6-N-acetyl-8-oxoadenosine | 3868-35-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-N-acetyl-8-oxoadenosine
• 英文别名: 6-acetylamino-9-β-D-ribofuranosyl-7,9-dihydro-purin-8-one；6-N-Acetylamino-9-β-D-ribofuranosyl-8-oxo-purin；N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-oxo-7H-purin-6-yl]acetamide
• CAS: 3868-35-7
• 化学式: C₁₂H₁₅N₅O₆
• 分子量: 325.281
• InChiKey: HYPVPPODKIUGFS-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-N-acetyl-8-oxoadenosine 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 15.0h， 生成 6-N-acetyl-2',3'-di-O-benzoyl-5'-O-tert-butyldimethylsilyl-8-oxoadenosine
  参考文献：
  名称：

  膦酰胺及其相关化合物的首次合成及其抗癌活性。

  摘要：

  本文描述了膦酰胺和膦嘧啶B的首次合成，即由8-氧代腺苷和L-脯氨酸组成的核苷酸抗生素，它们通过独特的N-酰基氨基磷酸酯键连接。膦酰胺在N-酰基氨基磷酸酯键的磷原子上具有尚未确定的手性中心。磷肌苷B是一种脱磷的磷肌苷衍生物，在磷上没有手性。在5-（3,5-二硝基苯基）-1H-四唑存在下，N-乙酰基-8-氧代腺苷5'-O-亚磷酰胺衍生物与N-保护的脯氨酰胺反应成功地合成了肌苷B。通过使用叔丁氧羰基（Boc）基团可以成功合成膦嘧啶 发现它被选择性地引入到8-氧代腺苷的7-NH官能团中，并由于其空间效应而以未保护的6-氨基未被磷酸化的方式用作假保护基团。8-氧代腺苷5'-亚磷酰胺衍生物与N-三苯甲基脯氨酰胺的最终偶联反应，然后完全脱保护，得到膦酰胺及其非对映异构体的混合物。非对映异构体的（13）C NMR光谱表明，缓慢洗脱的非对映异构体1b是天然存在的膦酰胺。通过MTT分析评价了膦肌苷1b，其非对

  DOI：

  10.1021/jo016176g
• 作为产物：
  描述：

  8-氧腺苷 在 pyridine amine 、 sodium acetate 、 溶剂黄146 作用下， 反应 9.0h， 生成 6-N-acetyl-8-oxoadenosine
  参考文献：
  名称：

  Synthesis and antitumor activities of phosmidosine A and its N-acetylated derivative

  摘要：

  A new antitumor active phosmidosine A, which was isolated from Streptomyces sp., was successfully synthesized by a series of reactions involving construction of the N-acyl phosphoramidate linkage which was achieved by the reaction of the 5'-O-phosphoramidite derivative with a prolinamide derivative in the presence of 5-(3,5-dinitrophenyl)-1H-tetrazole. The growth inhibitory effect of phosmidosine A and its N-acetyl analog on the various human cell lines was examined. These results showed that both compounds have a significant growth inhibitory activity and that the 6-amino group is not required for the growth inhibitory activity of phosmidosine A. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00926-6

文献信息

• Structure–activity relationship of phosmidosine: importance of the 7,8-dihydro-8-oxoadenosine residue for antitumor activity
  作者：Mitsuo Sekine、Kazuhisa Okada、Kohji Seio、Hideaki Kakeya、Hiroyuki Osada、Takuma Sasaki

  DOI：10.1016/j.bmc.2004.07.021

  日期：2004.10

  To study the structure-activity relationship of phosmidosine, a variety of phosmidosine derivatives 9a-g were synthesized by condensation of N-diisopropyl N'-(N-tritylprolyl)phosphorodiamidite 6 with appropriately protected nucleoside derivatives 7a-g. As the result, replacement of the 7,8-diliydro-8-oxoadenine base by adenine and 6-N-acetyladenine did not affect the antitumor activity. However, phosmidosine derivatives containing uracil, cytosine, and guanine in place of the 7,8-dibydro-8-oxoadenine base did not show significant activity. A plausible explanation for the selective expression of phosmidosine compared with that of phosmidosine analogs having other amino acids in place of proline is also discussed. These results suggest that phosmidosine serves as an inhibitor of prolyl adenosine 5'-phosphate (prolyl-AMP) to inhibit the peptide synthesis in cancer-related cells. (C) 2004 Elsevier Ltd. All rights reserved.
• First Synthesis and Anticancer Activity of Phosmidosine and Its Related Compounds
  作者：Tomohisa Moriguchi、Norio Asai、Kazuhisa Okada、Kohji Seio、Takuma Sasaki、Mitsuo Sekine

  DOI：10.1021/jo016176g

  日期：2002.5.1

  the presence of 5-(3,5-dinitrophenyl)-1H-tetrazole. The successful synthesis of phosmidosine was achieved by use of a tert-butoxycarbonyl (Boc) group, which was found to be selectively introduced into the 7-NH function of 8-oxoadenosine and to serve as a pseudo-protecting group due to its steric effect in such manner that the unmasked 6-amino group was not phosphitylated. Final coupling reaction of the

  本文描述了膦酰胺和膦嘧啶B的首次合成，即由8-氧代腺苷和L-脯氨酸组成的核苷酸抗生素，它们通过独特的N-酰基氨基磷酸酯键连接。膦酰胺在N-酰基氨基磷酸酯键的磷原子上具有尚未确定的手性中心。磷肌苷B是一种脱磷的磷肌苷衍生物，在磷上没有手性。在5-（3,5-二硝基苯基）-1H-四唑存在下，N-乙酰基-8-氧代腺苷5'-O-亚磷酰胺衍生物与N-保护的脯氨酰胺反应成功地合成了肌苷B。通过使用叔丁氧羰基（Boc）基团可以成功合成膦嘧啶 发现它被选择性地引入到8-氧代腺苷的7-NH官能团中，并由于其空间效应而以未保护的6-氨基未被磷酸化的方式用作假保护基团。8-氧代腺苷5'-亚磷酰胺衍生物与N-三苯甲基脯氨酰胺的最终偶联反应，然后完全脱保护，得到膦酰胺及其非对映异构体的混合物。非对映异构体的（13）C NMR光谱表明，缓慢洗脱的非对映异构体1b是天然存在的膦酰胺。通过MTT分析评价了膦肌苷1b，其非对
• Synthesis and antitumor activities of phosmidosine A and its N-acetylated derivative
  作者：Tomohisa Moriguchi、Norio Asai、Takeshi Wada、Kohji Seio、Takuma Sasaki、Mitsuo Sekine

  DOI：10.1016/s0040-4039(00)00926-6

  日期：2000.7

  A new antitumor active phosmidosine A, which was isolated from Streptomyces sp., was successfully synthesized by a series of reactions involving construction of the N-acyl phosphoramidate linkage which was achieved by the reaction of the 5'-O-phosphoramidite derivative with a prolinamide derivative in the presence of 5-(3,5-dinitrophenyl)-1H-tetrazole. The growth inhibitory effect of phosmidosine A and its N-acetyl analog on the various human cell lines was examined. These results showed that both compounds have a significant growth inhibitory activity and that the 6-amino group is not required for the growth inhibitory activity of phosmidosine A. (C) 2000 Elsevier Science Ltd. All rights reserved.