Periodical
Alkyne-Allene Transformation: Density Functional and in silicoStudies of 5-bromo-1-(Propargyl)-7-azabenzimidazole and its 1,2-propadiene Analogue
| العنوان: | Alkyne-Allene Transformation: Density Functional and in silicoStudies of 5-bromo-1-(Propargyl)-7-azabenzimidazole and its 1,2-propadiene Analogue |
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| المؤلفون: | Oluwafemi, Kola A., Oyeneyin, Oluwatoba E., Ojo, Nathanael D., Aigbogun, Jane A. |
| المصدر: | Chemistry Africa; 20220101, Issue: Preprints p1-7, 7p |
| مستخلص: | Allenes are important precursors for various cycloaddition reactions and they are present in several natural and synthetic medicinal compounds. One of the simplest ways of allenes preparation is through alkyne transformation. An earlier report described the base-catalyzed (Cs2CO3or K2CO3) isomerization of 5-bromo-1-(propargyl)-7-azabenzimidazole to 5-bromo-1-(1,2-propadiene)-7-azabenzimidazole. The current work probes this transformation by computational methods at the DFT/B3LYP(M06-2X)/6–31(d) level of theory. The two isomers were docked in malaria kinase enzyme model (PbCDPK-1). The molecular descriptors such as energy gap (ΔE), global softness (S), chemical potential (σ), electrophilicity (ω) were calulated. Relative energy of the isomers (ΔEiso), free energy change (ΔGiso), enthalpy change (ΔHiso) and entropy change (ΔSiso) for the propargyl-propadiene isomerization. Results obtained indicated that the isomers were polar and strong electrophiles with charge transfer tendency. 5-bromo-1-(1,2-propadiene)-7-azabenzimidazole exhibits improved chemical softness and kinetic instability. The propargyl-propadiene isomer showed negative values for ΔEiso, ΔGiso, ΔHisoand ΔSiso. Malaria enzyme binding data were also obtained for these isomers and the 5-bromo-1-(1,2-propadiene)-7-azabenzimidazole gave a better scoring function which may be attributed to its chemical softness. |
| قاعدة البيانات: | Supplemental Index |
| تدمد: | 25225758 25225766 |
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| DOI: | 10.1007/s42250-022-00538-7 |