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【结 构 式】 
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【分子编号】63838 【品名】8-(9-hydroxytricyclo[3.3.1.0~3,7~]non-3-yl)-1-(2-oxopropyl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione 【CA登记号】 |
【 分 子 式 】C20H26N4O4 【 分 子 量 】386.451 【元素组成】C 62.16% H 6.78% N 14.5% O 16.56% |
合成路线1
该中间体在本合成路线中的序号：M3The condensation of 9-oxotricyclo[3.3.1.03,7]nonane-3-carboxylic acid methyl ester (II) with 5,6-diamino-1-propylpyrimidine-2,4(1H,3H)-dione (VI) by means of LiOH gives the expected condensation product (VII), which by reduction with NaBH4 and HPLC separation yields the exo-hydroxy isomer (VIII). The condensation of (VIII) with bromoacetone (IX) by means of cesium carbonate affords compound (X), which is cyclized with Ca(OH)2 as before to give metabolite M3. Finally, this compound is reduced with NaBH4 to afford metabolite M2.
| 【1】 Shimada, J.; Eguchi, T.; Yasuzawa, T.; Nakamura, A.; Horiguchi, A.; Mochida, K.; Suzuki, F.; Synthesis of rat metabolites of a adenosine A1 antagonist, KW-3902. Symp Med Chem 1996, Abst 1-P-24. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IIa) | 20541 | methyl 9-oxotricyclo[3.3.1.0(3,7)]nonane-3-carboxylate | C11H14O3 | 详情 | 详情 | |
| M3 | 63838 | 8-(9-hydroxytricyclo[3.3.1.0~3,7~]non-3-yl)-1-(2-oxopropyl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione | C20H26N4O4 | 详情 | 详情 | |
| M2 | 63839 | 1-(2-hydroxypropyl)-8-(9-hydroxytricyclo[3.3.1.0~3,7~]non-3-yl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione | C20H28N4O4 | 详情 | 详情 | |
| (V) | 20545 | 8-(9-oxotricyclo[3.3.1.0(3,7)]non-3-yl)-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione | C20H26N4O3 | 详情 | 详情 | |
| (VI) | 20546 | 5,6-diamino-1-propyl-2,4(1H,3H)-pyrimidinedione | C7H12N4O2 | 详情 | 详情 | |
| (VII) | 20547 | N-(6-amino-2,4-dioxo-1-propyl-1,2,3,4-tetrahydro-5-pyrimidinyl)-9-oxotricyclo[3.3.1.0(3,7)]nonane-3-carboxamide | C17H22N4O4 | 详情 | 详情 | |
| (VIII) | 20548 | N-(6-amino-2,4-dioxo-1-propyl-1,2,3,4-tetrahydro-5-pyrimidinyl)-9-hydroxytricyclo[3.3.1.0(3,7)]nonane-3-carboxamide | C17H24N4O4 | 详情 | 详情 | |
| (IX) | 20549 | 1-bromoacetone | 598-31-2 | C3H5BrO | 详情 | 详情 |
| (X) | 20550 | N-[6-amino-2,4-dioxo-3-(2-oxopropyl)-1-propyl-1,2,3,4-tetrahydro-5-pyrimidinyl]-9-hydroxytricyclo[3.3.1.0(3,7)]nonane-3-carboxamide | C20H28N4O5 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：M3The selective biological hydroxylation of compounds (XI) by means of Absidia ramosa FERM BP-4605 in corn steep liquor, glucose, Brig 35 at 28 C, 5-7 days gives metabolites M3.
| 【1】 Shimada, J.; Eguchi, T.; Yasuzawa, T.; Nakamura, A.; Horiguchi, A.; Mochida, K.; Suzuki, F.; Synthesis of rat metabolites of a adenosine A1 antagonist, KW-3902. Symp Med Chem 1996, Abst 1-P-24. |