SCH-48461

SCH-48461

Names
IUPAC name (3R,4S)-1,4-bis(4-methoxyphenyl)-3-(3-phenylpropyl)-2-azetidinone
Identifiers
CAS Number	148260-92-8 Y
ChEMBL	ChEMBL23541 N
ChemSpider	117230 N
Jmol 3D model	Interactive image
PubChem	132832
InChI InChI=1S/C26H27NO3/c1-29-22-15-11-20(12-16-22)25-24(10-6-9-19-7-4-3-5-8-19)26(28)27(25)21-13-17-23(30-2)18-14-21/h3-5,7-8,11-18,24-25H,6,9-10H2,1-2H3/t24-,25-/m1/s1 N Key: IMNTVVOUWFPRSB-JWQCQUIFSA-N N InChI=1/C26H27NO3/c1-29-22-15-11-20(12-16-22)25-24(10-6-9-19-7-4-3-5-8-19)26(28)27(25)21-13-17-23(30-2)18-14-21/h3-5,7-8,11-18,24-25H,6,9-10H2,1-2H3/t24-,25-/m1/s1 Key: IMNTVVOUWFPRSB-JWQCQUIFBU
SMILES COc1ccc(cc1)[C@@H]2[C@H](C(=O)N2c3ccc(cc3)OC)CCCc4ccccc4
Properties
Chemical formula	C26H27NO3
Molar mass	401.49748
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox 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.