Synthesis and alkylation of 6-(1H-benzimidazol-2-yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-ones

Authors

  • S. V. Vlasov National University of Pharmacy, Ukraine
  • S. M. Kovalenko National University of Pharmacy, Ukraine
  • V. P. Chernykh National University of Pharmacy, Ukraine
  • K. Yu. Krolenko National University of Pharmacy, Ukraine

DOI:

https://doi.org/10.24959/ophcj.15.822

Keywords:

thiophene, pyrimidine, imidazole, alkylation

Abstract

The one-step method for preparation of 6-(1H-benzimidazol-2-yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-ones by interaction of 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid with ortho-pnenylediamines using 1,1’-carbonyldiimidazole as a coupling-reagent has been developed. The procedure proposed allows to obtain easily the target products using common reagents and solvents; and it also requires the simple isolation methods. The selectivity of 6-(1H-benzimidazol-2-yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one interaction with benzyl chlorides in DMF – K2CO3 conditions has been studied using the NOESY spectroscopic method and alternative synthetic approaches; it has been determined that the reaction occurs at position 3 of the thieno[2,3-d] pyrimidine system. The study of the antimicrobial activity by the agar diffusion method for the compounds obtained has shown that 6-(1H-benzimidazol-2-yl)-3-benzyl-5-methylthieno[2,3-d]pyrimidin-4(3H)-ones reveal the antimicrobial activity against the strains of Escherichia coli, Proteus vulgaris, Pseudomonas aeruginosa; while the compound with unsubstituted position 3 appeared to be inactive against these strains of microorganisms. However, this compound exhibited the higher inhibitory activity against the Candida albicans fungi.

Downloads

Download data is not yet available.

References

  1. Пат. DE2411273 (1975). Заявл.: 06.03.1974. Опубл.: 18.09.1975. Chem. abs. vol. 83, №206324. [Электронный ресурс] Режим доступа http:// worldwide.espacenet.com/publicationDetails/originalDocument?CC=DE&NR=2411273A1&KC=A1&FT=D&ND=3&date=19750918&DB=EPODOC&locale=en_EP.
  2. Пат. US2013/123231 (2013). Заявл.: 09.11.2012. Опубл.: 16.05.2013. [Электронный ресурс] Режим доступа http://worldwide.espacenet.com/ publicationDetails/originalDocument?CC=US&NR=2013123231A1&KC=A1&FT=D&ND=3&date=20130516&DB=EPODOC&locale=en_EP.
  3. Пат. US 2007208040 (2007). Заявл.: 02.03.2007. Опубл.: 06.09.2007. [Электронный ресурс] Режим доступа http://worldwide.espacenet.com/ publicationDetails/originalDocument?CC=US&NR=2007208040A1&KC=A1&FT=D&ND=3&date=20070906&DB=EPODOC&locale=en_EP.
  4. Lu J., Yang B., Bai Y. Synth. Commun., 2002, Vol. 32, No.24, pp.3703-3710.
  5. Lim C. J., Kim N., Lee E. K. et al. Bioorg. Med. Chem. Lett., 2011, Vol. 21, No.8, pp.2309-2312.
  6. Sluka J., Danek J., Bedrnik P., Budesinsky Z. Collect. Czech. Chem.Commun., 1981,. Vol. 46, No.11, pp.2703-2708.
  7. Lee I.-S. H., Jeoung E. H., Kreevoy M. M. J. Am. Chem. Soc., 1997, Vol. 119, No.11, pp.2722-2728.
  8. Pareek S., Vyas S., Seth G., Vyas P. C. Heteroact. Chem., 2008, Vol. 19, No.2, pp.154-157.
  9. Grinev A. N., Kaplina N. V. Chem. of Heterocycl. Compnd., 1985, Vol. 21, No.7, pp.767-770.
  10. Clinical and Laboratory Standards Institute. Performance Standards for Antimicrobial Susceptibility Testing; Twenty-Second Informational Supplement. Document M100-S22, 2012, Vol. 32, No.3, CLSI, Wayne, PA, January.
  11. American Society for Microbiology, Coyle M.B. Manual of Antimicrobial Susceptibility Testing. American Society for Microbiology: Washington; 2005, p.236.

Downloads

Published

2015-06-10

How to Cite

(1)
Vlasov, S. V.; Kovalenko, S. M.; Chernykh, V. P.; Krolenko, K. Y. Synthesis and Alkylation of 6-(1H-Benzimidazol-2-Yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-Ones. J. Org. Pharm. Chem. 2015, 13, 30-34.

Issue

Section

Original Researches