2-amino-6-chloro-9-(2-C-cyano-2-deoxy-β-D-arabino-pentofuranosyl)purine | 937802-79-4

• 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: 2-amino-6-chloro-9-(2-C-cyano-2-deoxy-β-D-arabino-pentofuranosyl)purine
• 英文别名: (2R,3S,4S,5R)-2-(2-amino-6-chloropurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolane-3-carbonitrile
• CAS: 937802-79-4
• 化学式: C₁₁H₁₁ClN₆O₃
• 分子量: 310.7
• InChiKey: ZKXMXJMRADONFY-CBPNBUAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-amino-6-chloro-9-(2-C-cyano-2-deoxy-β-D-arabino-pentofuranosyl)purine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以42%的产率得到2-amino-9-(2-C-cyano-2-deoxy-β-D-arabino-pentofuranosyl)purine
  参考文献：
  名称：

  9-(2-C-Cyano-2-deoxy-β-d-arabino- pentofuranosyl)guanine, a Potential Antitumor Agent against B-Lymphoma Infected with Kaposi's Sarcoma-Associated Herpesvirus

  摘要：

  Several 9-(2-C-cyano-2-deoxy-l-beta-D-arabino-pentofuranosyl)purine derivatives were tested against Kaposi's sarcoma-associated herpesvirus (KSHV)-infected primary effusion lymphoma (PEL) cells. The guanine derivative (3, CNDAG), as well as the 2-amino-6-substituted-purine derivatives 4, 5, and 6, exhibited cell growth inhibitory activity against KSHV-infected cells, but showed no cytotoxicity against KSHV-negative cells at > 15 mu M concentrations. Therefore, it was found that compounds 3, 4, 5, and 6 showed selective cytotoxicity against PEL cells infected with KSHV.

  DOI：

  10.1021/jm070032y
• 作为产物：
  描述：

  2-amino-6-chloro-9-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]purine 在 乙酸酐 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 4 A molecular sieve 、 四丁基氟化铵 、 三正丁基氢锡 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 2-amino-6-chloro-9-(2-C-cyano-2-deoxy-β-D-arabino-pentofuranosyl)purine
  参考文献：
  名称：

  9-(2-C-Cyano-2-deoxy-β-d-arabino- pentofuranosyl)guanine, a Potential Antitumor Agent against B-Lymphoma Infected with Kaposi's Sarcoma-Associated Herpesvirus

  摘要：

  Several 9-(2-C-cyano-2-deoxy-l-beta-D-arabino-pentofuranosyl)purine derivatives were tested against Kaposi's sarcoma-associated herpesvirus (KSHV)-infected primary effusion lymphoma (PEL) cells. The guanine derivative (3, CNDAG), as well as the 2-amino-6-substituted-purine derivatives 4, 5, and 6, exhibited cell growth inhibitory activity against KSHV-infected cells, but showed no cytotoxicity against KSHV-negative cells at > 15 mu M concentrations. Therefore, it was found that compounds 3, 4, 5, and 6 showed selective cytotoxicity against PEL cells infected with KSHV.

  DOI：

  10.1021/jm070032y

文献信息

• 9-(2-<i>C</i>-Cyano-2-deoxy-β-<scp>d</scp>-<i>arabino</i>- pentofuranosyl)guanine, a Potential Antitumor Agent against B-Lymphoma Infected with Kaposi's Sarcoma-Associated Herpesvirus
  作者：Masaki Ohtawa、Satoshi Ichikawa、Yasuhiro Teishikata、Masahiro Fujimuro、Hideyoshi Yokosawa、Akira Matsuda

  DOI：10.1021/jm070032y

  日期：2007.5.1

  Several 9-(2-C-cyano-2-deoxy-l-beta-D-arabino-pentofuranosyl)purine derivatives were tested against Kaposi's sarcoma-associated herpesvirus (KSHV)-infected primary effusion lymphoma (PEL) cells. The guanine derivative (3, CNDAG), as well as the 2-amino-6-substituted-purine derivatives 4, 5, and 6, exhibited cell growth inhibitory activity against KSHV-infected cells, but showed no cytotoxicity against KSHV-negative cells at > 15 mu M concentrations. Therefore, it was found that compounds 3, 4, 5, and 6 showed selective cytotoxicity against PEL cells infected with KSHV.