166182-17-8Relevant academic research and scientific papers
Hypoxia-selective 3-alkyl 1,2,4-benzotriazine 1,4-dioxides: The influence of hydrogen bond donors on extravascular transport and antitumor activity
Hay, Michael P.,Pchalek, Karin,Pruijn, Frederik B.,Hicks, Kevin O.,Siim, Bronwyn G.,Anderson, Robert F.,Shinde, Sujata S.,Phillips, Victoria,Denny, William A.,Wilson, William R.
, p. 6654 - 6664 (2008/09/18)
Tirapazamine (TPZ) and related 1,2,4-benzotriazine 1,4 dioxides (BTOs) are selectively toxic under hypoxia, but their ability to kill hypoxic cells in tumors is generally limited by their poor extravascular transport. Here we show that removing hydrogen b
New and versatile syntheses of 3-alkyl- and 3-aryl-1,2,4-benzotriazine 1,4-dioxides: Preparation of the bioreductive cytotoxins SR 4895 and SR 4941
Hay, Michael P.,Denny, William A.
, p. 9569 - 9571 (2007/10/03)
Palladium-mediated coupling of 3-chloro-1,2,4-benzotriazine 1-oxide with a variety of stannanes in the presence of Pd(PPh3)4 gives 3-alkyl derivatives in good yields. Suzuki reaction of the 3-chloro compound with phenylboronic acids gives 3-aryl-1,2,4-benzotriazine 1-oxides. Oxidation of 1-oxides with trifluoroperacetic acid gives the 1,4-dioxides. This method provides a better route to the potential anti-cancer agents SR 4895 and SR 4941.
Process for preparing 1,2,4-benzotriazine oxides
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, (2008/06/13)
A method of using 1,2,4-benzotriazine oxides, some of which are novel compounds, as radiosensitizers and selective cytotoxic agents is disclosed. These compounds are shown to specifically radiosensitize hypoxic tumor cells. Some are additionally disclosed to be useful as specific cytotoxic agents for these cells. They also show an unexpected ability to radiosensitize aerobic cells following or preceding a hypoxic incubation of the cells with the drug. This provides a basis for selective radiosensitization of tumors compared to normal cells. A novel method for preparing the 1,2,4-benzotriazine oxides is also disclosed.
