Synthesis, structure, cytotoxic and antioxidant properties of 6-ethoxy-4-methylcoumarin

Çelikezen, Fatih Çağlar; Örek, Cahit; Parlak, Akif Evren; Sarac, Kamiran; Türkez, Hasan; Tozlu, Özlem Özdemir

doi:10.1016/j.molstruc.2019.127577

Cited by 14 publications

(4 citation statements)

References 53 publications

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“…: 116−117.5 °C (from 96% ethanol), ref. : [2] 161-162 °C (from 96% ethanol). IR (KBr), ν (cm −1 ) 1715 (νC=O lactone), 1572, 1485 (νC=C arene), 1165 &1067 (νCOC lactone); 1 H NMR (500 MHz, DMSO-d6, ppm), δ (ppm): 7.27 (d, J = 9.0 Hz, 1H, H-8), 7.16 (dd, J = 9.0, 2.5 Hz, 1H, H-7), 7.11 (d, J = 2.5 Hz, 1H, H-5), 6.34 (s, 1H, H-3), 4.07 (q, J = 7.0 Hz, 2H, 6-OCH2CH3), 2.39 (s, 3H, 4-CH3), 1.35 (t, J = 7.0 Hz, 3H, 6-OCH2CH3);…”

Section: Me Omentioning

confidence: 99%

Synthesis of 6- and 7-alkoxy-4-methylcoumarins from corresponding hydroxy coumarins and their conversion into 6- and 7-alkoxy-4-formylcoumarin derivatives

Toan

Thành

2020

Synthetic Communications

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Section: Me Omentioning

confidence: 99%

Synthesis of 6- and 7-alkoxy-4-methylcoumarins from corresponding hydroxy coumarins and their conversion into 6- and 7-alkoxy-4-formylcoumarin derivatives

Toan

Thành

2020

Synthetic Communications

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“…The concept of the molecular orbital characteristic is the relationship between highest occupied molecular (HOMO) orbital and unoccupied molecular orbital (LUMO) with HOMO-1 and LUMO+1 [37,38]. The frontier molecular orbital theory plays an essential role in quantum chemistry [20]. It can be used for clarifying the interactions, i.e., it helps to identify molecular attributes that is associated with the discrepancy between the HOMO and LUMO [39].…”

Section: Frontier Molecular Orbitalsmentioning

confidence: 99%

“…Density Functional Theory (DFT) is one of the theoretical methods used for simulating the synthesized compounds [13][14][15][16][17] . The DFT method is a significant area of interest because it has a perfect analytical capacity for the structural, spectral, and electronic properties of many molecules and has a high agreement with the experimental data [15,[18][19][20]. B3LYP method is one of the DFT functions that showed an important precision in predicting the electronic, energetic, and spectral properties of various molecules; therefore, it's called the brain of quantum chemistry [21][22][23][24] .…”

Section: Introductionmentioning

confidence: 99%

Theoretical Analysis of the Reactivity of Carmustine and Lomustine Drugs

Omer

Ahmed

Qader

et al. 2022

Journal of Physical Chemistry and Functional Materials

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Carmustine and lomustine nitrosoureas disintegrate to produce reactive intermediates that serve as classic alkylating agents in the body. Carmustine is given intravenously, while lomustine is administered orally. They both act as anti-cancer drugs; both could be used to treat brain tumors. To know the correct synthesis and reactivity of the molecules, structural analysis is very important. This research indicates the characterization of carmustine and lomustine drugs by quantum chemical measurements. The aforementioned compounds were optimized and the bandgap energies were calculated using DFT and HF methods at various basis sets. For all calculations, the B3LYP/6-311++G level has been chosen. For the two molecules, some parameters such as bond length, bond angle, and dihedral angle were calculated. Also, HOMO – LUMO energies were calculated to predict the more reactive molecule; the calculations included ionization potential, electron affinity, electronegativity, dipole moment properties, chemical hardness, and chemical softness. Moreover, electrostatic molecular potentials and Mulliken atomic charges were also described. All calculation results showed that lomustine is more reactive compared to carmustine.

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“…The principle characterizing of the molecular orbital is the relationship between HOMO and LUMO with HOMO-1 and LUMO+1. In quantum chemistry, the frontier molecular orbital theory is critical [19]. The maximum straight-forward of such interactions, which helps to identify molecular qualities, is the one linked to the discrepancy between a natural system's highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) [20,21].…”

Section: Frontier Molecular Orbitalsmentioning

confidence: 99%

Structure reactivity analysis for Phenylalanine and Tyrosine

Omer

Koparır

Qader

et al. 2021

Cumhuriyet Science Journal

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Phenylalanine (Phe) is one of the amino acids that cannot be produced in the body and must be ingested through diet. Tyrosine (Tyr) is also a non-essential amino acid and can be produced by Phe hydroxylation in the liver when the dietary intake of Tyr is low. Structure analysis is very important to know the correct synthesis and the reactivity of the molecule. In this study, the characterization of Phe and Tyr molecules were investigated using quantum chemical calculations. The molecular geometry for both molecules was determined using density functional theory (B3LYP) by handling the 6-311++G(d,p) basis set. The method of TD-DFT which is based on the B3LYP/6-31++G(d,p) level, was utilized in ethanol solvent to find the electronic absorption spectra. In addition, frontier molecular orbitals, electrostatic potential and molecular charge distributions analysis were carried out by B3LYP/6-311++G(d,p) theory. The energy differences between HOMO and LUMO for Phe were obtained as 0.19851 eV, which have a good argument with the reactivity compared with tyrosine, and energy band gap was 0.20501 eV.

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Synthesis, structure, cytotoxic and antioxidant properties of 6-ethoxy-4-methylcoumarin

Cited by 14 publications

References 53 publications

Synthesis of 6- and 7-alkoxy-4-methylcoumarins from corresponding hydroxy coumarins and their conversion into 6- and 7-alkoxy-4-formylcoumarin derivatives

Synthesis of 6- and 7-alkoxy-4-methylcoumarins from corresponding hydroxy coumarins and their conversion into 6- and 7-alkoxy-4-formylcoumarin derivatives

Theoretical Analysis of the Reactivity of Carmustine and Lomustine Drugs

Structure reactivity analysis for Phenylalanine and Tyrosine

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