Desferrioxamine, Deferoxamine, ICL-749B(depot formulation), CGH-749B(depot formulation), DFO, Ba-33112(mesylate), Ba-29837(HCl), NSC-527604, Desferin, Desferal

合成路线:A culture broth of Streptomyces pilosus ETH 21748 is treated with Hyflo-Supercel and aqueous ferric sulfate,and the clear solution obtained is extracted with phenol-CHCl3 to obtain,after purification a crude mixture of ferrioxamins A,B,C,D1,D2,E and F.This crude product is chromatographed through Dowex 50 WX2 using an ammonium acetate buffer and the different ferrioxamins are separated.The treatment of ferrioxamin B (I) with aqueous NaOH gives a precipitate of Fe(OH)3 which is filtered off,and the remaining solution is then treated with HCl and extracted with phenol-CHCl3.Finally,this extract is worked up to give the pure product.

参考文献标题:260.Stoffwechselprodukte von actinomyceten.Uber die isolierung und charakterisierung der ferrioxamine A-F,neuer wuchsstadde der sideramin-gruppe
文献作者:Bickel,H.; et al.
参考来源:Helv Chim Acta 1960,432118-28


合成路线:A culture broth of Streptomyces pilosus ETH 21748 is treated with Hyflo-Supercel and aqueous ferric sulfate,and the clear solution obtained is extracted with phenol-CHCl3 to obtain,after purification a crude mixture of ferrioxamins A,B,C,D1,D2,E and F.This crude product is chromatographed through Dowex 50 WX2 using an ammonium acetate buffer and the different ferrioxamins are separated.The treatment of ferrioxamin B (I) with aqueous NaOH gives a precipitate of Fe(OH)3 which is filtered off,and the remaining solution is then treated with HCl and extracted with phenol-CHCl3.Finally,this extract is worked up to give the pure product.

参考文献标题:261.Stoffweschselprodukte von actinomyceten,Uber die konstitution von ferrioxamine B
文献作者:Bickel,H.; et al.
参考来源:Helv Chim Acta 1960,432129-38


合成路线:The reaction of 1-amino-5-nitropentane (I) with benzyloxycarbonyl chloride (A) by means of NaOH in water gives 1-carbobenzoxyamino-5-nitropentane (II),which by reduction with Zn and ammonium chloride in ethanol - water yields 1-carbobenzoxyamino-5-hydroxylaminopentane (III).The reaction of (III) with succinic anhydride (B) by means of NaOH in pyridine water affords 1-carbobenzoxyamino-5-(N-succinylhydroxylamino)pentane (IV),which is cyclized with hot acetic anhydride giving 2-(5-carbobenzoxyaminopentyl)-3,6-dioxotetrahydro-1,2-oxazine (V).The reaction of (V) with the nitroamine (I) by means of sodium methoxide in methanol yields 1-carbobenzoxy-6-hydroxy-16-nitro-7,10-dioxo-6,11-diazahexadecane (VI),which is reduced with Zn and acetylated as before affording 1-carboxybenzoxyamino-6-hydroxy-16-(N-acetylhydroxylamino)-7,10-dioxo-6,11-diazahexadecane (VII).

合成路线:The acetylation of (III) as before gives 1-carbobenzoxyamino-5-(N-acetylhydroxylamino)pentane (X),which is debenzylated as usual yielding 1-amino-5-(N-acetylhydroxylamino)pentane (XI).Finally,this compound is condensed with (V) to afford (VII).

合成路线:The debenzylation of (VII) by hydrogenation with H2 over Pd/C gives 1-amino-6-hydroxy-16-(N-acetylhydroxylamino)-7,10-dioxo-6,11-diazahexadecane (VIII),which condensed with (V) as before yields 1-carbobenzoxyamino-6,17-dihydroxy-7,10,18,21-tetraoxo-27-(N-acetylhydroxylamino)-6,11,17,22-tetrazaheptaeicosane (IX).Finally,this compound is debenzylated by means H2 over Pd/C.

参考文献标题:75.Stoffweschselprodukte con actinomyceten.Uber die synthese der ferrioxamine B und D1
文献作者:Prelog,V.; Walser,A.
参考来源:Helv Chim Acta 1962,45631-637


合成路线:A culture broth of Streptomyces pilosus ETH 21748 is treated with Hyflo-Supercel and aqueous ferric sulfate,and the clear solution obtained is extracted with phenol-CHCl3 to obtain,after purification a crude mixture of ferrioxamins A,B,C,D1,D2,E and F.This crude product is chromatographed through Dowex 50 WX2 using an ammonium acetate buffer and the different ferrioxamins are separated.The treatment of ferrioxamin B (I) with aqueous NaOH gives a precipitate of Fe(OH)3 which is filtered off,and the remaining solution is then treated with HCl and extracted with phenol-CHCl3.Finally,this extract is worked up to give the pure product.

合成路线:The reaction of 1-amino-5-nitropentane (I) with benzyloxycarbonyl chloride (A) by means of NaOH in water gives 1-carbobenzoxyamino-5-nitropentane (II),which by reduction with Zn and ammonium chloride in ethanol - water yields 1-carbobenzoxyamino-5-hydroxylaminopentane (III).The reaction of (III) with succinic anhydride (B) by means of NaOH in pyridine water affords 1-carbobenzoxyamino-5-(N-succinylhydroxylamino)pentane (IV),which is cyclized with hot acetic anhydride giving 2-(5-carbobenzoxyaminopentyl)-3,6-dioxotetrahydro-1,2-oxazine (V).The reaction of (V) with the nitroamine (I) by means of sodium methoxide in methanol yields 1-carbobenzoxy-6-hydroxy-16-nitro-7,10-dioxo-6,11-diazahexadecane (VI),which is reduced with Zn and acetylated as before affording 1-carboxybenzoxyamino-6-hydroxy-16-(N-acetylhydroxylamino)-7,10-dioxo-6,11-diazahexadecane (VII).

合成路线:The acetylation of (III) as before gives 1-carbobenzoxyamino-5-(N-acetylhydroxylamino)pentane (X),which is debenzylated as usual yielding 1-amino-5-(N-acetylhydroxylamino)pentane (XI).Finally,this compound is condensed with (V) to afford (VII).

合成路线:The debenzylation of (VII) by hydrogenation with H2 over Pd/C gives 1-amino-6-hydroxy-16-(N-acetylhydroxylamino)-7,10-dioxo-6,11-diazahexadecane (VIII),which condensed with (V) as before yields 1-carbobenzoxyamino-6,17-dihydroxy-7,10,18,21-tetraoxo-27-(N-acetylhydroxylamino)-6,11,17,22-tetrazaheptaeicosane (IX).Finally,this compound is debenzylated by means H2 over Pd/C.
参考文献标题:153.Stoffweschselprodukte von mikroorganismen.Zur henntnis von desferrioxamin B
文献作者:Bickel,H.; et al.
参考来源:Helv Chim Acta 1963,461385-89