ChemInform Abstract: SUBSTITUENTENEFFEKTE AUF IR‐ UND (1)H‐NMR‐SPEKTREN VON M‐ UND P‐SUBSTITUIERTEN DIPHENYLAMINEN

Kasai, Michio; Hirota, Minoru; Hamada, Y.; Matsuoka, Hirotaka

doi:10.1002/chin.197316059

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“…For NPPA, the N-H stretching vibration is around 3448 cm À1 , a value that is in the cited range. Comparison with other molecules with similar structural characteristics, such as diphenylamine (3421-3429 cm À1 ; Kasai et al, 1973), shows that the stretching vibration shifts to low wavenumber values, even when the nature of the substituents is changed (electron attractor or electron donor). From this behaviour it could be rationalized that the pyrimidine ring plays an important role in shifting the N-H vibrational frequency to higher wavenumber values, causing an effect similar to that caused by a methyl group.…”

Section: Theoretical/experimental Vibrational Analysismentioning

confidence: 90%

Synthesis, spectroscopic characterization, structural studies, thermal analysis and molecular docking ofN-(2-methyl-5-nitrophenyl)-4-(pyridin-2-yl)pyrimidin-2-amine, a precursor for drug design against chronic myeloid leukemia

Moreno-Fuquen¹,

Arango-Daraviña²,

Kennedy³

2021

Acta Crystallogr C

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The synthesis, crystal structure and spectroscopic and electronic properties of N-(2-methyl-5-nitrophenyl)-4-(pyridin-2-yl)pyrimidin-2-amine (NPPA), C16H13N5O2, a potential template for drug design against chronic myelogenous leukemia (CML), is reported. The design and construction of the target molecule were carried out starting from the guanidinium nitrate salt (previously synthesized) and the corresponding enaminone. X-ray diffraction analysis and a study of the Hirshfeld surfaces revealed important interactions between the nitro-group O atoms and the H atoms of the pyridine and pyrimidine rings. A crystalline ordering in layers, by the stacking of rings through interactions of the π–π type, was observed and confirmed by a study of the shape-index surfaces and dispersion energy calculations. Quantitative electrostatic potential studies revealed the most positive value of the molecule on regions close to the N—H groups (34.8 kcal mol−1); nevertheless, steric impediments and the planarity of the molecule do not allow the formation of hydrogen bonds from this group. This interaction is however activated when the molecule takes on a new extended conformation in the active pocket of the enzyme kinase (PDB ID 2hyy), interacting with protein residues that are fundamental in the inhibition process of CML. The most negative values of the molecule are seen in regions close to the nitro group (−35.4 and −34.0 kcal mol−1). A molecular docking study revealed an energy affinity of ΔG = −10.3 kcal mol−1 for NPPA which, despite not having a more negative value than the control molecule (Imatinib; ΔG = −12.8 kcal mol−1), shows great potential to be used as a template for new drugs against CML.

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Section: Theoretical/experimental Vibrational Analysismentioning

confidence: 90%