166282-70-8

Basic information

• Product Name: 2H-Cycloocta[b]pyran-2-one, 3-[(3-aminophenyl)cyclopropylmethyl]-5,6,7,8,9,10-hexahydro-4-hydroxy -
• CAS NO: 166282-70-8
• Molecular Formula: C21H25NO3
• Molecular Weight: 339.434
• Mol File: 166282-70-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2H-Cycloocta[b]pyran-2-one, 3-[(3-aminophenyl)cyclopropylmethyl]-5,6,7,8,9,10-hexahydro-4-hydroxy -(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Cycloocta[b]pyran-2-one, 3-[(3-aminophenyl)cyclopropylmethyl]-5,6,7,8,9,10-hexahydro-4-hydroxy -(166282-70-8)
• EPA Substance Registry System: 2H-Cycloocta[b]pyran-2-one, 3-[(3-aminophenyl)cyclopropylmethyl]-5,6,7,8,9,10-hexahydro-4-hydroxy -(166282-70-8)

Safety Data

• Hazardous Substances Data: 166282-70-8(Hazardous Substances Data)

Upstream product

• 162174-77-8 m-<(benzyloxycarbonyl)amino>phenyl cyclopropyl carbinol 
• 166282-28-6 <3-pyran-3-yl)methyl>phenyl>carbamic acid, phenylmethyl ester 
• 100058-82-0 5,6,7,8,9,10-Hexahydro-4-hydroxy-2H-cyclooctapyran-2-on 

Downstream Products

• 166335-75-7 (E)-2-Phenyl-ethenesulfonic acid {3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-methyl]-phenyl}-amide 
• 174485-25-7 N-methyl-3[(3-aminophenyl)cyclopropylmethyl]-5,6,7,8,9,10-hexahydro-4-hydroxy-2H-cycloocta[b]pyran-2-one 
• 166335-00-8 3-[Cyclopropyl-[3-[(phenylmethyl)amino]phenyl]methyl]-5,6,7,8,9,10-hexahydro-4-hydroxy-2H-cycloocta[b]pyran-2-one 
• 166335-01-9 3-[Cyclopropyl-[3-[(2-phenylethyl)amino]phenyl]methyl]-5,6,7,8,9, 10-hexahydro-4-hydroxy-2H-cycloocta[b]pyran-2-one 
• 166336-03-4 4-amino-N-[3-[cyclopropyl(5,6,7,8,9,10-hexahydro-4-hydroxy-2-oxo-2H-cycloocta[b]pyran-3-yl)methyl]phenyl]-benzenesulfonamide 

Relevant articles and documents

PYRANONE COMPOUNDS USEFUL TO TREAT RETROVIRAL INFECTIONS

The present invention relates to compounds of formulae (I) and (II) which are pyran-2-ones, 5,6-dihydro-pyran-2-ones, 4-hydroxy-benzopyran-2-ones, 4-hydroxy-cycloalkyl[b]pyran-2-ones, and derivatives thereof, useful for inhibiting a retrovirus in a mammalian cell infected with said retrovirus, wherein R 10 and R 20 taken together are formulae (III) and (IV). STR1

Structure-based design of nonpeptidic HIV protease inhibitors: The sulfonamide-substituted cyelooctylpyranones

Recently, cyclooctylpyranone derivatives with m-carboxamide substituents (e.g. 2c) were identified as potent, nonpeptidic HIV protease inhibitors, but these compounds lacked significant antiviral activity in cell culture. Substitution of a sulfonamide group at the meta position, however, produces compounds with excellent HIV protease binding affinity and antiviral activity. Guided by an iterative structure-based drug design process, we have prepared and evaluated a number of these derivatives, which are readily available via a seven-step synthesis. A few of the most potent compounds were further evaluated for such characteristics as pharmacokinetics and toxicity in rats and dogs. From this work, the p-cyanophenyl sulfonamide derivative 35k emerged as a promising inhibitor, was selected for further development, and entered phase I clinical trials.

Structure-based design of nonpeptidic HIV protease inhibitors from a cyclooctylpyranone lead structure

Recently, the novel cyclooctylpyranone HIV protease inhibitor 1 was identified in our labs, and an X-ray structure of this inhibitor complexed with HIV-2 protease was obtained. This crystal structure was used to develop two strategies for creating derivat