174484-81-2

Basic information

• Product Name: N-[3-[1-(2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide
• Synonyms: N-[3-[1-(2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide;2-Pyridinesulfonamide, N-[3-[1-[5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-;Aids059126;Aids-059126
• CAS NO: 174484-81-2
• Molecular Formula: C31H33F3N2O5S
• Molecular Weight: 0
• Mol File: 174484-81-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 680°Cat760mmHg
• Flash Point: 365.1°C
• Appearance: /
• Density: 1.313g/cm³
• Vapor Pressure: 2.01E-19mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: N-[3-[1-(2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[3-[1-(2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide(174484-81-2)
• EPA Substance Registry System: N-[3-[1-(2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide(174484-81-2)

Safety Data

• Hazardous Substances Data: 174484-81-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36,38H,3-4,15-17,19H2,1-2H3

Upstream product

• 213014-25-6 3-[1-(3-Nitro-phenyl)-meth-(Z)-ylidene]-6-phenethyl-6-propyl-dihydro-pyran-2,4-dione 
• 162174-87-0 5,6-dihydro-4-hydroxy-6-phenethyl-6-propyl-2H-pyran-2-one 
• 99-61-6 3-nitro-benzaldehyde 
• 29898-25-7 1-phenylhexan-3-one 
• 174485-72-4 5-trifluoromethyl-pyridin-2-ylsulfonylchloride 
• 174486-10-3 (S)-3-[(S)-1-(3-Amino-phenyl)-propyl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-pyran-2-one 
• 174590-56-8 (S)-3-[(R)-1-(3-Amino-phenyl)-propyl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-pyran-2-one 
• 174590-54-6 (R)-3-[(S)-1-(3-Amino-phenyl)-propyl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-pyran-2-one 
• 188559-05-9 (R)-N-[(E)-EtCHCHC(O)]-4-phenyl-1,3-oxazolidin-2-one 
• 188559-22-0 (2S,5R)-2-[(S)-1-(3-Dibenzylamino-phenyl)-propyl]-5-hydroxy-1-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-5-phenethyl-oct-6-yne-1,3-dione 
• 188559-10-6 (S)-2-[(S)-1-(3-Dibenzylamino-phenyl)-propyl]-1-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-butane-1,3-dione 
• 188559-25-3 (R)-3-[(R)-1-(3-Dibenzylamino-phenyl)-propyl]-4-hydroxy-6-phenethyl-6-prop-1-ynyl-5,6-dihydro-pyran-2-one 
• 174590-40-0 (R)-3-[(S)-3-(3-Dibenzylamino-phenyl)-pentanoyl]-4-phenyl-oxazolidin-2-one 
• 33698-85-0 (E)-pent-2-enoyl chloride 

Relevant articles and documents

Process for asymmetric hydrogenation

The present invention is a process for the preparation of a compound of the formula: where R3, R4 and n are defined in the specification which comprises hydrogenating a compound of the formula: the E-geometrical isomer thereof or a mixture of the Z- and E-isomers in the presence of catalyst containing Rh, a chiral ligand with at least one phosphorous atom where the hydrogenation is conducted in the presence of a base.

Tipranavir (PNU-140690): A potent, orally bioavailable nonpeptidic HIV protease inhibitor of the 5,6-dihydro-4-hydroxy-2-pyrone sulfonamide class

A broad screening program previously identified phenprocoumon (1) as a small molecule template for inhibition of HIV protease. Subsequent modification of this lead through iterative cycles of structure-based design led to the activity enhancements of pyrone and dihydropyrone ring systems (II and V) and amide-based substitution (III). Incorporation of sulfonamide substitution within the dihydropyrone template provided a series of highly potent HIV protease inhibitors, with structure-activity relationships described in this paper. Crystallographic studies provided further information on important binding interactions responsible for high enzymatic binding. These studies culminated in compound VI, which inhibits HIV protease with a K(i) value of 8 pM and shows an IC90 value of 100 nM in antiviral cell culture. Clinical trials of this compound (PNU-140690, Tipranavir) for treatment of HIV infection are currently underway.

A convergent, scalable synthesis of HIV protease inhibitor PNU-140690

PNU-140690, an inhibitor of the HIV protease enzyme undergoing clinical evaluation as a chemotherapeutic agent for treatment of AIDS, was synthesized by a convergent approach amenable to large-scale preparation in a pilot plant environment. The key step is the aldol addition of nitroaromatic ester (+)-8 to aldehyde 19e. The two stereocenters present in the target molecule were each set independently by resolution of enantiomers. Intermediates along the synthetic routes were chosen to maximize opportunities for isolation and purification by crystallization.