny, M. T., et al., Acid-catalyzed synthesis of oxathiolone fused chalcones. Comparison of their activity toward various microorganisms and human cancer cells line. European Journal of Medicinal Chemistry 2007, 42, 729.   DOI
2 Kumar, D., et al., Synthesis and biological evaluation of indolyl chalcones as antitumor agents. Bioorganic & Medicinal Chemistry Letters 2010, 20, 3916.   DOI
3 Aboelnaga, A.; EL-Sayed, T. H. Click synthesis of new 7-chloroquinoline derivatives by using ultrasound irradiation and evaluation of their biological activity. Green Chemistry Letters and Reviews 2018, 11, 254.   DOI
4 Asiri, A. M.; Khan, S. A. Synthesis and anti-bacterial activities of a bis-chalcone derived from thiophene and its biscyclized products. Molecules 2011, 16, 523.   DOI
5 Echeverria, C., et al., Structural antitumoral activity relationships of synthetic chalcones. International Journal of Molecular Sciences 2009, 10, 221.   DOI
6 Biradar, J.; Sasidhar, B.; Parveen, R. Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives. European Journal of Medicinal Chemistry 2010, 45, 4074.   DOI
7 Sharshira, E. M.; Hamada, N. M. M. Synthesis, antibacterial and antifungal activities of some pyrazole-1-carbothioamides and pyrimidine-2 (1H)-thiones. Am. J. Org. Chem. 2012, 2, 26.   DOI
8 Gokhan-Kelekci, N., et al., A new therapeutic approach in Alzheimer disease: some novel pyrazole derivatives as dual MAO-B inhibitors and antiinflammatory analgesics. Bioorganic & Medicinal Chemistry 2007, 15, 5775.   DOI
9 Aboelnaga, A.; Amer, N.; Zakaria, N. Polyaniline/Aza-Bicyclo Composites Containing P, S, and Si Atoms: Synthesis, Characterization, Molecular Orbital Calculations, Electrical Conductivity, and Biocidal Activities against Some Biofouling-Causing Organisms. Polycyclic Aromatic Compounds 2020; p. 1-18.
10 Sabzevari, O., et al., Phloretin and hydroxychalcones hepatoprotective activity against acetaminophen-induced liver damage in mice. Toxicology Letters 2010(196): p. S213.
11 Mansour, E., et al., A new series of thiazolyl pyrazoline derivatives linked to benzo [1, 3] dioxole moiety: Synthesis and evaluation of antimicrobial and anti-proliferative activities. Synthetic Communications 2019; p. 1-12.
12 Sapra, S., et al., Chalconoid Derived Heterocycles as Potent Bioactive Molecules: A Review. Chem. Sci. J, 2016, 7, 129.
13 Farag, A. M.; Fahim, A. M. Synthesis, biological evaluation and DFT calculation of novel pyrazole and pyrimidine derivatives. Journal of Molecular Structure 2019, 1179, 304.   DOI
14 Nepali, K., et al., Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones. Medicinal Chemistry Research 2012, 21, 2990.   DOI
15 Syam, S., et al., Synthesis of chalcones with anticancer activities. Molecules 2012, 17, 6179.   DOI
16 Aponte, J.C., et al., In vitro and in vivo anti-Leishmania activity of polysubstituted synthetic chalcones. Bioorganic & Medicinal Chemistry Letters 2010, 20, 100.   DOI
17 Illicachi, L., et al., Synthesis and DFT Calculations of Novel Vanillin-Chalcones and Their 3-Aryl-5-(4-(2-(dimethylamino)-ethoxy)-3-methoxyphenyl)-4, 5-dihydro-1H-pyrazole-1-carbaldehyde Derivatives as Antifungal Agents. Molecules 2017, 22, 1476.   DOI
18 Kaddouri, Y., et al., Pyrazole Compounds: Synthesis, molecular structure, chemical reactivity, experimental and theoretical DFT FTIR spectra. Materials Today: Proceedings 2019, 13, 956.   DOI
19 Maliyappa, M., et al., 6-Substituted benzothiazole based dispersed azo dyes having pyrazole moiety: Synthesis, characterization, electrochemical and DFT studies. Journal of Molecular Structure 2020, 1199, 126959.   DOI
20 Hagar, M., et al., N-alkyl 2-pyridone versus O-alkyl 2-pyridol: Ultrasonic synthesis, DFT, docking studies and their antimicrobial evaluation. Journal of Molecular Structure 2020, 1199, 126926.   DOI
21 Nafee, S. S.; Ahmed, H. A.; Hagar, M. New architectures of supramolecular H-bonded liquid crystal complexes based on dipyridine derivatives. Liquid Crystals 2020; p. 1-14.
22 Nafee, S. S., et al., New two rings Schiff base liquid crystals; ball mill synthesis, mesomorphic, Hammett and DFT studies. Journal of Molecular Liquids 2020, 299, 112161.   DOI
23 Ahmed, H.; Hagar, M.; Alhaddad, O. Mesomorphic and geometrical orientation study of the relative position of fluorine atom in some thermotropic liquid crystal systems. Liquid Crystals 2019; p. 1-10.
24 Alhaddad, O.; Ahmed, H.; Hagar, M. Experimental and Theoretical Approaches of New Nematogenic Chair Architectures of Supramolecular H-Bonded Liquid Crystals. Molecules 2020, 25, 365.   DOI
25 Nafee, S. S.; Ahmed, H.; Hagar, M. Theoretical, experimental and optical study of new thiophene-based liquid crystals and their positional isomers. Liquid Crystals 2020; p. 1-12.
26 Alnoman, R. B., et al., A new chiral Boron-dipyrromethene (BODIPY)-based fluorescent probe: molecular docking, DFT, antibacterial and antioxidant approaches. Journal of Biomolecular Structure and Dynamics 2019 (just-accepted); p. 1-19.
27 Nafee, S. S., et al., The synthesis of new thermal stable schiff base/ester liquid crystals: A computational, mesomorphic, and optical study. Molecules 2019, 24, 3032.   DOI
28 Alnoman, R.; Ahmed, H. A.; Hagar, M. Synthesis, optical, and geometrical approaches of new natural fatty acids' esters/Schiff base liquid crystals. Molecules 2019, 24, 4293.   DOI
29 Elsisy, M.; El Sayed, M. Fuzzy rough bi-level multi-objective nonlinear programming problems. Alexandria Engineering Journal 2019, 58, 1471.   DOI
30 Kobayashi, R.; Amos, R. D. Theoretical investigation of the isomerisation of merocyanine. Molecular Physics, 2013, 111, 1574.   DOI
31 Gokhan-Kelekc, N., et al., Synthesis and biological evaluation of some thiazole and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial. Bioorg Med Chem 2007, 15, 5775.   DOI
32 Hawaiz, F. E. Synthesis and characterization of some new 4, 5-dihydropyrazolyl thiazoles. Chemical Science Transactions 2014, 3, 1583.
33 Gokhan-Kelekc, N., et al., Synthesis and biological evaluation of some thiazole and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial. Bioorg. Med. Chem. 2007, 15, 5775.   DOI