93006-85-0

Upstream product

• 4217-66-7 1,2-dihydroxy-2-phenylpropane 
• 98-59-9 p-toluenesulfonyl chloride 
• 515-30-0 2-phenyllactic acid 
• 20731-95-7 methyl 2-hydroxy-2-phenylpropanoate 

Downstream Products

• 1187978-26-2 5-methyl-5-phenyl-3-m-tolyloxazolidin-2-one 

Relevant academic research and scientific papers

Dibutyltin oxide catalyzed selective sulfonylation of α-chelatable primary alcohols

(equation presented) The reaction of substituted glycols with catalytic dibutyltin oxide, stoichiometric p-toluenesulfonyl chloride, and triethylamine in CH2Cl2 resulted in the complete and rapid sulfonylation at the primary alcohol. The α-heterosubstituted primary alcohol moiety appeared optimal for best results, supporting the intermediacy of a five-membered chelate. The role of the amine is discussed, in addition to catalyst requirements and solvent effects.

Development of novel LP1-based analogues with enhanced delta opioid receptor profile

Pain relief achieved by co-administration of drugs acting at different targets is more effective than that obtained with conventional MOR selective agonists usually associated to relevant side effects. It has been demonstrated that simultaneously targeting different opioid receptors is a more effective therapeutic strategy. Giving the promising role for DOR in pain management, novel LP1-based analogues with different N-substituents were designed and synthesized with the aim to improve DOR profile. For this purpose, we maintained the phenyl ring in the N-substituent of 6,7-benzomorphan scaffold linked to an ethyl spacer bearing a hydroxyl/methyl or methoxyl group at carbon 2 or including it in a 1,4-benzodioxane ring. LP1 analogues were tested by competition binding assays. Compounds 6 (KiMOR = 2.47 nM, KiDOR = 9.6 nM), 7 (KiMOR = 0.5 nM and KiDOR = 0.8 nM) and 9 (KiMOR = 1.08 nM, KiDOR = 6.6 nM) retained MOR affinity but displayed an improved DOR binding capacity as compared to LP1 (KiMOR = 0.83 nM, KiDOR = 29.1 nM). Moreover, GPI and MVD functional assays indicated that compounds 6 (IC50 = 49.2 and IC50 = 10.8 nM), 7 (IC50 = 9.9 and IC50 = 11.8 nM) and 9 (IC50 = 21.5 and IC50 = 4.4 nM) showed a MOR/DOR agonist profile, unlike LP1 that was a MOR agonist/DOR antagonist (IC50 = 1.9 and IC50 = 1240 nM). Measurements of their antinociceptive effect was evaluated by mice radiant tail flick test displaying for compounds 6, 7 and 9 ED50 values of 1.3, 1.0 and 0.9 mg/kg, i.p., respectively. Moreover, the antinociceptive effect of compound 9 was longer lasting with respect to LP1. In conclusion the N-substituent nature of compounds 6, 7 and 9 shifts the DOR profile of LP1 from antagonism to agonism.

INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1

This invention relates to novel compounds of the Formula (I) and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of

A concise synthesis of (S)-(+)-1-(4-{2-[bis-(4-fluorophenyl)methoxy]-ethyl} piperazin-1-yl)-2-phenylpropan-2-ol dimaleate

(S)-(+)-1-(4-{2-[Bis-(4-fluorophenyl)methoxy]-ethyl}piperazin-1-yl) -2-phenylpropan-2-ol dimaleate was prepared in several steps from (S)-(+)-atrolactic acid by a process permitting synthesis of multigram quantities. With the information provided by asymmetric synthesis, the X-ray crystal structure was solved.

Catalytic regioselective sulfonylation of α-chelatable alcohols: Scope and mechanistic insight

This paper describes a convenient protocol for the regioselective sulfonylation of α-chelatable alcohols. Typically, the reaction of α-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pKa of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of 119Sn NMR studies.

Selective sulfonylation of 1,2-diols and derivatives catalyzed by a recoverable fluorous tin oxide

Fluorous tin oxide (C6F13CH2CH2)2SnO is readily synthesized, exhibits spectra that are generally similar to dibutyltin oxide and appears to exist as an oligomer or polymer. The fluorous tin oxide can be used catalytically to effect the selective monotosylation of 1,2-diols with TsCl/Et3N, and it can be readily recovered and reused. (C) 2000 Published by Elsevier Science Ltd.