13451-80-4

Usage

InChI:InChI=1/C8H4F3NOS/c9-8(10,11)4-1-2-6-5(3-4)12-7(14)13-6/h1-3H,(H,12,14)

Upstream product

• 75-15-0 carbon disulfide 
• 454-81-9 2-amino-4-(trifluoromethyl)phenol 
• 121-17-5 2-chloro-3-nitro-5-trifluoromethylbenzene 
• 109-01-3 1-methyl-piperazine 
• 22876-19-3 5-chloro-2-mercaptobenzoxazole 
• 400-99-7 2-nitro-4-trifluoromethylphenol 
• 140-89-6 potassium ethyl xanthogenate 

Downstream Products

• 114997-91-0 2-chloro-5-(trifluoromethyl)benzo[d]oxazole 
• 213685-32-6 N-(2,6-diisopropylphenyl)-6-((5-(trifluoromethyl)benzo[d]oxazol-2-yl)thio)hexanamide 
• 1421257-27-3 C₂₁H₂₆F₃N₃O₃ 
• 143925-49-9 2-phenyl-5-(trifluoromethyl)benzo[d]oxazole 

Relevant academic research and scientific papers

HMOX1 inducers

The present invention is related to compounds of structure (I) as heme oxygenase 1 (HMOX 1) inducers. The present invention is also related a method of controlling the activity or the amount, or both the activity and the amount, of heme-oxygenase 1 in a mammalian subject. The definitions of the variables are provided herein.

ISOINDOLINES AS HDAC INHIBITORS

The present disclosure relates to inhibitors of zinc-dependent histone deacetylases (HDACs), having the formula: (I) wherein Z, X1, X2, Y1, Y2, Y3, L, Z, and R are described herein.

ANTIBIOTIC COMPOUNDS

The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.

Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors

We describe our molecular design of aortic-selective acyl-coenzyme A:cholesterol O-acyltransferase (ACAT, also abbreviated as SOAT) inhibitors, their structure–activity relationships (SARs) and their pharmacokinetic (PK) and pharmacological profiles. The connection of two weak ligands—N-(2,6-diisopropylphenyl)acetamide (50% inhibitory concentration [IC50] = 8.6 μM) and 2-(methylthio)benzo[d]oxazole (IC50 = 31 μM)—via a linker comprising a 6 methylene group chains yielded a highly potent molecule, 9-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)nonanamide (3h) that exhibited high potency (IC50 = 0.004 μM) toward aortic ACAT. This head-to-tail design made it possible to markedly enhance the activity to 2150- to 7750-fold and to discriminate the isoform-selectivity based on the double-induced fit mechanism. At doses of 1 and 3 mg/kg, 3h significantly decreased the lipid-accumulation areas in the aortic arch to 74 and 69%, respectively without reducing the plasma total cholesterol level in high fat- and cholesterol-fed F1B hamsters. Here, we demonstrate the antiatherosclerotic effect of 3h in vivo via its direct action on aortic ACAT and its powerful modulator of cholesterol level. This molecule is a potential therapeutic agent for the treatment of diseases involving ACAT-1 overexpression.

Discovery and SAR of PF-4693627, a potent, selective and orally bioavailable mPGES-1 inhibitor for the potential treatment of inflammation

Inhibition of mPGES-1, the terminal enzyme in the arachidonic acid/COX pathway to regulate the production of pro-inflammatory prostaglandin PGE2, is considered an attractive new therapeutic target for safe and effective anti-inflammatory drugs. The discovery of a novel series of orally active, selective benzoxazole piperidinecarboxamides as mPGES-1 inhibitors is described. Structure-activity optimization of lead 5 with cyclohexyl carbinols resulted in compound 12, which showed excellent in vitro potency and selectivity against COX-2, and reasonable pharmacokinetic properties. Further SAR studies of the benzoxazole ring substituents lead to a novel series of highly potent compounds with improved PK profile, including 23, 26, and 29, which were effective in a carrageenan-stimulated guinea pig air pouch model of inflammation. Based on its excellent in vitro and in vivo pharmacological, pharmacokinetic and safety profile and ease of synthesis, compound 26 (PF-4693627) was advanced to clinical studies.

Synthesis and insecticidal activity of novel dihalopropene derivatives containing benzoxazole moiety: A structure-activity relationship study

Ten dichloropropene derivatives containing benzoxazole moiety were synthesized and bioassayed in order to determine their in vivo insecticidal activity. The structures of obtained compounds were identified by 1H NMR, MS and elemental analyses. The bioassay results indicated that compound 2-(3-(2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy)propoxy)-5-(trifluoromethyl) benzo[d]oxazole (5i, R1 is trifluoromethyl, R2 is H and n is 3) had the optimal structure with best insecticidal activity against Spodoptera exigua (100%) at 1 mg/L concentration, highlighting the importance of trifluoromethyl group. The structure-activity relationship of the synthesized compounds was discussed as well.

DIAZEPANE COMPOUNDS WHICH MODULATE THE CB2 RECEPTOR

Compounds of formula (I) are disclosed. Compounds according to the invention bind to and are agonists, antagonists or inverse agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.

Regulatory molecules for the 5-HT3 receptor ion channel gating system

Substituted benzoxazole derivatives which possess a nitrogen-containing heterocycle at C2 are selective partial agonists of the 5-HT3 receptor. Alteration of substituents on the benzoxazole nucleus affords both agonist-like and antagonist-like compounds, and uniquely modifies the function of the 5-HT3 receptor ion channel gating system. SAR and corroborative computational docking study for these partial agonists successfully explained structure and function of the 5-HT3 receptor.

Design and synthesis of highly potent and selective human peroxisome proliferator-activated receptor α agonists

A combination of benzoxazole, phenoxyalkyl side chain, and phenoxybutyric acids was identified as a highly potent and selective human peroxisome proliferator-activated receptor α (PPARα) agonist. The synthesis, structure-activity relationship (SAR) studies, and in vivo activities of the representative compounds are described.

NOVEL PIPERAZINES, PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE THEREOF

Disclosed are novel piperazine derivatives that act as agonists of the α7 nAChR. Also disclosed are phannaceutical compositions, methods of treating inflammatory conditions, methods of treating CNS disorders, methods for inhibiting cytokine release from mammalian cells and methods for the preparation of the novel compounds.