【药物名称】Minamestane, FCE-24928
化学结构式(Chemical Structure):
参考文献No.1153
标题:Process for the preparation of 4-amino-androstenedione derivs
作者:(Microbial Chemistry Research Foundation)
来源:JP 1984186996
合成路线图解说明:

This compound can be obtained by three related ways: 1) The chlorination of androsta-1,4-diene-3,17-dione (I) with SO2Cl2 in pyridine gives 4-chloroandrosta-1,4-diene-3,17-dione (II), which is brominated with N-bromosuccinimide (NBS) in refluxing carbon tetrachloride yielding the 5-bromo derivative. The reaction of (III) with LiCl and Li2CO3 in hot DMF affords 4-chloroandrosta-1,4,6-triene-3,17-dione (IV), which is finally treated with NH4OH in dioxane at 90 C in a pressure vessel. 2) The reaction of 7alpha-acetoxy-6beta-bromoandrosta-1,4-diene-3,17-dione (V) with sodium azide in hot DMF gives 4-azidoandrosta-1,4,6-triene-3,17-dione (VI), which is then reduced with propane-1,3-dithiol and triethylamine in anhydrous methanol. 3) The reaction of 6beta,7alpha-dibromoandrosta-1,4-diene-3,17-dione (VII) with sodium azide as before also yields the azido derivative (VI).

参考文献No.4722
标题:4-Substd. androst-4-en-3,17-dione derivs. useful as aromatase inhibitors and their manufacturing
作者:Faustini, F.; D'Alessio, R.; Villa, V.; Di Salle, E.; Lombardi, P. (Pharmacia Corp.)
来源:AU 8653433; BE 0904226; CH 669199; DE 3604179; ES 8706165; ES 8708235; FR 2577556; GB 2171100; JP 1986189295
合成路线图解说明:

This compound can be obtained by three related ways: 1) The chlorination of androsta-1,4-diene-3,17-dione (I) with SO2Cl2 in pyridine gives 4-chloroandrosta-1,4-diene-3,17-dione (II), which is brominated with N-bromosuccinimide (NBS) in refluxing carbon tetrachloride yielding the 5-bromo derivative. The reaction of (III) with LiCl and Li2CO3 in hot DMF affords 4-chloroandrosta-1,4,6-triene-3,17-dione (IV), which is finally treated with NH4OH in dioxane at 90 C in a pressure vessel. 2) The reaction of 7alpha-acetoxy-6beta-bromoandrosta-1,4-diene-3,17-dione (V) with sodium azide in hot DMF gives 4-azidoandrosta-1,4,6-triene-3,17-dione (VI), which is then reduced with propane-1,3-dithiol and triethylamine in anhydrous methanol. 3) The reaction of 6beta,7alpha-dibromoandrosta-1,4-diene-3,17-dione (VII) with sodium azide as before also yields the azido derivative (VI).

参考文献No.154829
标题:Synthesis of novel 4-aminoandrostenediones
作者:Colombo, M.; Longo, A.; Lombardi, P.; Orzi, F.
来源:7th IUPAC Conf Org Synth (July 4-7, Nancy) 1988,Abst 7-R7
合成路线图解说明:

This compound can be obtained by three related ways: 1) The chlorination of androsta-1,4-diene-3,17-dione (I) with SO2Cl2 in pyridine gives 4-chloroandrosta-1,4-diene-3,17-dione (II), which is brominated with N-bromosuccinimide (NBS) in refluxing carbon tetrachloride yielding the 5-bromo derivative. The reaction of (III) with LiCl and Li2CO3 in hot DMF affords 4-chloroandrosta-1,4,6-triene-3,17-dione (IV), which is finally treated with NH4OH in dioxane at 90 C in a pressure vessel. 2) The reaction of 7alpha-acetoxy-6beta-bromoandrosta-1,4-diene-3,17-dione (V) with sodium azide in hot DMF gives 4-azidoandrosta-1,4,6-triene-3,17-dione (VI), which is then reduced with propane-1,3-dithiol and triethylamine in anhydrous methanol. 3) The reaction of 6beta,7alpha-dibromoandrosta-1,4-diene-3,17-dione (VII) with sodium azide as before also yields the azido derivative (VI).

