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Also known as: Azd1152, 722543-31-9, Azd-1152, Barasertib [inn], Azd 1152, 957881-03-7

Molecular Formula

C₂₆H₃₁FN₇O₆P

Molecular Weight

587.5 g/mol

InChI Key

GBJVVSCPOBPEIT-UHFFFAOYSA-N

FDA UNII

16XC2U7W8N

Barasertib is an orally bioavailable, small-molecule, dihydrogen phosphate prodrug of the pyrazoloquinazoline Aurora kinase inhibitor AZD1152-hydroxyquinazoline pyrazol anilide (AZD1152-HQPA) with potential antineoplastic activity. Upon administration and rapid conversion from the prodrug form in plasma, AZD1152-HQPA specifically binds to and inhibits Aurora kinase B, which results in the disruption of spindle checkpoint functions and chromosome alignment and, so, the disruption of chromosome segregation and cytokinesis. Consequently, cell division and cell proliferation are inhibited and apoptosis is induced in Aurora kinase B-overexpressing tumor cells. Aurora kinase B, a serine/threonine protein kinase that functions in the attachment of the mitotic spindle to the centromere, is overexpressed in a wide variety of cancer cell types.

1 2D Structure

Barasertib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[ethyl-[3-[4-[[5-[2-(3-fluoroanilino)-2-oxoethyl]-1H-pyrazol-3-yl]amino]quinazolin-7-yl]oxypropyl]amino]ethyl dihydrogen phosphate

2.1.2 InChI

InChI=1S/C26H31FN7O6P/c1-2-34(10-12-40-41(36,37)38)9-4-11-39-21-7-8-22-23(16-21)28-17-29-26(22)31-24-14-20(32-33-24)15-25(35)30-19-6-3-5-18(27)13-19/h3,5-8,13-14,16-17H,2,4,9-12,15H2,1H3,(H,30,35)(H2,36,37,38)(H2,28,29,31,32,33)

2.1.3 InChI Key

GBJVVSCPOBPEIT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN(CCCOC1=CC2=C(C=C1)C(=NC=N2)NC3=NNC(=C3)CC(=O)NC4=CC(=CC=C4)F)CCOP(=O)(O)O

2.2 Other Identifiers

2.2.1 UNII

16XC2U7W8N

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-((3-((4-((5-(2-((3-fluorophenyl)amino)-2-oxoethyl)-1h-pyrazol-3-yl)amino)quinazolin-7-yl)oxy)propyl)(ethyl)amino)ethyl Dihydrogen Phosphate

2. Azd 1152

3. Azd-1152

4. Azd1152

2.3.2 Depositor-Supplied Synonyms

1. Azd1152

2. 722543-31-9

3. Azd-1152

4. Barasertib [inn]

5. Azd 1152

6. 957881-03-7

7. Barasertib (who-dd)

8. 2-(ethyl(3-((4-((5-(2-((3-fluorophenyl)amino)-2-oxoethyl)-1h-pyrazol-3-yl)amino)quinazolin-7-yl)oxy)propyl)amino)ethyl Dihydrogen Phosphate

9. 16xc2u7w8n

10. Chembl415049

11. Barasertib [who-dd]

12. 2-(ethyl(3-(4-(5-(2-(3-fluorophenylamino)-2-oxoethyl)-1h-pyrazol-3-ylamino)quinazolin-7-yloxy)propyl)amino)ethyl Dihydrogen Phosphate

13. 5-[[7-[3-[ethyl[2-(phosphonooxy)ethyl]amino]propoxy]-4-quinazolinyl]amino]-n-(3-fluorophenyl)-1h-pyrazole-3-acetamide

14. 2-(ethyl(3-((4-((3-(2-((3-fluorophenyl)amino)-2-oxoethyl)-1h-pyrazol-5-yl)amino)quinazolin-7-yl)oxy)propyl)amino)ethyl Dihydrogen Phosphate

15. 2-[ethyl-[3-[4-[[5-[2-(3-fluoroanilino)-2-oxoethyl]-1h-pyrazol-3-yl]amino]quinazolin-7-yl]oxypropyl]amino]ethyl Dihydrogen Phosphate

16. Azd1152 (barasertib)

17. Barasertibum

18. Unii-16xc2u7w8n

19. 2-{ethyl[3-({4-[(5-(2-[(3-fluorophenyl)amino]-2-oxoethyl}-1h-pyrazol-3-yl)amino]quinazolin-7-yl}oxy)propyl]amino}ethyl Dihydrogen Phosphate

20. Kinome_3324

21. 2-naphthylacrylate

22. Schembl613582

23. Gtpl7332

24. Schembl16671950

25. Dtxsid00222583

26. Chebi:167636

27. Bcpp000362

28. Hms3674c21

29. Hms3747e05

30. Bcp01734

31. Bcp13793

32. Cs-d0326

33. Ex-a3656

34. Azd1152-hqpa Dihydrogen Phosphate

35. Bdbm50241089

36. Nsc799355

37. Zinc43129461

38. Bcp9000360

39. Cs-0978

40. Cs-w000582

41. Db11747

42. Nsc-799355

43. Sb16659

44. Azd1152, 33

45. Ncgc00378734-03

46. Ac-35703

47. As-17018

48. Hy-10127

49. Db-074538

50. A9414

51. Ft-0662378

52. Ft-0736007

53. A15011

54. 543e319

55. 881a037

56. Q27074865

57. 1h-pyrazole-3-acetamide, 5-((7-(3-(ethyl(2- (phosphonooxy)ethyl)amino)propoxy)-4-quinazolinyl)amino)-n-(3-fluorophenyl)-

58. 1h-pyrazole-3-acetamide, 5-((7-(3-(ethyl(2-(phosphonooxy)ethyl)amino)propoxy)-4-quinazolinyl)amino)-n-(3-fluorophenyl)-

59. 1h-pyrazole-3-acetamide,5-[[7-[3-[ethyl[2-(phosphonooxy)ethyl]amino]propoxy]-4-quinazolinyl]amino]-n-(3-fluorophenyl)-

60. 2-[ethyl(3-{[4-({5-[2-(3-fluoroanilino)-2-oxoethyl]-1h-pyrazol-3-yl}amino)quinazolin-7-yl]oxy}propyl)amino]ethyl Dihydrogen Phosphate

61. 2-ethyl3-4-5-2-3-fluorophenylamino)-2-oxoethyl)-1h-pyrazol-3-ylamino)quinazolin-7-yloxy)propyl)amino)ethyl Dihydrogen Phosphate

62. N-(3-fluorophenyl)-3-[[7-[3-[ethyl[2-(phosphonooxy)ethyl]amino]propyloxy]quinazoline-4-yl]amino]-1h-pyrazole-5-acetamide

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₁FN₇O₆P
Molecular Weight	587.5 g/mol
XLogP3	-0.4
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	15
Exact Mass	587.20574689 g/mol
Monoisotopic Mass	587.20574689 g/mol
Topological Polar Surface Area	175 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	859
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1