Details

Autor(en) / Beteiligte

• Kramarova, Eugene P
• Borisevich, Sophia S
• Khamitov, Edward M
• Korlyukov, Alexander A
• Dorovatovskii, Pavel V
• Shagina, Anastasia D
• Mineev, Konstantin S
• Tarasenko, Dmitri V
• Novikov, Roman A
• Lagunin, Alexey A
• Boldyrev, Ivan
• Ezdoglian, Aiarpi A
• Karpechenko, Natalia Yu
• Shmigol, Tatiana A
• Baukov, Yuri I
• Negrebetsky, Vadim V

Titel

Pyridine Carboxamides Based on Sulfobetaines: Design, Reactivity, and Biological Activity

Ist Teil von

• Molecules (Basel, Switzerland), 2022-11, Vol.27 (21), p.7542

Ort / Verlag

Basel: MDPI AG

Erscheinungsjahr

2022

Quelle

EZB-FREE-00999 freely available EZB journals

Beschreibungen/Notizen

• The synthesis of the products of the 1,3-propanesultone ring opening during its interaction with amides of pyridinecarboxylic acids has been carried out. The dependence of the yield of the reaction products on the position (ortho-, meta-, para-) of the substituent in the heteroaromatic fragment and temperature condition was revealed. In contrast to the meta- and para-substituted substrates, the reaction involving ortho-derivatives at the boiling point of methanol unexpectedly led to the formation of a salt. On the basis of spectroscopic, X-Ray, and quantum-chemical calculation data, a model of the transition-state, as well as a mechanism for this alkylation reaction of pyridine carboxamides with sultone were proposed in order to explain the higher yields obtained with the nicotinamide and its N-methyl analog compared to ortho or meta parents. Based on the analysis of ESP maps, the positions of the binding sites of reagents with a potential complexing agent in space were determined. The in silico evaluation of possible biological activity showed that the synthetized compounds revealed some promising pharmacological effects and low acute toxicity.