753022-28-5

Basic information

• Product Name: (R)-3-(3-benzyloxy-2-naphthoxy)-1,2-propanediol
• Synonyms: (R)-3-(3-benzyloxy-2-naphthoxy)-1,2-propanediol
• CAS NO: 753022-28-5
• Molecular Weight: 324.376
• Mol File: 753022-28-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-3-(3-benzyloxy-2-naphthoxy)-1,2-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(3-benzyloxy-2-naphthoxy)-1,2-propanediol(753022-28-5)
• EPA Substance Registry System: (R)-3-(3-benzyloxy-2-naphthoxy)-1,2-propanediol(753022-28-5)

Safety Data

• Hazardous Substances Data: 753022-28-5(Hazardous Substances Data)

Upstream product

• 92-44-4 2,3-naphthalenediol 
• 100-44-7 benzyl chloride 
• 98793-02-3 3-benzyloxynaphthalen-2-ol 
• 83461-40-9 methanesulfonic acid (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 

Downstream Products

• 753022-30-9 (S)-3-(3-hydroxy-2-naphthoxy)-1,2-bis(tosyloxy)propane 
• 753023-11-9 (2S)-2-[((2-(2,6-dimethoxyphenoxy)ethyl)amino)methyl]-2,3-dihydronaphtho[2,3-b][1,4]dioxine 
• 753022-31-0 (R)-2-((tosyloxy)methyl)-2,3-dihydronaphtho[2,3-b][1,4]dioxine 
• 753022-29-6 (S)-3-(3-benzyloxy-2-naphthoxy)-1,2-bis(tosyloxy)propane 

Relevant articles and documents

Structure-affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the α1a-AR with respect to the other two α1 subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the α1a-AR, α1b-AR, α1d-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific α1a affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high α1a affinity of (S)-1 and its α1a versus α1b selectivity slightly increasing the α1a/α1d and α1a/5HT 1A affinity ratios. The SAR data were evaluated in the light of known α1 subtype pharmacophores and of the α1a-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models.