Synthesis and antimicrobial activity of novel fused [1,2,4]triazino[5,6-b]indole derivatives
- Authors: Al Osaimi A.G.1, Ali R.S.1,2, Saad H.A.1, El Sayed Aly M.R.1,3
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Affiliations:
- Chemistry Department, Faculty of Science
- Department of Basic Science
- Chemistry Department, Faculty of Applied Science
- Issue: Vol 87, No 6 (2017)
- Pages: 1246-1255
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/220284
- DOI: https://doi.org/10.1134/S1070363217060202
- ID: 220284
Cite item
Abstract
Synthesis of new fused systems of triazino[5,6-b]indole starting with preparation of 3-amino[1,2,4]-triazino[5,6-b]indole 1 by reaction of isatin with 2-aminoguanidinium carbonate in boiling acetic acid is presented [1]. Intermediate compound 1 reacted with aldehyde, ethyl chloroformate, triethyl orthoformate, and ninhydrine and gave new heterotetracyclic nitrogen systems, such as 3-(N2-guanidinylimino)indole-2(1H)-one 2, 3-(N-ethoxycarbonylamino)-4H-[1,2,4]triazino[5,6-b]indole 3, 3-(N-ethoxymethyleneamino)-4H-[1,2,4]-triazino[5,6-b]indole 4, 3-(hydrazinothiocarbonylamino)-4H-[1,2,4]triazino[5,6-b]indole 5, respectively. N-(1,3-dioxoindene-2-ylidene)-4H-[1,2,4]triazino[5,6-b]indol-3-amine 6 was synthesized by reaction of compound 1 with aldehyde, ethyl chloroformate, triethyl orthoformate, and ninhydrine. New fused indole systems, pyrimido[2′,1′:3,4][1,2,4]triazino[5,6-b]indol-3(4H)-one 8, 9, 11, 12 and 1H-imidazo[2′,1′:3,4][1,2,4]triazino-[5,6-b]indol-2(3H)-one 10, were synthesized in the reaction of the intermediate 1 with bifunctional compounds. Structures of the products were elucidated from their elemental analysis and spectral data (IR, 1H and 13C NMR and mass spectra). Antimicrobial activity of some synthesized compounds was tested.
About the authors
A. G. Al Osaimi
Chemistry Department, Faculty of Science
Email: raniaelatar2010@gmail.com
Saudi Arabia, Taif, 21974
R. S. Ali
Chemistry Department, Faculty of Science; Department of Basic Science
Author for correspondence.
Email: raniaelatar2010@gmail.com
Saudi Arabia, Taif, 21974; Cairo
H. A. Saad
Chemistry Department, Faculty of Science; Chemistry Department, Faculty of Science
Email: raniaelatar2010@gmail.com
Saudi Arabia, Taif, 21974; Zagazig
M. R. El Sayed Aly
Chemistry Department, Faculty of Science; Chemistry Department, Faculty of Applied Science
Email: raniaelatar2010@gmail.com
Saudi Arabia, Taif, 21974; Port Said