251322-95-9

Basic information

• Product Name: 3-amino-1,2,4-benzotriazine 4-oxide
• Synonyms: 3-amino-1,2,4-benzotriazine 4-oxide
• CAS NO: 251322-95-9
• Molecular Weight: 162.151
• Mol File: 251322-95-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-amino-1,2,4-benzotriazine 4-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-amino-1,2,4-benzotriazine 4-oxide(251322-95-9)
• EPA Substance Registry System: 3-amino-1,2,4-benzotriazine 4-oxide(251322-95-9)

Safety Data

• Hazardous Substances Data: 251322-95-9(Hazardous Substances Data)

Upstream product

• 20028-80-2 SR 4330 
• 27314-97-2 3-amino-1,2,4-benzotriazine-1,4-dioxide 

Relevant articles and documents

Time-resolved spectroscopy of the excited singlet states of tirapazamine and desoxytirapazamine

Laser flash photolysis (LFP, 400 nm excitation) of the anti-cancer drug tirapazamine (TPZ) in acetonitrile produces the singlet excited-state S 1 with λmax = 544 nm. The lifetime of this state is 130 ps, in good agreement with the reported fluorescence lifetime. The excited state is reduced to the corresponding radical anion by KSCN or KI. The spectrum of the radical anion is in good agreement with previously reported pulse radiolysis studies and time-dependent density functional theory (TD-DFT) calculations. LFP of desoxytirapazamine (dTPZ) also produces the first excited singlet state, S1. The fluorescence quantum yield and lifetime (5.4 ns) of the dTPZ singlet excited state are both much greater than the corresponding values of TPZ. This is explained by DFT calculations that predict that cyclization of TPZ to form an oxaziridine is thermodynamically facile but that cyclization of dTPZ to form an oxadiaziridine is not. Thus, the S 1 state of TPZ has a short lifetime and low fluorescence quantum yield due to ready cyclization whereas the cyclization of the S1 state of dTPZ is unimportant and does not limit either the fluorescence quantum yield or the fluorescence lifetime. This conclusion is confirmed by studies of dTPZ', an isomer of dTPZ containing the C=N-O moiety which has a low quantum yield and short fluorescence lifetime similar to that of TPZ.

Benzoazine mono-N-oxides and benzoazine 1,4 dioxides and compositions therefrom for the therapeutic use in cancer treatments

The present invention relates to a synergetistic composition comprising one or more benzoazine-mono-N-oxides, and one or more benzoazine 1,4 dioxides for use in cancer therapy. The invention also provides a range of novel 1,2,4 benzoazine-mono-N-oxides and related analogues. These can be used as potentiators of the cytotoxicity of existing anticancer drugs and therapies for cancer treatment.