83648-76-4

Upstream product

• 68767-14-6 loxoprofen 
• 89675-47-8 methyl 2-<4-(trans-2-acetoxycyclopentylmethyl)phenyl>propionate 
• 89631-53-8 methyl 2-<4-(cis-2-acetoxycyclopentylmethyl)phenyl>propionate 
• 83599-42-2 (2S)-2-<4-((1R)-2-oxocyclopentylmethyl)phenyl>propionic acid 
• 72748-99-3 (R)-1-Amino-2-(methoxymethyl)pyrrolidine 
• 589-29-7 p-xylylene glycol 
• 1333080-48-0 4-((4-methoxybenzyloxy)methyl)benzaldehyde 
• 1333080-45-7 (R)-2-[4-((S)-2-hydroxy-1-methylethyl)benzyl]cyclopentanone 
• 1333080-43-5 C₃₁H₃₈O₂Si 
• 1333080-42-4 [(S)-2-(4-bromomethylphenyl)propoxy]-tert-butyldiphenylsilane 
• 1333080-41-3 {4-[(S)-2-(tert-butyldiphenylsilanyloxy)-1-methylethyl]phenyl}methanol 
• 1333080-40-2 tert-butyl{(S)-2-[4-(4-methoxybenzyloxymethyl)phenyl]propoxy}diphenylsilane 
• 1333080-39-9 (S)-2-(4-(4-methoxybenzyloxy)phenyl)propan-1-ol 
• 1333080-31-1 (4-((4-methoxybenzyloxy)methyl)phenyl)methanol 

Downstream Products

• 88378-27-2 {2-[4-((1S,2R)-2-Hydroxy-cyclopentylmethyl)-phenyl]-propionylamino}-acetic acid 
• 88378-26-1 2-{2-[4-((1S,2R)-2-Hydroxy-cyclopentylmethyl)-phenyl]-propionylamino}-ethanesulfonic acid 
• 88378-29-4 {2-[4-((1R,2S)-2-Acetoxy-cyclopentylmethyl)-phenyl]-propionylamino}-acetic acid ethyl ester 
• 89631-57-2 methyl (+/-)-2-<4-(trans-2-hydroxycyclopentylmethyl)phenyl>propionate 
• 89631-57-2 methyl (+/-)-2-<4-(cis-2-hydroxycyclopentylmethyl)phenyl>propionate 
• 290331-99-6 Acetic acid (1S,2R)-2-{4-[(S)-1-((S)-1-phenyl-ethylcarbamoyl)-ethyl]-benzyl}-cyclopentyl ester 
• 88378-28-3 2-[4-((1R,2S)-2-Acetoxy-cyclopentylmethyl)-phenyl]-propionic acid 

Relevant academic research and scientific papers

Asymmetric synthesis of the active form of loxoprofen and its analogue

The asymmetric synthesis of the active form of the antiinflammatory drug loxoprofen has been reported in this article. Enzymatic kinetic resolution/racemization of a substituted homo-benzylic primary alcohol with lipase-PS, asymmetric alkylation of cyclic ketones using either Enders' or Meyers' strategy followed by a stereoselective biocatalytic reduction of carbonyl group are the key reactions employed successfully to achieve the target molecule and one of its analogue.

Properties and synthesis of 2-{2-fluoro (or bromo)-4-[(2-oxocyclopentyl) methyl]phenyl}propanoic acid: Nonsteroidal anti-inflammatory drugs with low membrane permeabilizing and gastric lesion-producing activities

We previously proposed that membrane permeabilization activity of NSAIDs is involved in NSAID-induced gastric lesions. We here synthesized derivatives of loxoprofen that have lower membrane permeabilization activity than other NSAIDs. Compared to loxoprofen, the derivatives 10a and 10b have lower membrane permeabilization activity and their oral administration produced fewer gastric lesions but showed an equivalent anti-inflammatory effect. These results suggest that 10a and 10b are likely to be therapeutically beneficial as safer NSAIDs.

Synthesis of the active form of loxoprofen by using allylic substitutions in two steps

High regioselectivity for allylic substitution of the cyclopentenyl picolinate 5 with benzylcopper reagent was attained with ZnBr2, and the finding was applied to the p-BrC6H4CH2 reagent. The cyclopentene moiety in the product was reduced to the cyclopentane, and the p-BrC6H4 was converted to the "Cu"C6H4 for the second allylic substitution with picolinate 8 to furnish the title compound after oxidative cleavage of the resulting olefin moiety.

Evaluation of loxoprofen and its alcohol metabolites for potency and selectivity of inhibition of cyclooxygenase-2

Loxoprofen, its trans-alcohol and cis-alcohol metabolites were evaluated for selectivity of inhibition of COX-2 over COX-1. The (2S,1′R,2′S)- trans-alcohol derivative was found to be the most active metabolite and to be a potent and nonselective inhibitor of COX-2 and COX-1 in both enzyme and human whole blood assays.

An efficient synthesis of (2S)-2-[4-((1R, 2S)-2- hydroxycyclopentylmethyl)phenyl]propionic acid

An efficient synthesis of (2S)-2-[4-((1R,2S)-2- hydroxycyclopentylmethyl)phenyl]propionic acid via lipase-catalyzed kinetic resolution of (-)-N-[(1S)-1-phenylethyl]-(±)-2-[4-(trans-2- hydroxycyclopentylmethyl)phenyl] propionamide is successfully accomplished.

Reduction of drug ketones by dihydrodiol dehydrogenases, carbonyl reductase and aldehyde reductase of human liver

In this study, we compared the enzymatic reduction of 10 drugs with a ketone group by homogeneous carbonyl reductase, aldehyde reductase and three dihydrodiol dehydrogenases of human liver cytosol. At least one and in some cases all of the three dihydrodi

Synthesis of the eight possible optically active isomers of 2-[4-(2-hydroxycyclopentylmethyl)phenyl]propionic acid

A recently synthesized compound, (±)-2-[4-(2-oxocyclopentylmethyl)phenyl]propionic acid, had good anti-inflammatory and analgesic activities. One of the metabolites of this compound showed more potent prostaglandin synthetase inhibitory activity than the