158647-85-9

Basic information

• Product Name: α-(tetrahydropyran-2-yloxy)-4-(trifluoromethyl)propiophenone
• Synonyms: α-(tetrahydropyran-2-yloxy)-4-(trifluoromethyl)propiophenone
• CAS NO: 158647-85-9
• Molecular Weight: 302.293
• Mol File: 158647-85-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: α-(tetrahydropyran-2-yloxy)-4-(trifluoromethyl)propiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: α-(tetrahydropyran-2-yloxy)-4-(trifluoromethyl)propiophenone(158647-85-9)
• EPA Substance Registry System: α-(tetrahydropyran-2-yloxy)-4-(trifluoromethyl)propiophenone(158647-85-9)

Safety Data

• Hazardous Substances Data: 158647-85-9(Hazardous Substances Data)

Upstream product

• 711-33-1 4-trifluoromethyl propiophenone 
• 67081-98-5 (+/-)-1-<4-(trifluoromethyl)phenyl>-1-propanol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 144-55-8 sodium hydrogencarbonate 
• 158558-35-1 (+/-)-α-hydroxy-4-(trifluoromethyl)propiophenone 
• 75-09-2 dichloromethane 
• 95728-57-7 2-bromo-1-(4-trifluoromethylphenyl)propan-1-one 
• 455-19-6 4-Trifluoromethylbenzaldehyde 

Downstream Products

• 150803-04-6 (+/-)-2-<1-(tetrahydropyran-2-yloxy)ethyl>-2-<4-(trifluoromethyl)phenyl>oxirane 

Relevant articles and documents

Synthesis and antifungal activity of new azole derivatives containing an N-acylmorpholine ring

A series of azole derivatives carrying an N-acylmorpholine ring are described. The compounds were chemically designed to simulate the lanosterol D ring, taking advantage of the conformational preferences of 2-alkyl-1- acylmorpholines. Three structural variables, the nature of the N-benzoyl group, the phenyl substituents, and the degree of oxidation at carbon 2 of the morpholine, were optimized for maximum activity. Only the (5R,6R) isomers showed antifungal activity. Cyclic hemiacetal (-)-39a (UR-9746) and cyclic ether (-)-41 (UR-9751) were selected for further development. In vitro, (-)- 41 was clearly more active than (-)-39a and somewhat less active than the acyclic counterpart (-)-7. In vivo activity was assessed by a systemic (mouse) and a vaginal (rat) candidosis model. In the former, (-)-39a, (-)- 41, and (-)-7 at 1 mg/kg given 1, 4, and 24 h postinfection displayed 90- 100% protection from mortality on day 9. Compound (-)-39a was slightly more potent than (-)-41 and similar in potency to (-)-7. The three compounds were superior in potency to fluconazole and similar in potency to SCH-42427 in this test. In the vaginal model, (-)-39a and (-)-41 given daily during 3 days after infection at 0.5 mg/kg showed high levels of protection on days 10 and 15. At 0.25 mg/kg, (-)-39a was slightly more potent than SCH-42427 and (-)-7 and superior in potency to (-)-41 and fluconazole in this model. Preliminary 28-day toxicity tests at 100 mg/kg/day po in rats indicated no or very mild adverse effects for the two UR compounds.

Novel orally active antifungal agents

The present invention relates to novel orally active antifungal agents of general formula Iwherein R1 represents hydrogen and R2 represents hydrogen or C1 4 alkyl, or R1 and R2 together represent a group -(CH2)-; p is 0 or 1, and the salts and solvates thereof.