7-methyl-8-oxoadenine

• 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: 7-methyl-8-oxoadenine
• 英文别名: 6-amino-7-methyl-9H-purin-8-one
• 化学式: C₆H₇N₅O
• 分子量: 165.154
• InChiKey: CKMRTJFKEVFFIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-Methyl-8-oxoadenosine 在 盐酸 作用下， 反应 48.0h， 以45%的产率得到7-methyl-8-oxoadenine
  参考文献：
  名称：

  Purines. LXXIV. Syntheses and Rearrangements of 8-Oxoadenines Monomethylated at the N6-, 1-, and 3-Positions.

  摘要：

  用沸腾的 2 N 盐酸处理 48 小时后，N6-甲基-8-氧代腺嘌呤核苷（1）、1-甲基-8-氧代腺嘌呤核苷（5）和 7-甲基-8-氧代腺嘌呤核苷（8）发生糖苷水解，但速度比相应的 8-未取代化合物慢得多，生成的缩醛（2、6 和 9）的产率为 45%-63%。在这些条件下，N6-甲基-8-氧代腺嘌呤（2）重新排列为 9-甲基-8-氧代腺嘌呤（3）（收率 8%），这可能是通过咪唑环的裂变和再封闭实现的。3- 甲基-8-羟基腺嘌呤（7）也发生了明显的甲基迁移，在类似条件下，用盐酸处理后可得到 1-甲基-8-氧代腺嘌呤（6），产率为 9%。

  DOI：

  10.1248/cpb.44.2318

文献信息

• Purines. LXXVI. Alkylation of 8-Oxoadenine Derivatives: Syntheses of 3,7-Dialkyl-, 3,9-Dialkyl-, and 3,7,9-Trialkyl-8-oxoadenines.
  作者：Taisuke ITAYA、Yasutaka TAKADA、Tae KANAI、Miki KANEKO、Tozo FUJII

  DOI：10.1248/cpb.45.1582

  日期：——

  3-Alkyl-8-hydroxyadenines (5) have been shown to undergo regioselective methylation at the 7- or 9-position depending on the reaction conditions. Thus, treatment of 5a, c with dimetyl sulfate in aqueous NaOH provided 3-alkyl-7-methyl-8-oxoadenines (6b, h) in 48-60% yields, together with 3-alkyl-8-methoxyadenines 4d, h), whereas treatment of 5a-c with MeI in AcNMe2 at 40°C for 48h and subsequent anion exchange afforded 3-alkyl-9-methyl-8-oxoadenine hydrochlorides (7d, g, h·HCl) in 50-59% yieds. However, the reactions of 5a, c with EtI or PhCH2Br took place slowly, giving complex mixtures of products.Compounds 6d, h were alternatively prepared in 51% and 31% yields, respectively, together with 3-alkyl-7, 9-dimethyl-8-oxoadenine hydrochlorides (11d, h·HCl), by treatment of 3-alkyl-8-methoxyadenines (4d, h) with MeI in AcNMe2 at room temperature for 6 h, followed by hydrolysis with boiling aqueous HCl. This method was applicable to ethylation with EtI, and 7-ethyl-3-methyl-8-oxoadenine (6e) was obtained in 70% yield from 8-ethoxy-3-methyladenine (4e). Compound 11h was shown to be obtainable through futher methylation of 6h. Thus, 11d, h were prepared in good yields by treatment of 6d, h with MeI in AcNMe2.Compounds 7, to which zwitterionic structures were assigned, were stable in 0.1 N aqueous NaOH at room temperature, whereas 11d, h were no longer stable under such conditions.

  d, h·HCl·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H
• CYCLIC DINUCLEOTIDE ANALOGUE, PHARMACEUTICAL COMPOSITION THEREOF, AND APPLICATION
  申请人：Shanghai de Novo Pharmatech Co., Ltd.

  公开号：EP3854799A1

  公开（公告）日：2021-07-28

  A cyclic dinucleotide analogue, a pharmaceutical composition thereof, and application. A cyclic dinucleotide analogue (I), an isomer thereof, a prodrug, a stable isotope derivative, or a pharmaceutically acceptable salt has the following structure. The cyclic dinucleotide analogue can be used as a regulator of a stimulator of interferon genes (STING) and a related signal path thereof, and can effectively treat and/or relieve multiple types of diseases, including but not limited to malignant tumors, inflammations, autoimmune diseases, and infectious diseases. In addition, the STING regulator can also be used as a vaccine adjuvant.

  一种环二核苷酸类似物、其药物组合物及应用。一种环二核苷酸类似物（I）、其异构体、原药、稳定同位素衍生物或药学上可接受的盐具有如下结构。环二核苷酸类似物可用作干扰素基因刺激物（STING）及其相关信号通路的调节剂，可有效治疗和/或缓解多种类型的疾病，包括但不限于恶性肿瘤、炎症、自身免疫性疾病和传染性疾病。此外，STING 调节剂还可用作疫苗佐剂。
• CYCLIC MOLECULES AS BRUTON'S TYROSINE KINASE INHIBITOR
  申请人：Minghui Pharmaceutical (Shanghai) Limited

  公开号：EP3912980A1

  公开（公告）日：2021-11-24

  The present invention relates to a novel molecule with protein tyrosine kinase inhibitory activity, and the synthesis and usage thereof. Specifically, the present invention relates to compound by formula A, pharmaceutically acceptable salts, hydrates or solvates thereof, and the synthesis and usage thereof.

  本发明涉及一种具有蛋白酪氨酸激酶抑制活性的新型分子及其合成和使用方法。具体地说，本发明涉及式 A 的化合物、其药学上可接受的盐、水合物或溶液及其合成和使用方法。
• [EN] CYCLIC DINUCLEOTIDE ANALOGUE, PHARMACEUTICAL COMPOSITION THEREOF, AND APPLICATION<br/>[FR] ANALOGUE DINUCLÉOTIDIQUE CYCLIQUE, COMPOSITION PHARMACEUTIQUE ASSOCIÉE ET UTILISATION<br/>[ZH] 环状二核苷酸类似物、其药物组合物及应用
  申请人：SHANGHAI DE NOVO PHARMATECH CO LTD

  公开号：WO2020057546A1

  公开（公告）日：2020-03-26

  一种环状二核苷酸类似物、其药物组合物及应用。环状二核苷酸类似物(I)、其异构体、前药、稳定的同位素衍生物或药学上可接受的盐具有如下结构。环状二核苷酸类似物可用作干扰素基因刺激因子STING及其相关信号通路的调节剂，可有效治疗和/或缓解多种类型的疾病，包括且不限于恶性肿瘤，炎症、自身免疫性疾病、传染性疾病。另外，STING调节剂还可以作为疫苗佐剂。
• [EN] CYCLIC MOLECULES AS BRUTON'S TYROSINE KINASE INHIBITOR<br/>[FR] MOLÉCULES CYCLIQUES SERVANT D'INHIBITEUR DE LA TYROSINE KINASE DE BRUTON<br/>[ZH] 作为布鲁顿酪氨酸激酶抑制剂的环状分子
  申请人：MINGHUI PHARMACEUTICAL SHANGHAI LTD

  公开号：WO2020147798A1

  公开（公告）日：2020-07-23

  本发明描述了具有蛋白酪氨酸激酶抑制活性的新型分子，以及该化合物的合成和使用方法。具体地，本发明描述了式（A）化合物或其药学上可接受的盐、水合物或溶剂合物，以及该化合物的合成和使用方法。