2(R)-adenin-9-yl-2,3-dihydrofuran | 37076-65-6

• 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(R)-adenin-9-yl-2,3-dihydrofuran
• 英文别名: (2R')-9-(2,3-dihydrofuran-2-yl)adenine；(R)-9-(2,3-Dihydro-2-furanyl)-9H-purin-6-amine；9-[(2R)-2,3-dihydrofuran-2-yl]purin-6-amine
• CAS: 37076-65-6
• 化学式: C₉H₉N₅O
• 分子量: 203.203
• InChiKey: DUFUESFZQXXUHZ-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2(R)-adenin-9-yl-2,3-dihydrofuran 生成 N-[9-[(2R,4S,5S)-5-(dimethoxyphosphorylmethoxy)-4-iodooxolan-2-yl]purin-6-yl]-2,2-dimethylpropanamide
  参考文献：
  名称：

  KIM, CHOUNG UN;LUH, BING Y.;MISCO, PETER F.;MARTIN, JOHN C., NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 371-375

  摘要：

  DOI：
• 作为产物：
  描述：

  1-β-(adenin-9-yl)-D-riburonic acid 在 neopentylacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以65%的产率得到2(R)-adenin-9-yl-2,3-dihydrofuran
  参考文献：
  名称：

  Isosteric triphosphonate analogues of dNTP: Synthesis and substrate properties toward various DNA polymerases

  摘要：

  Isosteric triphosphonate derivatives of 2',3'-dideoxy-2',3'-didehydroadenosine and 3'-deoxy-2',3'-didehydrothymidine and their beta,gamma-substituted analogues were synthesized. Their substrate properties toward a number of reverse transcriptases of the human immunodeficiency and avian myeloblastosis viruses, human DNA polymerases alpha and beta, and the Klenow fragment of Escherichia coli DNA polymerase I were studied.

  DOI：

  10.1134/s1068162007050056

文献信息

• Nucleoside analogs
  申请人：Institute of Organic Chemistry and Biochemistry of the Academy of

  公开号：US05686611A1

  公开（公告）日：1997-11-11

  Provided are compounds of the following formulae: A phosphonomethoxymethyoxymethyl purine/pyrimidine derivative of the formula ##STR1## wherein X and X' are the same or different and are hydrogen or alkyl. R and R' are the same or different and are hydrogen, alkyl, hydroxyalkyl or alkanoyl and B is a purine or pyrimidine base. A compound of formula (VI) ##STR2## wherein X is halogen, Y is S-phenyl, Se-phenyl or halogen and B is hypoxanthine, xanthine, guanine, 8-bromoguanine, 8-chloroguanine, 8-methylguanine, 8-thioguanine, 3-deazaguanine, purine, 2-aminopurine, 2,6-diaminopurine, adenine, 3-deazaadenine, 8-aminoguanine, 8-hydrazinoguanine, 8-hydroxyguanine, cytosine, 5-ethylcytosine, 5-methylcytosine, thymine, uracil, 5-chlorouracil, 5-bromouracil, 5-ethyluracil, 5-iodouracil, 5-propyluracil or 5-vinyluracil, 2-acetamido-6-diphenylcarbamoylpurine, 6-N-dimethylamino-methyladenine or 6-N-pivaloyladenine. A compound of formula (VII) ##STR3## wherein B is guanine, 8-guanine, 8-bromoguanine, 8-chloroguanine, 8-methylguanine, 8-thioguanine, 3-deazaguanine, 8-aminoguanine, 8-hydrazinoguanine, 8-hydroxyguanine, cytosine, 5-ethylcytosine, or 5-methylcytosine.

  提供以下式的化合物：A磷酸甲氧甲氧甲氧基嘌呤/嘧啶衍生物，其化学式为##STR1##其中X和X'相同或不同，为氢或烷基。R和R'相同或不同，为氢、烷基、羟基烷基或烷酰基，B为嘌呤或嘧啶碱基。化学式为(VI)的化合物##STR2##其中X为卤素，Y为S-苯基、Se-苯基或卤素，B为咖啡碱、黄嘌呤、鸟嘌呤、8-溴鸟嘌呤、8-氯鸟嘌呤、8-甲基鸟嘌呤、8-硫鸟嘌呤、3-去氮鸟嘌呤、嘌呤、2-氨基嘌呤、2,6-二氨基嘌呤、腺嘌呤、3-去氮腺嘌呤、8-氨基鸟嘌呤、8-叠氮鸟嘌呤、8-羟基鸟嘌呤、胞嘧啶、5-乙基胞嘧啶、5-甲基胞嘧啶、胸腺嘧啶、尿嘧啶、5-氯尿嘧啶、5-溴尿嘧啶、5-乙基尿嘧啶、5-碘尿嘧啶、5-丙基尿嘧啶或5-乙烯基尿嘧啶、2-乙酰胺基-6-二苯基氨基嘌呤、6-N-二甲氨基甲基腺嘌呤或6-N-戊酰基腺嘌呤。化学式为(VII)的化合物##STR3##其中B为鸟嘌呤、8-鸟嘌呤、8-溴鸟嘌呤、8-氯鸟嘌呤、8-甲基鸟嘌呤、8-硫鸟嘌呤、3-去氮鸟嘌呤、8-氨基鸟嘌呤、8-叠氮鸟嘌呤、8-羟基鸟嘌呤、胞嘧啶、5-乙基胞嘧啶或5-甲基胞嘧啶。
• 2'3' CYCLIC DINUCLEOTIDES WITH PHOSPHONATE BOND ACTIVATING THE STING ADAPTOR PROTEIN
  申请人：INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY ASCR,V.V.I.

