2-amino-6-mercapto-7-methylpurine | 7329-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-amino-6-mercapto-7-methylpurine
• 英文别名: 2-amino-7-methyl-6-purinethiol；6-thio-7-methylguanine；7-methyl-6-thioguanine；7-methylthioguanine；6H-Purine-6-thione, 1,7-dihydro-2-amino-7-methyl-；2-amino-7-methyl-3H-purine-6-thione
• CAS: 7329-79-5
• 化学式: C₆H₇N₅S
• 分子量: 181.221
• InChiKey: AJOUMKDWEVWIEU-UHFFFAOYSA-N

物化性质

• 沸点：
  488.1±37.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 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：
  100
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-6-mercapto-7-methylpurine 、 碘甲烷 在 sodium hydroxide 作用下， 反应 0.33h， 以62.2%的产率得到2-amino-6-methylthio-7-methylpurine
  参考文献：
  名称：

  天然嘌呤代谢产物含硫衍生物的合成及辐射防护性能

  摘要：

  鉴于氯在 7-甲基腺嘌呤中的低反应性，这些化合物被转化为它们的盐 (II, III)。质子化时带正电的碳正离子的形成增强了分子的亲电性，并促进了氯被硫置换。除 2-硫腺嘌呤 (IV) 外，盐 (II) 与硫脲缩合得到一些硫化物 (V)。2-氨基-6-氯-7-甲基嘌呤(IX)得到6-硫-7-甲基鸟嘌呤(X)和2-氨基-6-甲硫-7-甲基嘌呤(XI)。

  DOI：

  10.1007/bf00776334
• 作为产物：
  描述：

  7-甲基鸟嘌呤 在 吡啶 、 tetraphosphorus decasulfide 作用下， 反应 10.0h， 以57%的产率得到2-amino-6-mercapto-7-methylpurine
  参考文献：
  名称：

  Purine Nucleoside Phosphorylase-Catalyzed, Phosphate-Independent Hydrolysis of 2-Amino-6-mercapto-7-methylpurine Ribonucleoside

  摘要：

  In the presence of 1 mM phosphate, 2-amino-6-mercapto-7-methylpurine ribonucleoside (MESG) is a well-behaved substrate for calf spleen purine nucleoside phosphorylase (PNP). In the absence of phosphate, calf spleen PNP catalyzes a slow hydrolysis of MESG, which is accompanied by inactivation of the enzyme, analogous to the previously observed PNP-catalyzed hydrolysis of inosine and guanosine with formation, in the former case, of a stable PNP.hypoxanthine complex (P. C. Kline and V. L. Schramm (1992) Biochemistry 31, 5964-5973). Qualitative and semiquantitative features of calf spleen PNP-catalyzed hydrolysis of MESG are accounted for by the following model. First, in the absence of phosphate and at pH 7.4, the enzyme exists as an equilibrium mixture of monomer and trimer with a dissociation constant for the trimer of 3 x 10(14) M-2. Second, a stoichiometric reaction between three molecules of MESG and the PNP trimer results in the formation of a stable PNP.purinethiol complex. Third, the PNP.purinethiol complex initially formed with the monomeric enzyme partitions between product release and formation of a stable complex with 55 turnovers per inactivation event. Fourth, the stable PNP.purinethiol complexes are rapidly dissociated by phosphate to regenerate active enzyme. This dissociation is accompanied by an increase in absorbance at 356 nm consistent with a pK(a) for the purinethiol base on the enzyme of 8.1, compared to a corresponding value of 8.8 in aqueous solution. (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1999.1137

文献信息

• [EN] NEW DERIVATIVES OF INDOLE FOR THE TREATMENT OF CANCER, VIRAL INFECTIONS AND LUNG DISEASES<br/>[FR] NOUVEAUX DÉRIVÉS D'INDOLE UTILES DANS LE TRAITEMENT DU CANCER, DES INFECTIONS VIRALES ET DES MALADIES PULMONAIRES
  申请人：BIOKINESIS

  公开号：WO2014086964A1

  公开（公告）日：2014-06-12

  The present invention relates to a new class of indole derivatives, having a particular MKlp2 inhibition profile and useful as a therapeutic agent, in particular for the treatment of cancer, viral infections and lung diseases.

  本发明涉及一类新的吲哚衍生物，具有特定的MKlp2抑制剂作用，并可用作治疗剂，特别是用于癌症、病毒感染和肺部疾病的治疗。
• [EN] METHOD FOR SYNTHESISING AMIDES<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'AMIDES
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2018029097A1

  公开（公告）日：2018-02-15

  The present invention relates to a method for synthesising amides that is of general applicability. The method may be performed in vitro or in vivo. Cell lines for use in the in vivo methods also form aspects of the invention. The method for synthesising a non-natural amide comprises: a. reaction of a carboxylic acid with a naturally occurring CoA ligase or a variant thereof; and b. reaction of the product of step a with an amine in the presence of a naturally occurring acyltransferase or a variant thereof; with the proviso that where the CoA ligase and acyltransferase are both naturally occurring, they are not derived from the same source species and do not act sequentially in a metabolic pathway; and with the proviso that the non-natural product is not N-(E)-p-coumaroyl-3-hydroxyanthranilic acid or N-(E)-p-caffeoyl-3-hydroxyanthranilic acid. Further, a method for producing an active pharmaceutical ingredient by the aforementioned method and host cells for carrying out said methods are envisaged.

