Acetic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester | 102219-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Acetic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester
• CAS: 102219-53-4
• 化学式: C₃₉H₃₇N₃O₈
• 分子量: 675.738
• InChiKey: VNLOKSDEZNVSNN-GABYNLOESA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  127.21
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 在 吡啶 、 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 硝基甲烷 为溶剂， 生成 O^3'-acetyl-N⁴-benzoyl-O^5'-(toluene-4-sulfonyl)-2'deoxy-cytidine
  参考文献：
  名称：

  三唑基13α-雌激素-核苷生物共轭物的合成及生物学评价。

  摘要：

  通过应用铜催化的炔-叠氮化物点击反应（CuAAC）合成了13α-雌酮的2'-脱氧核苷共轭物。为了引入叠氮基，选择了核苷的5'-位和13α-雌酮的3-羟基上的炔丙基醚官能团。当核苷的3'-羟基被乙酰基保护并且5'-羟基通过甲苯磺酰叠氮化物交换法进行修饰时，我们的手中获得了最佳收率。受保护的5'-叠氮核苷和甾类炔烃之间单击反应的常用条件通过使用1.5当量的Cu（I）催化剂进行了轻微修饰。所有制备的缀合物均通过MTT分析法在体外评估，其针对一组人类粘附细胞系（HeLa，通过体外放射性底物孵育研究了MCF-7和A2780）以及新缀合物对人17β-羟基类固醇脱氢酶1（17β-HSD1）的潜在抑制活性。一些受保护的缀合物对一组人类粘附癌细胞系表现出中等的抗增殖特性（受保护的胞苷缀合物被证明是最有效的，IC50值为9μM）。胸苷偶联物显示出相当大的17β-HSD1抑制活性（IC50 = 19μM）。一些

  DOI：

  10.3390/molecules21091212
• 作为产物：
  描述：

  乙酸酐 、 N4-苯甲酰基-5′-O-(4,4′-二甲氧基三苯基)-2′-脱氧胞苷 在 吡啶 作用下， 反应 4.0h， 生成 Acetic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  三唑基13α-雌激素-核苷生物共轭物的合成及生物学评价。

  摘要：

  通过应用铜催化的炔-叠氮化物点击反应（CuAAC）合成了13α-雌酮的2'-脱氧核苷共轭物。为了引入叠氮基，选择了核苷的5'-位和13α-雌酮的3-羟基上的炔丙基醚官能团。当核苷的3'-羟基被乙酰基保护并且5'-羟基通过甲苯磺酰叠氮化物交换法进行修饰时，我们的手中获得了最佳收率。受保护的5'-叠氮核苷和甾类炔烃之间单击反应的常用条件通过使用1.5当量的Cu（I）催化剂进行了轻微修饰。所有制备的缀合物均通过MTT分析法在体外评估，其针对一组人类粘附细胞系（HeLa，通过体外放射性底物孵育研究了MCF-7和A2780）以及新缀合物对人17β-羟基类固醇脱氢酶1（17β-HSD1）的潜在抑制活性。一些受保护的缀合物对一组人类粘附癌细胞系表现出中等的抗增殖特性（受保护的胞苷缀合物被证明是最有效的，IC50值为9μM）。胸苷偶联物显示出相当大的17β-HSD1抑制活性（IC50 = 19μM）。一些

  DOI：

  10.3390/molecules21091212

文献信息

• 2-(4-Nitrophenyl)ethyl Methylenebis(phosphonate):  A Versatile Reagent for the Synthesis of Nucleoside 5‘-Methylenebis(phosphonate)s
  作者：Krystyna Lesiak、Kyoichi A. Watanabe、Jay George、Krzysztof W. Pankiewicz

  DOI：10.1021/jo971859a

  日期：1998.3.1

  2-(4-Nitrophenyl)ethyl methylenebis(phosphonate) (6) was prepared by reaction of equimolar amounts of 2-(4-nitrophenyl)ethyl alcohol and methylenebis(phosphonyl) tetrachloride in the presence of tetrazole. Compound 6 was further converted into the corresponding 4-nitrophenylethyl trisanhydride intermediate 7 by dehydration with diisopropylcarbodiimide (DIC). Reaction of 7 with either 2',3'-O-isopropylideneadenosine (8a) or 2',3'-O-isopropylideneguanosine (8b) afforded, after hydrolysis, the desired P-1-[2-(4-nitrophenyl)ethyl]-P-2-(2',3'-O-isopropylideneadenosin-5'-yl)methylenebis(phosphonate) (9a) and guanosine analogue 9b, respectively. A similar treatment of intermediate 7 with 3'-O-acetylthymidine (12a), 3'-O-acetyl-2'-deoxy-N-4-benzoylcytidine (12b), 3'-O-acetyl-2'-deoxy-N-6-benzoyladenosine (12c), and 3'-O-acetyl-2'-deoxy-N-2-isobutyrylguanosine (12d) gave the corresponding 2-(4-nitrophenyl)ethyl methylenebis(phosphonate)s 13a-d. These compounds as well as 9a,b were treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) which caused elimination of the 2-(4-nitrophenyl)ethyl group. The base labile 3'-O-acetyl, N-4-acetyl, N-6-benzoyl, and N-2-isobutyryl groups of 12a-d were also removed during the DBU treatment. Thus, the 5'-methylenebis(phosphonate)s of 2',3'-O-isopropylideneadenosine (10a), 2',3'-O-isopropylideneguanosine (10b), thymidine (14a), 2'-deoxycytidine (14b), 2'-deoxyadenosine (14c), and 2'-deoxyguanosine (14d) were prepared in good yield. De-O-isopropylidenation of 10a and 10b afforded adenosine 5'-methylenebis(phosphonate) (11a) and guanosine 5'-methylenebis(phosphonate) (11b), respectively.
• Synthesis of 2′-Deoxynucleoside 5′-Methylenebis-(phosphonate)s Using 2-(4-Nitrophenyl)ethyl Methylenebis(phosphonate) as the Phosphonylating Agent.
  作者：Krystyna Lesiak、Kyoichi A. Watanabe、Krzysztof W. Pankiewicz

  DOI：10.1080/07328319808004723

  日期：1998.9

  2-(4-Nitrophenylethyl) methylenebis(phosphonate) (1) has been prepared by reaction of 2-(4-nitrophenyl)ethyl alcohol with methylenebis(phosphonyl) tetrachloride. Compound 1 was treated with diisopropylcarbodiimide (DIC) to give bicyclic intermediate 2, which in reaction with suitably protected 2'-deoxynucleosides 3 gave P-1,P-2-disubstituted methylenebis(phosphonate)s 4. Removal of the nitrophenylethyl group by beta-elimination with DBU afforded the corresponding 2'-deoxynucleoside 5'-methylene-bis(phosphonate) analogues 5.