10554-65-1

Usage

Uses

6-(2-Nitrovinyl)-1,4-benzodioxan can be prepared to have anti-parasitic activity.

InChI:InChI=1/C10H9NO4/c12-11(13)4-3-8-1-2-9-10(7-8)15-6-5-14-9/h1-4,7H,5-6H2/b4-3+

Upstream product

• 29668-44-8 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 75-52-5 nitromethane 

Downstream Products

• 380636-86-2 6-(3,4,5-trimethoxyphenyl)-2,3-dihyhydro[1,4]dioxino[2,3-g]isoquinoline 
• 380636-90-8 6-(3,4,5-trimethoxyphenyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline 
• 10554-64-0 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethan-1-amine 
• 1026151-62-1 4-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-2-(4-methoxy-phenyl)-4,5-dihydro-3H-pyrrole-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Substituted tetrahydroisoquinolines: synthesis, characterization, antitumor activity and other biological properties

This work deals with the molecular design, synthesis and biological activity of a series of tetrahydro[1,4]dioxanisoquinolines and dimethoxyisoquinoline analogues. This study describes the synthesis strategy of these potential antitumor compounds, their multi-step synthesis and their optimization. A series of tetrahydroisoquinolines was synthesized and their cytotoxicity evaluated. Some of these tetrahydroisoquinolines showed promising KRas inhibition, antiangiogenesis activity and antiosteoporosis properties. Molecular modeling studies showed that compound 12 bind in the p1 pocket of the KRas protein making interactions with the hydrophobic residues Leu56, Tyr64, Tyr71 and Thr74 and hydrogen bonds with residues Glu37 and Asp38.

N-heterocyclic derivatives as NOS inhibitors

N-Heterocyclic derivatives of the formula (I): are described herein, as well as other N-heterocycles, as inhibitors of nitric oxide synthase. Pharmaceutical compositions containing these compounds, methods of using these compounds as inhibitors of nitric oxide synthase and processes for synthesizing these compounds are also described herein.

Pyrrolidine-3-carboxylic acids as endothelin antagonists. 5. Highly selective, potent, and orally active ETA antagonists

The synthesis and structure-activity relationships (SAR) of a series of pyrrolidine-3-carboxylic acids as endothelin antagonists are described. The data shows an increase in selectivity when the methoxy of Atrasentan (ABT-627) is replaced with methyl, and the benzodioxole is replaced with dihydrobenzofuran. Adding a fluorine further increases the binding activity and provides a metabolically stable and orally bioavailable ETA-selective antagonist.

Potent and selective non-benzodioxole-containing endothelin-A receptor antagonists

The benzodioxole ((methylenedioxy)benzene) group is present in a number of endothelin (ET) receptor antagonists thus far reported. As part of our own endothelin antagonist program we have developed (2R*,3R*,4S*)-1-(N,N- dibutylacetamido)-4-(1,3-benzodioxol-5-yl)-2-(4-methoxyphenyl)pyrrolidine-3- carboxylic acid (A-127722). This is a potent antagonist, binding to the ET(A) and ET(B) receptor subtypes with affinities (IC50) of 0.4 and 520 nM, respectively, and also contains the aforementioned benzodioxole. While this compound was seemingly optimized at its N-terminus, no effort had been directed toward understanding the contributions to binding affinity or receptor subtype selectivity conferred by the benzodioxole. Substitution by 1- or 2-naphthyl yielded weak antagonists. Oxygenated benzenes, such as p- anisyl, were potent compounds with IC50s in the low-nanomolar range. Simple deletion of either of the two oxygen atoms (dihydrobenzofurans) yielded extremely potent agents, possessing subnanomolar affinity for the ET(A) receptor. Additionally, the compounds showed enhanced selectivity, binding to the ET(B) receptor subtype in the micromolar range. This paper describes the development of this novel class of compounds.