3-Phenyl/Pyridinyl Derivatives of &amp;lt;i&amp;gt;Trans&amp;lt;/i&amp;gt;-2-(aryl/heteryl)vinyl-3&amp;lt;i&amp;gt;H&amp;lt;/i&amp;gt;-quinazolin-4-ones: Synthesis and Fluorescent Properties

Носова, Э. В.; Stupina, Tatyana V.; Lipunova, G. N.; Валова, М. С.; Слепухин, П. А.; Чарушин, В. Н.

doi:10.4236/ijoc.2012.21010

Cited by 11 publications

(7 citation statements)

References 26 publications

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“…6.91 ppm (R = H, F) or 6.99 ppm (R = Cl, OMe) and in the δ 7.91–7.93 ppm region with coupling constant values J = 16.0 Hz, which indicates that the double bond exists in an E -geometry in agreement with the literature assignment for the analogous compounds [20,21,22,23]. The analogous 3-phenyl/pyridinyl substituted trans -2-(aryl/hetearyl)vinylquinazolin-4(3 H )-ones exhibited significantly reduced emission intensities in solution at room temperature due to competitive quenching through trans-cis C=C photo-isomerization [24]. However, these conformational changes were found to be suppressed at 77 K in a frozen glass leading to significantly enhanced emission intensity [24].…”

Section: Resultssupporting

confidence: 83%

Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones

et al. 2015

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Suzuki-Miyaura cross-coupling of 6-bromo-2-styrylquinazolin-4(3H)-ones with arylboronic acids afforded a series of novel 6-aryl-2-styrylquinazolin-4(3H)-ones. These compounds were evaluated for potential anticancer properties against the human renal (TK-10), melanoma (UACC-62) and breast cancer (MCF-7) cell lines. Their antimicrobial properties were also evaluated against six Gram-positive and four Gram-negative bacteria, as well as two strains of fungi. Molecular docking studies (in silico) were conducted on compounds 5a, b, d and 6a, b, d-f to recognize the hypothetical binding motif of the title compounds within the active site of the dihydrofolate reductase and thymidylate synthase enzymes.

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Section: Resultssupporting

confidence: 83%

Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones

et al. 2015

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“…Analytical characteristics of (E) 3 phenyl 2 styryl quinazolin 4(3H) one (3a) (93% yield, 0.4 g) and (E) 2 (2 (naphthalen 1 yl)vinyl) 3 phenylquinazolin 4(3H) one (3b) (89% yield, 0.43 g) agreed with those given in the works. 10 (19)); 119.86 (C()); 120.43 (C(4a)); 121.69 (C(15)); 126.25 (C(6)); 126.38 (C(5)); 127.10 (C(8)); 128.86 (C(20)); 128.92 (C(10), C(14)); 129.02 (C(12)); 129.58 (C(11), C(13)); 130.81 (C(18)); 134.67 (C(7)); 135.42 (C()); 137.24 (C(9)); 147.54 (C(8a)); 152.18 (C(2)); 156.60 (C(16)); 161.36 (C(4)). IR (DRA), /cm 20 .…”

Section: Methodsmentioning

confidence: 99%

Synthesis, photochemical and luminescent properties of (E)-2-(2-hydroxyarylethylene)-3-phenylquinazolin-4(3H)-ones

