(3S)-morpholin-3-ylmethyl N-[4-({1-[(3-fluorophenyl)methyl]-1H-indazol-5-yl}amino)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamate

• ChemBase ID: 162457
• Molecular Formular: C27H27FN8O3
• Molecular Mass: 530.5534832
• Monoisotopic Mass: 530.21901498
• SMILES: O1CCN[C@@H](C1)COC(=O)Nc1c(c2n(c1)ncnc2Nc1cc2c(cc1)n(nc2)Cc1cccc(c1)F)C
• Canonical SMILES: O=C(Nc1cn2c(c1C)c(ncn2)Nc1ccc2c(c1)cnn2Cc1cccc(c1)F)OC[C@@H]1COCCN1
• InChI: InChI=1S/C27H27FN8O3/c1-17-23(34-27(37)39-15-22-14-38-8-7-29-22)13-36-25(17)26(30-16-32-36)33-21-5-6-24-19(10-21)11-31-35(24)12-18-3-2-4-20(28)9-18/h2-6,9-11,13,16,22,29H,7-8,12,14-15H2,1H3,(H,34,37)(H,30,32,33)/t22-/m0/s1
• InChIKey: LUJZZYWHBDHDQX-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-morpholin-3-ylmethyl N-[4-({1-[(3-fluorophenyl)methyl]-1H-indazol-5-yl}amino)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamate
• IUPAC Traditional name: (3S)-morpholin-3-ylmethyl N-[4-({1-[(3-fluorophenyl)methyl]indazol-5-yl}amino)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamate
• Synonyms: N-[4-[[1-[(3-Fluorophenyl)methyl]-1H-indazol-5-yl]amino]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamic Acid (3S)-3-Morpholinylmethyl Ester; AC 480; BMS 599626

Database IDs

• CAS Number: 714971-09-2
• PubChem SID: 162256592
• PubChem CID: 10437018

CALCULATED PROPERTIES

• Acid pKa: 12.238873
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.9732387
• LogD (pH = 7.4): 3.6462848
• Log P: 3.9929276
• Molar Refractivity: 166.6558 cm^3
• Polarizability: 55.314674 Å^3
• Polar Surface Area: 119.63 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B596300

It is a highly selective and potent inhibitor of HER1 and HER2 kinases and inhibits tumor cell proliferation through modulation of receptor signaling. BMS-599626 inhibits HER1/HER2 receptor heterodimerization and provides an additional mechanism of inhib

REFERENCES

• Wiseman, L., et al.: Eur. J. Cancer, 29A, 2256 (1993)
• Wittman, M., et al.: J. Med. Chem., 48, 5639 (1993)
• Allen, G., et al.: Cancer Res., 67, 1155 (1993)