121484-76-2

Upstream product

• 100-39-0 benzyl bromide 
• 14755-02-3 3-hydroxycinnamic acid 
• 621-54-5 3-(3-hydroxyphenyl)-propanoic acid 
• 96251-92-2 (E)-3-(3-hydroxyphenyl)acrylic acid ethyl ester 
• 34708-60-6 3-(3-hydroxy-phenyl)propionic acid ethyl ester 
• 14755-02-3 3-hydroxy-trans-cinnamic acid 
• 57668-34-5 3-(3-(benzyloxy)phenyl)propanoic acid 
• 100-44-7 benzyl chloride 
• 75849-10-4 ethyl 3-<3-(benzyloxy)phenyl>propanoate 

Downstream Products

• 1380328-05-1 (R)-2-((2R,3R)-7-(3-(benzyloxy)phenyl)-3-((4-methoxybenzyl)oxy)heptan-2-yl)oxirane 
• 1380328-08-4 (R)-7-(2-(((2R,4S,5R,6R)-6-(4-(3-(benzyloxy)phenyl)butyl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)methyl)-1,3-dithian-2-yl)-7-methyloct-1-en-4-ol 
• 1160697-43-7 ethyl 5-(3-(benzyloxy)phenyl)pentanoate 
• 1380327-88-7 (1R,3R,4R,5S,9R,13R)-9-(hydroxymethyl)-3-(4-(3-hydroxyphenyl)butyl)-4,16,16-trimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1^1,5]octadecane-7,11-dione 
• 75849-11-5 1-(benzyloxy)-3-(3-bromopropyl)benzene 
• 289034-17-9 C₁₈H₂₀O₂ 
• 1380328-03-9 (3S,4R)-8-(3-(benzyloxy)phenyl)-3-methyloct-1-en-4-ol 
• 946136-58-9 C₂₂H₂₇NO₂ 

Relevant academic research and scientific papers

SYNTHESIS AND CHEMISTRY OF AN IRON(III) TETRAPHENYLPORPHYRIN WITH A COVALENTLY-ATTACHED PHENOLATE TAIL

We report the synthesis of a phenolate-tailed iron(III) tetraphenylporphyrin, 1.The phenolate ligand is covalently-attached to the porphyrin ring and is coordinated to the iron(III) center.This phenolate ligand increases the rate of oxygen atom transfer to the metal center.

Improved and large-scale synthesis of 10-methyl-aplog-1, a potential lead for an anticancer drug

10-Methyl-aplog-1 (1), a simplified analog of tumor-promoting aplysiatoxin, is a potential lead for cancer therapy that exhibits marked and selective growth inhibitory effects against several human cancer cell lines and negligible tumor-promoting activity in vivo. However, more detailed evaluations of its toxicity and anticancer activity in vivo are hampered by supply problems associated with a non-optimal synthetic method. We here addressed this issue through a more practical and reliable synthetic method that afforded several hundred milligrams of 1 with high purity (>98%) in 23 steps from commercially available m-hydroxycinnamic acid with an overall yield of 1.1%. The utilization of two key reactions, substrate-controlled epoxidation and the oxidative cleavage of alkene with a free hydroxyl group, successfully reduced the existing five synthetic steps and markedly improved the handling of large amounts of intermediates. We also demonstrated for the first time that such an analog was synthetically accessible in reliable quantities and also that this large supply could advance in vivo trials for the treatment of cancer.

Macrocyclic BACE inhibitors: Optimization of a micromolar hit to nanomolar leads

We have identified macrocyclic inhibitors of the aspartic protease BACE, implicated in the etiology of Alzheimer's disease. An X-ray structure of screening hit 1 in the BACE active site revealed a hairpin conformation suggesting that constrained macrocycl

Discovery of azetidinone acids as conformationally-constrained dual PPARα/γ agonists

A novel class of azetidinone acid-derived dual PPARα/γ agonists has been synthesized for the treatment of diabetes and dyslipidemia. The preferred stereochemistry in this series for binding and functional agonist activity against both PPARα and PPARγ receptors was shown to be 3S,4S. Synthesis, in vitro and in vivo activities of compounds in this series are described. A high-yielding method for N-arylation of azetidinone esters is also described.

Structure-activity relationships of α-ketooxazole inhibitors of fatty acid amide hydrolase

A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1-napthyl, K, - 2.6 nM), with 5hh (aryl -3-ClPh, Ki = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, Ki = 3 nM, or 13d, 2-position OH, Ki = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of >100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.

INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME

Compounds of formula (I) are hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors, and are useful in therapeutic and prophylactic treatment of persons infected with hepatitis C virus.