NU2013 | 146331-47-7

• 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: NU2013
• 英文别名: 6-(allyloxy)-9H-purine；6-allyloxy-9H-purine；6-Allyloxypurine；6-prop-2-enoxy-7H-purine
• CAS: 146331-47-7
• 化学式: C₈H₈N₄O
• 分子量: 176.178
• InChiKey: KQTMKEHKXBCEMK-UHFFFAOYSA-N

物化性质

• 沸点：
  315.7±52.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  NU2013 在 叔丁基过氧化氢 、 Mn(dpm)₃ 、 苯硅烷 作用下， 以 癸烷 、 异丙醇 为溶剂， 以56%的产率得到6-N-丙氧基嘌呤
  参考文献：
  名称：

  Simple, Chemoselective Hydrogenation with Thermodynamic Stereocontrol

  摘要：

  Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.

  DOI：

  10.1021/ja412342g
• 作为产物：
  描述：

  烯丙醇 、 6-氯嘌呤 在 sodium hydride 作用下， 以 mineral oil 为溶剂， 反应 16.5h， 以73%的产率得到NU2013
  参考文献：
  名称：

  双头核苷酸的碱基配对性质

  摘要：

  包含两个核碱基（双头核苷酸）的核苷酸有可能将两个独立核苷酸的信息浓缩为一个。前提是两个碱基都必须与同源链成功配对。在这里，开发并详细研究了具有胞嘧啶，鸟嘌呤，胸腺嘧啶，腺嘌呤，次黄嘌呤和二氨基嘌呤与阿拉伯糖支架的C2'-位相连的双头核苷酸。通过聚合合成有效地制备了这些单体单元，并通过自动亚磷酰胺方法将其掺入DNA寡核苷酸中。在几种情况下，通过基于紫外线的熔融温度分析和广泛的分子动力学研究，评估了它们的配对效率。共，

  DOI：

  10.1002/chem.201901077

文献信息

• Base‐Pairing Properties of Double‐Headed Nucleotides
  作者：Mick Hornum、Julie Stendevad、Pawan K. Sharma、Pawan Kumar、Rasmus B. Nielsen、Michael Petersen、Poul Nielsen

  DOI：10.1002/chem.201901077

  日期：2019.5.28

  Nucleotides that contain two nucleobases (double‐headed nucleotides) have the potential to condense the information of two separate nucleotides into one. This presupposes that both bases must successfully pair with a cognate strand. Here, double‐headed nucleotides that feature cytosine, guanine, thymine, adenine, hypoxanthine, and diaminopurine linked to the C2′‐position of an arabinose scaffold were

  包含两个核碱基（双头核苷酸）的核苷酸有可能将两个独立核苷酸的信息浓缩为一个。前提是两个碱基都必须与同源链成功配对。在这里，开发并详细研究了具有胞嘧啶，鸟嘌呤，胸腺嘧啶，腺嘌呤，次黄嘌呤和二氨基嘌呤与阿拉伯糖支架的C2'-位相连的双头核苷酸。通过聚合合成有效地制备了这些单体单元，并通过自动亚磷酰胺方法将其掺入DNA寡核苷酸中。在几种情况下，通过基于紫外线的熔融温度分析和广泛的分子动力学研究，评估了它们的配对效率。共，
• Gold(I)-Triphenylphosphine Complexes with Hypoxanthine-Derived Ligands: In Vitro Evaluations of Anticancer and Anti-Inflammatory Activities
  作者：Radka Křikavová、Jan Hošek、Ján Vančo、Jakub Hutyra、Zdeněk Dvořák、Zdeněk Trávníček

  DOI：10.1371/journal.pone.0107373

  日期：——

  series of gold(I) complexes involving triphenylphosphine (PPh3) and one N-donor ligand derived from deprotonated mono- or disubstituted hypoxanthine (HLn) of the general composition [Au(Ln)(PPh3)] (1-9) is reported. The complexes were thoroughly characterized, including multinuclear high resolution NMR spectroscopy as well as single crystal X-ray analysis (for complexes 1 and 3). The complexes were screened

  报道了一系列涉及三苯基膦 (PPh3) 和一个 N-供体配体的金 (I) 配合物，该配体来源于一般组成 [Au(Ln)(PPh3)] (1-9) 的去质子化单或二取代次黄嘌呤 (HLn) . 对配合物进行了彻底的表征，包括多核高分辨率 NMR 光谱以及单晶 X 射线分析（配合物 1 和 3）。筛选了复合物对人癌细胞系 MCF7（乳腺癌）、HOS（骨肉瘤）和 THP-1（单核细胞白血病）的体外细胞毒性，确定复合物 4-6 是最有希望的代表，其抗增殖活性是进一步针对 A549（肺腺癌）、G-361（黑色素瘤）、HeLa（宫颈癌）、A2780（卵巢癌）、A2780R（对顺铂耐药的卵巢癌）进行了测试，22Rv1（前列腺癌）细胞系。与商业使用的抗癌药物顺铂相比，复合物 4-6 对所用癌细胞（G-361 除外）显示出显着更高的体外抗癌作用，IC50 ≈ 1-30 µM。通过评估复合物调节促炎细胞因子（
• Cyclin dependent kinase inhibiting purine derivatives
  申请人：Cancer Research Campaign Technology Limited

  公开号：US06303618B1

  公开（公告）日：2001-10-16

  Method of treating a tumour or other cell proliferation disorder which comprises administering an effective amount of a purine compound which inhibits cyclic dependent kinase activity. Novel purine compounds and pharmaceutical compositions are also disclosed.

  治疗肿瘤或其他细胞增殖紊乱的方法，包括给予有效量的嘌呤化合物，该化合物抑制环状依赖性激酶活性。此外还揭示了新的嘌呤化合物和制药组合物。
• CYCLIC DI-NUCLEOTIDES COMPOUNDS FOR THE TREATMENT OF CANCER
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP4008403A1

  公开（公告）日：2022-06-08

  Provided herein are compounds useful for the treatment of cancer.

  本文提供的化合物可用于治疗癌症。
• 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.