- Synthesis, spectroscopic characterization, and computational studies of 2-cyano-6-hydroxybenzothiazole: A key synthetic intermediate of firefly luciferin
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Firefly luciferin is widely applied as a biotechnological tool for visualizing various biological processes in vitro and in vivo. Chemically, 2-cyano-6-hydroxybenzothiazole, as a key synthetic intermediate of firefly luciferin, is obtained from 2-cyano-6-methoxybenzothiazole by changing the methoxy with a hydroxy group. However, this approach is costly and not suited for large-scale synthesis. Here we report cost-effective and efficient syntheses of 2-cyano-6-hydroxybenzothiazole through the catalytic Sandmeyer-type cyanation reaction. Our approach employs diazonium tetrafluoroborate salt of 2-amino-6-hydroxybenzothiazole as a cyanation substrate. The cyanation reaction proceeds efficiently under mild conditions by using Cu(I)/Cu(II)/N,N,N',N'-tetramethylethylenediamine as a catalyst. In addition, computational studies of the 2-cyano-6-hydroxybenzothiazole structure were performed based on the density functional theory method. The theoretical parameters of the optimized geometry were derived from the B3LYP/6-311 ++ G(d, p) method. Time-dependent density functional theory was applied to assign the electronic absorption bands observed experimentally and the1 H NMR chemical shifts were computed using the GIAO method. There was a significant relationship between computational studies and experimental results.
- Shahmoradi, Ghasem,Amani, Saeid
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p. 1499 - 1517
(2019/01/03)
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- SOLID FORMS COMPRISING N-(5-TERT-BUTYL-ISOXAZOL-3-YL)-N'-{4-[7-(2-MORPHOLIN-4-YL-ETHOXY)IMIDAZO[2,1-B][1,3]BENZOTHIAZOL-2-YL]PHENYL}UREA, COMPOSITIONS THEREOF, AND USES THEREWITH
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Solid forms comprising N-(5-tert-butyl-isoxazol-3-yl)-N'-{4-[7-(2-morpholin- 4-yl-ethoxy)imidazo[2,l-b][l,3]benzothiazol-2-yl]phenyl}urea, compositions comprising the solid forms, methods of making the solid forms and methods of their use for the treatmen
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Page/Page column 84
(2009/04/25)
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- Imidazolothiazole compounds for the treatment of disease
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Compounds, compositions and methods are provided for modulating the activity of receptor kinases and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder mediated by receptor kinases.
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Page/Page column 39
(2008/06/13)
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