N-[3-(morpholin-4-yl)propyl]-5,7-diphenylpyrazolo[1,5-a]pyrimidine-3-carboxamide

• ChemBase ID: 153298
• Molecular Formular: C26H27N5O2
• Molecular Mass: 441.52488
• Monoisotopic Mass: 441.21647513
• SMILES: c1ccc(cc1)c1cc(n2c(n1)c(cn2)C(=O)NCCCN1CCOCC1)c1ccccc1
• Canonical SMILES: O=C(c1cnn2c1nc(cc2c1ccccc1)c1ccccc1)NCCCN1CCOCC1
• InChI: InChI=1S/C26H27N5O2/c32-26(27-12-7-13-30-14-16-33-17-15-30)22-19-28-31-24(21-10-5-2-6-11-21)18-23(29-25(22)31)20-8-3-1-4-9-20/h1-6,8-11,18-19H,7,12-17H2,(H,27,32)
• InChIKey: JTRXWCLQFAZHGP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[3-(morpholin-4-yl)propyl]-5,7-diphenylpyrazolo[1,5-a]pyrimidine-3-carboxamide
• IUPAC Traditional name: N-[3-(morpholin-4-yl)propyl]-5,7-diphenylpyrazolo[1,5-a]pyrimidine-3-carboxamide
• Synonyms: N-[3-(4-Morpholinyl)propyl]-5,7-diphenylpyrazolo[1,5-a]pyrimidine-3-carboxamide; Reversan; CBLC4H10; N-[3-(4-Morpholinyl)propyl]-5,7-diphenyl-pyrazolo[1,5-a]pyrimidine-3-carboxamide; Reversan

Database IDs

• CAS Number: 313397-13-6
• MDL Number: MFCD01528184
• PubChem SID: 162247437
• PubChem CID: 2298706

CALCULATED PROPERTIES

• Acid pKa: 12.77142
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.7901117
• LogD (pH = 7.4): 3.072365
• Log P: 3.187695
• Molar Refractivity: 139.4856 cm^3
• Polarizability: 51.55358 Å^3
• Polar Surface Area: 71.76 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: ≥8 mg/mL at ~60 °C
• Apperance: faint yellow to yellow powder; Pale Yellow Solid
• Melting Point: 176-180°C

Safety Information

• Storage Condition: Refrigerator
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C26H27N5O2

DETAILS

Sigma Aldrich - SML0173

Biochem/physiol Actions
Reversan is a selective and nontoxic multidrug resistance-associated protein 1 (MRP1) and P-glycoprotein (P-gp) inhibitor.

Toronto Research Chemicals - R279800

Reversan represents a new class of nontoxic MRP1 inhibitor, which may be clinically useful for the treatment of neuroblastoma.

REFERENCES

• Sengupta, S., et al.: Pharmacol. Res., 42, 459 (2000)
• Norris, M., et al.: Med. Pediatr. Oncol., 36, 177 (2000)
• Haber, M., et al.: J. Clin. Oncol., 24, 1546 (2000)
• O'Connor, R., et al.: Cancer Chemother. Pharmacol., 59, 79 (2000)