【药物名称】D-64131
化学结构式(Chemical Structure):
参考文献No.52164
标题:2-Acyl indol derivs. and their use as anti-tumour agents
作者:Burger, A.; Mahboobi, S.; Pongratz, H.; Hufsky, H.; B鰄mer, F.-D.; Beckers, T.; Klenner, T.; Baasner, S.; Frieser, M.; Hockemeyer, J.; Fiebig, H.-H. (Asta Medica AG)
来源:DE 10020852; WO 0182909
合成路线图解说明:

Protection of 5-methoxyindole (I) with benzenesulfonyl chloride (II) in the presence of NaH affords the N-sulfonyl indole (III). Acylation of the 2-lithio derivative of (III) with benzoyl chloride (IV) gives rise to ketone (V). Finally, removal of the phenylsulfonyl protecting group of (V) is achieved by either basic hydrolysis or by treatment with tetrabutylammonium fluoride.

参考文献No.645566
标题:Synthetic 2-aroylindole derivatives as a new class of potent tubulin-inhibitory, antimitotic agents
作者:Mahboobi, S.; Pongratz, H.; Hufsky, H.; Hockemeyer, J.; Frieser, M.; Lyssenko, A.; Paper, D.H.; Burgermeister, J.; Bohmer, F.D.; Fiebig, H.H.; Burger, A.M.; Baasner, S.; Beckers, T.
来源:J Med Chem 2001,44(26),4535
合成路线图解说明:

Protection of 5-methoxyindole (I) with benzenesulfonyl chloride (II) in the presence of NaH affords the N-sulfonyl indole (III). Acylation of the 2-lithio derivative of (III) with benzoyl chloride (IV) gives rise to ketone (V). Finally, removal of the phenylsulfonyl protecting group of (V) is achieved by either basic hydrolysis or by treatment with tetrabutylammonium fluoride.

参考文献No.654249
标题:Bis(1H-2-indolyl) methanones as a novel class of inhibitors of the platelet-derived growth factor receptor kinase
作者:Mahboobi, S.; Teller, S.; Pongratz, H.; Hufsky, H.; Sellmer, A.; Botzki, A.; Uecker, A.; Beckers, T.; Baasner, S.; Schachtele, C.; Uberall, F.; Kassack, M.U.; Dove, S.; Bohmer, F.D.
来源:J Med Chem 2002,45(5),1002
合成路线图解说明:

Protection of 5-methoxyindole (I) with benzenesulfonyl chloride (II) in the presence of NaH affords the N-sulfonyl indole (III). Acylation of the 2-lithio derivative of (III) with benzoyl chloride (IV) gives rise to ketone (V). Finally, removal of the phenylsulfonyl protecting group of (V) is achieved by either basic hydrolysis or by treatment with tetrabutylammonium fluoride.

合成路线图解说明:

In a related method, the 2-lithio derivative of 5-methoxy-1-(phenylsulfonyl)indole (I) is condensed with benzaldehyde (II) to produce carbinol (III). Subsequent oxidation of (III) to the corresponding ketone (IV) is accomplished by treatment with pyridinium dichromate (PDC) in the presence of pyridinium trifluoroacetate (PTFA). Finally, the N-phenylsulfonyl group of (IV) is deprotected by treatment with tetrabutylammonium fluoride.

参考文献No.713661
标题:A simple synthesis of 2-acyl indoles from isatins
作者:Black, D.S.C.; Wong, L.C.H.
来源:J Chem Soc Chem Commun 1980,(4),200
合成路线图解说明:

The alkaline hydrolysis of 5-methoxyisatin (I) provides the ortho-(aminophenyl)glyoxylic acid salt (II), which is then alkylated by 2-bromoacetophenone (III) to furnish the N-phenacylisatin (IV). Rearrangement of (IV) in the presence of NaOH gives rise to a 40:60 mixture of the indolecarboxylic acid (V) and the target decarboxylated compound.

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