9-(2-deoxy-5-O-phosphonopentofuranosyl)-2-{[(1R,2R,3S,4R)-2,3,4-trihydroxy-7-methyl-1,2,3,4-tetrahydrotetraphen-1-yl]amino}-3,9-dihydro-6H-purin-6-one | 133551-48-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 9-(2-deoxy-5-O-phosphonopentofuranosyl)-2-{[(1R,2R,3S,4R)-2,3,4-trihydroxy-7-methyl-1,2,3,4-tetrahydrotetraphen-1-yl]amino}-3,9-dihydro-6H-purin-6-one
• 英文别名: 9-(2-Deoxy-5-O-phosphonopentofuranosyl)-2-{[(1R,2R,3S,4R)-2,3,4-trihydroxy-7,12-dimethyl-1,2,3,4-tetrahydro-1-tetraphenyl]amino}-3,9-dihydro-6H-purin-6-one；9-(2-Deoxy-5-O-phosphonopentofuranosyl)-2-{[(1S,2R,3S,4R)-2,3,4-trihydroxy-7,12-dimethyl-1,2,3,4-tetrahydro-1-tetraphenyl]amino}-3,9-dihydro-6H-purin-6-one；[3-hydroxy-5-[6-oxo-2-[[(1R,2S,3R,4S)-2,3,4-trihydroxy-7,12-dimethyl-1,2,3,4-tetrahydrobenzo[a]anthracen-1-yl]amino]-3H-purin-9-yl]oxolan-2-yl]methyl dihydrogen phosphate
• CAS: 133551-48-1；133645-08-6；133645-09-7；133645-10-0
• 化学式: C₃₀H₃₂N₅O₁₀P
• 分子量: 653.585
• InChiKey: QTLGKGTYSHMEFZ-MXSPZODLSA-N

物化性质

• 密度：
  1.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  46.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  232.51
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  9-(2-deoxy-5-O-phosphonopentofuranosyl)-2-{[(1R,2R,3S,4R)-2,3,4-trihydroxy-7-methyl-1,2,3,4-tetrahydrotetraphen-1-yl]amino}-3,9-dihydro-6H-purin-6-one 生成 Guanosine, 2'-deoxy-N-(1,2,3,4-tetrahydro-2,3,4-trihydroxy-7,12-dimethylbenz[a]anthracen-1-yl)- (9CI) 、 9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-((1S,2R,3S,4R)-2,3,4-trihydroxy-7,12-dimethyl-1,2,3,4-tetrahydro-benzo[a]anthracen-1-ylamino)-1,9-dihydro-purin-6-one 、 Guanosine, 2'-deoxy-N-(1,2,3,4-tetrahydro-2,3,4-trihydroxy-7,12-dimethylbenz[a]anthracen-1-yl)- (9CI) 、 Guanosine, 2'-deoxy-N-(1,2,3,4-tetrahydro-2,3,4-trihydroxy-7,12-dimethylbenz[a]anthracen-1-yl)- (9CI)
  参考文献：
  名称：

  Effect of bay region methyl group on reactions of anti-benz[a]anthracene 3,4-dihydrodiol 1,2-epoxides with DNA

  摘要：

  The NMR spectroscopic characterization of seven 7-methylbenz[a]anthracene-deoxyribonucleoside adducts and eight 7,12-dimethylbenz[a]anthracene-deoxyribonucleoside adducts, derived from the reaction of the corresponding anti-dihydrodiol epoxides and deoxyguanylic and deoxyadenylic acids, is described. The epoxide ring is opened by the purine amino groups to yield both cis and trans products from each enantiomer in the racemic dihydrodiol epoxides. Circular dichroism and NMR spectra allow the conformations of the products to be established. Interesting differences between the products from the two hydrocarbons are as follows: the dimethyl derivative is distributed fairly evenly over adenine and guanine residues in DNA, whereas guanine is the principal site for reaction of the monomethyl derivative; the conformation of the tetrahydro ring system is similar in trans products for both hydrocarbons with the hydrogens on C3 and C4 being pseudodiaxial; in cis adducts, these hydrogens are pseudodiaxial for 7,12-dimethylbenz[a]anthracene adducts but pseudodiequatorial for the 7-methylbenz[a]anthracene adducts; in reactions with nucleotides, trans adducts predominate for 7-methylbenz[a]anthracene derivatives but trans and cis adducts form to similar extents for 7,12-dimethylbenz[a]anthracene derivatives. This latter differs substantially from previous findings with other bay region substituted hydrocarbons where cis adducts have been obtained only in low yields.

  DOI：

  10.1021/jo00013a020
• 作为产物：
  描述：

  7,12-dimethylbenz[a]anthracene anti-diol epoxide 、 2ˊ-脱氧鸟苷-5ˊ-一磷酸 在 tris-HCl-buffer 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 生成 9-(2-deoxy-5-O-phosphonopentofuranosyl)-2-{[(1R,2R,3S,4R)-2,3,4-trihydroxy-7-methyl-1,2,3,4-tetrahydrotetraphen-1-yl]amino}-3,9-dihydro-6H-purin-6-one
  参考文献：
  名称：

  Effect of bay region methyl group on reactions of anti-benz[a]anthracene 3,4-dihydrodiol 1,2-epoxides with DNA

  摘要：

  The NMR spectroscopic characterization of seven 7-methylbenz[a]anthracene-deoxyribonucleoside adducts and eight 7,12-dimethylbenz[a]anthracene-deoxyribonucleoside adducts, derived from the reaction of the corresponding anti-dihydrodiol epoxides and deoxyguanylic and deoxyadenylic acids, is described. The epoxide ring is opened by the purine amino groups to yield both cis and trans products from each enantiomer in the racemic dihydrodiol epoxides. Circular dichroism and NMR spectra allow the conformations of the products to be established. Interesting differences between the products from the two hydrocarbons are as follows: the dimethyl derivative is distributed fairly evenly over adenine and guanine residues in DNA, whereas guanine is the principal site for reaction of the monomethyl derivative; the conformation of the tetrahydro ring system is similar in trans products for both hydrocarbons with the hydrogens on C3 and C4 being pseudodiaxial; in cis adducts, these hydrogens are pseudodiaxial for 7,12-dimethylbenz[a]anthracene adducts but pseudodiequatorial for the 7-methylbenz[a]anthracene adducts; in reactions with nucleotides, trans adducts predominate for 7-methylbenz[a]anthracene derivatives but trans and cis adducts form to similar extents for 7,12-dimethylbenz[a]anthracene derivatives. This latter differs substantially from previous findings with other bay region substituted hydrocarbons where cis adducts have been obtained only in low yields.

  DOI：

  10.1021/jo00013a020