3-(Benzo[<i>d</i>]thiazol-2-yl)-2<i>H</i>-chromen-2-one

Abdallah, Amira E. M.; Elgemeie, Galal H.; Jones, Peter G.

doi:10.1107/s2414314622003327

Cited by 4 publications

(7 citation statements)

References 23 publications

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“…Therefore, the X-ray crystal structure was determined, indicating the formation of 3-(benzo[d]thiazol-2-yl)-6-methyl-2H-chromen-2-one (4) as the sole product, presumably arising via the initial formation of adduct 3 and the subsequent elimination of benzohydrazide rather than water. This is consistent with our recent observation that the desmethyl compound mentioned above is also formed as an unintended product by an exactly analogous reaction (Abdallah et al, 2022). The products thus represent, by coincidence, a continuation of our research on developing new benzothiazole and coumarin derivatives as organic fluorescent constituents (Elgemeie et al, 2015).…”

Section: Chemical Contextsupporting

confidence: 90%

“…A short intramolecular S11Á Á ÁO2 contact of 2.792 (1) A ˚is observed. The desmethyl analogue (Abdallah et al, 2022) has, as expected, a closely similar molecular structure, with an SÁ Á ÁO C contact of 2.727 (2) A ˚and an interplanar angle of 6.47 (6) , but is not isotypic to 4.…”

Section: Structural Commentarysupporting

confidence: 73%

“…In two recent papers (Abdallah et al, 2022(Abdallah et al, , 2023, we have given a more extensive list of references concerning the properties of benzothiazoles and coumarins, including many of our own publications in these fields.…”

Section: Chemical Contextmentioning

confidence: 99%

“…In all of these, the benzothiazole was bonded via its 2-position. The structure with refcode AKUCUG (Bakthadoss & Selvakumar, 2016) involved a linkage via the 8-position of the coumarin; the other 6 hits [VIVWEF and VIWDOX (Shi et al, 2019); WINZAU (Jasinski & Paight, 1995); SECSEC (Abdallah et al, 2022); PEGMEX and PEGMIB (Singh et al, 2022)] all had this linkage at the 3-position, as in compound 4. In all cases, a short intramolecular SÁ Á ÁO C contact was observed, with distances in the range 2.681-2.786 A ˚.…”

Section: Database Surveymentioning

confidence: 99%

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Crystal structure of 3-(benzo[d]thiazol-2-yl)-6-methyl-2H-chromen-2-one

2023

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Section: Chemical Contextsupporting

confidence: 90%

Section: Structural Commentarysupporting

confidence: 73%

Section: Chemical Contextmentioning

confidence: 99%

Section: Database Surveymentioning

confidence: 99%

See 2 more Smart Citations

Crystal structure of 3-(benzo[d]thiazol-2-yl)-6-methyl-2H-chromen-2-one

2023

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“…X-ray single crystal structure of the compound 9a . Reproduced with permission of the International Union of Crystallography under the,open-access license …”

Section: Resultsmentioning

confidence: 99%

Novel Fluorescent Benzothiazolyl-Coumarin Hybrids as Anti-SARS-COVID-2 Agents Supported by Molecular Docking Studies: Design, Synthesis, X-ray Crystal Structures, DFT, and TD-DFT/PCM Calculations

2023

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This study revealed the design and preparation of new 3-(benzo[d]thiazol-2-yl)-2H-chromen-2-one derivatives 9a–h. The structures of the synthesized products were elucidated by their spectroscopic data and X-ray crystallography for compounds 9a and 9d. The prepared new compounds were measured for their fluorescence, and a good result indicated that the emission efficiency was decreased by increasing the electron-withdrawing groups from the unsubstituted compound 9a to the highly substituted derivative 9h (2 Br heavy atoms). On the other hand, the B3LYP/6-311G** theoretical level of theory was used to optimize the quantum mechanical calculations of the geometrical characteristics and energy of the novel compounds 9a–h under study. The electronic transition was investigated using the TD-DFT/PCM B3LYP approach, which uses time-dependent density functional calculations. Moreover, the compounds exhibited nonlinear optical properties (NLO) and a small HOMO–LUMO energy gap, which makes them easy to polarize. Furthermore, the acquired infrared spectra were compared with the expected harmonic vibrations of the substances 9a–h. On the other hand, binding energy analyses of compounds 9a–h with human corona virus nucleocapsid protein Nl63 (PDB ID: 5epw) were predicted using molecular docking and virtual screening tools. The results showed a promising binding and how these potent compounds were inhibiting the COVID-19 virus. Compound 9h was the most active anti-COVID-19 agent among all the synthesized benzothiazolyl-coumarin derivatives, as it forms five bonds. The presence of the two bromine atoms in its structure was responsible for the potent activity.

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Crystal structure of N-[3-(benzo[d]thiazol-2-yl)-6-bromo-2H-chromen-2-ylidene]-4-methylbenzenamine

2023

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The title compound, C23H15BrN2OS, was the unexpected product in an attempted synthesis of the isomeric 3-(benzo[d]thiazol-2-yl)-6-bromo-1-p-tolylquinolin-2(1H)-one. The Cchromene=N—C angle is wide [125.28 (8)°]. The benzothiazole and chromene ring systems are almost coplanar, with their planes parallel to (1\overline{1}0); the toluene ring system is rotated by ca 40° out of the chromene plane. The molecular packing involves layers with π-stacking, borderline `weak' hydrogen bonds and possible C—H...π contacts.

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3-(Benzo[d]thiazol-2-yl)-2H-chromen-2-one

Abstract: In the title compound, C16H9NO2S, the interplanar angle is 6.47 (6)°. An intramolecular S...O=C contact of 2.727 (2) Å is observed. The packing is determined by several types of weak interaction (`weak' hydrogen bonds, S...S contacts and π–π stacking).

Cited by 4 publications

References 23 publications

Crystal structure of 3-(benzo[d]thiazol-2-yl)-6-methyl-2H-chromen-2-one

Crystal structure of 3-(benzo[d]thiazol-2-yl)-6-methyl-2H-chromen-2-one

Novel Fluorescent Benzothiazolyl-Coumarin Hybrids as Anti-SARS-COVID-2 Agents Supported by Molecular Docking Studies: Design, Synthesis, X-ray Crystal Structures, DFT, and TD-DFT/PCM Calculations

Crystal structure of N-[3-(benzo[d]thiazol-2-yl)-6-bromo-2H-chromen-2-ylidene]-4-methylbenzenamine

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