A facile one-pot expeditious synthesis of triazolothiadiazines and anticancer activity. (27th May 2019)

• Record Type: Journal Article
• Authors: Arandkar, Varun; Vedula, Rajeswar Rao
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 194:Number 4/6(2019)
• Page Start: 533
• Page End: 539
• Publication Date: 2019-05-27
• Subjects: Traiazolothiadiazines -- phenacyl bromides -- multicomponent approach -- anticancer activity; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2018.1542394
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: A novel, one-pot, multicomponent synthesis of triazolothiadiazine derivatives have been achieved starting from 4-amino-4 H -1, 2, 4-triazole-3, 5-dithiol and variously substituted phenacyl bromides. The synthesis involves the simultaneous formation of two C–S and one C = N bond. The newly synthesized compounds were characterized by IR, 1 H NMR, 13 C NMR, and mass spectral data. The advantages of this method are good yields, high purity, shorter reaction times and simple purification technique. The synthesized target compounds were screened for their in vitro anticancer activity at concentration 10 −5 M against 60 cancer cell lines. Among all the compounds, 1-(4-Fluorophenyl)-2-((6-(4-fluorophenyl)-7H-[1, 2, 4]triazolo[3, 4-b][1, 3, 4]thiadiazin-3-yl) thio)ethanone (4d), 1-(4-Bromophenyl)-2-((6-(4-bromophenyl)-7H-[1, 2, 4]triazolo[3, 4-b][1, 3, 4]thiadiazin-3-yl)thio) ethanone (4f), and 2-((6-(4-Chlorophenyl)-7H-[1, 2, 4] triazolo[3, 4-b][1, 3, 4]thiadiazin-3-yl)thio)-1-(4-fluorophenyl)ethanone (4l) exhibited significant activity in terms of growth percent against renal cancer OU-31 cell line with 47.42%, 46.76%, 48.14%. The compound 2-((6-(4-Chlorophenyl)-7H-[1, 2, 4]triazolo[3, 4-b][1, 3, 4]thiadiazin-3-yl)thio)-1-(4-fluorophenyl) ethanone (4l) also exhibited significant activity on leukemia MOLT-4 cell line with 49.82%. Graphical Abstract: UF0001