52779-81-4

Usage

Definition

ChEBI: A thiophene substituted at C-2 by a 4-ethylbenzoyl group.

InChI:InChI=1/C13H12OS/c1-2-10-5-7-11(8-6-10)13(14)12-4-3-9-15-12/h3-9H,2H2,1H3

Upstream product

• 40828-46-4 2-[4-(thien-2-ylcarbonyl)phenyl]propanoic acid 
• 16331-45-6 p-ethylbenzoyl chloride 
• 63139-21-9 4-ethylphenylboronic acid 
• 527-72-0 2-thiophenylcarboxylic acid 

Relevant academic research and scientific papers

Time-resolved spectroscopic and density functional theory investigation of the photochemistry of suprofen

The photochemistry of suprofen (SPF) was investigated by femtosecond transient absorption (fs-TA), resonance Raman (RR) and nanosecond time-resolved resonance Raman (ns-TR3) spectroscopic methods to gain additional information so as to better elucidate the possible photochemical reaction mechanism of suprofen in several different solvents. In neat acetonitrile (MeCN), the fs-TA and ns-TR3 experimental data indicated that the lowest lying excited singlet state S1 (np?) underwent an efficient intersystem crossing process (ISC) to the excited triplet state T3 (pp?), followed by an internal conversion (IC) process to T1 (pp?). In the aqueous solution, a triplet biradical species (3ETK-1) was obtained as the product of a decarboxylation process from triplet suprofen anion (3SPF-) and the reaction rate of the decarboxylation processwas determined by the concentration of H2O. A protonation process for 3ETK-1 leads to formation of a neutral species (3ETK-3) that was directly observed by ns-TR3 spectra, then this 3ETK-3 species decayed via ISC process to generate final product.

Antibodies directed to drug epitopes to investigate the structure of drug-protein photoadducts. Recognition of a common photobound substructure in tiaprofenic acid/ketoprofen cross-photoreactivity

Drug-induced photoallergy is an immune adverse reaction to the combined effect of drugs and light. From the mechanistic point of view, it first involves covalent binding of drug to protein resulting in the formation of a photoantigen. Hence, determination of the structures of drug-protein photoadducts is of great relevance to understand the molecular basis of photoallergy and cross-immunoreactivity among drugs. Looking for new strategies to investigate the covalent photobinding of drugs to proteins, we generated highly specific antibodies to drug chemical substructures. The availability of such antibodies has allowed us to discriminate between the different modes by which tiaprofenic acid (TPA), suprofen (SUP), and ketoprofen (KTP) photobind to proteins. The finding that the vast majority of the TPA photoadduct can be accounted for by means of antibody anti-benzoyl strongly supports the view that the drug binds preferentially via the thiophene ring, leaving the benzene ring more accessible. By contrast, selective recognition of SUP-protein photoadducts by antibody anti-thenoyl evidences a preferential coupling via the benzene ring leaving the thiophene moiety more distant from the protein matrix. In the case of KTP, photoadducts are exclusively recognized by antibody anti-benzoyl, indicating that the benzene ring is again more accessible. As a result of this research, we have been able to identify a common substructure that is present in TPA-albumin and KTP-albumin photoadducts. This is remarkable since, at a first sight, the greatest structural similarities can be found between TPA and SUP as they share the same benzoylthiophene chromophore. These findings can explain the previously reported observations of cross-reactivity to KTP (or TPA) in patients photosensitized to TPA (or KTP).

One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling

A palladium-catalyzed one-pot procedure for the synthesis of aryl ketones has been developed. Triazine esters when coupled with aryl boronic acids provided aryl ketones in moderate to excellent yields (up to 95%) in the presence of 1 mol % Pd(PPh3)2Cl2 for 30 min. (Chemical Equation Presented).

Structure and photochemical behavior of the cyclodextrin inclusion complexes of the benzoylthiophene-derived drugs tiaprofenic acid (= 5-benzoyl-α-methylthiophene-2-acetic acid) and suprofen (=α-methyl-4-(2-thienylcarbonyl)benzeneacetic acid)

The effect of β-cyclodextrin (β-CD) on the excited-state reactivity of the two benzoylthiophene derivatives, tiaprofenic acid (TPA; 2) and suprofen (SPF; 3) in their carboxylate forms is studied. The presence of βcyclodextrin does not affect the nature of the photoproduced transients and the photoproducts, but increases the photodegradation quantum yields of both drugs. The efficiency of the photodecarboxylation process is enhanced. This effect is rationalized in the light of the inclusion of 2 and 3 in the β-CD cavity, affecting the energy of the lowest excited states of the drugs. The structure of the complexes is determined by induced circular dichroism, and molecular-mechanics and dynamic Monte Carlo calculations. The photoreactivity of the decarboxylated photoproduct 7 of tiaprofenic acid (2) in presence of β-CD is also examined.

Triplet photochemistry of suprofen in aqueous environment and in the beta-cyclodextrin inclusion complex.

The photodecarboxylation of suprofen in the carboxylate form was studied in aqueous medium as a function of the temperature, the concentration and the presence of oxygen by steady-state and time-resolved photochemical techniques. The process is characterized by an activation energy of 9-10 kcal/mol, the precursor state being the lowest triplet which is of pi-pi* nature. The reactivity of the drug was also studied in the beta-cyclodextrin inclusion complex and an additional photoreaction involving the macrocycle as reactive species was observed. Representative NMR and circular dichroism measurements were performed. Singlet molecular oxygen formation was also investigated.

Aroyl-substituted phenylacetic acid derivatives

Compounds of the class of aroyl-substituted phenylacetic acids and corresponding esters, amides and hydroxamic acids, useful as anti-inflammatory agents and certain novel precursors therefor.

Synthesis of α methyl 4 (2 thienylcarbonyl)benzeneacetic acid, suprofen, and derivatives

A series of compounds with general structure Het CO Ar CH(CH3)COOH was prepared for pharmacological screening. Different synthetic approaches are described. α Methyl 4 (2 thienylcarbonyl)benzeneacetic acid (compound III-l, suprofen), was found to show a marked antiwrithing activity. Furthermore this compound proved to be a potent inhibitor of prostaglandin biosynthesis.