Tocladesine, Adenazole, ICN-1256, NSC-614491, 8-Cl-cAMP
8-氯腺苷-3',5'-环状磷酸钠盐Chemical Name: 8-Chloroadenosine-3',5'-O-monophosphate
CAS No. 41941-56-4
项目整合开发状态: Phase II
项目研究机构: Cancer Research UK (Originator), National Cancer Institute (Originator), Ribapharm (Originator)
合成路线:Direct chlorination of adenosine 3',5'-cyclic phosphate (I) was carried out by treatment with anhydrous HCl and m-chloroperbenzoic acid (m-CPBA) in DMF or with N-chlorosuccinimide and NaCl in aqueous HOAc.Chlorination of adenosine (II) was achieved by treatment with HCl in the presence of m-CPBA or in the absence of the oxidating reagent m-CPBA at a higher temperature and longer reaction times.The resultant 8-chloroadenosine (III) was converted to the monophosphate (IV) by means of POCl3,and this was further cyclized to the title compound using DCC.8-Chloroadenosine monophosphate (IV) was also accessible by chlorination of adenosine monophosphate (V).Optionally,the chlorinated adenosine (III) was directly converted to the title cyclic phosphate by phosphorylation with POCl3 in the presence of NaOH in triethyl phosphate as the solvent.
合成路线:The title chloro derivative was also obtained by halogen exchange of the previously reported 8-bromoadenosine cyclic phosphate (VI) with CaCl2 in hot DMF.Alternatively,the 8-thioadenosine derivative (VII) was converted into the target compound by treatment with elemental chlorine in methanolic HCl at -15 C.
📌 参考资料/链接：
参考文献标题:Treatment of malignant tumours with 8-chloroadenosine 3'-5'-cyclic phosphate,8-aminoadenosine 3',5'-cyclic phosphate and preparation thereof
文献作者:Robins,R.K.; Revankar,G.R.; Chang,Y.(Nucleic Acid Res.Inst.,Costa Mesa)
参考来源:EP 0499291; WO 8905648
📄 详细内容
合成路线:Direct chlorination of adenosine 3',5'-cyclic phosphate (I) was carried out by treatment with anhydrous HCl and m-chloroperbenzoic acid (m-CPBA) in DMF or with N-chlorosuccinimide and NaCl in aqueous HOAc.Chlorination of adenosine (II) was achieved by treatment with HCl in the presence of m-CPBA or in the absence of the oxidating reagent m-CPBA at a higher temperature and longer reaction times.The resultant 8-chloroadenosine (III) was converted to the monophosphate (IV) by means of POCl3,and this was further cyclized to the title compound using DCC.8-Chloroadenosine monophosphate (IV) was also accessible by chlorination of adenosine monophosphate (V).Optionally,the chlorinated adenosine (III) was directly converted to the title cyclic phosphate by phosphorylation with POCl3 in the presence of NaOH in triethyl phosphate as the solvent.
参考文献标题:The facile and efficient synthesis of 8-chloroadenosine 3',5'-cyclic monophosphate by phosphorylative cyclization of 8-chloroadenosine and its characterization by 1H and 13C NMR spectroscopy
文献作者:Woo,N.-T.; et al.
参考来源:Arch Pharmacal Res 1997,20(2),176
合成路线:The title chloro derivative was also obtained by halogen exchange of the previously reported 8-bromoadenosine cyclic phosphate (VI) with CaCl2 in hot DMF.Alternatively,the 8-thioadenosine derivative (VII) was converted into the target compound by treatment with elemental chlorine in methanolic HCl at -15 C.
参考文献标题:Synthesis and biological activity of 8-haloadenosine 3',5'-cyclic phosphates
文献作者:Muneyama,K.; et al.
参考来源:J Carbohydr Nucleosides Nucleotides 1974,1(1),55
产品链接: CAS No. 41941-56-4››