4-amino-5-cyano-7-(5-chloro-5-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine | 65562-54-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-5-cyano-7-(5-chloro-5-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• 英文别名: 5'-chloro-5'-deoxytoyocamycin
• CAS: 65562-54-1
• 化学式: C₁₂H₁₂ClN₅O₃
• 分子量: 309.712
• InChiKey: UJGHDRLYRXDWQE-WOUKDFQISA-N

物化性质

• 沸点：
  692.2±55.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  130.21
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-amino-5-cyano-7-(5-chloro-5-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 溶剂黄146 、 sodium nitrite 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 4-chloro-5-cyano-7-(5-deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyriomidine
  参考文献：
  名称：

  Deoxy Sugar Analogues of Triciribine:  Correlation of Antiviral and Antiproliferative Activity with Intracellular Phosphorylation

  摘要：

  Triciribine (TCN) and triciribine monophosphate (TCN-P) have antiviral and antineoplastic activity at low micromolar or submicromolar concentrations. In an effort to improve and better understand this activity, we have conducted a structure-activity relationship study to explore requirements for the number of hydroxyl groups on the ribosyl moiety for biological activity. 2'-Deoxytriciribine (2'-dTCN), 3'-deoxytriciribine (3'-dTCN), 2',3'-epoxytriciribine (2',3'-epoxyTCN), 2',3'-dideoxy-2',3'-didehydrotriciribine (2',3'-d4TCN), and 2',3'-dideoxytriciribine (2',3'-ddTCN) were synthesized and evaluated for activity against human immunodeficiency virus (HIV-1), herpes simplex virus type 1 (HSV-1), and human cytomegalovirus (HCMV). Antiproliferative activity of the compounds also was tested in murine L1210 cells and three human tumor cell lines. All compounds were either less active than TCN and TCN-P or inactive at the highest concentration tested (100 mu M) in both antiviral and antiproliferative assays. Reverse-phase HPLC of extracts from uninfected cells treated with the deoxytriciribine analogues only detected the conversion of 3'-dTCN and 2',3'-ddTCN to their respective monophosphates. Therefore, either the deoxytriciribine analogues were not transported across the cell membrane or, more likely, they were not substrates for a nucleoside kinase or phosphotransferase. We have concluded that the hydroxyl groups on the ribosyl ring system of TCN and TCN-P must be intact in order to obtain significant antiviral and antineoplastic activity.

  DOI：

  10.1021/jm990205m
• 作为产物：
  描述：

  4-氨基-5-氰基-7-(beta-d-呋喃核糖)吡咯并[2,3-d]嘧啶 在 氯化亚砜 作用下， 反应 5.0h， 以50%的产率得到4-amino-5-cyano-7-(5-chloro-5-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  新型的组蛋白甲基转移酶DOT1L的小分子抑制剂，具有腈作为重卤素原子的非传统替代物。

  摘要：

  公开了许多新的核苷衍生物作为DOT1L活性的抑制剂。SARs证实，可以通过在5位（5、6、12）掺入极性基团和小的杂环或通过使用其他含氮碱基（18）来实现DOT1L抑制。根据这些结果，CN-SAH（19）被确定为DOT1L活性的有效和选择性抑制剂，其中结晶晶体显示极性5腈基结合在DOT1L的疏水口袋中。此外，我们表明极性腈基可以用作重卤素原子的非传统替代物。

  DOI：

  10.1016/j.bmcl.2016.07.041

文献信息

• 5’-脱氧-5’-异丙基取代氨基核苷类化合物、 其制备方法和用途
  申请人：中国科学院上海药物研究所

  公开号：CN109748944B

  公开（公告）日：2021-12-10

  本发明公开了通式7所示的5’‑脱氧‑5’‑异丙基取代氨基核苷类化合物，该类化合物7的制备方法，以及该类化合物7作为中间体在制备5’‑脱氧‑5’‑多取代氨基核苷类化合物1中的应用。