Design, synthesis, molecular modeling, and biological evaluation of novel α-aminophosphonates based quinazolinone moiety as potential anticancer agents: DFT, NBO and vibrational studies

Awad, Mohamed K.; Abdel-Aal, Mahmoud F.; Atlam, Faten M.; Hekal, Hend A.

doi:10.1016/j.molstruc.2018.06.094

Cited by 36 publications

(12 citation statements)

References 41 publications

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“…Furthermore, the natural bond orbital (NBO) study of the title molecule 3 was computed at B3LYP/6-31+ G(d,p) level of model. To understanding into delocalization of electron density, intra- and inter-molecular bonding relations between the bonds, and investigate the charge transfer (CT) or conjugative relations in molecular structure 40 . The structure of the calculated compound was exhibited a type of Lewis structure (97.7%), 2.12% of valence non-Lewis, and 0.16% of Rydberg non-Lewis (Fig.…”

Section: Resultsmentioning

confidence: 99%

A comparison between observed and DFT calculations on structure of 5-(4-chlorophenyl)-2-amino-1,3,4-thiadiazole

Kerru

Gummidi

Bhaskaruni

et al. 2019

Sci Rep

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The crystal and molecular structure of 5-(4-chlorophenyl)-2-amino-1,3,4-thiadiazole 3 was reported, which was characterized by various spectroscopic techniques (FT-IR, NMR and HRMS) and single-crystal X-ray diffraction. The crystal structure 3 (C8H6ClN3S) crystallized in the orthorhombic space group Pna21 and the unit cell consisted of 8 asymmetric molecules. The unit cell parameters were a = 11.2027(2) Å, b = 7.6705(2) Å, c = 21.2166(6) Å, α = β = γ = 90°, V = 1823.15(8) Å3, Z = 8. In addition, the structural geometry (bond lengths, bond angles, and torsion angles), the electronic properties of mono and dimeric forms of compound 3 were calculated by using the density functional theory (DFT) method at B3LYP level 6-31+ G(d,p), 6-31++ G(d,p) and 6-311+ G(d,p) basis sets in ground state. A good correlation was found (R2 = 0.998) between the observed and theoretical vibrational frequencies. Frontier molecular orbitals (HOMO and LUMO) and Molecular Electrostatic Potential map of the compound was produced by using the optimized structures. The NBO analysis was suggested that the molecular system contains N-H…N hydrogen bonding, strong conjugative interactions and the molecule become more polarized owing to the movement of π-electron cloud from donor to acceptor. The calculated structural and geometrical results were in good rational agreement with the experimental X-ray crystal structure data of 1,3,4-thiadiazol-2-amine, 3. The compound 3 exhibited n→π* UV absorption peak of UV cutoff edge, and great magnitude of the first-order hyperpolarizability was observed. The obtained results suggest that compound 3 could have potential application as NLO material. Therefore, this study provides valuable insight experimentally and theoretically, for designing new chemical entities to meet the demands of specific applications.

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Section: Resultsmentioning

confidence: 99%

A comparison between observed and DFT calculations on structure of 5-(4-chlorophenyl)-2-amino-1,3,4-thiadiazole

Kerru

Gummidi

Bhaskaruni

et al. 2019

Sci Rep

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“…Many 3,4-dihydroquinazolin-2(1 H )-one derivatives have been previously synthesized (Huang et al, 2008; Khan et al, 2014, 2015, 2016; Kshirsagar, 2015; Camacho et al, 2016; Maiden and Harrity, 2016; Awad et al, 2018; Zhang et al, 2018; Elkholy et al, 2019; Gatadi et al, 2019; Long et al, 2019; Wang et al, 2019). For example, Wang et al (2009) reported the synthesis of 4-alkyl-2(1H)-quinazolinones via the cyclization of 1-(2-alkynyl-phenyl)ureas catalyzed by TfOH and Saunthwal et al (2015) described a green and catalyst-free straightforward tandem synthesis of functionalized tetrahydroquinazolines from 2-aminophenylacrylate.…”

Section: Introductionmentioning

confidence: 99%

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

et al. 2019

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A new series of 3-substituted 4-methylene-quinazolinthiones and 4-methylene-quinazolinones were synthesized in moderate to excellent yield through a simple reaction of 2-aminoacetophenones with isocyanates or isothiocyanates. The reaction shows good tolerance of many important functional groups in the presence of air and water under metal-free conditions. Only water is produced as a coproduct, rendering this “green” methodology a highly versatile and eco-friendly alternative to the existing methods for the construction of the quinazolinone/quinazolinthione framework. We have interpreted the reaction mechanism by use of quantum chemical calculations on the basis of state-of-the-art computational methods SMD-B3LYP-D3(BJ)/BS1//B3LYP/BS1.

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“…A number of reviews have been published on various aspects of the biological properties of α‐aminophosphonates . Certain α‐aminophosphonates and copper(II) complexes with α‐aminophosphonates as tridentate ligands exhibit significant anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

Stereochemistry of the Kabachnik‐Fields Condensation of Terpenic Amino Oximes with Aldehydes and Dimethyl Phosphite

et al. 2020

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Three-component condensation of aldehydes and dimethyl phosphite with α-amino oximes derived from (À)-α-pinene and (+)-3-carene (Kabachnik-Fields reaction) resulted in amino phosphonates as pairs of diastereomers. Diastereomeric ratio depends on the catalyst used (SnCl 2 × 2H 2 O, SiO 2 , Al 2 O 3-H +) and the heating type (conventional or microwave). The best results were achieved by MW irradiation with simultaneous cooling. Stereochemical assignment of the key derivatives was made by X-ray diffractometry. According to quantum chemical calculations (DFT PBE0/def2-TZVPP) and spectroscopic data, the terpenic α-amino phosphonates should be conformationally inhomogeneous, exhibiting a tendency to form H-bonded dimers (DFT M06/def2-SVP, IR). One-bond spin-spin coupling 1 J P-C was found to be diagnostic for the configuration assignment since the value 1 J P-C depends on the dihedral angle between bond CÀ P and axis of the electron lone pair at the neighboring nitrogen (NMR, DFT PBE0/aug-cc-pVTZÀ J).

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Design, synthesis, molecular modeling, and biological evaluation of novel α-aminophosphonates based quinazolinone moiety as potential anticancer agents: DFT, NBO and vibrational studies

Cited by 36 publications

References 41 publications

A comparison between observed and DFT calculations on structure of 5-(4-chlorophenyl)-2-amino-1,3,4-thiadiazole

A comparison between observed and DFT calculations on structure of 5-(4-chlorophenyl)-2-amino-1,3,4-thiadiazole

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

Stereochemistry of the Kabachnik‐Fields Condensation of Terpenic Amino Oximes with Aldehydes and Dimethyl Phosphite

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