2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study

Abstract

The X-ray crystal structure of the title phthalazin-1-one derivative, C17H16N2O3S {systematic name: 2-[(2,4,6-trimethylbenzene)sulfonyl]-1,2-dihydrophthalazin-1-one}, features a tetrahedral sulfoxide-S atom, connected to phthalazin-1-one and mesityl residues. The dihedral angle [83.26 (4)°] between the organic substituents is consistent with the molecule having the shape of the letter V. In the crystal, phthalazinone-C6-C—H...O(sulfoxide) and π(phthalazinone-N2C4)–π(phthalazinone-C6) stacking [inter-centroid distance = 3.5474 (9) Å] contacts lead to a linear supramolecular tape along the a-axis direction; tapes assemble without directional interactions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of the C—H...O and π-stacking interactions but, also H...H and C—H...C contacts. The calculation of the interaction energies indicate the importance of dispersion terms with the greatest energies calculated for the C—H...O and π-stacking interactions.

Synthesis of novel phthalazine-based derivatives with potent cytotoxicity against HCT-116 cells through apoptosis and VEGFR2 inhibition

“…1 H NMR and 13 C NMR were used to elucidate the synthetic construction of N-allyl-3-(4-benzyl-1-oxophthalazin-2(1H)-yl) propanamide (7a), which yielded the following signals: the olenic methylene protons (CH]CH 2 ) appeared as two doublet at 5.06 ppm for the cis proton with coupling constant values J cis = 10.4, while the trans proton appeared at 5.14 ppm with coupling constant J trans = 17.4. The olenic CH (CH]CH 2 ) appeared as multiplet at 5.85-5.75 ppm and NHCH 2 appeared as triplet at 4.59 ppm; the 13 Hydrazide 5 was reacted with different amino acid hydrochloride in presence of NaNO 2 /HCl; methyl (3-[4-benzyl-1oxophthalazin-2(1H)-yl) propanoyl amino] alkanoates 8a-c were obtained (Scheme 4).…”

“…20 The esters 8a-c was believed to be a major stage in the chemical structure modication of the phthalazinone nucleus. Hydrazides 9a-c were obtained via reaction of esters 13 C NMR. The IR showed the addition of new carbonyl at 1630 cm −1 .…”

N'-(Pyridin-3-ylmethylene)benzenesulfonohydrazide: Crystal structure, DFT, Hirshfeld surface and in silico anticancer studies

“…The 2-D Fingerprint plots illustrate the overall and percentage contributions of the intermolecular contacts in the molecule [32,33]. The overall fingerprint plot for PMB and those delineated into H 5a-f, and their percentage contributions are presented in Table 5.…”

Role of pharmacological active phthalazine scaffolds in medicinal chemistry

“…It's a flexible lead for novel medication development [11][12][13][14]. Because of their pharmacological activity and therapeutic potential, heterocyclic-containing hydrazine has gotten a lot of interest among the many nitrogen-containing heterocyclic compounds.…”