Gimatecan, LBQ-707, CPT-184, ST-1481
吉马替康Chemical Name: 7-(tert-Butoxyiminomethyl)camptothecin; (4S)-4-Ethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-11-carbaldehyde O-(tert-butyl)oxime
CAS No. 292618-32-7
项目整合开发状态: Phase II
项目研究机构: Sigma-Tau (Orphan Drug), Istituto Nazionale Studio e Cura Tumori (Originator), Sigma-Tau (Originator), Novartis (Licensee)
合成路线:Radical hydroxymethylation of camptothecin (I) by means of MeOH in the presence of H2O2 and FeSO4 provided (II).Subsequent heating of alcohol (II) in acetic acid gave rise to 7-formylcamptothecine (III).Finally,condensation of aldehyde (III) with O-t-butylhydroxylamine afforded the corresponding oxime.
合成路线:The title imine derivative was prepared by condensation of the known 7-formylcamptothecin (I) with aniline (II) in the presence of ytterbium triflate and molecular sieves in CH2Cl2.
📌 参考资料/链接：
参考文献标题:Camptothecin derivs.having antitumor activity
文献作者:Carminati,P.; Penco,S.; Zunino,F.; Merlini,L.(Istituto Nazionale per lo Studio e la Cura dei Tumori; Sigma-Tau Industrie Farmaceutiche Riunite SpA)
参考来源:EP 1044977; WO 0053607
📄 详细内容
合成路线:Semisynthesis: Treatment of camptothecin (XI) with tert-butylhydroperoxide in the presence of FeSO4,conc.H2SO4 and acetic acid in water gives (S)-7-methylcamptothecin (XII).Mannich reaction of compound (XII) with isopropylamine hydrochloride in DMSO as a formaldehyde source gives CKD-602.
合成路线:Radical hydroxymethylation of camptothecin (I) by means of MeOH in the presence of H2O2 and FeSO4 provided (II).Subsequent heating of alcohol (II) in acetic acid gave rise to 7-formylcamptothecine (III).Finally,condensation of aldehyde (III) with O-t-butylhydroxylamine afforded the corresponding oxime.
参考文献标题:Chemical modification of an antitumor alkaloid camptothecin: Synthesis and antitumor activity of 7-C-substituted camptothecins
文献作者:Sawada,S.; Nokata,K.; Furuta,T.; Yokokura,T.; Miyasaka,T.
参考来源:Chem Pharm Bull 1991,39(10),2574
合成路线:Radical hydroxymethylation of camptothecin (I) by means of MeOH in the presence of H2O2 and FeSO4 provided (II).Subsequent heating of alcohol (II) in acetic acid gave rise to 7-formylcamptothecine (III).Finally,condensation of aldehyde (III) with O-t-butylhydroxylamine afforded the corresponding oxime.
参考文献标题:Novel 7-oxyiminomethyl derivatives of camptothecin with potent in vitro and in vivo antitumor activity
文献作者:Dallavalle,S.; Ferrari,A.; Biasotti,B.; Merlini,L.; Penco,S.; Gallo,G.; Marzi,M.; Tinti,M.O.; Martinelli,R.; Pisano,C.; Carminati,P.; Carenini,N.; Beretta,G.; Perego,P.; De Cesare,M.; Pratesi,G.; Zunino,F.
参考来源:J Med Chem 2001,44(20),3264
产品链接: CAS No. 292618-32-7››