N-苯甲酰基-3'-脱氧腺苷 | 76902-49-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: N-苯甲酰基-3'-脱氧腺苷
• 英文名称: 3'-deoxy-N⁶-benzoyladenosine
• 英文别名: N-(9-((2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide；N6-Benzoyl-3'-deoxyadenosine；N-[9-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• CAS: 76902-49-3
• 化学式: C₁₇H₁₇N₅O₄
• 分子量: 355.353
• InChiKey: GNPRDDYSJSKPJF-XWCIJXRUSA-N

物化性质

• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-苯甲酰基-3'-脱氧腺苷 在 吡啶 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 27.5h， 生成 N⁶-benzoyl-3'-deoxy-5'-O-(monomethoxytrityl)adenosine 2'-<2,5-dichlorophenyl 2-(p-nitrophenyl)ethyl phosphate>
  参考文献：
  名称：

  核苷酸。第二十八部分。2'-5'-cordycepin-trimer核的化学合成†

  摘要：

  3'-脱氧腺苷-（2'-5'）-3'-脱氧腺苷基-（2'-5'）-3'-脱氧腺苷（30；三聚虫草素）的化学合成通过使用不同保护基团的三种不同途径进行描述并应用磷酸三酯方法。中间体已通过元素分析和光谱学手段进行了分离和表征。通过脱保护获得了高收率的30，使得该具有生物学活性的化合物可以制备规模获得。

  DOI：

  10.1002/hlca.19870700808
• 作为产物：
  描述：

  虫草素 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 N-苯甲酰基-3'-脱氧腺苷
  参考文献：
  名称：

  O-Alkyl-5',5'-dinucleoside phosphates as prodrugs of 3'-azidothymidine and cordycepin

  摘要：

  The syntheses of two O-alkyl-5',5'-dinucleoside phosphotriesters 2a and 2b as combined prodrugs of the antiviral drug AZT (1) and the antibiotic agent cordycepin (3) are described. 2a,b were obtained as a 1:1 diastereomeric mixture. The absolute configuration of the isolated diastereomers was determined by NOE NMR experiments and correlated with the migration characteristics on silica gel as well as the P-31-NMR chemical shift. The conformational features of 2b(R) and 2b(S) were determined m deuteriated dodecylphosphocholine micelles in aqueous solution using 2D-NOESY spectra and shown to be dependent on the configuration at phosphorus. Additionally, all new compounds were tested for their antiviral activities in HIV-1-infected CEM C113 and H9 cell systems. Although all compounds were able to significantly inhibit the HIV-1-induced cytopathogenic effect, only the phosphodiester 12 gave a selectivity index (SI(RT) = 2000) comparable to the reference compound AZT (1) (SI(RT) = 3000).

  DOI：

  10.1021/jo00052a053

文献信息

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

  公开号：WO2017027645A1

  公开（公告）日：2017-02-16

  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.

  提供一类多环化合物，其一般化学式为(II)，一般化学式为(II')或一般化学式为(II")，其中在此处定义了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和R8a，这些化合物可能作为I型干扰素的诱导剂，特别是作为STING活性剂。还提供了合成和使用这些化合物的方法。
• Efficient synthesis of protected 3′-deoxyadenosine and 3′-deoxyguanosine from adenosine and guanosine
  作者：Zhiyong Cui、Lei Zhang、Biliang Zhang

  DOI：10.1016/s0040-4039(00)02041-4

  日期：2001.1

  Highly efficient synthesis of protected 3′-deoxyadenosine and 3′-deoxyguanosine from adenosine and guanosine were described. The 2′,3′-diol of protected adenosine and guanosine were reacted with α-acetoxyisobutyryl bromide to yield 9-(2′-O-acetyl-3′-bromo-5′-O-tert-butyldiphenylsilyl-3′-deoxy-β-d-xylofuranosyl)-6-N-benzoyl adenine and 9-(2′-O-acetyl-3′-bromo-5′-O-tert-butyldiphenylsilyl-3′-deoxy-β

  描述了由腺苷和鸟苷高效合成保护的3'-脱氧腺苷和3'-脱氧鸟苷。2'，3'-二醇保护的腺苷和鸟苷，用α-乙酰氧基异丁酰溴反应，得到9-（2'- ø -乙酰基3'-溴-5'- ø -叔-butyldiphenylsilyl -3'-脱氧-β-d呋喃木糖基）-6- ñ -苯甲酰基腺嘌呤和9-（2'- ø -乙酰基3'-溴-5'- ø -叔-butyldiphenylsilyl -3'-脱氧-β-d呋喃木糖基） -2- ñ - （ñ '，ñ '-dimethylaminomethylene）鸟嘌呤，随后用三-加热ñ-丁基氢化锡在2,2'-偶氮二异丁腈的存在下，以全部收率提供66-73％的受保护的3'-脱氧腺苷和3'-脱氧鸟苷。
• Asymmetric Synthesis of Nucleosides via Molybdenum-Catalyzed Alkynol Cycloisomerization Coupled with Stereoselective Glycosylations of Deoxyfuranose Glycals and 3-Amidofuranose Glycals
  作者：Frank E. McDonald、Mark M. Gleason

  DOI：10.1021/ja960581l

  日期：1996.1.1

  effects of 3-amido-2,3-dideoxyfuranose glycals were exploited in a novel and highly stereoselective synthesis strategy for a variety of biologically active 3‘-amino-2‘,3‘-dideoxy- and 3‘-amino-3‘-deoxy-β-nucleosides, including puromycin aminonucleoside. In addition, the mechanism of the molybdenum-catalyzed alkynol cycloisomerization reaction has been studied. Evidence is p...

  脱氧呋喃糖糖可以通过五羰基钼催化的炔醇环异构化有效制备，炔醇很容易通过短合成序列制备成手性非外消旋形式，其特征是市售烯丙醇的不对称环氧化。环异构化反应被证明与酯和酰胺官能团相容。2,3-二脱氧呋喃糖苷被立体选择性地转化为抗艾滋病 β-核苷司他夫定 (2',3'-didehydro-2',3'-dideoxythymidine, d4T) 和抗病毒药物 3'-脱氧-β-核苷虫草素. 3-amido-2,3-dideoxyfuranose 聚糖的异嵌合和氢键导向作用被用于各种具有生物活性的 3'-amino-2',3'-dideoxy-和3'-氨基-3'-脱氧-β-核苷，包括嘌呤霉素氨基核苷。此外，还研究了钼催化炔醇环异构化反应的机理。证据是...
• Synthesis and properties of 3′-deoxyadenylate trimer dA2′p5′A2′p5′A
  作者：Ramamurthy Charubala、Wolfgang Pfleiderer

  DOI：10.1016/0040-4039(80)88070-1

  日期：1980.1

  The trimeric 3′-deoxyadenylyl-(2′→5′)-3′-deoxyadenylyl-(2′→5′)-3′-deoxyadenosine () was synthesized via the phosphotriester approach starting from cordycepine (). Various physical data have been determined and compared with those of the ribo-A2′p5′A2′p5′A analog.

  从虫草素（）开始，通过磷酸三酯法合成了三聚体3'-脱氧腺苷基-（2'→5'）-3'-脱氧腺苷基-（2'→5'）-3'-脱氧腺苷（）。已经确定了各种物理数据，并将其与ribo-A2'p5'A2'p5'A类似物的数据进行了比较。
• 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。