参考文献No.154831
标题:Synthesis and in vitro evaluation of novel aromatase inhibitors
作者:Lombardi, P.; DiSalle, E.; D'Alessio, R.; Faustini, F.; Villa, V.
来源:J Steroid Biochem 1986,25(suppl)(Suppl.),Abst 128
合成路线图解说明:

This compound can be obtained by three related ways: 1) The chlorination of androsta-1,4-diene-3,17-dione (I) with SO2Cl2 in pyridine gives 4-chloroandrosta-1,4-diene-3,17-dione (II), which is brominated with N-bromosuccinimide (NBS) in refluxing carbon tetrachloride yielding the 5-bromo derivative. The reaction of (III) with LiCl and Li2CO3 in hot DMF affords 4-chloroandrosta-1,4,6-triene-3,17-dione (IV), which is finally treated with NH4OH in dioxane at 90 C in a pressure vessel. 2) The reaction of 7alpha-acetoxy-6beta-bromoandrosta-1,4-diene-3,17-dione (V) with sodium azide in hot DMF gives 4-azidoandrosta-1,4,6-triene-3,17-dione (VI), which is then reduced with propane-1,3-dithiol and triethylamine in anhydrous methanol. 3) The reaction of 6beta,7alpha-dibromoandrosta-1,4-diene-3,17-dione (VII) with sodium azide as before also yields the azido derivative (VI).

参考文献No.211471
标题:Minamestane
作者:Prous, J.; Mealy, N.; Casta馿r, J.
来源:Drugs Fut 1993,18(6),510
合成路线图解说明:

This compound can be obtained by three related ways: 1) The chlorination of androsta-1,4-diene-3,17-dione (I) with SO2Cl2 in pyridine gives 4-chloroandrosta-1,4-diene-3,17-dione (II), which is brominated with N-bromosuccinimide (NBS) in refluxing carbon tetrachloride yielding the 5-bromo derivative. The reaction of (III) with LiCl and Li2CO3 in hot DMF affords 4-chloroandrosta-1,4,6-triene-3,17-dione (IV), which is finally treated with NH4OH in dioxane at 90 C in a pressure vessel. 2) The reaction of 7alpha-acetoxy-6beta-bromoandrosta-1,4-diene-3,17-dione (V) with sodium azide in hot DMF gives 4-azidoandrosta-1,4,6-triene-3,17-dione (VI), which is then reduced with propane-1,3-dithiol and triethylamine in anhydrous methanol. 3) The reaction of 6beta,7alpha-dibromoandrosta-1,4-diene-3,17-dione (VII) with sodium azide as before also yields the azido derivative (VI).

参考文献No.212373
标题:Synthesis of novel aromatase inhibitors from bromosteroidal intermediates
作者:Colombo, M.; Longo, A.; Orzi, F.; Buzzetti, F.; Lombardi, P.
来源:Ind Chem Libr 1991,3119-25
合成路线图解说明:

This compound can be obtained by three related ways: 1) The chlorination of androsta-1,4-diene-3,17-dione (I) with SO2Cl2 in pyridine gives 4-chloroandrosta-1,4-diene-3,17-dione (II), which is brominated with N-bromosuccinimide (NBS) in refluxing carbon tetrachloride yielding the 5-bromo derivative. The reaction of (III) with LiCl and Li2CO3 in hot DMF affords 4-chloroandrosta-1,4,6-triene-3,17-dione (IV), which is finally treated with NH4OH in dioxane at 90 C in a pressure vessel. 2) The reaction of 7alpha-acetoxy-6beta-bromoandrosta-1,4-diene-3,17-dione (V) with sodium azide in hot DMF gives 4-azidoandrosta-1,4,6-triene-3,17-dione (VI), which is then reduced with propane-1,3-dithiol and triethylamine in anhydrous methanol. 3) The reaction of 6beta,7alpha-dibromoandrosta-1,4-diene-3,17-dione (VII) with sodium azide as before also yields the azido derivative (VI).

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