(1R,cis)-3-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-1-cyclopentane-1-methanol | 267668-72-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1R,cis)-3-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-1-cyclopentane-1-methanol
• 英文别名: (1R,3S)-3-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopentanemethanol；[(1R,3S)-3-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopentyl]methanol
• CAS: 267668-72-4
• 化学式: C₁₄H₂₀N₆O
• 分子量: 288.352
• InChiKey: TYPRESGPNUCUCA-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,cis)-3-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-1-cyclopentane-1-methanol 在 吡啶 、 亚磷酸二苯酯 、 碘 、 氯磷酸二苯酯 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.74h， 生成 triethylammonium (1S,cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methyl [N-(4-methylthiazol-2-yl)]phosphoramidate
  参考文献：
  名称：

  Aryl H-Phosphonates 18. Synthesis, properties, and biological activity of 2′,3′-dideoxynucleoside (N-heteroaryl)phosphoramidates of increased lipophilicity

  摘要：

  Recently, AZT (N-pyridyl)phosphoramidates were reported as a new type of potential anti-HIV therapeutics. In continuation of that work, here we present new (N-heteroaryl)phosphoramidate derivatives of antiviral 2',3'-dideoxynucleosides containing other types of N-heteroaryl moieties, particularly those with higher lipophilicity. The present studies comprise mechanistic investigations using P-31 NMR correlation analysis, which permitted improvements in the synthetic procedures. The obtained compounds were tested in biological systems to establish their cytotoxicity and anti-HIV activity. The results were analyzed with respect to possible correlations between biological and physico-chemical properties of the phosphoramidates studied, to get some,insight into their antiviral mode of action. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.004
• 作为产物：
  描述：

  阿巴卡韦 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以98%的产率得到(1R,cis)-3-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-1-cyclopentane-1-methanol
  参考文献：
  名称：

  An Efficient, Scalable Synthesis of the HIV Reverse Transcriptase Inhibitor Ziagen® (1592U89)

  摘要：

  Ziagen(R), (IS, cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol, was synthesized from (IS,4R)-azabicyclo[2.2.1]hept-5-en-3-one by efficient processes which bypass problematic steps in earlier routes. 2-Amino-4,6-dichloro-5-formamidopyrimidine is a key intermediate which makes possible an efficient construction of the purine from a chiral cyclopentenyl precursor.

  DOI：

  10.1080/15257770008033011

文献信息

• [EN] STABILIZATION OF MHC COMPLEXES<br/>[FR] STABILISATION DE COMPLEXES CMH
  申请人：UNIV CALIFORNIA

  公开号：WO2021133742A1

  公开（公告）日：2021-07-01

  Provided, inter alia, are methods and compositions for treating cancer.

  提供了治疗癌症的方法和组合物，包括但不限于。
• Composition and method to prevent or reduce diarrhea and steatorrhea in HIV patients
  申请人：SIPOS TIBOR

  公开号：US20100021505A1

  公开（公告）日：2010-01-28

  Method of preventing or reducing diarrhea and/or steatorrhea in HIV-positive patients being treated with High Activity Antiretroviral drugs containing protease inhibitors, nucleoside reverse transcriptase inhibitors or non-nucleoside reverse transcriptase inhibitors. The method includes the steps of: administering to the HIV-positive patient a High Activity Antiretroviral drug containing a protease inhibitor, a nucleoside reverse transcriptase inhibitor or a non-nucleoside reverse transcriptase inhibitor; and co-administering with the HAART drug a gastric acid-resistant polymer-coated and buffered digestive enzyme composition containing pancreatic proteases, lipases, co-lipases, nucleases, amylases and other bio-active substances produced by the pancreatic gland.

  预防或减少HIV阳性患者在接受含有蛋白酶抑制剂、核苷酸反转录酶抑制剂或非核苷酸反转录酶抑制剂的高活性抗逆转录病毒药物治疗时出现腹泻和/或脂肪泻的方法。该方法包括以下步骤：给HIV阳性患者口服含有蛋白酶抑制剂、核苷酸反转录酶抑制剂或非核苷酸反转录酶抑制剂的高活性抗逆转录病毒药物；同时与HAART药物联合给予一种胃酸耐受性聚合物包膜和缓冲的消化酶组合物，其中包含胰蛋白酶、脂肪酶、胆脂酶、核酸酶、淀粉酶和胰腺分泌的其他生物活性物质。