Synthesis, spectroscopic, in vitro cytotoxicity and crystal structures of novel fluorinated dispiroheterocycles: DFT approach

Satheeshkumar R., SAYIN K., Kaminsky W., Prasad K. J. R.

MONATSHEFTE FUR CHEMIE, cilt.149, sa.1, ss.141-147, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 149 Sayı: 1
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1007/s00706-017-2050-5
  • Dergi Adı: MONATSHEFTE FUR CHEMIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.141-147
  • Sivas Cumhuriyet Üniversitesi Adresli: Evet

Özet

The reaction of azomethine ylide generated in situ from ninhydrin and sarcosine/thiaproline with fluorinated cyclopent[b]indole dipolarophiles in refluxing dioxane and methanol afforded a novel class of fluorinated cyclopent[b]indole dispiroheterocycles via 1,3-dipolar cycloaddition. The crystal structures of 4'-[4-(trifluoromethyl)phenyl]-1',5-dimethyl-2,3-dihydrodispiro[cyclopent[b]-indol-2,3'-pyrrolidine-2',2aEuro(3)-indene]-1,1aEuro(3),3aEuro(3)-trione and 4'-(4-fluorophenyl)-5-methyl-2,3-dihydrodispiro[cyclopent[b]indol-2,3'-pyrrolizidine-2',2aEuro(3)-indene]-1,1aEuro(3),3aEuro(3)-trione are reported. New compounds are investigated theoretically via DFT calculations utilizing M062X hybrid function with 6-311++G(d,p) basis sets in vacuum. Results from in vitro cytotoxicity screening are compared with those of standard drugs.