N-(9-((3aR,4R,6aS)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)benzamide | 33962-29-7

• 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: N-(9-((3aR,4R,6aS)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)benzamide
• 英文别名: N⁶-benzoyl-9-(5-deoxy-2,3-O-isopropylidene-β-D-erythropent-4-enofuranosyl)adenine；6-N-benzoyl-9-(5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranosyl)adenine；N-[9-(O²,O³-isopropylidene-β-D-erythro-5-deoxy-pent-4-enofuranosyl)-9H-purin-6-yl]-benzamide；1-(6-benzoylamino-purin-9-yl)-O²,O³-isopropylidene-β-D-erythro-1,5-dideoxy-pent-4-enose；N6-Benzoyl-9-(5-deoxy-2,3-O-isopropyliden-β-D-erythro-pent-4-en-furanosyl)adenin；N-[9-[(3aS,6R,6aR)-2,2-dimethyl-4-methylidene-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-6-yl]purin-6-yl]benzamide
• CAS: 33962-29-7
• 化学式: C₂₀H₁₉N₅O₄
• 分子量: 393.402
• InChiKey: AUDJYCHFVYNLOC-SPYBWZPUSA-N

物化性质

• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(9-((3aR,4R,6aS)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)benzamide 在 18-冠醚-6 、 氨基磺酰氯 、 氨 、 碘 、 silver fluoride 、 三丁基氧化锡 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二甲基亚砜 、 乙腈 为溶剂， 反应 69.17h， 生成 Nucleocidin
  参考文献：
  名称：

  Maguire, Anita R.; Meng, Wei-dong; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1993, # 15, p. 1795 - 1808

  摘要：

  DOI：
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 7.0h， 生成 N-(9-((3aR,4R,6aS)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)benzamide
  参考文献：
  名称：

  Maguire, Anita R.; Meng, Wei-dong; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1993, # 15, p. 1795 - 1808

  摘要：

  DOI：

文献信息

• 4'-Substituted nucleosides. 2. Synthesis of the nucleoside antibiotic nucleocidin
  作者：Ian D. Jenkins、Julien P. H. Verheyden、John G. Moffatt

  DOI：10.1021/ja00427a049

  日期：1976.5

  gave the corresponding 4’-flUOrO nucleosides (20, 2Oa) which were converted to their sulfamoyl esters (22, 22a) by way of intermediate 5’-O-tributyltin (21, 21a, R = SnBuj ) derivatives. Following removal of protecting groups the nucleoside antibiotic nucleocidin (1) and its cu-L-lyxofuranosyl epimer la were isolated. Several alternative methods for conversion of the 5’-iodo function in 10 and 11 to

  氟化碘加成 N6,N6-dibenzoyl-9-(5-deoxy-2,3-O-isopropy~idene-~-D-er~f~ro-pent-4-enofuranosyl)adenine (9) 导致与 PD-呋喃核糖基 (10) 和 aL-lyxofuranosyl (11) 构型形成相应的 5'-脱氧-4'-氟-5'-碘核苷。5'-碘功能的亲核置换非常困难，但可以用叠氮离子完成，得到 5'-叠氮-4'-氟核苷 (18, Ma)。叠氮化物光解，然后温和水解和硼氢化物还原得到相应的 4'-氟代核苷 (20, 2Oa)，通过中间体 5'-O-三丁基锡 (21, 21a) 将其转化为其氨磺酰酯 (22, 22a) , R = SnBuj ) 导数。在去除保护基团后，分离出核苷抗生素亲核素 (1) 及其 cu-L-lyxofuranosyl 差向异构体 1a。研究了将 10 和 11 中的 5'-碘官能团转化为羟基对应物
• [EN] COMPOSITIONS AND METHODS OF MODULATING THE IMMUNE RESPONSE BY ACTIVATING ALPHA PROTEIN KINASE 1<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE MODULATION DE LA RÉPONSE IMMUNITAIRE PAR ACTIVATION DE LA PROTÉINE KINASE ALPHA 1
  申请人：SHANGHAI YAO YUAN BIOTECHNOLOGY CO LTD

