2-chloro-9-isopropyl-6H-purine-6-one

• 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-chloro-9-isopropyl-6H-purine-6-one
• 英文别名: 2-Chloro-9-isopropyl-9H-purin-6-ol；2-chloro-9-propan-2-yl-1H-purin-6-one
• 化学式: C₈H₉ClN₄O
• 分子量: 212.639
• InChiKey: BKBXSMOZZZFPDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-9-isopropyl-6H-purine-6-one 在 四(三苯基膦)钯 、 sodium carbonate 、 caesium carbonate 、 sodium iodide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 3-((2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-yl)oxy)propanamide
  参考文献：
  名称：

  WO2020113178A5

  摘要：

  公开号：

  WO2020113178A5
• 作为产物：
  描述：

  2,6-二氯-9-异丙基-9h-嘌呤 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以0.54 g的产率得到2-chloro-9-isopropyl-6H-purine-6-one
  参考文献：
  名称：

  WO2020113178A5

  摘要：

  公开号：

  WO2020113178A5

文献信息

• [EN] CYCLIC DI-NUCLEOTIDE COMPOUNDS AS STING AGONISTS<br/>[FR] COMPOSÉS DI-NUCLÉOTIDIQUES CYCLIQUES UTILISÉS EN TANT QU'AGONISTES DE STING
  申请人：MERCK SHARP & DOHME

  公开号：WO2020117625A1

  公开（公告）日：2020-06-11

  A class of polycyclic compounds of general formula (I), wherein Base1, Base2, Y, Ya, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2a, R3, R3a, R4, R4a, R5, R6, R6a, R7, R7a, R8, R8a, and R9 are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds. (I)

  提供一类多环化合物，其一般式为（I），其中Base1、Base2、Y、Ya、Xa、Xa1、Xb、Xb1、Xc、Xc1、Xd、Xd1、R1、R1a、R2a、R3、R3a、R4、R4a、R5、R6、R6a、R7、R7a、R8、R8a和R9在此处定义，可能有用作I型干扰素产生的诱导剂，特别是作为STING活性剂。还提供了合成和使用化合物的方法。（I）
• Cyclic di-nucleotide compounds as STING agonists
  申请人：Merck Sharp & Dohme Corp.

  公开号：US10738074B2

  公开（公告）日：2020-08-11

  A class of polycyclic compounds of general formula (II), of general formula (II′), or of general formula (II″), wherein Base1, Base2, Y, Ya, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2, R2a, R3a, R4, R4a, R5, R6, R6a, R7, R7a, R8, and R8a are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

  一类通式(II)、通式(II′)或通式(II″)的多环化合物，其中Base1、Base2、Y、Ya、Xa、Xa1、Xb、Xb1、Xc、Xc1、Xd、Xd1、R1、R1a、本文定义了 R2、R2a、R3a、R4、R4a、R5、R6、R6a、R7、R7a、R8 和 R8a，它们可用作 I 型干扰素产生的诱导剂，特别是 STING 活性剂。还提供了合成和使用这些化合物的工艺。
• Cyclic di-nucleotide compounds as sting agonists
  申请人：Merck Sharp & Dohme Corp.

  公开号：US10766919B2

  公开（公告）日：2020-09-08

  A class of polycyclic compounds of general formula (I), of general formula (I′), or of general formula (I″), wherein Base1, Base2, Y, Ya, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2, R2a, R3, R4, R4a, R5, R6, R6a, R7, R7a, R8, and R8a are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

  一类通式(I)、通式(I′)或通式(I″)的多环化合物，其中Base1、Base2、Y、Ya、Xa、Xa1、Xb、Xb1、Xc、Xc1、Xd、Xd1、R1、R1a、R2、本文定义的 R2a、R3、R4、R4a、R5、R6、R6a、R7、R7a、R8 和 R8a 可用作 I 型干扰素产生的诱导剂，特别是 STING 活性剂。还提供了合成和使用这些化合物的工艺。
• Methods of modulating immune activity
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US11376272B2

  公开（公告）日：2022-07-05

  In one aspect, the invention provides methods of increasing immune response by administering postcellular signaling factors produced by cells exposed to a stress condition. In one aspect, the invention provides methods of increasing immune response by administering in combination (a) a Stimulator of Interferon Genes (STING) agonist and (b) a purinergic receptor agonist. The increase in immune response may be used, for example, for treatment of infection or cancer. The invention also provides screening assays for identification of compounds that induce production of postcellular signaling factors which are also immunostimulatory agents. The invention further provides methods for identifying postcellular signaling factors with immunostimulatory activity. In another aspect, the invention provides methods of decreasing immune response by administering to a cell, tissue or subject a purinergic receptor antagonist alone or in combination with a Stimulator of Interferon Genes (STING) antagonist.

  一方面，本发明提供了通过施用暴露于应激条件下的细胞产生的细胞后信号因子来提高免疫应答的方法。在一个方面，本发明提供了通过联合施用(a)干扰素基因刺激剂（STING）激动剂和(b)嘌呤能受体激动剂来增加免疫反应的方法。免疫反应的增强可用于治疗感染或癌症等。本发明还提供了筛选测定法，用于鉴定能诱导产生细胞后信号因子的化合物，这些细胞后信号因子也是免疫刺激剂。本发明进一步提供了鉴定具有免疫刺激活性的细胞后信号因子的方法。在另一方面，本发明提供了通过向细胞、组织或受试者单独施用嘌呤能受体拮抗剂或与干扰素基因刺激剂（STING）拮抗剂联合施用来降低免疫反应的方法。
• N-Alkylation of 2,6-Dichloropurine Hydrochloride with a Variety of Alcohols over Alumina Catalyst
  作者：Harikrishna Tumma、N. Nagaraju、K. Vijayakumar Reddy

  DOI：10.1080/00397910903162791

  日期：2010.5.19

  2,6-Dichloropurine hydrochloride reacts with various types of alcohols using different alumina catalysts and converts into its N-9-alkyl-2-chloro-6-hydroxy-9H-purine products to an extent of 49-74%. The product selectivity depends on the stability of carbocation generated from the alcohol. More stable carbocation formulates both N-7 and N-9-alkyl-2,6-dichloropurine products, whereas the less stable carbocation results in exclusively N-9-alkyl-2-chloro-6-hydroxy-9H-purine. The catalytic activity of alumina prepared using the sol-gel method has larger Brunauer, Emmett, and Teller (BET) surface area and hence shows significantly greater catalytic activity than the commercially available alumina samples.