  本发明涉及一种合成酰胺的方法，具有普遍适用性。该方法可以在体外或体内进行。用于体内方法的细胞系也构成本发明的方面之一。合成非天然酰胺的方法包括：a. 将羧酸与天然存在的辅酶A连接酶或其变体反应；b. 在天然存在的酰基转移酶或其变体存在下，将步骤a的产物与胺反应；但辅酶A连接酶和酰基转移酶若均为天然存在，则不能来自相同源物种且不能在代谢途径中依次作用；并且非天然产物不是N-(E)-对香豆酰-3-羟基蒽醌酸或N-(E)-对咖啡酰-3-羟基蒽醌酸。此外，还可以通过上述方法生产活性药物成分的方法和用于执行该方法的宿主细胞。
• [EN] TETRAHYDROCARBOLINE DERIVATIVES AS EG5 INHIBITORS<br/>[FR] DÉRIVÉS DE TÉTRAHYDROCARBOLINE COMME INHIBITEURS DE L'EG5
  申请人：SANOFI SA

  公开号：WO2011084439A1

  公开（公告）日：2011-07-14

  The present invention relates to substituted tetrahydro-β-carbolines and substituted tetrahydro-γ-carbolines. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are inhibitors of Eg5 kinesin. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of diseases.

  本发明涉及替代的四氢-β-咔啉和替代的四氢-γ-咔啉。本发明还涉及制备这些化合物的方法，包括新颖的中间体。本发明的化合物是Eg5肌动蛋白的抑制剂。因此，本发明的化合物在药物制剂中具有用途，特别是在治疗和/或预防疾病方面。
• [EN] AURONES AND METHODS OF USING AURONES TO TREAT TUBERCULOSIS<br/>[FR] AURONES ET MÉTHODES D'UTILISATION D'AURONES POUR TRAITER LA TUBERCULOSE
  申请人：MIDDLE TENNESSEE STATE UNIV

  公开号：WO2020223439A1

  公开（公告）日：2020-11-05

  This disclosure describes compounds, compositions, and methods for treating or preventing infection or disease including, in some specific embodiments, treating or preventing tuberculosis and/or infection with Mycobacterium tuberculosis (Mtb). In one aspect, this disclosure describes aurones including, for example, aurone 9504, aurone 9505, aurone 9501, aurone 9510, aurone AA2A, and aurone AA8, compositions including aurones, and methods of using aurones for treating or preventing tuberculosis.

  这份披露描述了治疗或预防感染或疾病的化合物、组合物和方法，包括在某些具体实施例中，治疗或预防结核病和/或结核分枝杆菌（Mtb）感染。在一个方面，这份披露描述了包括aurone 9504、aurone 9505、aurone 9501、aurone 9510、aurone AA2A和aurone AA8在内的aurones，包括aurones的组合物，以及使用aurones治疗或预防结核病的方法。
• Synthesis of a C-phosphonate mimic of maltose-1-phosphate and inhibition studies on Mycobacterium tuberculosis GlgE
  作者：Sri Kumar Veleti、Jared J. Lindenberger、Donald R. Ronning、Steven J. Sucheck

  DOI：10.1016/j.bmc.2013.12.058

  日期：2014.2

  enzyme assay which measures orthophosphate release. The requirement of M1P for the assay necessitated the development of an expedited synthetic route to M1P from an intermediate used in the MCP 13 synthesis. In conclusion, we designed a substrate analogue of M1P that is the first to exhibit Mtb GlgE inhibition.

  广泛耐药结核病 (XDR-TB) 的出现需要确定新的抗结核药物靶点以及更好地了解基本的生物合成途径。GlgE 是一种结核分枝杆菌( Mtb ) 编码的麦芽糖基转移酶，参与 α-葡聚糖生物合成。Mtb中 GlgE 的缺失导致细胞内 M1P 的积累，导致生物体快速死亡。为了抑制 GlgE，麦芽糖-C-膦酸酯 (MCP) 13被设计为 M1P 的等排非水解模拟物。MCP 13，唯一已知的Mtb抑制剂使用 Wittig 烯化作为将麦芽糖转化为所需产品的关键步骤，成功合成了 GlgE。MCP 13抑制Mtb GlgE，IC 50  = 230 ± 24 μM，使用测量正磷酸盐释放的偶联酶测定法测定。M1P 用于测定需要开发一条从 MCP 13合成中使用的中间体到 M1P 的快速合成路线。总之，我们设计了 M1P 的底物类似物，它是第一个表现出Mtb GlgE 抑制的。