Unexpected kinetically controlled organoselenium-based isomaleimide: X-ray structure, hirshfeld surface analysis, 3D energy framework approach, and density functional theory calculation

Abstract

Reduction of 4,4′-diselanediyldianiline (1) followed by the reaction with bromo-4-(bromomethyl)benzene afforded the corresponding 4-((4-bromobenzyl)selanyl)aniline (2) in 85% yield. N-Maleanilic acid 3 was obtained in 94% yield via the reaction of selenoamine 2 with toxilic anhydride. Subsequent dehydration of N-maleanilic acid 3 using acetic anhydride furnished the unexpected isomaleimide 5-((4-((4-bromophenyl)selanyl)phenyl)imino)furan-2(5H)-one (4) instead of the maleimide 5. The molecular structure of compound 4 was confirmed by mass spectrometry, 1H- and 13C-NMR spectroscopy, and X-ray diffraction analysis. Their cytotoxicity was assessed against two oligodendrocytes, and their respective redox properties were evaluated using 2′,7′-dichlorodihydrofluorescein diacetate (H2-DCFDA) assay. Furthermore, their antiapoptotic potential was also evaluated by flow cytometry. The compound crystallizes in triclinic P-1 space group with unit cell parameters a = 5.7880 (4) Å, b = 9.8913 (6) Å, c = 14.5951 (9) Å, V = 1731.0 (3) Å3 and Z = 2. The crystal packing is stabilized by intermolecular hydrogen bonding, π···π, C-Br···π stacking interactions, and other non-covalent interactions. The mapping of different Hirshfeld surfaces and 2D-fingerprint were used to investigate intermolecular interactions. The interaction energies that stabilize the crystal packing were calculated and graphically represented as framework energy diagrams. We present a computational investigation of compound 4’s molecular structure at the Density Functional Theory level using the B3LYP method and the 6-31G ++ basis set in this paper. The optimized structure matches the experimental outcome. The global reactivity descriptors and molecular electrostatic potential (M.E.P.) map emphasize the molecule’s reactive locations, allowing reactivity prediction. The charge transfer properties of molecules can be estimated by examining Frontier molecular orbitals.

Synthesis and Experimental Structure of a Multifunctional Catechol‐Azomethinebenzoic Acid, DFT/DMol3Calculations, and Molecular Docking with Hsp90

“…The so-called chemical reactivity descriptors, which we have detailed in previous publications, [50,51] have been widely used to understand and predict the chemical behavior of compounds. [52][53][54][55] They are essentially calculated from the Experimental [a] DFT-calculated [b] Bond lengths (Å) [a] Symmetry codes: (i) -x,-y,1-z; (iii) 2-x,1-y,2-z.…”

Repurposed organoselenium tethered amidic acids as apoptosis inducers in melanoma cancer via P53, BAX, caspases-3, 6, 8, 9, BCL-2, MMP2, and MMP9 modulations

“…15,16 The reaction typically involves a nucleophilic attack of the amine on the anhydride carbonyl (C]O) carbon, followed by ring opening and the formation of the corresponding amidic acid intermediates i.e., N-maleanilic and N-succinanilic carboxylic acid derivatives. 17,18 The latter is either subjected to further reaction with amines to furnish dicarboxamides or subsequent dehydration and intramolecular cyclization to give the corresponding cyclic imides (e.g., maleimides and succinimides). 19 Within this context, dicarboxamides are important synthetic intermediates and have shown prevalent applications in coordination, agrochemicals, and polymer chemistry.…”

“…16,23,24 Additionally, maleimides and succinimides are found in many natural products and pharmaceutical active drug molecules such as the farinomalein (II) natural pesticide and Zarontin (III), and oxaleimide A (IV) which are used as anticonvulsant drug candidates. 17,25,26 Furthermore, scientists are increasingly excited about developing new compounds containing selenium (Se) (organoselenium (OSe) compounds). These compounds hold promise for preventing cancer due to their potential ability to ght cancer development (chemoprevention) and protect cells from damage (antioxidant activity).…”

“…, N -maleanilic and N -succinanilic carboxylic acid derivatives. 17,18 The latter is either subjected to further reaction with amines to furnish dicarboxamides or subsequent dehydration and intramolecular cyclization to give the corresponding cyclic imides ( e.g. , maleimides and succinimides).…”

“…16,23,24 Additionally, maleimides and succinimides are found in many natural products and pharmaceutical active drug molecules such as the farinomalein ( II ) natural pesticide and Zarontin ( III ), and oxaleimide A ( IV ) which are used as anticonvulsant drug candidates. 17,25,26…”