NSC-D699127

合成路线:Acetylation of aniline (I) with acetic anhydride (Ac2O) in HOAc followed by reaction with mercurium acetate (Hg(OAc)2) and HClO4 in HOAc provides derivative (II),which is first subjected to dimerization by treatment with Cu and PdCl2 in pyridine and then nitrated by means of HNO3 in HOAc to afford substituted biphenyl (III).Hydrolysis of (III) with H2SO4 gives 4,4'-diamino-3,3'-dinitrobiphenyl (IV),which is converted into tetraaminobiphenyl (V) by hydrogenation over Raney-Ni in acetone.Mitsunobu reaction between p-hydroxybenzaldehyde (VI) and 3-dimethylamino propan-1-ol (VII) with PPh3 and DEAD in THF gives substituted benzaldehyde (VIII),which is finally cyclized with biphenyl derivative (V) by heating in nitrobenzene to furnish the target product.

参考文献标题:A new class of symmetric bisbenzimidazole-based DNA minor groove-binding agents showing antitumor activity
文献作者:Mann,J.; Baron,A.; Opoku-Boahen,Y.; johansson,E.; Parkinson,G.; Kelland,L.R.; Neidle,S.
参考来源:J Med Chem 2001,44(2),138


合成路线:Acetylation of aniline (I) with acetic anhydride (Ac2O) in HOAc followed by reaction with mercurium acetate (Hg(OAc)2) and HClO4 in HOAc provides derivative (II),which is first subjected to dimerization by treatment with Cu and PdCl2 in pyridine and then nitrated by means of HNO3 in HOAc to afford substituted biphenyl (III).Hydrolysis of (III) with H2SO4 gives 4,4'-diamino-3,3'-dinitrobiphenyl (IV),which is converted into tetraaminobiphenyl (V) by hydrogenation over Raney-Ni in acetone.Mitsunobu reaction between p-hydroxybenzaldehyde (VI) and 3-dimethylamino propan-1-ol (VII) with PPh3 and DEAD in THF gives substituted benzaldehyde (VIII),which is finally cyclized with biphenyl derivative (V) by heating in nitrobenzene to furnish the target product.
参考文献标题:Symmetric bis-benzimidazoles: New sequence-selective DNA-binding molecules
文献作者:Neidle,S.; et al.
参考来源:Chem Commun (London) 1999,(10),929