α-Chymotrypsin is selectively and irreversibly inactivated by 2-bromomethyl-3,i-benzoxazin-4-one (Compd Ib) at neutral pH. Reaction of the enzyme with this activated ester leads rapidly to a relatively stable acyl-enzyme in which intramolecular alkylation of a single methionine residue (likely ...

The free fatty acid receptor 1 (FFA1) is a potential target due to its function in enhancement of glucose-stimulated insulin secretion. Takeda’s compound 1 has robustly in vitro activity for FFA1, but it has been suffered from poor pharmacokinetic (PK) profiles because the phenylpropanoic acid ...

The aldo-keto reductase 1C3 (AKR1C3) isoform plays a vital role in the biosynthesis of androgens and is considered an attractive target in prostate cancer (PCa). No AKR1C3-targeted agent has to date been approved for clinical use. Flufenamic acid and indomethacine are non-steroidal anti-inflamma...

4-{[2-[(2-Furylsulfonyl)(isobutyl)amino]-5-(trifluoromethyl)phenoxy]methyl}benzoic acid analogs 2a and b and a series of the acid analogs, in which the carboxylic acid residue of 2b was replaced with various kinds of carboxylic acid bioisosteres, were synthesized and evaluated as EP1 receptor an...

G protein-coupled receptor 52 (GPR52) agonists are expected to improve the symptoms of psychiatric disorders. During exploration for a novel class of GPR52 agonists with good pharmacokinetic profiles, we synthesized 4-(3-(3-fluoro-5-(trifluoromethyl)benzyl)-5-methyl-1H-1,2,4-triazol-1-yl)-2-meth...

GPR40, also known as free fatty acid receptor 1 (FFAR1), is a member of G protein-coupled receptors (GPCR) family and has emerged as an attractive target for the treatment of type 2 diabetes mellitus. So far, most of the synthetic GPR40 agonists, including several drug candidates discontinued in...

Poly(2-amino-4-tert-butylphenol), poly(2A-4TBP), was synthesized from monomer aqueous solution using either electrochemical or chemical oxidation procedures. Several spectroscopic characterization techniques were employed to gain information on the chemical structure and redox behavior of the ob...

Tests of antiproliferative activity of Mannich adducts of aromatic nucleophiles and a chiral bicyclic imine revealed a di-tert-butylphenol derivative as a promising compound for further exploration. To study the influence of substitution pattern and a configuration of stereogenic centers on the ...

The natural product 2,4‑di‑tert‑butylphenol (DTBP) has a wide spectrum of biological functions, including anticancer activities, although the underlying mechanisms are poorly understood. Here, we found that DTBP induces senescence in human gastric adenocarcinoma AGS cells as evidenced by upregul...

Novel gold(I) complexes, PPh3AuSR (1) and [(Ph3PAu)2SR]2(BF4)2 (2), with a protective antioxidant group R (R = 3,5-di-tert-butyl-4-hydroxyphenyl) were synthesized and characterized by 1H, 13C, 31P NMR, IR and elemental analyses. The crystal structures of compounds 1 and 2 were determined by X-ra...

A series of rare-earth metal carboxylates M(RCOO)3 (M = La (1), Eu (2), Gd (3), Tb (4), Er (5); R = 3,5-di-tert-butyl-4-hydroxyphenyl) was synthesized and characterized by elemental analysis, NMR, IR spectroscopy and MALDI-TOF spectroscopy. The photoluminescent (PL) properties of 1–5 were inves...

In the present paper, the liquid–liquid micro extraction of 4-tert-butylphenol from aqueous solution to trioctyl phosphate organic phase in carbon paste electrode was studied by potentiometry and semi-empirical quantum chemistry with MOPAC2009. The extraction dynamic process was monitored by op...

The reactivity of the previously reported pentadentate low-spin (S = 1) oxoiron(IV) complex, [FeIV(O)(asN4Py)] (2) (asN4Py = N,N-bis(2-pyridylmethyl)-1,2-di(2-pyridyl)ethylamine), has been investigated in the oxidation reaction of 2,6-di-tert-butylphenol derivatives. Detailed kinetic, and mechan...

The tert-butylphenols (TBPs) are one group of alkylated phenolic compounds with wide applications in UV absorbers and antioxidants. They are becoming contaminants of emerging concern with residues frequently detected in natural surface water or drinking water. The direct sunlight may photolyze T...

In this study, two water-soluble iron porphyrins bearing sulfonate and carboxylate functionalities (FePTS and FePTC, respectively) and their supported analogues were used as catalysts for the oxidation of 2,6-di-tert-butylphenol (DTBP) in a water-methanol mixture. tert-Butyl hydroperoxide (TBHP)...

Synthetic phenolic antioxidants (SPAs) have received increasing attention due to the reports of toxicity and environmental contamination. Nevertheless, limited information was available on human burdens of these SPAs, with the exception of 2,6-di-tert-butyl-4-methylphenol (BHT). In our study, BH...

To develop SAR at both the cannabinoid CB1 and CB2 receptors for 3-(1-naphthoyl)indoles bearing moderately electron withdrawing substituents at C-4 of the naphthoyl moiety, 1-propyl and 1-pentyl-3-(4-fluoro, chloro, bromo and iodo-1-naphthoyl) derivatives were prepared. To study the steric and e...

An inherently regiospecific synthesis of isatins (1H-indole-2,3-diones) starting from 1-halo-2-nitrobenzenes is described. The isatins are formed by an intramolecular palladium-catalyzed annulation of 2-(2-haloethynyl)-1-nitrobenzenes via the formation of 2-haloisatogens.

New synthetic pathways have been elaborated to 1-methyl-1H-pyridazino[3,4-b]indoles starting from halopyridazin-3(2H)-ones. Suzuki cross-coupling reaction of chloro, iodo, dichloro, and dibromo substituted pyridazin-3(2H)-ones with 2-pivaloylaminophenylboronic acid followed by hydrolysis of the ...

A facile and general approach to the synthesis of 2,5,7-trisubstituted indoles from readily available 2-bromo-6-iodo-4-substituted and 2-bromo-4-chloro-6-iodoanilines is reported. The assembly of the indole rings is accomplished via a one-pot Sonogashira cross-coupling with terminal alkynes foll...