2-{4-[(1S,4R)-bicyclo[2.2.2]octa-2,5-diene-2-carbonyl]piperazin-1-yl}-6,7-dimethoxyquinazolin-4-amine

• ChemBase ID: 176872
• Molecular Formular: C23H27N5O3
• Molecular Mass: 421.49218
• Monoisotopic Mass: 421.21138975
• SMILES: c1(c(cc2c(c1)nc(nc2N)N1CCN(CC1)C(=O)C1=C[C@H]2C=C[C@@H]1CC2)OC)OC
• Canonical SMILES: COc1cc2nc(nc(c2cc1OC)N)N1CCN(CC1)C(=O)C1=C[C@@H]2CC[C@H]1C=C2
• InChI: InChI=1S/C23H27N5O3/c1-30-19-12-17-18(13-20(19)31-2)25-23(26-21(17)24)28-9-7-27(8-10-28)22(29)16-11-14-3-5-15(16)6-4-14/h3,5,11-15H,4,6-10H2,1-2H3,(H2,24,25,26)/t14-,15+/m0/s1
• InChIKey: MXXRJJCMLRPJOF-LSDHHAIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[(1S,4R)-bicyclo[2.2.2]octa-2,5-diene-2-carbonyl]piperazin-1-yl}-6,7-dimethoxyquinazolin-4-amine
• IUPAC Traditional name: 2-{4-[(1S,4R)-bicyclo[2.2.2]octa-2,5-diene-2-carbonyl]piperazin-1-yl}-6,7-dimethoxyquinazolin-4-amine
• Synonyms: 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-bicyclo[2.2.2]octa-2,5-dienyl-carbonyl)-piperazine; SZL-49; Prazobind

Database IDs

• CAS Number: 107021-36-3
• PubChem SID: 164232782
• PubChem CID: 40428214

CALCULATED PROPERTIES

• Molar Refractivity: 121.9264 cm^3
• Polarizability: 45.830177 Å^3
• Polar Surface Area: 93.81 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.9421417
• LogD (pH = 7.4): 2.2229514
• Log P: 2.448376

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Ethanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 245-247°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: -200C

DETAILS

Toronto Research Chemicals - P702150

α1-Adrenoceptor alkylating reagent. A Prazosin analog. An antihypertensive.

REFERENCES

• Piascik, M.T., et al.: J. Pharmacol. Exp. Ther., 251, 878 (1989)
• Pitha, J., et al.: J. Med. Chem., 32, 96 (1989)
• Mante, S., et al.: Eur. J. Pharmacol., 208, 113 (1989)