(7S,8R)-7-Bromo-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-8-hydroxy-4,6,7,8-tetrahydropyrimido[1,2-a]purin-10(3H)-one | 111189-87-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (7S,8R)-7-Bromo-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-8-hydroxy-4,6,7,8-tetrahydropyrimido[1,2-a]purin-10(3H)-one
• 英文别名: (7R,8S)-7-bromo-8-hydroxy-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4,6,7,8-tetrahydropyrimido[1,2-a]purin-10-one；3-(2-deoxy-β-D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-7-bromo-8-hydroxypyrimido<1,2-a>purin-10(3H)-one；3-(2-deoxy-β-D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-7-bromo-8-hydroxypyrimido[1,2-a]purin-10(3H)-one
• CAS: 111189-87-8；111265-78-2
• 化学式: C₁₃H₁₆BrN₅O₅
• 分子量: 402.205
• InChiKey: PUAGWHJRLJMCLX-RDDMABQCSA-N

物化性质

• 沸点：
  782.5±70.0 °C(Predicted)
• 密度：
  2.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.09
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  134.66
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2'-脱氧鸟苷 、 2-溴丙烯醛 以 甲醇 、 水 为溶剂， 反应 0.33h， 生成 (7S,8R)-7-Bromo-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-8-hydroxy-4,6,7,8-tetrahydropyrimido[1,2-a]purin-10(3H)-one 、 (6S,7R)-7-bromo-6-hydroxy-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4,6,7,8-tetrahydropyrimido[1,2-a]purin-10-one 、 (6R,7S)-7-溴-3-(2-脱氧-β-D-赤藓-五呋喃糖基)-6-羟基-4,6,7,8-四氢嘧啶并[1,2-a]嘌呤-10(3H)-酮 、 (6S,7S)-7-bromo-6-hydroxy-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4,6,7,8-tetrahydropyrimido[1,2-a]purin-10-one
  参考文献：
  名称：

  Formation of six cyclic 1,N2-hydroxybromopropanodeoxyguanosine isomers upon reaction of 2-bromoacrolein with 2'-deoxyguanosine

  摘要：

  DOI：

  10.1021/jo00236a008

文献信息

• 1,N 2-Cyclic deoxyguanosine adducts and guanine adducts of 2-haloacroleins. Isolation, characterization, isomerization and stability
  作者：Erwin Eder、Christian Hoffman

  DOI：10.1007/s002040050099

  日期：1994.8

  The reaction of the mutagenic 2-haloacroleins, 2-fluoroacrolein, 2-chloroacrolein and 2-bromoacrolein, with nucleosides and 5'-mononucleotides was studied. We found two different regioisomers of 1,N-2-cyclic deoxyguanosine adducts of 2-chloroacrolein and 2-bromoacrolein: type A, the 6-hydroxy, 7-haloadduct in which the OH-substituent is vicinal to the N-2-atom of the guanine moiety and type B, the 8-hydroxy, 7-haloadduct in which the OH-group is adjacent to the N-1-atom of the guanine moiety. The major adducts were the trans pairs of diastereomers of type A and type B in which the 6,7-substituents as well as the 7,8-substituents are in the energetically favoured diaxial position of the newly formed tetrahydropyrimidine ring. In the case of the type A regioisomers, the cis pairs of diastereomers (traces with chloroacrolein and about 4% with bromoacrolein) were also found in which the halosubstituent probably takes the equatorial position. Due to the anomeric effect, the OH-group takes the axial position in both regioisomers. No cis isomers of the type B regioisomers could be isolated. Acid hydrolysis of the deoxyguanosine adducts released deoxyribose, and the respective guanine adducts were isolated and characterized. Besides the vicinal halo, hydroxy adducts, trace amounts of the corresponding dihydroxy adducts were formed by hydrolysis of the chlorine or bromine substituents. The dihydroxy compounds possess the same structures and conformations in the newly formed tetrahydropyrimidine ring as do the halo, hydroxy adducts. Under our conditions no adducts other than those with deoxyguanosine and guanine could be identified. We found, however, indication for the formation of deoxyadenosine adducts when using dimethylsulfoxide as a solvent. No adducts in substantical amounts could be isolated with fluoroacrolein due to its rapid polymerization.