  公开号：WO2019080898A1

  公开（公告）日：2019-05-02

  The disclosure provides compositions and methods related to activating alpha-kinase 1 (ALPK1) for modulating an immune response and treating or preventing cancer, infection, inflammation and related diseases and disorders as well as potentiating an immune response to a target antigen. The disclosure also provides heterocyclic compounds of formula (I) as agonists of alpha protein kinase 1 (ALPK1) and their use in activating ALPK1, modulating an immune response and treating diseases such as cancer, wherein A1, A2, L1, L2, L3, Z1, Z2, W1, W2, R1, R2, R3, R4, R5, R6 and R7 are defined herein.

  该披露提供了与激活α-激酶1（ALPK1）相关的组合物和方法，用于调节免疫应答，治疗或预防癌症、感染、炎症和相关疾病和疾病，以及增强对靶抗原的免疫应答。该披露还提供了式（I）的杂环化合物作为α蛋白激酶1（ALPK1）的激动剂，并其在激活ALPK1、调节免疫应答和治疗癌症等疾病中的应用，其中A1、A2、L1、L2、L3、Z1、Z2、W1、W2、R1、R2、R3、R4、R5、R6和R7在此定义。
• Compositions and methods of modulating the immune response by activating alpha protein kinase 1
  申请人：Shanghai Yao Yuan Biotechnology Co., Ltd.

  公开号：US11149051B2

  公开（公告）日：2021-10-19

  The disclosure provides compositions and methods related to activating alpha-kinase 1 (ALPK1) for modulating an immune response and treating or preventing cancer, infection, inflammation and related diseases and disorders as well as potentiating an immune response to a target antigen. The disclosure also provides heterocyclic compounds of formula (I) as agonists of alpha protein kinase 1 (ALPK1) and their use in activating ALPK1, modulating an immune response and treating diseases such as cancer, wherein A1, A2, L1, L2, L3, Z1, Z2, W1, W2, R1, R2, R3, R4, R5, R6 and R7 are defined herein.

  本公开提供了与激活α蛋白激酶1（ALPK1）有关的组合物和方法，用于调节免疫反应和治疗或预防癌症、感染、炎症及相关疾病和失调，以及增强对靶抗原的免疫反应。本公开还提供了作为α蛋白激酶1（ALPK1）激动剂的式(I)杂环化合物及其在激活ALPK1、调节免疫应答和治疗癌症等疾病中的用途，其中A1、A2、L1、L2、L3、Z1、Z2、W1、W2、R1、R2、R3、R4、R5、R6和R7在本文中定义。
• Ozonolysis of 6-N-benzoyl-9-(5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranosyl)adenine and related compounds
  作者：Bhalchandra V. Joshi、Colin B. Reese

  DOI：10.1016/s0040-4039(00)73866-4

  日期：1993.9

  The nucleoside 4',5'-olefins 3, 5, 7 and 9 are readily converted into the corresponding lactones 4, 6, 8 and 10, respectively, by ozonolysis in dichloromethane solution at -78-degrees-C.
• COMPOSITIONS AND METHODS OF MODULATING THE IMMUNE RESPONSE BY ACTIVATING ALPHA PROTEIN KINASE 1
  申请人：Shanghai Yao Yuan Biotechnology Co., Ltd.

  公开号：US20200283468A1

  公开（公告）日：2020-09-10

  The disclosure provides compositions and methods related to activating alpha-kinase 1 (ALPK1) for modulating an immune response and treating or preventing cancer, infection, inflammation and related diseases and disorders as well as potentiating an immune response to a target antigen. The disclosure also provides heterocyclic compounds of formula (I) as agonists of alpha protein kinase 1 (ALPK1) and their use in activating ALPK1, modulating an immune response and treating diseases such as cancer, wherein A 1 , A 2 , L 1 , L 2 , L 3 , Z 1 , Z 2 , W 1 , W 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are defined herein.