6-异丙氧基-1H-嘌呤 | 66085-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 6-异丙氧基-1H-嘌呤
• 英文名称: 6-isopropoxypurine
• 英文别名: 6-isopropoxy-7(9)H-purine；6-isopropoxy-1H-purine；6-propan-2-yloxy-7H-purine
• CAS: 66085-16-3
• 化学式: C₈H₁₀N₄O
• mdl: MFCD00520064
• 分子量: 178.194
• InChiKey: NXBUZBZGNABKHN-UHFFFAOYSA-N

物化性质

• 沸点：
  298.4±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-异丙氧基-1H-嘌呤 在 氢氧化钾 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.83h， 生成 7-<2-deoxy-β-D-erythro-pentofuranosyl>-6-isopropoxy-7H-purine
  参考文献：
  名称：

  N7-DNA: Base-Pairing Properties ofN7-(2′-Deoxy-β-D-erythro-pentofuranosyl)-Substituted Adenine, Hypoxanthine, and Guanine in Duplexes with Parallel Chain Orientation

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2244::aid-hlca2244>3.0.co;2-i
• 作为产物：
  描述：

  6-氯嘌呤 、 异丙醇 在 sodium 作用下， 以45%的产率得到6-异丙氧基-1H-嘌呤
  参考文献：
  名称：

  一种嘌呤衍生物及其合成方法和应用

  摘要：

  本发明属于生物医药领域，具体涉及一种嘌呤衍生物及其合成方法和应用。该嘌呤衍生物的结构如式I所示，R1为饱和烃基、链烯基、炔基、环烷基、芳基、杂环基或烷氧基羰基；R2为氢、卤素、烷基、芳基、氨基、烃氨基或烷氧基；R3为氢、烷基、氨基、烃氨基、烷氧基，氨基磺酰基、硫烷基、芳基、杂环基或羧基；n为1、2、3、4、5或6。该嘌呤衍生物对于5‑脂氧合酶和5‑脂氧合酶具有很好的抑制活性，能够用于制备脂氧合酶抑制剂，也能够用于制备治疗脂氧合酶介导的疾病的药物，具备很好的临床应用前景。

  公开号：

  CN116003415A

文献信息

• Anti-HIV Pyrimidine Nucleosides
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0317128A2

  公开（公告）日：1989-05-24

  Certain 3′-fluoro pyrimidine and purine nucleosides have been found to have potent antiviral activity particularly against Human Immunodeficiency Virus (HIV).

  某些3'-氟嘧啶和嘌呤核苷可以具有强效的抗病毒活性，特别是对人类免疫缺陷病毒（HIV）有效。
• Therapeutic nucleosides
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0286425A2

  公开（公告）日：1988-10-12

  This invention relates to certain 6-substituted 2ʹ,3ʹ-dideoxypurine nucleosides and pharmaceutically acceptable derivatives thereof and their use in the treatment and prophylaxis of HIV infections. Also provided are pharmaceutical formulations and processes for the production of the compounds according to the invention.

  本发明涉及某些6-取代的2ʹ,3ʹ-二脱氧嘌呤核苷及其药学上可接受的衍生物，以及它们在治疗和预防HIV感染中的用途。还提供了根据本发明的化合物的药物制剂和生产工艺。
• Therapeutic Nucleosides
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0669341A1

  公开（公告）日：1995-08-30

  Certain 3'-fluoro pyrimidine and purine nucleosides have been found to have potent antiviral activity particularly against Human Immunodeficiency Virus (HIV).

  研究发现，某些 3'-氟嘧啶和嘌呤核苷具有很强的抗病毒活性，特别是对人类免疫缺陷病毒（HIV）。
• Novel 6-alkoxypurine 2',3'-dideoxynucleosides as inhibitors of the cytopathic effect of the human immunodeficiency virus
  作者：Charlene L. Burns、Marty H. St. Clair、Lloyd W. Frick、Thomas Spector、Devron R. Averett、Michael L. English、Timothy J. Holmes、Thomas A. Krenitsky、George W. Koszalka

  DOI：10.1021/jm00055a009

  日期：1993.2

  Twenty-one 6-alkoxypurine 2',3'-dideoxynucleosides were enzymatically synthesized with nucleoside phosphorylases purified from E. coli. Eighteen analogs exhibited anti-HIV-1 activity in MT4 cells. Two analogs,6-(hexyloxy)-(17) and 6-(heptyloxy)-(18) purine 2',3'-dideoxynucleoside, were as potent as 2',3'-dideoxyinosine (ddI, didanosine, Videx). Although the antiviral activities of 17 and 18 were equivalent, 18 was more cytotoxic. Analogs containing less than four carbons in the 6-alkoxypurine substituent exhibited weak anti-HIV-1 activity. Analogs containing more than seven carbons in the 6-alkoxypurine substituent were too cytotoxic to be effectively evaluated for antiviral activity. Several 6-alkoxypurine 2',3'-dideoxynucleosides were evaluated for substrate activity with calf intestinal adenosine deaminase (ADA). Increasing the carbon chain length of the 6-alkoxypurine substituent decreased the rate of dealkoxylation. The best substrate in this series was 6-methoxypurine 2',3'-dideoxynucleoside (1); however, the rate of dealkoxylation of 100 muM 1 was 0.17 % of the rate of deamination of 100 muM 2',3'-dideoxyadenosine. Compound 17, the most potent anti-HIV-1 analog, was not a substrate for ADA. EHNA (erythro-9-(2-hydroxy-3-nonyl) adenine), a potent inhibitor of ADA, had little effect on the antiviral activities of 17 and ddI. In contrast, coformycin, a potent inhibitor of both ADA and AMP deaminase, dramatically decreased the antiviral activity of 17, but not the antiviral activity of ddI. Thus, AMP deaminase appeared to be involved in the anabolism of 17. The pharmacokinetic profile of 17, the most promising analog in this series, was determined in the rat. At least seventeen metabolites of 17, including ddI, were detected in plasma samples. This analog also had poor oral bioavailability.
• 6-Oxo and 6-thio purine analogs as antimycobacterial agents
  作者：Ashish K. Pathak、Vibha Pathak、Lainne E. Seitz、William J. Suling、Robert C. Reynolds

  DOI：10.1016/j.bmc.2013.01.054

  日期：2013.4

  6-Oxo and 6-thio analogs of purine were prepared based on the initial activity screening of a small, diverse purine library against Mycobacterium tuberculosis (Mtb). Certain 6-oxo and 6-thio-substituted purine analogs described herein showed moderate to good inhibitory activity. N-9-substitution apparently enhances the anti-mycobacterial activity in the purine series described herein. Several 2-amino and 2-chloro purine analogs were also synthesized that showed moderate inhibitory activity against Mtb. (C) 2013 Elsevier Ltd. All rights reserved.