54448-50-9

Basic information

• Product Name: 1,2,4-Benzotriazine, 3-chloro-7-methyl-, 1-oxide
• Synonyms: 3-chloro-7-methylbenzo[e][1,2,4]triazine 1-oxide;3-chloro-7-methyl-1,2,4-benzotriazin 1-oxide;1,2,4-Benzotriazine,3-chloro-7-methyl-,1-oxide;3-chloro-7-methyl-1,2,4-benzotriazine 1-oxide
• CAS NO: 54448-50-9
• Molecular Formula: C8H6ClN3O
• Molecular Weight: 195.608
• Mol File: 54448-50-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1,2,4-Benzotriazine, 3-chloro-7-methyl-, 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-Benzotriazine, 3-chloro-7-methyl-, 1-oxide(54448-50-9)
• EPA Substance Registry System: 1,2,4-Benzotriazine, 3-chloro-7-methyl-, 1-oxide(54448-50-9)

Safety Data

• Hazardous Substances Data: 54448-50-9(Hazardous Substances Data)

Usage

Uses

3-Chloro-7-methyl-1,2,4-benzotriazine 1-Oxide is an intermediate in the synthesis of Azapropazone which is a non-steroidal anti-inflammatory drug.

Upstream product

• 27446-11-3 7-Methyl-1-oxy-4H-benzo[1,2,4]triazin-3-one 
• 27446-11-3 7-methyl-1-oxy-4H-benzo[e][1,2,4]triazin-3-one 
• 27281-74-9 3-Amino-7-methylbenzo-1,2,4-triazin 1-Oxide 

Downstream Products

• 921933-29-1 C₁₅H₁₄N₄O 
• 1259019-65-2 3-(1-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)-2-methoxy-2-oxoethyl)-7-methylbenzo[e][1,2,4]triazine 1-oxide 

Relevant articles and documents

Stille coupling reactions in the synthesis of hypoxia-selective 3-alkyl-1,2,4-benzotriazine 1,4-dioxide anticancer agents

The introduction of a 3-alkyl substituent is a key step in the synthesis of 1,2,4-benzotriazine 1,4-dioxide hypoxia-selective anticancer agents, such as SN29751. The Stille reaction of 3-chloro-1,2,4-benzotriazine 1-oxides (BTOs) 5 was inhibited by the presence of electron donating substituents on the benzo ring, thus limiting the range of compounds available for SAR studies. The use of 3-iodo-BTOs 8 did not provide a significant improvement in the yields of 3-ethyl-BTOs 6. Microwave-assisted Stille coupling of chlorides 5 gave dramatically improved yields, which were consistently superior to those from the corresponding iodides 8. The application of microwave-assisted synthesis extended the range of substituted BTOs available for SAR studies and provided an efficient, scalable synthesis of the investigational anticancer agent, SN29751 (1).

NOVEL 1,2,4-BENZOTRIAZINE-1,4-DIOXIDES

The present invention provides a simplified set of characteristics that can be used to select 1,2,4 benzotriazine 1,4 dioxide compounds (TPZ analogues) with therapeutic activity against hypoxic cells in human tumour xenografts, and to further provide a no

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.