Bradyzide

Chemical Name: N-[2-[N-[2-(Dimethylamino)ethyl]-N-methylamino]ethyl]-1-[4-[4-(diphenylmethyl)thiosemicarbazido]-3-nitrophenylsulfonyl]pyrrolidine-2(S)-carboxamide
CAS No. 263011-13-8
项目整合开发状态: Preclinical
项目研究机构: Novartis (Originator)
合成路线:Ethanolamine (I) was protected as the N-benzyloxycarbonyl derivative (II) and subsequently converted to tosylate (III).Alkylation of N,N,N'-trimethylethylenediamine (IV) with tosylate (III) produced triamine (V).The benzyloxycarbonyl protecting group was then removed by transfer hydrogenolysis with ammonium formate and Pd/C to yield triamine (VI).

合成路线:Condensation of 4-chloro-3-nitrobenzenesulfonyl chloride (VII) with L-proline tert-butyl ester (VIII) yielded sulfonamide (IX).Displacement of the chloro group of (IX) with hydrazine hydrate furnished the aryl hydrazine (X),which was reacted with benzhydryl isothiocyanate (XI) to produce the thiosemicarbazide (XII).After acid cleavage of the tert-butyl ester of (XII),the resulting carboxylic acid (XIII) was activated with isobutyl chloroformate and then coupled with triamine (VI) to furnish the title amide.