Novel Benzylic Substituted Imidazolinium, Tetrahydropyrimidinium and Tetrahydrodiazepinium Salts: Potent Carbonic Anhydrase and Acetylcholinesterase Inhibitors

Creative Commons License

Yiğit B., Yiğit M., Barut Celepci D., Gök Y., Aktaş A., Aygün M., ...More

CHEMISTRYSELECT, vol.3, no.27, pp.7976-7982, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 3 Issue: 27
  • Publication Date: 2018
  • Doi Number: 10.1002/slct.201801019
  • Journal Name: CHEMISTRYSELECT
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7976-7982
  • Keywords: Acetylcholinesterase, carbonic anhydrase, crystal structure, enzyme inhibition, novel imidazolinium, HETEROCYCLIC CARBENE COMPLEXES, ANTIOXIDANT, BUTYRYLCHOLINESTERASE, BROMOPHENOLS, BIOACTIVITY, ISOENZYMES, CHLORIDES, ISOZYMES
  • Dokuz Eylül University Affiliated: Yes

Abstract

The new imidazolinium, tetrahydropyrimidinium and tetrahydrodiazepinium salts were synthesized in good yield by the reaction of the corresponding N,N'-dialkylalkanediamine with triethyl orthoformate in the presence of ammonium chloride. All of the compounds were obtained, and spectroscopically characterized. The crystal structure for the 1,3-bis(4-benzyloxy-3-methoxybenzyl)-3,4,5,6-tetrahydropyrimidinium chloride (5g) was determined by single-crystal X-ray diffraction. The biological properties of all novel compounds were tested and the influence of ring size and benzylic N-substituents on the biological activities were examined. Also, they were found as effective inhibitors against cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and acetylcholinesterase (AChE) enzyme. Among these compounds, 1,3-bis(4-(1-piperidinyl)benzyl)-3,4,5,6-tetrahydropyrimidinium chloride (5f) demonstrated the the best inhibition effects against hCA I, 1,3-bis(4-benzyloxy-3-methoxybenzyl)-3,4,5,6-tetrahydropyrimidinium chloride (5g) demonstrated the the best inhibition effects against cytosolic hCA II isoenzyme. On the other hand, 1,3-Bis(4-methylthiobenzyl)-3,4,5,6-tetrahydropyrimidinium chloride, (5e) demonstrated the the best inhibition effects against AChE enzyme.