(2R)-1-{4-[(2R,4S,11R)-3,3-difluorotetracyclo[10.4.0.02,4.05,10]hexadeca-1(12),5(10),6,8,13,15-hexaen-11-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol

• ChemBase ID: 179681
• Molecular Formular: C32H31F2N3O2
• Molecular Mass: 527.6042464
• Monoisotopic Mass: 527.23843369
• SMILES: [C@@H]12[C@@H](c3c([C@H](c4c1cccc4)N1CCN(CC1)C[C@H](COc1c4c(ccc1)nccc4)O)cccc3)C2(F)F
• Canonical SMILES: O[C@H](CN1CCN(CC1)[C@@H]1c2ccccc2[C@@H]2[C@H](c3c1cccc3)C2(F)F)COc1cccc2c1cccn2
• InChI: InChI=1S/C32H31F2N3O2/c33-32(34)29-22-7-1-3-9-24(22)31(25-10-4-2-8-23(25)30(29)32)37-17-15-36(16-18-37)19-21(38)20-39-28-13-5-12-27-26(28)11-6-14-35-27/h1-14,21,29-31,38H,15-20H2/t21-,29-,30+,31-/m1/s1
• InChIKey: IHOVFYSQUDPMCN-DBEBIPAYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-{4-[(2R,4S,11R)-3,3-difluorotetracyclo[10.4.0.0^2,^4.0^5,^1^0]hexadeca-1(12),5(10),6,8,13,15-hexaen-11-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol
• IUPAC Traditional name: (2R)-1-{4-[(2R,4S,11R)-3,3-difluorotetracyclo[10.4.0.0^2,^4.0^5,^1^0]hexadeca-1(12),5(10),6,8,13,15-hexaen-11-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol
• Synonyms: (αR)-4-[(1aα,6α,10bα)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]-α-[(5-quinolinyloxy)methyl]-1-piperazineethanol Hydrochloride; Zosuquidar Hydrochloride; LY 335979; RS 33295-198; Zosuquidar Trihydrochloride

Database IDs

• CAS Number: 167465-36-3
• PubChem SID: 164235591
• PubChem CID: 3036703

CALCULATED PROPERTIES

• Acid pKa: 14.07888
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.281876
• LogD (pH = 7.4): 4.1407084
• Log P: 4.8176975
• Molar Refractivity: 146.6752 cm^3
• Polarizability: 57.740555 Å^3
• Polar Surface Area: 48.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 172-176°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - Z700870

Multi-drug resistance (MDR) modulator; selective inhibitor of P-glycoprotein (P-gp). Antineoplastic adjunct (chemosensitizer).

REFERENCES

• Green, L.J., et al.: Biochem. Pharmacol., 61, 1393 (2001)
• Shepard, R.L., et al.: Int. J. Cancer, 103, 121 (2001)