Synthesis and antimicrobial activity of novel fused [1,2,4]triazino[5,6-b]indole derivatives
- Autores: Al Osaimi A.1, Ali R.1,2, Saad H.1, El Sayed Aly M.1,3
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Afiliações:
- Chemistry Department, Faculty of Science
- Department of Basic Science
- Chemistry Department, Faculty of Applied Science
- Edição: Volume 87, Nº 6 (2017)
- Páginas: 1246-1255
- Seção: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/220284
- DOI: https://doi.org/10.1134/S1070363217060202
- ID: 220284
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Resumo
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.
Sobre autores
A. Al Osaimi
Chemistry Department, Faculty of Science
Email: raniaelatar2010@gmail.com
Arábia Saudita, Taif, 21974
R. Ali
Chemistry Department, Faculty of Science; Department of Basic Science
Autor responsável pela correspondência
Email: raniaelatar2010@gmail.com
Arábia Saudita, Taif, 21974; Cairo
H. Saad
Chemistry Department, Faculty of Science; Chemistry Department, Faculty of Science
Email: raniaelatar2010@gmail.com
Arábia Saudita, Taif, 21974; Zagazig
M. El Sayed Aly
Chemistry Department, Faculty of Science; Chemistry Department, Faculty of Applied Science
Email: raniaelatar2010@gmail.com
Arábia Saudita, Taif, 21974; Port Said