  公开号：US20190185510A1

  公开（公告）日：2019-06-20

  The present disclosure relates to 2′3′ cyclic phosphonate dinucleotides of general formula (J), their pharmaceutically acceptable salts, their pharmaceutical composition and combinations of said substances and other medicaments or pharmaceuticals. The disclosure also relates to the use of said compounds for the treatment or prevention of diseases or conditions modifiable by STING protein modulation, such as cancer or viral, allergic and inflammatory diseases. In addition, these substances can be used as adjuvants in vaccines.

  本公开涉及一般式（J）的2′3′环磷酸二核苷酸，其药用可接受盐，其药物组合物以及所述物质与其他药物或药品的组合物。该公开还涉及使用所述化合物治疗或预防可通过STING蛋白调节改变的疾病或状况，如癌症或病毒性、过敏性和炎症性疾病。此外，这些物质可用作疫苗的辅助剂。
• 3'3' CYCLIC DINUCLEOTIDES WITH PHOSPHONATE BOND ACTIVATING THE STING ADAPTOR PROTEIN
  申请人：INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY ASCR, V.V.I.

  公开号：US20190183917A1

  公开（公告）日：2019-06-20

  Provided herein are the 3′3′ cyclic phosphonate dinucleotides of general formula J, their pharmaceutically acceptable salts, a pharmaceutical composition containing them and combinations of said substances and other medicaments or pharmaceuticals. The disclosure also relates to the use of said compounds for the treatment or prevention of diseases or conditions modifiable by STING protein modulation, such as cancer or viral, allergic and inflammatory diseases. In addition, these substances can be used as adjuvants in vaccines.

  本文提供了一般式J的3′3′环磷酸二核苷酸及其药学上可接受的盐、包含它们的制药组合物以及与其他药物或制药品的混合物。本文还涉及使用这些化合物治疗或预防可通过STING蛋白调节改变的疾病或病症，例如癌症或病毒性、过敏性和炎症性疾病。此外，这些物质可以用作疫苗佐剂。
• 2'2' CYCLIC DINUCLEOTIDES WITH PHOSPHONATE BOND ACTIVATING THE STING ADAPTOR PROTEIN
  申请人：INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY ASCR, V.V.I.

  公开号：US20190185509A1

  公开（公告）日：2019-06-20

  Provided herein are 2′2′ cyclic phosphonate dinucleotides of formula (J), their pharmaceutically acceptable salts, hydrates or solvates, a pharmaceutical composition containing them and combinations of said substances and other medicaments or pharmaceuticals. The disclosure also relates to the use of said compounds for the treatment or prevention of diseases or conditions modifiable by STING protein modulation, such as cancer or viral, allergic and inflammatory diseases. In addition, the dinucleotides can be used as adjuvants in vaccines.

  本文提供了式（J）的2′2′环磷酸二核苷酸，它们的药学上可接受的盐、水合物或溶剂化物，以及含有它们的药物组合物和其他药物或制药品的组合物。本文还涉及使用这些化合物治疗或预防STING蛋白调节可改变的疾病或病情，如癌症或病毒性、过敏性和炎症性疾病。此外，这些二核苷酸可以用作疫苗佐剂。
• Phosphonate nucleoside analogs
  申请人：Institute of Organic Chemistry and Biochemistry of the Academy of

  公开号：US05693798A1

  公开（公告）日：1997-12-02

  Provided are compounds of the following formulae: A phosphonomethoxymethyoxymethyl purine/pyrimidine derivative of the formula ##STR1## wherein X and X' are the same or different and are hydrogen or alkyl. R and R' are the same or different and are hydrogen, alkyl, hydroxyalkyl or alkanoyl and B is a purine or pyrimidine base. A 4'-phosphonomethoxytetrahydrofuranyl-1'-purine-pyrimidine of the formula ##STR2## wherein X and X' are the same or different and are hydrogen or alkyl, Y and Z are the same or different and are hydrogen, hydroxyl or alkyl or Y+Z is an alkenyl, an epoxide or cyclopropyl, and B is a purine or pyrimidine base.

  提供以下式子的化合物：公式为A的磷酸甲氧甲氧甲基嘌呤/嘧啶衍生物##STR1##其中X和X'相同或不同，是氢或烷基。R和R'相同或不同，是氢、烷基、羟基烷基或脂肪酰基，B是一种嘌呤或嘧啶碱基。公式为##STR2##其中X和X'相同或不同，是氢或烷基，Y和Z相同或不同，是氢、羟基或烷基，或Y+Z是烯烃、环氧化物或环丙基，B是一种嘌呤或嘧啶碱基。