Theprubicin, Pirarubicin, THP-ADM, Therarubicin, Pinorubicin, -Drug Synthesis Database

【结构式】

【药物名称】Theprubicin, Pirarubicin, THP-ADM, Therarubicin, Pinorubicin

【化学名称】(8S,10S)-10-[[3-Amino-2,3,6-trideoxy-4-O-(2R-tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl]oxy]-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
　　　　　　(8S-cis)-10-[[3-Amino-2,3,6-trideoxy-4-O-(tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
　　　　　　4'-O-Tetrahydropyranyladriamycin
　　　　　　4'-O-Tetrahydropyranyldoxorubicin

【CA登记号】72496-41-4

【分子式】C₃₂H₃₇NO₁₂

【分子量】627.65119

【开发单位】Meiji Seika (Originator), Nippon Kayaku (Originator), Sanraku (Originator), Almirall Prodesfarma (Licensee)

【药理作用】Antibiotics and Alkaloids, Antineoplastic Antibiotics, ONCOLYTIC DRUGS

合成路线1

This compound can be obtained by two related ways: 1) By reaction of adriamycin (I) with 2,3-dihydropyran (II) by means of p-toluenesulfonic acid as a catalyst in DMF. 2) The reaction of adriamycin (I) with 2,3-dihydropyran (II) under stronger conditions yields 14,4'-O-bistetrahydropyranyladriamycin (III), which is selectively hydrolyzed with aqueous 10% acetic acid.

参考文献中间体

【1】 Kinoshita, M.; Ishizuka, M.; Takeuchi, T.; Tatsuta, K.; Takahashi, Y.; Umezawa, H.; Naganawa, H.; Masuda, T.; Tetrahydropyranyl derivatives of daunomycin and adriamycin. J Antibiot 1979, 32, 10, 1082-85.
【2】 Umezawa, H.; Takeuchi, T.; Naganawa, H.; Tatsuka, K. (Microbial Chemistry Research Foundation); Anthracycline derivatives, a process for their preparation and pharmaceutical compositions containing them. AT 369384B; CA 1136618; EP 0014853; ES 488209; US 4303785 .
【3】 Blancafort, P.; Castaner, J.; Serradell, M.N.; THP-ADM. Drugs Fut 1983, 8, 7, 610.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	11675	(8S,10S)-10-[[(2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-8-glycoloyl-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione		C₂₇H₂₉NO₁₁	详情	详情
(II)	13684	3,4-Dihydro-2H-pyran;2,3-Dihydro-4H-pyran; 5,6-Dihydro-4H-pyran;Dihydropyran	110-87-2	C₅H₈O	详情	详情
(III)	31091	(8S,10S)-10-[[(2R,4S,5S,6S)-4-amino-6-methyl-5-(tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yl]oxy]-6,8,11-trihydroxy-1-methoxy-8-[2-(tetrahydro-2H-pyran-2-yloxy)acetyl]-7,8,9,10-tetrahydro-5,12-naphthacenedione		C₃₇H₄₅NO₁₃	详情	详情

Extended Information