Structure via PubChem · Public domain (PubChem)
sch-48461
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Chemical data
- Formula
- C26H27NO3
- Molecular weight
- 401.5 g/mol
- IUPAC name
- (3R,4S)-1,4-bis(4-methoxyphenyl)-3-(3-phenylpropyl)azetidin-2-one
- SMILES
- COC1=CC=C(C=C1)[C@@H]2[C@H](C(=O)N2C3=CC=C(C=C3)OC)CCCC4=CC=CC=C4
- InChIKey
- IMNTVVOUWFPRSB-JWQCQUIFSA-N
- XLogP
- 5.3
- Polar surface area
- 38.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 401.199
Show 3 more facts
- canonical SMILES
- COC1=CC=C(C=C1)C2C(C(=O)N2C3=CC=C(C=C3)OC)CCCC4=CC=CC=C4
- chemical formula
- C₂₆H₂₇NO₃
- isomeric SMILES
- COC1=CC=C(C=C1)[C@@H]2[C@H](C(=O)N2C3=CC=C(C=C3)OC)CCCC4=CC=CC=C4
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
SCH-48461 is a cholesterol absorption inhibitor.
During the early phases of an NPC1L1 inhibitor discovery program at Schering-Plough, conformationally restricted analogs based on the 2-azetidinone backbone were targeted by Burnett and co-workers. Early in the biological evaluation, it became apparent that even though the in vitro ACAT inhibitory activity of these analogs was modest (e.g., IC50 values of 2–50 mM), they exhibited significant activity in a cholesterol-fed hamster model (CFH). The discovery of the prototypical 2-azetidinone CAI, SCH-48461 (ACAT IC50 ~26 mM, ED50 of CE reduction in hamsters ~2.2 mpk) and the details of the first-generation SAR have been described in detail.
Excerpted from Wikipedia’s “sch-48461” article, available under the CC BY-SA 4.0 licence.
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