68287-22-9

Upstream product

• 106-95-6 allyl bromide 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 107-05-1 3-chloroprop-1-ene 
• 4873-09-0 allyl tosylate 

Downstream Products

• 856106-96-2 3-allyl-2,4-dihydroxybenzaldehyde 
• 68287-16-1 2-Phenyl-4-(2'-acetoxy-4'-allyloxybenzal)oxazolone 
• 132803-49-7 2-hydroxy-3-(2-propenyloxy)benzaldehyde 
• 1352526-75-0 C₁₄H₁₂O₃ 
• 813414-08-3 4-(allyloxy)-2-methoxybenzaldehyde 
• 1620146-71-5 (Z)-5-(5-allyl-4-hydroxy-2-methoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-70-4 (Z)-5-(5-allyl-4-hydroxy-2-methoxybenzylidene)-3-benzylthiazolidine-2,4-dione 
• 1620146-69-1 (Z)-5-(5-allyl-4-hydroxy-2-methoxybenzylidene)-3-butylthiazolidine-2,4-dione 
• 1620146-68-0 (Z)-5-(5-allyl-4-hydroxy-2-methoxybenzylidene)-3-(3-methylbut-2-en-1-yl)thiazolidine-2,4-dione 
• 1620146-67-9 (Z)-5-(5-allyl-4-hydroxy-2-methoxybenzylidene)-3-allylthiazolidine-2,4-dione 
• 1620146-66-8 (Z)-5-(5-allyl-4-hydroxy-2-methoxybenzylidene)-3-isopropylthiazolidine-2,4-dione 
• 1620146-65-7 (Z)-5-(5-allyl-4-hydroxy-2-methoxybenzylidene)-3-methylthiazolidine-2,4-dione 
• 1620146-64-6 (Z)-5-(5-allyl-2-methoxy-4-((tetrahydro-2H-pyran-2-yl)oxy)benzylidene)-3-benzylthiazolidine-2,4-dione 
• 1620146-63-5 (Z)-5-(5-allyl-2-methoxy-4-((tetrahydro-2H-pyran-2-yl)oxy)benzylidene)-3-butylthiazolidine-2,4-dione 

Relevant academic research and scientific papers

Hg based on rhodamine derivatives2 + Fluorescent probe as well as preparation method and application thereof

The invention provides a Hg2+ fluorescence probe based on a rhodamine derivative. The probe is of a structure shown in the formula I. The fluorescence probe based on rhodamine compounds is used for Hg2+ detection. The probe can detect Hg2+ in a n ethyl al

Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship

In our earlier study, we have reported that a phenolic compound 2-hydroxy-4-methoxybenzaldehyde from Janakia arayalpatra root extract was active against Viper and Cobra envenomations. Based on the structure of this natural product, libraries of synthetic structurally variant phenolic compounds were studied through molecular docking on the venom protein. To validate the activity of eight selected compounds, we have tested them in in vivo and in vitro models. The compound 21 (2-hydroxy-3-methoxy benzaldehyde), 22 (2-hydroxy-4-methoxybenzaldehyde) and 35 (2-hydroxy-3-methoxybenzylalcohol) were found to be active against venom-induced pathophysiological changes. The compounds 20, 15 and 35 displayed maximum anti-hemorrhagic, anti-lethal and PLA2 inhibitory activity respectively. In terms of SAR, the presence of a formyl group in conjunction with a phenolic group was seen as a significant contributor towards increasing the antivenom activity. The above observations confirmed the anti-venom activity of the phenolic compounds which needs to be further investigated for the development of new anti-snake venom leads.

Condensation of salicylaldehydes with ethyl 4,4,4-trichloro-3-oxobutanoate: A facile approach for the synthesis of substituted 2H-chromene-3-carboxylates

A highly efficient and simple protocol has been developed for the preparation of ethyl 2-oxo-2H-chromene-3-carboxylates 3a-v by the condensation of salicylaldehydes 1a-v with ethyl 4,4,4-trichloro-3-oxobutanoate 2 for the first time. The reaction is proceeding via Knoevenagel pathway followed by a selective addition of the phenolic hydroxyl group to the carbonyl group adjacent to the CCl3 group rather than ester carbonyl due to a strong electron withdrawing effect and produced coumarin derivative 3a with the elimination of CHCl3.

