9-乙酰基-1,9-二氢-6H-嘌呤-6-酮 | 408531-05-5

• 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: 9-乙酰基-1,9-二氢-6H-嘌呤-6-酮
• 英文名称: 9-Acetyl-1H-purin-6(9H)-one
• 英文别名: 9-acetyl-1H-purin-6-one
• CAS: 408531-05-5
• 化学式: C₇H₆N₄O₂
• 分子量: 178.15
• InChiKey: CMHKDVSDWIISHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319
• 储存条件：
  室温且干燥

反应信息

• 作为产物：
  描述：

  乙酸酐 、 肌苷 在 三氟乙酸 作用下， 以90%的产率得到四乙酰核糖
  参考文献：
  名称：

  一种改进的利巴韦林制备方法

  摘要：

  4-三唑3-羧酸酯得到1-(2,3,5-三-O-乙酰基-β-D-呋喃核糖基)-1H-1,2,4-三唑-3-羧酸甲酯(3)，随后将其转化为利巴韦林( 4）通过脱乙酰和氨解（方案1）。由1制备2的方法存在成本高、产率低、需要大量催化剂和后处理不适合工业生产等缺点。10影响该反应的主要因素是催化剂的酸度；如果催化剂酸性太强，产物会分解，而低酸性的催化剂会导致反应时间长或核苷键断裂不完全。在此，我们报道了一种实用、方便且有效的方法，用于从肌苷 (1a, R1 = OH, R2 = H)、腺苷 (1b, R1 = NH2, R2 = H) 或鸟​​苷 (1c, R1 = OH) 合成 4 , R2 = NH2) 分三步。表1显示了各种催化剂促进的嘌呤核苷乙酰化和裂解的结果。根据已发表的结果，肌苷、腺苷和鸟苷可以转化为 2 和相应的乙酰基嘌呤，同时使用过量的乙酸作为催化剂和溶剂（表 1，条目 2-4）。获得了更好的结果

  DOI：

  10.1080/00304948.2012.697741

文献信息

• NOVEL NANOCARRIER DELIVERED CANCER CHEMOTHERAPEUTIC AGENTS
  申请人：UNIVERSITY OF CINCINNATI

  公开号：US20160101188A1

  公开（公告）日：2016-04-14

  Compositions and methods for treating cancer in a subject are described herein. The composition includes modified nucleobases and nucleosides that are converted in the cell to nucleotides that are incorporated into growing DNA and result in termination of DNA elongation. The nucleobases and nucleotides are incorporated with a drug delivery system (DDS). The DDS includes β-cyclodextrin. The nucleobases and nucleotides are conjugated to the β-cyclodextrin by an acid labile linker that releases the nucleobases and nucleotides in the acidic environment of cancer cells. The DDS may also include a targeting ligand that targets the DDS/nucleobase or nucleotide conjugate to cancer cells. The DDS/nucleobase or nucleotide conjugate may self form into nanoparticles and may be administered to a subject with cancer in an amount effective to treat said cancer.

  本文描述了用于治疗患者癌症的组合物和方法。该组合物包括经过修饰的核碱基和核苷，这些核碱基和核苷在细胞中转化为核苷酸，并被合并到正在生长的DNA中，导致DNA延伸终止。这些核碱基和核苷与药物输送系统（DDS）一起使用。DDS包括β-环糊精。核碱基和核苷通过酸敏链连接到β-环糊精上，该链在癌细胞的酸性环境中释放核碱基和核苷。DDS还可以包括靶向配体，将DDS/核碱基或核苷共轭物靶向癌细胞。DDS/核碱基或核苷共轭物可以自行形成纳米粒子，并可以以有效治疗癌症的剂量给患者服用。
• [EN] NOVEL NANOCARRIER DELIVERED CANCER CHEMOTHERAPEUTIC AGENTS<br/>[FR] NOUVEAUX AGENTS CHIMIOTHÉRAPEUTIQUES ANTICANCÉREUX DÉLIVRÉS PAR NANO-PORTEUR
  申请人：UNIV CINCINNATI

  公开号：WO2014194250A2

  公开（公告）日：2014-12-04

  Compositions and methods for treating cancer in a subject are described herein. The composition includes modified nucleobases and nucleosides that are converted in the cell to nucleotides that are incorporated into growing DNA and result in termination of DNA elongation. The nucleobases and nucleotides are incorporated with a drug delivery system (DDS). The DDS includes β-cyclodextrin. The nucleobases and nucleotides are conjugated to the β-cyclodextrin by an acid labile linker that releases the nucleobases and nucleotides in the acidic environment of cancer cells. The DDS may also include a targeting ligand that targets the DDS/ nucleobase or nucleotide conjugate to cancer cells. The DDS/ nucleobase or nucleotide conjugate may self form into nanoparticles and may be administered to a subject with cancer in an amount effective to treat said cancer.
• An Improved Procedure for the Preparation of Ribavirin
  作者：Y. S. Li、J. J. Zhang、L. Q. Mei、C. X. Tan

  DOI：10.1080/00304948.2012.697741

  日期：2012.1

  acetylation of inosine (1a), with methyl 1,2,4-triazole3-carboxylate gave methyl 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3carboxylate (3) which is subsequently converted to ribavirin (4) by deacetylation and ammonolysis (Scheme 1). The process for the preparation of 2 from 1 suffer from drawbacks such as high cost, low yields, need for large amounts of catalyst and work-ups unsuitable for industrial

  4-三唑3-羧酸酯得到1-(2,3,5-三-O-乙酰基-β-D-呋喃核糖基)-1H-1,2,4-三唑-3-羧酸甲酯(3)，随后将其转化为利巴韦林( 4）通过脱乙酰和氨解（方案1）。由1制备2的方法存在成本高、产率低、需要大量催化剂和后处理不适合工业生产等缺点。10影响该反应的主要因素是催化剂的酸度；如果催化剂酸性太强，产物会分解，而低酸性的催化剂会导致反应时间长或核苷键断裂不完全。在此，我们报道了一种实用、方便且有效的方法，用于从肌苷 (1a, R1 = OH, R2 = H)、腺苷 (1b, R1 = NH2, R2 = H) 或鸟​​苷 (1c, R1 = OH) 合成 4 , R2 = NH2) 分三步。表1显示了各种催化剂促进的嘌呤核苷乙酰化和裂解的结果。根据已发表的结果，肌苷、腺苷和鸟苷可以转化为 2 和相应的乙酰基嘌呤，同时使用过量的乙酸作为催化剂和溶剂（表 1，条目 2-4）。获得了更好的结果