81580-84-9

Basic information

• Product Name: 4-(2',3'-dimethoxyphenyl)-3-butenoic acid
• Synonyms: 4-(2',3'-dimethoxyphenyl)-3-butenoic acid
• CAS NO: 81580-84-9
• Molecular Weight: 222.241
• Mol File: 81580-84-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-(2',3'-dimethoxyphenyl)-3-butenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2',3'-dimethoxyphenyl)-3-butenoic acid(81580-84-9)
• EPA Substance Registry System: 4-(2',3'-dimethoxyphenyl)-3-butenoic acid(81580-84-9)

Safety Data

• Hazardous Substances Data: 81580-84-9(Hazardous Substances Data)

Upstream product

• 51114-94-4 (2-carboxyethyl)triphenylphosphonium bromide 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 845519-27-9 2-(2,3-dimethoxyphenyl)-5-oxo-tetrahydrofuran-3-carboxylic acid 

Downstream Products

• 24039-89-2 5,6-dimethoxy-1-tetralone 
• 59515-92-3 5,6-dihydroxy-3,4-dihydronaphthalen-1(2H)-one 
• 64400-76-6 4-(2',3'-dimethoxyphenyl)-3-butanoic acid 

Relevant articles and documents

Mapping the catechol binding site in dopamine D1 receptors: Synthesis and evaluation of two parallel series of bicyclic dopamine analogues

A novel class of isochroman dopamine analogues, originally reported by Abbott Laboratories, have >100-fold selectivity for D1-like over D2-like receptors. We synthesized a parallel series of chroman compounds and showed that repositioning the oxygen atom in the heterocyclic ring decreases potency and confers D2-like receptor selectivity to these compounds. Insilico modeling supports the hypothesis that the altered pharmacology for the chroman series is due to potential intramolecular hydrogen bonding between the oxygen in the chroman ring and the meta-hydroxy group of the catechol moiety. This interaction realigns the catechol hydroxy groups and disrupts key interactions between these ligands and critical serine residues in TM5 of the D1-like receptors. This hypothesis was tested by the synthesis and pharmacological evaluation of a parallel series of carbocyclic compounds. Our results suggest that if the potential for intramolecular hydrogen bonding is removed, D1-like receptor potency and selectivity are restored. What a difference an H bond makes: Structurally related chromans, isochromans, and their carbocyclic analogues were assessed for dopamine D1 and D2 receptor affinity. Isochromans and carbocyclic analogues had high D1 receptor affinity. Poor affinity for the chromans was attributed to an intramolecular hydrogen bond, which disrupts the ligand-receptor hydrogen bonding network.

OCTAHYDROBENZOISOQUINOLINE MODULATORS OF DOPAMINE RECEPTORS AND USES THEREFOR

Octahydrobenzoisoquinoline modulators of dopamine receptors are described herein. Methods for using octahydrobenzoisoquinoline modulators of dopamine receptors in the treatment of dopamine dysfunction are also described herein.

Inhibitors of Bllod Platelet Aggregation. Activity of Some 1H-Benzisoquinolinecarboximidamides on the in Vivo Blood Platelet Aggregation Induced by Collagen

A series of 33-1H-benzisoquinolinecarboximidamides has been prepared and tested in the rat after intraperitoneal (ip) and/or oral (po) administration for their ability to inhibit the in vivo blood platelet aggregation induced by colagen.In this aggregation test, a considerable number of active compounds were found.Fourteen compounds were active when administred ip , five of which also exhibited significant po activity.One compound was toxic after ip administration but was found to be active after po administration without apparent toxicity.Itis thought that the solubility of the drug in water is an important factor for the resorption after oral administration and, hence, for its oral activity.