Design, synthesis and docking study of 5-(substituted benzylidene) thiazolidine-2,4-dione derivatives as inhibitors of protein tyrosine phosphatase 1B

A series of novel 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives was designed, and synthesized based on our previous studies. Also their activities were evaluated as competitive inhibitors of protein tyrosine phosphatase 1B (PTP1B). Compounds 6d-6g, 7b, 7c, 7e, 7j, 7k, 7m, 14b and 14e-14f showed potent inhibitory effects against PTP1B, and compound 7e, the most potent among the series, had an IC50 of 4.6 μM. Also a Surflex-Dock docking model of 7e was studied. Compound 7e showed a negative binding energy of -7.35 kcal/mol and a high affinity to PTP1B residues (Gly220, Ala217, Arg221, Asp181, Ser216, Cys215, Phe182, Gln262 and Ile219) in the active sites, indicating that it may stabilize the open form and generate tighter binding to the catalytic sites of PTP1B.

Regioselective alkylation of hydroxysalicylaldehydes

Schiff-base ligands are often used as backbone ligands for mono- and dinuclear complexes that serve as catalysts during aerobic oxidation reactions. However, their water solubility is low and limits their applicability as catalysts to transform highly water-soluble biomolecules, such as carbohydrates or amino alcohols. A new method to regioselectively incorporate water solubility-promoting polyethylene glycol side chains into a frequently used aldehyde building block of Schiff-base ligands has been developed.

Selective ET(A) antagonists. 5. Discovery and structure-activity relationships of phenoxyphenylacetic acid derivatives

The fifth paper in this series describes the culmination of our investigations into the development of a potent and selective ETA receptor antagonist for the treatment of diseases mediated by ET-1. Receptor site mapping of several ETA antagonists prepared previously identified a common cationic binding site which prompted synthesis of phenoxyphenylacetic acid derivative 13a, which showed good in vitro activity (IC50 59 nM, rat aortic ET(A)). Optimization of 13a led to the identification of 27b, which exhibited an IC50 of 4 nM. Although this did not translate into the expected in vivo potency, a compound of comparable in vitro activity, 27a (RPR118031A), showed a far better pharmacokinetic profile and in vivo potency (75 μmol/kg) and was duly proposed and accepted as a development candidate.

SUBSTITUTED PHENYL COMPOUNDS WITH A SUBSTITUENT HAVING A 1,3-BENZODIOXOLE RING

This invention is directed to compounds of formula I STR1 wherein R 1 is CN, CH 2 CN, CH=CHCN, CHO, or CH=CHCO. sub. 2 H;R 2 is aryl lower alkoxy, heteroaryl lower alkoxy, aryl lower alkylthio or heteroaryl lower alkylthio wherein each of the aryl and heteroaryl moieties is optionally substituted;R 3 is halogen;R 4 is optionally substituted aryl or optionally substituted heteroaryl;R. sup.5 is carboxy or an acid isostere; X is oxygen or sulphur; and n is zero or 1; or an N-oxide thereof, prodrug thereof solvate thereof, or pharmaceutically acceptable salt thereof, which compounds have endothelin antagonist activity. The invention is also directed to methods for preparing the compounds of formula I and their pharmaceutical use.

Substituted phenyl compounds with a substituent having a thienyl ring

This invention is directed to compounds of formula I wherein R1 is CN, CH2CN, CH=CHCN, CHO, or CH=CHCO2H; R2 is aryl lower alkoxy, heteroaryl lower alkoxy, aryl lower alkylthio or heteroaryl lower alkylthio wherein each of the aryl and heteroaryl moieties is optionally substituted; R3 is halogen; R4 is optionally substituted aryl or optionally substituted heteroaryl; R5 is carboxy or an acid isostere; X is oxygen or sulphur; and n is zero or 1; or an N-oxide thereof, prodrug thereof solvate thereof, or pharmaceutically acceptable salt thereof, which compounds have endothelin antagonist activity. The invention is also directed to methods for preparing the compounds of formula I and their pharmaceutical use.

A mild and chemoselective dealkylation of alkyl aryl ethers by cerium(III) chloride-NaI

The alkoxy groups present ortho to carbonyl group in alkoxybenzaldehydes are selectively deprotected in high yields leaving other alkoxy groups unaffected by cerium(III) chloride-NaI in refluxing acetonitrile under neutral reaction conditions.

Antidiabetic agents

The instant invention is concerned with acetylphenols which are useful as antiobesity and antidiabetic compounds. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering or modulating triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility or for treating atherosclerosis are also disclosed.