Compound 1 is a uniquely substituted ketone prepared via addition of a thiazole anion to an aromatic nitrile in good overall yield. An exploration into the generality of the addition of thiazole anions to nitriles allowed us to make a variety of thiazole ketones in good to excellent yields. The ...

This chapter is a review of the scientific literature from 1995 to 2007. In conjunction with the corresponding chapters in CHEC(1984) and CHEC-II(1996), it constitutes a thorough review of the chemistry of thiazoles. Structures discussed include thiazoles, thiazolines, thiazolidines, thiazolium ...

Publisher SummaryThiazoles play a prominent role in nature. For example, the thiazolium ring present in vitamin B1 serves as an electron sink and its coenzyme form is important for the decarboxylation of α-keto-acids. Furthermore, thiazoles are useful building blocks in pharmaceutical agents as...

With anticipation of the improvement in biological aspects in our SGLT2 program, novel pyridazinyl and thiazolyl analogs were designed and efficiently synthesized. The installation of the pyridazine ring at the anomeric carbon of d-glucopyranose was carried out in a stereoselective fashion. On t...

The most common CF mutation, F508del, impairs the processing and gating of CFTR protein. This deletion results in the improper folding of the protein and its degradation before it reaches the plasma membrane of epithelial cells. Present correctors, like VX809 only induce a partial rescue of the ...

In 1996, we reported that benzeneboronic acids bearing electron-withdrawing groups at the meta- or para-position are highly effective catalysts for the amide condensation reaction in less-polar solvents. In this paper, we report that N-alkyl-4-boronopyridinium halides are more effective catalyst...

An efficient acylative kinetic resolution of racemic aromatic β-hydroxy esters with cyclohexanecarboxylic anhydride was achieved using newly designed (R)-N-methylbenzoguanidine ((R)-NMBG) derivatives. A series of (R)-NMBG derivatives was synthesized by modifying the original (R)-NMBG catalyst w...

The adducts obtained through the Diels-Alder cycloadditions of (Z)-2-phenyl-4-benzyliden-5(4H)-oxazolone 1 with Danishefsky's diene and of methyl (E)-2-cyanocinnamate 9 with 2-methoxy-1,3-butadiene, were subsequently transformed allowing the synthesis of both stereoisomers of 2-phenyl-4-oxo...

An efficient synthetic approach is proposed to construct 4′,5,5″-triaryl-2,2′:6′,2″-terpyridines using two methods of pyridine ring construction, that is, the Weiss method and the ‘1,2,4-triazine’ methodology. Due to the use of ‘1,2,4-triazine’ methodology in the last step, aza-analogue...

A series of 2,6-di(thiazol-2-yl)pyridines (dtpy) functionalized at 4-position with 1-naphtyl (1), 2-naphtyl (2), 9-anthryl (3), 2-anthryl (4), 9-phenantryl (5) and 1-pyrenyl (6) groups has been synthesized and thoroughly investigated. The molecular formulas of 1–6 were determined by 1H and 13C ...

Efficient and convenient methods for the preparation of thienyl-substituted 2,2′:6′,2″-terpyridines are reported. The formation and characterization of Fe(II), Ru(II), Os(II) and Co(II) complexes containing the isomeric ligands 4′-(2-thienyl)-2,2′:6′,2″-terpyridine (1) and 4′-(3-thienyl)...

The imidazoline p-iodoclonidine is a high-affinity partial agonist at the alpha-2A adrenoceptors …

The imidazoline p-iodoclonidine is a high-affinity partial agonist at the alpha-2 adrenergic receptors and is routinely used as a radioligand for characterizing alpha-2 adrenergic receptors. The high specific activity of [125I]iodoclonidine makes it particularly useful for studying tissues with ...

Triphenylphosphine-catalyzed [3 + 2] cycloaddition between ethyl buta-2,3-dienoate and adamantane-containing N-substituted maleimides affords substituted bicyclic succinimides in excellent yields.

An efficient and transition-metal-free method for the synthesis of the structurally diversified pyrroles is described. Various α,β-unsaturated ynones reacted with N-substituted ethyl glycine ethyl ester hydrochlorides in the presence of DBU to form the corresponding products in good yields. Th...

Benzoic acid and pyridine derivatives inhibit recombinant trans-sialidase from Trypanosoma cruzi with I50 values between 0.4 and 1 mM. The best compounds, 4-acetylamino-3-hydroxymethylbenzoic acid and 5-acetylamino-6-aminopyridine-2-carboxylic acid, provide new leads to inhibitors not containing...

The toxicities of benzoic acids to Vibrio fischeri, Daphnia magna and carp were measured. The results showed that the toxicity to V. fischeri and Daphnia decreased in the order of bromo>chloro>fluoro≈aminobenzoic acids. The toxicity of substituted benzoic acids to carp and Daphnia was much lowe...

The relative importance of the liver and kidney for glycine conjugation of ortho-substituted benzoic acids was investigated. Glycine conjugation of ortho-substituted benzoic acids was investigated in mouse liver and kidney mitochondria. The extent of glycine conjugation of benzoic acids with the...

Continued SAR optimization of a series of 3-methylpyridine-2-carbonyl amino-2,4-dimethyl-benzoic acid led to the selection of compound 4f for clinical studies. Compound 4f showed an IC50 of 123 nM for inhibition of PGE2-induced TNFα reduction in an ex vivo LPS-stimulated human whole blood assay...

A series of novel cyclic amine-substituted benzoic acid derivatives were synthesized and evaluated for their PPARα agonist activity. Strucure-activity relationship studies led to the identification of (S)-3-[3-[2-(4-chlorophenyl)-4-methylthyazole-5-carboxamido]piperidin-1-yl]benzoic acid (S)-4f...