Synthesis, characterization, anticancer, antimicrobial and carbonic anhydrase inhibition profiles of novel (3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl)acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives

KOÇYİĞİT, ÜMİT MUHAMMET; Budak, Yakup; Gurdere, Meliha Burcu; Tekin, Saban; Koprulu, Tugba Kul; Erturk, Fatih; Ozcan, Kezban; Gülçin, İlhami; Ceylan, Mustafa

doi:10.1016/j.bioorg.2016.12.001

Makale Tam Makale Uluslararası 2017

Synthesis, characterization, anticancer, antimicrobial and carbonic anhydrase inhibition profiles of novel (3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl)acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives

ÜMİT MUHAMMET KOÇYİĞİT, Yakup Budak, Meliha Burcu Gurdere, Saban Tekin, Tugba Kul Koprulu, Fatih Erturk, Kezban Ozcan, İlhami Gülçin, Mustafa Ceylan

Bioorganic Chemistry Cilt 70 · ss. 118–125 · 01.02.2017

DOI ile aç

Özet

In the present study, a series of new hybrid compounds containing chalcone and methanoisoindole units 7a-n ((3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl) acryloyl) phenyl)-3a, 4,7,7a-tetrahydro-1H-4,7-methanoisoin dole-1,3(2H)-dione) were synthesized, characterized and investigated for their anticancer activity against C6 gliocarcinoma cell in rats, and antimicrobial activity against some human pathogen microorganisms. The compounds 7e, 7h, 7j, 7k, 7L and 7n showed very high anticancer activity with the inhibition range of 80.51-97.02% compared to 5-FU. Some of the compounds exhibited anti-microbial activity. Also, they evaluated for inhibition effects against human carbonic anhydrase I, and II isoenzymes (hCA I and II) with Ki values in the range of 405.26-635.68 pM for hCA I, and 245.40-489.60 pM for hCA II, respectively. These results demonstrated that 3aR, 4S, 7R, 7aS)-2-(4-((E)-3-(3-aryl) acryloyl) phenyl)-3a, 4,7,7a-tetrahy dro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives could be used in different biomedical applications. (C) 2016 Elsevier Inc. All rights reserved.

Anahtar kelimeler

carbonic anhydrase antioxidant antimicrobial Butyrylcholinesterase ISOENZYMES I CHALCONE anticancer DISCOVERY CHALCONE DERIVATIVES SULFAMIDES POTENT ACETYLCHOLINE ESTERASE GLUTATHIONE-S-TRANSFERASE Isoindole Lactoperoxidase C6

Atıf için künye

KOÇYİĞİT, Ü. M., Budak, Y., Gurdere, M. B., Tekin, S., Koprulu, T. K., Erturk, F., Ozcan, K., Gülçin, İ., & Ceylan, M. (2017). Synthesis, characterization, anticancer, antimicrobial and carbonic anhydrase inhibition profiles of novel (3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl)acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives. Bioorganic Chemistry, 70, 118–125. https://doi.org/10.1016/j.bioorg.2016.12.001

BibTeX

@article{kocyigit2017-67998,
  author = {KOÇYİĞİT, ÜMİT MUHAMMET and Budak, Yakup and Gurdere, Meliha Burcu and Tekin, Saban and Koprulu, Tugba Kul and Erturk, Fatih and Ozcan, Kezban and Gülçin, İlhami and Ceylan, Mustafa},
  title = {Synthesis, characterization, anticancer, antimicrobial and carbonic anhydrase inhibition profiles of novel (3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl)acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives},
  journal = {Bioorganic Chemistry},
  year = {2017},
  volume = {70},
  pages = {118--125},
  issn = {0045-2068},
  doi = {10.1016/j.bioorg.2016.12.001},
  url = {https://akademik.atauni.edu.tr/yayinlar/67998-synthesis-characterization-anticancer-antimicrobial-and-carbonic-anhydrase}
}