205499-60-1

Basic information

• Product Name: 2-benzylsulfinylphenylmethanol
• Synonyms: 2-benzylsulfinylphenylmethanol
• CAS NO: 205499-60-1
• Molecular Weight: 246.33
• Mol File: 205499-60-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-benzylsulfinylphenylmethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzylsulfinylphenylmethanol(205499-60-1)
• EPA Substance Registry System: 2-benzylsulfinylphenylmethanol(205499-60-1)

Safety Data

• Hazardous Substances Data: 205499-60-1(Hazardous Substances Data)

Upstream product

• 4521-45-3 2-(phenylmethylthio)benzenemethanol 
• 1531-80-2 2-(benzylthio)benzoic acid 
• 100-39-0 benzyl bromide 
• 4521-31-7 o-hydroxymethyl thiophenol 

Downstream Products

• 100-52-7 benzaldehyde 
• 205499-67-8 2-phenyl-4H-3,1-benzoxathiin 

Relevant articles and documents

Cyclic analogue of S-benzylisothiourea that suppresses kynurenine production without inhibiting indoleamine 2,3-dioxygenase activity

Kynurenine is biosynthesised from tryptophan catalysed by indoleamine 2,3-dioxygenase (IDO). The abrogation of kynurenine production is considered a promising therapeutic target for immunological cancer treatment. In the course of our IDO inhibitor programme, formal cyclisation of the isothiourea moiety of the IDO inhibitor 1 afforded the 5-Cl-benzimidazole derivative 2b-6, which inhibited both recombinant human IDO (rhIDO) activity and cellular kynurenine production. Further derivatisation of 2b-6 provided the potent inhibitor of cellular kynurenine production 2i (IC50 = 0.34 μM), which unexpectedly exerted little effect on the enzymatic activity of rhIDO. Elucidation of the mechanism of action revealed that compound 2i suppresses IDO expression at the protein level by inhibiting STAT1 expression in IFN-γ-treated A431 cells. The kynurenine-production inhibitor 2i is expected to be a promising starting point for a novel approach to immunological cancer treatment.

A one step conversion of sulfoxides to aldehydes by the neighboring group participation in the pummerer rearrangement of ortho-hydroxymethyl aryl benzyl sulfoxides

Benzyl 2-(hydroxymethyl)phenyl sulfoxides (1) treated with ptoluenesulfonic acid monohydrate (TsOH?H2O) undergo the Pummerer-type rearrangement to give benzaldehydes in one step. The reaction was found to proceed via the oxosulfonium salt (6) as an intermediate.