Synthesis and biological evaluation of 5-[[3,5-bis(1,1-dimethylethyl)- 4-hydroxyphenyl]methylene]oxazoles, -thiazoles, and -imidazoles: novel dual 5-lipoxygenase and cyclooxygenase inhibitors with antiinflammatory activity.

  title={Synthesis and biological evaluation of 5-[[3,5-bis(1,1-dimethylethyl)- 4-hydroxyphenyl]methylene]oxazoles, -thiazoles, and -imidazoles: novel dual 5-lipoxygenase and cyclooxygenase inhibitors with antiinflammatory activity.},
  author={Paul C. Unangst and David T. Connor and Wiaczeslaw A. Cetenko and Roderick J. Sorenson and Catherine R. Kostlan and Jagadish C. Sircar and Clifford D. Wright and Denis J. Schrier and Richard D. Dyer},
  journal={Journal of medicinal chemistry},
  volume={37 2},
A variety of benzylideneoxazoles, -thiazoles, and -imidazoles derived from 2,6-di-tert-butylphenol were prepared and evaluated as dual inhibitors of 5-lipoxygenase and cyclooxygenase in rat basophilic leukemia (RBL-1) cells. The target compounds exhibit varying degrees of selectivity toward the two enzymes. Several compounds are orally active in the rat carageenan footpad edema (CFE) and mycobacterium footpad edema (MFE) antiinflammatory models. Structure-activity relationships are discussed… Expand
Synthesis and biological evaluation of acyclic triaryl (Z)-olefins possessing a 3,5-di-tert-butyl-4-hydroxyphenyl pharmacophore: dual inhibitors of cyclooxygenases and lipoxygenases.
Structural-activity data indicate acyclic triaryl (Z)-olefins constitute a suitable template for the design of dual COX-2/LOX inhibitors. Expand
Synthesis and biological evaluation of a class of 5-benzylidene-2-phenyl-thiazolinones as potent 5-lipoxygenase inhibitors.
A class of 5-lipoxygenase (5-LO) inhibitors characterized by a central 5-benzylidene-2-phenyl-thiazolinone scaffold synthesized as a new series of molecular modifications and extensions of a previously reported series turned out to be essential for both the 5-LO inhibitory activity and the non-cytotoxic profile. Expand
Synthesis and three-dimensional qualitative structure selectivity relationship of 3,5-disubstituted-2,4-thiazolidinedione derivatives as COX2 inhibitors
Docking results suggested that several new 2,4-thiazolidinedione derivatives are active COX inhibitors with a significant preference for COX2. Expand
5-(4-Hydroxy-2,3,5-trimethylbenzylidene) thiazolidine-2,4-dione attenuates atherosclerosis possibly by reducing monocyte recruitment to the lesion
HMB-TZD ameliorates atherosclerotic lesion formation possibly by reducing the expression of proinflammatory molecules and monocyte/macrophage recruitment to the lesion. Expand
Development and evaluation of ST-1829 based on 5-benzylidene-2-phenylthiazolones as promising agent for anti-leukotriene therapy.
This study presents the synthesis and development of a potent and direct 5-LO inhibitor based on the well characterized 5-benzylidene-2-phenylthiazolone C06, whose further pharmacological investigation was precluded due to its low solubility. Expand
Design, synthesis and pharmacobiological evaluation of novel acrylic acid derivatives acting as lipoxygenase and cyclooxygenase-1 inhibitors with antioxidant and anti-inflammatory activities.
Docking simulations performed on LOX inhibitor 4I and COX-1 inhibitor 1I indicated that hydrophobic key interactions may govern the enzyme-inhibitor binding. Expand
One-Pot Synthesis of Pyrimidinothiazolidinones and Their Anti-Inflammatory and Antimicrobial Studies
In the present investigation, we report a one-pot synthesis of the title compounds, 2-arylidene-5-(2,3,6-trimethyl-4-methoxyphenyl)-7-substituted-5H-pyrimidino-[2,3-b]thiazolidine-3-ones 6a–j andExpand
Synthesis of Derivatives of of Δ2-Imidazolin-5-one and Imidazolidine Containing Residues of Sterically-hindered Phenols
Abstract1-Substituted 4-benzylidene-2-{β-[3,5-di(tert-butyl)-4-hydroxyphenyl]vinyl}-4-benzylidene-Δ2-imidazolin-5-ones have been synthesized by the interaction of azomethines and N-acylhydrazonesExpand
Design, synthesis, DFT, molecular modelling studies and biological evaluation of novel 3-substituted (E)-5-(arylidene)-1-methyl-2-thioxoimidazolidin-4-ones with potent cytotoxic activities against breast MCF-7, liver HepG2, and lung A549
Abstract We report the synthesis of novel 3-substituted (E)-5-(arylidene)-1-methyl-2-thioxoimidazolidin-4-ones 6-11, and their biological evaluation. Based on structural and pharmacophore analyses ofExpand
Synthesis, pharmacological screening and in silico studies of new class of Diclofenac analogues as a promising anti-inflammatory agents.
A novel series of 5-[2,6-dichlorophenylamino)benzyl]-3-(substituted)-1,3,4-oxadiazol-2(3H)-thione derivatives (4a-k) derivatives have been synthesized by the Mannich reaction with an appropriately substituted primary/secondary amines, in the presence of formaldehyde and absolute ethanol. Expand