(2R,3R)-1-[(7-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-3-{[(2H7)propan-2-yl]amino}butan-2-ol hydrochloride

• ChemBase ID: 171503
• Molecular Formular: C17H28ClNO2
• Molecular Mass: 313.86272
• Monoisotopic Mass: 313.18085682
• SMILES: Cl.c1cc(c2c(c1C)CCC2)OC[C@@H]([C@H](NC(C)C)C)O
• Canonical SMILES: CC(N[C@@H]([C@H](COc1ccc(c2c1CCC2)C)O)C)C.Cl
• InChI: InChI=1S/C17H27NO2.ClH/c1-11(2)18-13(4)16(19)10-20-17-9-8-12(3)14-6-5-7-15(14)17;/h8-9,11,13,16,18-19H,5-7,10H2,1-4H3;1H/t13-,16+;/m1./s1
• InChIKey: KBXMBGWSOLBOQM-CACIRBSMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-1-[(7-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-3-{[(^2H₇)propan-2-yl]amino}butan-2-ol hydrochloride
• IUPAC Traditional name: (2R,3R)-1-[(7-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-3-[(^2H₇)propan-2-ylamino]butan-2-ol hydrochloride
• Synonyms: (2R,3R)-rel-1-[(2,3-Dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methylethyl-d7)amino]-2-butanol Hydrochloride; (R*,R*)-1-[(2,3-Dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methylethyl-d7)amino]-2-butanol Hydrochloride; ICI 111581-d7; ICI 118551-d7 Hydrochloride

Database IDs

• PubChem SID: 164227413
• PubChem CID: 71749440

CALCULATED PROPERTIES

• Acid pKa: 13.816111
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.329761
• LogD (pH = 7.4): 1.2247218
• Log P: 3.5319011
• Molar Refractivity: 82.7167 cm^3
• Polarizability: 32.452805 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I163852

The labelled (R,R)-enantiomer of ICI 118551 as highly selective β2-adrenoceptor antagonist. The S,S-enantiomer is the most potent.

REFERENCES

• Bilski, A., et al.: J. Cardiovasc. Pharmacol., 5, 430 (1983)
• Furse, K., et al.: J. Med. Chem., 46, 4450 (1983)
• Cherezov, V., et al.: Science, 318, 1258 (1983)