Abstract
Derivatives based on pyridine-2-6- and furan-2,5-dicarboxamide scaffolds reveal numerous chemical properties and biological activities. This fact makes them an exciting research topic in supramolecular and coordination chemistry and in discovering new pharmacologically-active compounds. This work aimed to obtain a series of symmetrical pyridine-2-6- and furan-2,5-dicarboxamides through a condensation reaction of the appropriate acyl chlorides and aromatic amides. Successful syntheses were confirmed with NMR spectroscopy. We solved their crystal structures for seven compounds; two pyridine and five furan derivatives. Based on our crystallographic studies, we were able to indicate supramolecular features of the crystals under investigation. Additionally, Hirshfeld surface analysis allowed us to calculate a distribution of intermolecular contacts in the dicarboxamide crystals.
Highlights
The synthesis of heterocyclic dicarboxamides and N-nitrophenyldicarboxamides was performed based on a simple condensation of acyl chlorides A or B, with the appropriate aromatic amines according to Schemes 1 and 2, starting from furan-2,5-dicarboxylic or pyridine-2,6-dicarboxylic acid, respectively
Dicarboxamides with nitro groups were catalytically reduced to the corresponding diaminodicarboxamides with the use of hydrazine monohydrate (100%) and Pd/C (10%)
Synthesis of aromatic furan-2,5-dicarboxamides: (a) (CO)2Cl2 (4–6 eq), DMF, DCM, RT; (b) 3 or 4-nitroaniline, or 2, 3, 4-aminopyridine (2.0 eq), Et3N (2.0 eq), DCM/THF (1/1; v/v), 0 ◦C ÷ RT, 24 h; (c) 2-aminopyrazine or 2-amino, or 5-aminopyrimidine (4 eq), DCM/THF (1/1; v/v), 0 ◦C ÷ RT, 24 h; (d) N2H4·H2O (7 mL), Pd/C (10% w/w), MeOH, RT
Summary
The continuous need for medically and pharmacologically important scaffolds prompts chemists to constantly search for efficient and straightforward pathways to synthesize and modify different heterocycles This applies mainly to those heterocyclic systems for which some medical or pharmacological activity has already been demonstrated, but their use is still limited due to some structural constraints [1]. 2,6-Pyridinecarboxamide derivatives, macrocyclic oligoamides and hydrazides have been screened for their bactericidal and fungicidal potential [17,18] They exhibit significant antimicrobial activities against Gram-positive, Gram-negative bacteria and fungi comparable to reference antibiotics such as streptomycin, ciprofloxacin and ketoconazole. These properties give the opportunity to use such heterocycles in catalytic systems in supramolecular and coordination chemistry [19]. The synthetic derivatives of pyridine-2,6-dicarboxamide exhibit the ability to stabilize telomeric G-quadruplex DNA, which shows the potential of applying these compounds in a senescence-mediated anticancer therapy [21]
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