1245575-39-6

Basic information

• Product Name: 4-(2-(methylamino)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide
• Synonyms: 4-(2-(methylamino)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide
• CAS NO: 1245575-39-6
• Molecular Weight: 299.307
• Mol File: 1245575-39-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-(2-(methylamino)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-(methylamino)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide(1245575-39-6)
• EPA Substance Registry System: 4-(2-(methylamino)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide(1245575-39-6)

Safety Data

• Hazardous Substances Data: 1245575-39-6(Hazardous Substances Data)

Upstream product

• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 66074-00-8 3,4-bis(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide 

Relevant articles and documents

Design, synthesis and biological evaluation of nitro oxide donating N-hydroxycinnamamide derivatives as histone deacetylase inhibitors

Novel nitro oxide (NO)-donating N-hydroxycinnamamide derivatives 12a-j were designed and synthesized by coupling the carboxyl group of N-hydroxycinnamamides with phenylsulfonylfuroxan through various diols or alkylol amines, and their in vitro biological activities were evaluated. It was discovered that most of target compounds showed good histone deacetylases (HDACs) inhibition and anti-tumor activities, particularly for 12j, which had great HDACs inhibitory activities (IC50s=0.15-0.26 μm) and antiproliferative effects (IC50s=3.21-7.12 μm) comparable to suberoylanilide hydroxamic acid (SAHA) (IC50s=0.16-1.41 μm for HDACs, IC50s=3.15-7.45 μm for cancer cell inhibition). Furthermore, compound 12j with strong antitumor activities produced high levels of NO (up to 8.0 μm of nitrites/nitrates) in colon cancer cells, and its antiproliferative activity was nearly half-diminished by hemoglobin (10 μm), an NO scavenger. These results suggest that the strong antiproliferative activity of 12j could be attributed to the additive effects of high levels of NO production and inhibition of HDAC in the cancer cells.

Synthesis and in vitro biological evaluation of nitric oxide-releasing derivatives of hydroxylcinnamic acids as anti-tumor agents

Novel furoxan-based nitric oxide-releasing derivatives 6a-p of hydroxylcinnamic acids were synthesized by coupling the carboxyl group of hydroxylcinnamic acids with furoxan through various alkylol amines. Compounds 6a, e-i and m-p displayed more potent anti-tumor activities superior to control 5-fluorouracil (5-FU) in most cancer cells tested. Furthermore, 6f could selectively inhibit tumor cells, but not non-tumor cell proliferation. This inhibition was attributed to high levels of NO released in cancer cells and potentially synergistic effect of NO donor moieties and the bioactivity of hydroxylcinnamic acids.