et al. 2014

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Photoinduced transformations of 2 styrylquinazolinones in solutions were studied using absorption and NMR spectroscopy methods. A possibility of control of the photochemical isomerization rate of quinazolinone 2 (hydroxyaryl)ethenyl derivatives by changing the pH of the medium was demonstrated. The bases and the solvent nature also affect the luminescence intensity of solutions of these compounds in the wavelength range of 550-650 nm. The differ ences in the steric organization of the ortho hydroxystyryldiazinone system in crystals and in solutions related to the turn of the aryl group were found. Their influence on the competing processes of luminescence and photochemical transformation of the ethylene fragment were shown. The fact of reversible photo/thermal E-Z isomerization was established for (E) 2 (2 hydroxystyryl) 3 phenylquinazolin 4(3H) one.Key words: (E) 2 styrylquinazolin 4(3H) ones, ortho hydroxystyrylquinazolinones, lumi nescence, reversible photo/thermal isomerization, photoswitching.Diarylethenes and their heterocyclic analogues form the basis of modern electroluminescent and photochro mic materials, successfully used in nonlinear optics, lasers with tunable frequency, optoelectronic devices for record ing and storage of information, molecular photoswitch es. 1,2 Among hetarylstilbenes, their unsymmetric deriva tives 3,4 are of particular interest. Owing to the contribu tion of the n,* state, the presence of an acceptor azine (azinone) core in addition to the donor (aryl) one in stil bene molecules can have a considerable influence on photochemical and photophysical behavior of the lumi nophores. 5 However, there are fewer publications on the studies of the corresponding systems than of the symmetric (het)arylethenes. 4 In particular, there are several works on the synthesis of (E) 2 styrylquinazolin 4(3H) ones and the study of their photophysical properties. 4,6-10 It should be noted that compounds of this type with a specific emis sion ability and a tendency to a photoinduced E-Z iso merization 9,10 can be quite promising for the development of pH sensitive photochromic materials. We think that the introduction of a hydroxy group at the ortho position of the arylethenyl fragment of quinazolinones can gener ate photocontrolled processes related to the E-Z isomer ization with a proton transfer in the course of tautomeric transformations and heterocyclization to the correspond ing spiropyrans. ExperimentalIR spectra were recorded on a Perkin Elmer Spectrum One IR Fourier transform spectrometer using a diffuse reflectance sampling accessory (DRA). Electron absorption spectra were recorded on a UV 2401 PC double beam spectrophotometer (Shimadzu, Japan) in the range of 190-700 nm with the wave length setting accuracy of ±0.3 nm using a Shimadzu Scan stan dard program. Fluorescence spectra were recorded on a Varian Cary Eclipse fluorescence spectrophotometer with mutually per pendicular beams, the wavelength setting accuracy of 0.5 nm. The measurements were carried out in the range of 190-800 nm in SUP...

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“…The substituents at the ethylene fragment are located in transpositions. Unlike the structure reported by Nosova et al (2012), where the conjugation system of styrylquinazolinone is practically planar, in compound 1 the 2-phenyleth-(E)-enyl substituent is twisted with respect to the plane of the quinazolone ring. The phenyl (C21-C26) and the 4-hydroxyphenyl (C12-C17) rings are inclined to one another by 78.2 (2) , and to the quinazolone ring (N1/N2/C2/C4-C10) by 26.44 (19) and 81.25 (8) , respectively.…”

Section: Structural Commentarymentioning

confidence: 57%

“…Fig. 4) gave only three hits:Nosova et al (2012);Trashakhova et al (2011);Ovchinnikova et al (2014). However, none of the characterized single crystals contains a hydrogen-bond donor/acceptor in the aryl substituent at position 3 of the quinazolinone unit and information on intermolecular interactions of such structures is still missing.…”

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confidence: 99%

Crystal structure of 3-(4-hydroxyphenyl)-2-[(E)-2-phenylethenyl]quinazolin-4(3H)-one

et al. 2016

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3-Phenyl/Pyridinyl Derivatives of <i>Trans</i>-2-(aryl/heteryl)vinyl-3<i>H</i>-quinazolin-4-ones: Synthesis and Fluorescent Properties

Cited by 11 publications

References 26 publications

Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones

Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones

Synthesis, photochemical and luminescent properties of (E)-2-(2-hydroxyarylethylene)-3-phenylquinazolin-4(3H)-ones

Crystal structure of 3-(4-hydroxyphenyl)-2-[(E)-2-phenylethenyl]quinazolin-4(3H)-one

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