6-Ethylmercaptopurine riboside | 13286-04-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-Ethylmercaptopurine riboside
• 英文别名: 1-(6-ethylsulfanyl-purin-9-yl)-β-D-1-deoxy-ribofuranose；6-Ethylthio-9-β-D-ribofuranosylpurine；9-β-D-Ribofuranosyl-6-ethylmercapto-9H-purin；6-Ethylmercaptopurinribonucleosid；(2R,3R,4S,5R)-2-(6-(Ethylthio)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2R,3R,4S,5R)-2-(6-ethylsulfanylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 13286-04-9
• 化学式: C₁₂H₁₆N₄O₄S
• 分子量: 312.349
• InChiKey: SXDRPWJMWHDCLL-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

制备方法与用途

6-乙硫异黄嘌呤（6-ETI）

反应信息

• 作为反应物：
  描述：

  6-Ethylmercaptopurine riboside 在 间氯过氧苯甲酸 作用下， 以 水 、 乙腈 为溶剂， 以69 %的产率得到(2R,3R,4S,5R)-2-(6-(ethylsulfonyl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  10.1002/chem.202401774

  摘要：

  We present herein a novel photo‐mediated homolytic C‐S bond formation for the preparation of alkylthiopurines and alkylthiopurine nucleosides. Despite the presence of reactive sites for the Minisci reaction, chemoselective S‐alkylation remained the predominant pathway. This method allows for the late‐stage introduction of a broad spectrum of alkyl groups onto the sulfur atom of unprotective mercaptopurine derivatives, encompassing 2‐, 6‐, and 8‐mercaptopurine rings. Organoborons serve as efficient and eco‐friendly alkylating reagents, providing advantages in terms of readily availability, stability, and reduced toxicity. Further derivatization of the thioetherified nucleosides, together with anti‐tumor assays, led to the discovery of potent anti‐tumor agents with an IC50 value reaching 6.1 µM (Comp. 31 for Jurkat).

  DOI：

  10.1002/chem.202401774
• 作为产物：
  描述：

  2',3',5'-tri-O-acetyl-S6-(ethyl)thioinosine 在 三乙胺 作用下， 以 甲醇 为溶剂， 以87 %的产率得到6-Ethylmercaptopurine riboside
  参考文献：
  名称：

  Mitsunobu 反应对 6-硫嘌呤衍生物的烷基化

  摘要：

  摘要 据报道，通过 Mitsunobu 反应，硫嘌呤衍生物与醇的烷基化反应收率适中。将该方法应用于多种硫嘌呤和硫嘌呤核苷衍生物的合成。

  DOI：

  10.1080/15257770.2022.2163501

文献信息

• [EN] NOVEL NUCLEOSIDE ANALOGS AND USE THEREOF IN THERAPEUTIC TREATMENT<br/>[FR] NOUVEAUX ANALOGUES DE NUCLÉOSIDES ET LEUR UTILISATION DANS UN TRAITEMENT THÉRAPEUTIQUE
  申请人：UNIV CORNELL

  公开号：WO2017180981A1

  公开（公告）日：2017-10-19

  The present disclosure is directed to novel nucleoside analog compounds and methods for treating diseases characterized by high expression levels of adenosine kinase (ADK).

  本公开涉及新颖的核苷类似物化合物和用于治疗表达水平高的腺苷激酶(ADK)的疾病的方法。
• 6-Substituted purine 3',5'-cyclic nucleotides
  申请人：ICN Pharmaceuticals, Inc.

  公开号：US03948886A1

  公开（公告）日：1976-04-06

  Described herein are novel 6-alkylthio and 6-arylalkylthio purine 3',5' cyclic nucleotides variously exhibiting adenyl cyclase and (in animal studies) tumor inhibitory properties, interferon potentiation, antiviral activity, and the ability to activate adenosine 3',5'-cyclic phosphate-dependent protein kinase while enjoying resistance to phosphodiesterase hydrolysis superior to that of its naturally occuring analog. The compounds are obtained by alkylation of the corresponding 6-thio nucleotide, which is in turn provided by a novel synthetic route.

  本文介绍了新型的6-烷基硫基和6-芳基烷基硫基嘌呤3'，5'环状核苷酸，它们表现出腺苷酸环化酶和（在动物研究中）抑制肿瘤的特性，干扰素增强作用，抗病毒活性以及激活腺苷酸3'，5'-环磷酸依赖性蛋白激酶的能力，同时具有比其自然存在的类似物更强的磷酸二酯酶水解抵抗力。这些化合物是通过烷基化相应的6-硫代核苷酸获得的，这些核苷酸又是通过一种新的合成路线提供的。
• Compounds for use in treating or preventing primary and metastatic breast and prostate cancer
  申请人：Institut Univ. de Ciència i Tecnologia, S.A.

  公开号：EP2711009A1

  公开（公告）日：2014-03-26

  The present invention relates to the field of biotechnology. The present invention relates to a compound of formula (I) for use in the treatment or prevention of primary and metastatic breast and prostate cancer. The present invention also relates to a combination of a compound of formula (I) with at least one further compound for use in the treatment or prevention of primary and metastatic breast and prostate cancer. The present invention further relates to a pharmaceutical composition comprising the compound of formula (I) or the combination.

  本发明涉及生物技术领域。本发明涉及一种用于治疗或预防原发性和转移性乳腺癌和前列腺癌的式 (I) 化合物。本发明还涉及一种式（I）化合物与至少另一种化合物的组合物，用于治疗或预防原发性和转移性乳腺癌和前列腺癌。本发明还涉及一种包含式（I）化合物或组合物的药物组合物。
• TREATMENT OF TOXOPLASMOSIS
  申请人：UNIVERSITY OF ALABAMA, BIRMINGHAM RESEARCH FOUNDATION

  公开号：EP0755255A1

  公开（公告）日：1997-01-29
• EP0755255A4
  申请人：——

  公开号：EP0755255A4

  公开（公告）日：2002-07-24