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CAS 19916-73-5
PharmaCompass
CAS 19916-73-5
Also known as: O6-benzylguanine, 19916-73-5, 6-(benzyloxy)-7h-purin-2-amine, O(6)-benzylguanine, 2-amino-6-benzyloxypurine, O(6)-bgua
Molecular Formula
C12H11N5O
Molecular Weight
241.254  g/mol
InChI Key
KRWMERLEINMZFT-UHFFFAOYSA-N
FDA UNII
01KC87F8FE

6-O-benzylguanine has been used in trials studying the treatment of HIV Infection, Adult Gliosarcoma, Adult Glioblastoma, Stage I Adult Hodgkin Lymphoma, and Stage II Adult Hodgkin Lymphoma, among others.
1 2D Structure

CAS 19916-73-5

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
6-phenylmethoxy-7H-purin-2-amine
2.1.2 InChI
InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)
2.1.3 InChI Key
KRWMERLEINMZFT-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)COC2=NC(=NC3=C2NC=N3)N
2.2 Other Identifiers
2.2.1 UNII
01KC87F8FE
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. O6-benzylguanine

2. 19916-73-5

3. 6-(benzyloxy)-7h-purin-2-amine

4. O(6)-benzylguanine

5. 2-amino-6-benzyloxypurine

6. O(6)-bgua

7. 6-(benzyloxy)guanine

8. 6-(benzyloxy)-9h-purin-2-amine

9. 2-amino-6-(benzyloxy)purine

10. 6-benzyloxyguanine

11. 6-benzyloxy Guanine

12. 6-(phenylmethoxy)-1h-purin-2-amine

13. 2-amino-6-(phenylmethoxy)-9h-purine

14. 1h-purin-2-amine, 6-(phenylmethoxy)-

15. 6-benzylguanine

16. Purine, 2-amino-6-(benzyloxy)-

17. Nsc 637037

18. O6-bg

19. Chembl407874

20. 6-benzyloxy-7h-purin-2-amine

21. Mfcd00269931

22. Nsc637037

23. Sbb069180

24. 1000874-21-4

25. Smr000326791

26. 916b735

27. Unii-01kc87f8fe

28. Ccris 9383

29. 6-(benzyloxy)-3h-purin-2-amine

30. O6 -benzylguanine

31. O-6-benzylguanine

32. O(6) Benzylguanine

33. Pubchem9681

34. Purine, 8ci)

35. Ac1q4xue

36. Lopac-b-2292

37. D0b5bg

38. Ac1l1ih7

39. 6-benzyloxy-2-amino-purine

40. Lopac0_000181

41. Schembl61740

42. Ksc542o1r

43. Mls000859930

44. Mls001074887

45. Mls006010145

46. 01kc87f8fe

47. 6-benzyloxy-9h-purin-2-amine

48. Bdbm5491

49. 2-amino-6-benzyloxy-9h-purine

50. 0.4 Ch3oh

51. Ctk4e2718

52. 6-benzyloxy-9h-purin-2-ylamine

53. Dtxsid20173700

54. Or7851t

55. Krwmerleinmzft-uhfffaoysa-n

56. Molport-001-769-965

57. Molport-019-918-664

58. 6-(phenylmethoxy)purine-2-ylamine

59. 6-phenylmethoxy-7h-purin-2-amine

60. Hms2234p23

61. Hms3260f03

62. Hms3369a16

63. Krx-0402

64. Ks-00000dp7

65. O6-substituted Guanine Deriv. 31

66. Zinc5425464

67. 6-(benzyloxy)-7h-purin-2-ylamine

68. Tox21_500181

69. An-984

70. Anw-43110

71. Akos015919415

72. Akos015963409

73. Akos028109331

74. 9h-purin-2-amine,6-(phenylmethoxy)-

75. Ac-1076

76. Cb-1184

77. Ccg-204276

78. Cs-w002585

79. Db11919

80. Ks-5281

81. Lp00181

82. Ls20601

83. Nsc-637037

84. Rl02491

85. Rtr-030959

86. Ncgc00015144-01

87. Ncgc00015144-02

88. Ncgc00015144-03

89. Ncgc00015144-04

90. Ncgc00093660-01

91. Ncgc00093660-02

92. Ncgc00260866-01

93. Aj-54058

94. Ak-47518

95. Bc215630

96. Br-47518

97. H350

98. He051730

99. Nci60_012280

100. Purine, 2-amino-6-(benzyloxy)- (, )

101. Sc-02184

102. Sy008080

103. O6-benzylguanine, >=98% (tlc), Solid

104. Ab0013002

105. Ab1003839

106. Ls-126405

107. Tr-030959

108. 4ch-006286

109. Am20060538

110. Eu-0100181

111. Ft-0650712

112. St24033084

113. Y2972

114. A-1974

115. B 2292

116. J10132

117. S07-0157

118. W-201741

119. Obg

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 241.254 g/mol
Molecular Formula C12H11N5O
XLogP31.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass241.096 g/mol
Monoisotopic Mass241.096 g/mol
Topological Polar Surface Area89.7 A^2
Heavy Atom Count18
Formal Charge0
Complexity271
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Pharmacology

O6-Benzylguanine is a guanine analogue with antineoplastic activity. O6-benzylguanine binds the DNA repair enzyme O(6)-alkylguanine DNA alkyltransferase (AGT), transferring the benzyl moiety to the active-site cysteine and resulting in inhibition of AGT-mediated DNA repair. Co-administration of this agent potentiates the effects of other chemotherapeutic agents that damage DNA. (NCI04)


4.2 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS.


Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.


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