9-[(diisopropoxyphosphorylmethoxy)allyl]guanine | 1443683-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-[(diisopropoxyphosphorylmethoxy)allyl]guanine
• 英文别名: 2-amino-9-[2-[di(propan-2-yloxy)phosphorylmethoxymethyl]prop-2-enyl]-1H-purin-6-one
• CAS: 1443683-82-6
• 化学式: C₁₆H₂₆N₅O₅P
• 分子量: 399.387
• InChiKey: MAZREUZVOWIMGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-[(diisopropoxyphosphorylmethoxy)allyl]guanine 在 三甲基溴硅烷 、 四丁基溴化铵 、 三乙胺 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 9-[bis[O-(pivaloyoxymethyl)phosphorylmethoxy]allyl]guanine
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Anti-HBV Activity of Hybrid Molecules of Entecavir and Adefovir: Exomethylene Acycloguanine Nucleosides and Their Monophosphate Derivatives

  摘要：

  Exomethylene acycloguanine nucleosides 4, 6 and its monophosphate derivatives 5, 7, and 8 have been synthesized. Mitsunobu-type coupling of 2-N-acetyl-6-O-diphenylcarbamoylguanine (11) with primary alcohols proceeded regioselectively to furnish the desired N-9-substituted products in moderate yield. Evaluation of 4-8 for anti-HBV activity in HepG2 cells revealed that the phosphonate derivative 8 was found to exhibit moderated activity (EC50 value of 0.29 mu M), but cytotoxicity (CC50 value of 39 mu M) against the host cells was also observed.

  DOI：

  10.1080/15257770.2015.1037456
• 作为产物：
  描述：

  (2-hydroxymethyl-allyloxymethyl)-phosphonic acid diisopropyl ester 在 偶氮二甲酸二异丙酯 、 氨 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 9-[(diisopropoxyphosphorylmethoxy)allyl]guanine
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Anti-HBV Activity of Hybrid Molecules of Entecavir and Adefovir: Exomethylene Acycloguanine Nucleosides and Their Monophosphate Derivatives

  摘要：

  Exomethylene acycloguanine nucleosides 4, 6 and its monophosphate derivatives 5, 7, and 8 have been synthesized. Mitsunobu-type coupling of 2-N-acetyl-6-O-diphenylcarbamoylguanine (11) with primary alcohols proceeded regioselectively to furnish the desired N-9-substituted products in moderate yield. Evaluation of 4-8 for anti-HBV activity in HepG2 cells revealed that the phosphonate derivative 8 was found to exhibit moderated activity (EC50 value of 0.29 mu M), but cytotoxicity (CC50 value of 39 mu M) against the host cells was also observed.

  DOI：

  10.1080/15257770.2015.1037456

文献信息

• [EN] GUANINE ANALOGS AS TELOMERASE SUBSTRATES AND TELOMERE LENGTH AFFECTORS<br/>[FR] ANALOGUES DE GUANINE EN TANT QUE SUBSTRATS DE TÉLOMÉRASE ET AFFECTEURS DE LA LONGUEUR DE TÉLOMÈRES
  申请人：GERON CORP

  公开号：WO2013095684A1

  公开（公告）日：2013-06-27

  This invention relates to compounds useful for inhibiting telomere elongation. More specifically, the invention provides nucleotide analogs that are incorporated into telomeres by telomerase thereby inhibiting elongation of telomeres. The compounds are useful in treating cancer and other cell proliferative diseases.

  这项发明涉及用于抑制端粒延伸的化合物。更具体地说，该发明提供了一种通过端粒酶将核苷酸类似物嵌入端粒中，从而抑制端粒延伸的方法。这些化合物在治疗癌症和其他细胞增殖性疾病方面具有用途。
• Guanine analogs as telomerase substrates and telomere length affectors
  申请人：Geron Corporation

  公开号：US10035814B2

  公开（公告）日：2018-07-31

  This invention relates to compounds useful for inhibiting telomere elongation. More specifically, the invention provides nucleotide analogs that are incorporated into telomeres by telomerase thereby inhibiting elongation of telomeres. The compounds are use in treating cancer and other cell proliferative diseases.

  本发明涉及可用于抑制端粒伸长的化合物。更具体地说，本发明提供的核苷酸类似物通过端粒酶结合到端粒中，从而抑制端粒的伸长。这些化合物可用于治疗癌症和其他细胞增殖性疾病。
• GUANINE ANALOGS AS TELOMERASE SUBSTRATES AND TELOMERE LENGTH AFFECTORS
  申请人：Geron Corporation

  公开号：US20150299232A1

  公开（公告）日：2015-10-22

  This invention relates to compounds useful for inhibiting telomere elongation. More specifically, the invention provides nucleotide analogs that are incorporated into telomeres by telomerase thereby inhibiting elongation of telomeres. The compounds are useful in treating cancer and other cell proliferative diseases.
• Guanine Analogs as Telomerase Substrates and Telomere Length Affectors
  申请人：Geron Corporation

  公开号：US20170233419A1

  公开（公告）日：2017-08-17

  This invention relates to compounds useful for inhibiting telomere elongation. More specifically, the invention provides nucleotide analogs that are incorporated into telomeres by telomerase thereby inhibiting elongation of telomeres. The compounds are use in treating cancer and other cell proliferative diseases.
• US9593137B2
  申请人：——

  公开号：US9593137B2

  公开（公告）日：2017-03-14