Synthesis, and evaluation of α-amylase and α-glucosidase inhibitory potential of new pyrazolo[3,4-d]pyrimidine derivatives

A series of new pyrazolo[3,4-d]pyrimidine compounds were synthesized in excellent yields via sulfuration and 1,3-dipolar cycloaddition and confirmed by MS, FT-IR and NMR techniques. All the prepared compounds were screened in vitro for their α-amylase and α-glucosidase inhibitory activities. Preliminary results indicated that some target compounds exhibited promising α-amylase and α-glucosidase inhibitory activity potency. Among the tested products, the cycloadduct f was found most active inhibitor (IC50 = 134.30 μM) for α-amylase, and the sulphur product b is the most active inhibitor (IC50 = 16.37 μM) for α-glucosidase

4-Benzylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine

The pyrazolo[3,4-d]pyrimidine ring system of the title compound, C12H10N4S, is essentially planar [maximum deviation = 0.025 (1) Å for the C atom bearing the S atom] and almost perpendicular to the phenyl ring [dihedral angle = 71.42 (6)°]. In the crystal, molecules are linked via pairs of N—H...N hydrogen bonds, forming inversion dimers

Crystal structure of 4-allylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine

In the title compound, C8H8N4S, the pyrazolo[3,4-d]pyrimidine ring system is essentially planar, with a maximum deviation from the mean plane of 0.025 (3) Å. The allyl group is disordered over two sites in a 0.512 (6):0.488 (6) ratio. In the crystal, molecules are linked by pairs of N—H...N hydrogen bonds, forming inversion dimers with an R22(8) graph-set motif

2-{3-[2-(2-Chlorophenyl)ethyl]-2-oxo-1,2-dihydroquinoxalin-1-yl}acetohydrazide

In the title compound, C18H17ClN4O2, the dihydroquinoxaline moiety deviates slightly from planarity. The benzene ring and its chloro and methylene substituents are disordered over two sets of sites, with an occupancy ratio of 0.675 (3):0.325 (3). In the crystal, corrugated sheets parallel to (100) are formed by N—H...O, N—H...Cl and N—H...N hydrogen bonds. The structure was refined as a two-component inversion twin

The crystal structure of 1,5-dibenzyl-1H-pyrazolo[3,4-d]pyrimidine-4(5H)-thione

In the title compound, C19H16N4S, the pyrazolo[3,4-d]pyrimidine ring is close to being planar, with the greatest deviation from the mean plane being 0.023 (2) Å for the C atom bearing the thione S atom. The two phenyl rings are nearly perpendicular to the fused ring system [dihedral angles = 71.4 (2) and 78.1 (2)°], but are oriented in opposite directions; the dihedral angle between the phenyl rings is 32.22 (16)°. In the crystal, linear supramolecular chains along [101] are sustained by C—H...S interactions

4-[(1-Benzyl-1,2,3-triazol-5-yl)methyl]-2H-1,4-benzothiazin-3(4H)-one

The asymmetric unit of the title compound, C18H16N4OS, contains two independent molecules of similar conformation, the most relevant difference being the dihedral angle formed by the benzene rings [57.8 (2) and 52.7 (2)°]. The six-membered heterocycle of the benzothiazine fragment exhibits a screw-boat conformation in both molecules. The plane through the triazole ring is nearly perpendicular to those through the fused and terminal benzene rings [dihedral angles of 74.2 (2) and 83.2 (2)° in one molecule, and 77.8 (2) and 82.9 (2)° in the other]. In the crystal, molecules are linked by C—H...N and C—H...O hydrogen bonds into chains parallel to the a-axis direction. The crystal used was a non-merohedral twin, the refined ratio of twin components being 0.85 (10):15 (10)

(2Z)-2-Benzylidene-4-n-butyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

In the title compound, C19H19NOS, the six-membered heterocyclic ring of the benzothiazine fragment exhibits a screw boat conformation. The plane of the fused benzene ring makes a dihedral angle of 72.38 (12)° with that of the terminal phenyl ring, and is nearly perpendicular to the mean plane formed by the atoms through the n-butyl chain, as indicated by the dihedral angle of 88.1 (2)°. In the crystal, molecules are linked by C—H...O interactions to form supramolecular chains along [110]