N,N′-Diphenyldithiomalonodiamide: Structural Features, Acidic Properties, and In Silico Estimation of Biological Activity

Abstract

The spectral characteristics of dithiomalondianilide ( N , N ′-diphenyldithiomalonodiamide) were studied, and the dissociation constant was determined by potentiometric titration. Quantum-chemical methods at the B3LYP-D3BJ/6-311+G (2d,p) level were used to calculate the molecular geometry and vibrational spectra of the most stable tautomeric forms of dithiomalondianilide. The bioavailability parameters were calculated, and possible protein targets were predicted by the protein ligand docking method.

6-Amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamides: Synthesis, Biological Activity, Quantum Chemical Studies and In Silico Docking Studies

“…N,N ′ -Diphenyldithiomalondiamide (dithiomalondianilide) 1 was prepared from acetylacetone and phenyl isothiocyanate as reported in [33,34]. (E)-3-Aryl-2-cyanoacrylamides 2a-f were prepared via reaction of 2-cyanoacetamide with aromatic aldehydes in the presence of catalytic amounts of morpholine in EtOH at 40-50 • C [89] or in water in the presence of surfactants [90].…”

“…Recently, we have described the synthesis of functionalized [1,2]dithiolo [3,4 dines based on dithiomalondianilide 1 [30][31][32]. The starting thioamide 1 is readi able from the reaction of acetylacetone with phenyl isothiocyanate in the presenc dium ethoxide (Scheme 2) [33,34]. Dithiomalondianilide 1 is actively used as an S,S-or S,N-bidentate complexin [35][36][37][38][39][40][41][42][43], a lubricant [44,45] and a corrosion inhibitor [46].…”

Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies

“…Elemental analyses were carried out using a Carlo Erba 1106 Elemental Analyzer (Carlo Erba Strumentazione, Cornaredo, Italy) Reaction progress and purity of isolated compounds were controlled by TLC on Sorbfil-A plates (Imid Ltd, Krasnodar, Russia), eluent–acetone:hexane 1:1 or ethyl acetate:light petroleum 3:1; the spots were visualized with UV-light and iodine vapors. N,N’-Diphenyldithiomalondiamide (dithiomalondianilide) 12 was prepared from acetylacetone and phenyl isothiocyanate as described earlier [ 19 , 46 ]. Aldehydes, cyanoacetic esters, morpholine and solvents were purchased from commercial vendors and purified by distillation (Galachem, Moscow, Russia).…”

“…In the context of our interest in exploring the chemistry of dithiomalondianilide 12 and its transformations leading to [1,2]dithiolo[3,4-b]pyridines [ 16 , 19 , 20 , 21 ], it seemed reasonable to study the reactions of dithiomalondianilide 12 with other Michael acceptors. It is noteworthy that despite the long-standing and active use of thioamide 12 as a bidentate S,S-chelating agent towards heavy metals (e.g., [ 22 , 23 , 24 , 25 ]), the heterocyclization reactions of 12 have been little studied to date [ 26 , 27 , 28 , 29 ].…”

6-Amino-4-Aryl-7-Phenyl-3-(Phenylimino)-4,7-Dihydro-3H-[1,2]dithiolo[3,4-B]pyridine-5-Carboxamides: Synthesis, Biological Activity, Quantum Chemical Studies and In Silico Docking Studies

“…N,N′-Diphenyldithiomalondiamide (dithiomalondianilide) 1 was prepared from acetylacetone and phenyl isothiocyanate as reported [33,34]. (E)-3-Aryl-2-cyanoacrylamides 2a-f were prepared by reaction of 2-cyanoacetamide with aromatic aldehydes in the presence of catalytic amounts of morpholine in EtOH at 40-50 °С [89] or in water in the presence of surfactants [90].…”