ODC-188(free base), DU-1101(free base), ODC-218, DU-1102
Chemical Name: N1-(7-Chloroquinolin-4-yl)-N2-[6',7'a-diphenyl-7',7'a-dihydrospiro[cyclohexane-1,3'-4'aH-cyclopenta[1,2,4]trioxin]-4-yl]ethane-1,2-diamine dicitrate
CAS No. 324761-14-0, 324761-13-9 (free base)
项目整合开发状态: Preclinical
项目研究机构: CNRS (Originator), Palumed (Originator)
合成路线:The peroxidation of 1,4-diphenyl-1-cyclopentadiene (I) with O2,white light and activated by tetraphenylporphyrin in dichloromethane gives the peroxide (II),which is condensed with cyclohexane-1,4-dione (III) by means of trimethylsilyl trifluoromethanesulfonate in dichloromethane,yielding the adduct (IV).The reductocondensation of (IV) with N-(7-chloroquinolin-4-yl)ethylenediamine (V) by means of NaBH(OAc)3 in dichloromethane affords the tricyclic trioxane (VI),which is finally treated with citric acid in acetone to provide the target citrate.The intermediate N-(7-chloroquinolin-4-yl)ethylenediamine (V) has been obtained by reaction of 4,7-dichloroquinoline (VIII) with ethylenediamine by means of NaOH at 85 C.
📌 参考资料/链接：
参考文献标题:Dual molecules containing a peroxide deriv.,synthesis and therapeutic applications thereof
文献作者:Robert,A.; Dechy Cabaret,O.; Meunier,B.; Benoit Vical,F.(CNRS (Centre National de la Recherche Scientifique))
参考来源:FR 2807433; WO 0177105
📄 详细内容
合成路线:The peroxidation of 1,4-diphenyl-1-cyclopentadiene (I) with O2,white light and activated by tetraphenylporphyrin in dichloromethane gives the peroxide (II),which is condensed with cyclohexane-1,4-dione (III) by means of trimethylsilyl trifluoromethanesulfonate in dichloromethane,yielding the adduct (IV).The reductocondensation of (IV) with N-(7-chloroquinolin-4-yl)ethylenediamine (V) by means of NaBH(OAc)3 in dichloromethane affords the tricyclic trioxane (VI),which is finally treated with citric acid in acetone to provide the target citrate.The intermediate N-(7-chloroquinolin-4-yl)ethylenediamine (V) has been obtained by reaction of 4,7-dichloroquinoline (VIII) with ethylenediamine by means of NaOH at 85 C.
参考文献标题:Preparation of antimalarial activities of "trioxaquines",new modular molecules with a trioxane skeleton linked to a 4-aminoquinoline
文献作者:Dechy-Cabaret,O.; et al.
参考来源:ChemBioChem 2000,1(4),281