2',3',5'-三-O-乙酰基-8-溴腺苷 | 31281-86-4

• 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: 2',3',5'-三-O-乙酰基-8-溴腺苷
• 英文名称: 2',3',5'-tri-O-acetyl-8-bromoadenosine
• 英文别名: 8-bromo-2',3',5'-tri-O-acetyladenosine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-amino-8-bromopurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 31281-86-4
• 化学式: C₁₆H₁₈BrN₅O₇
• 分子量: 472.252
• InChiKey: HRCLVNMFELGYPE-SDBHATRESA-N

物化性质

• 熔点：
  188-189 °C
• 沸点：
  635.0±65.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2',3',5'-三-O-乙酰基-8-溴腺苷 在 亚硝酸正戊酯 作用下， 以 四氢呋喃 为溶剂， 反应 90.0h， 以27%的产率得到(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(8-bromo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  Synthesis and Biologic Evaluation of 8-Substituted Derivatives of Nebularine (9-β-D-Ribofuranosylpurine)

  摘要：

  A series of 8-substituted purine ribonucleosides were prepared from 2',3',5'-tri-O-acetyl-8-bromoadenosine and evaluated for cytotoxicity and antiviral activity. Four of these nucleosides (6b-9b) were significantly toxic to both HEp-2 and L1210 cells in culture but the most cytotoxic one (9b) was inactive against the P388 leukemia in mice. None of these nucleosides showed significant antiviral activity against Herpes Simplex 1 or 2, vaccinia, or influenza A.

  DOI：

  10.1080/15257779408011875
• 作为产物：
  描述：

  2',3',5'-三乙酰腺苷 在 disodium hydrogenphosphate 、 溴 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.25h， 以98%的产率得到2',3',5'-三-O-乙酰基-8-溴腺苷
  参考文献：
  名称：

  Distinct Solvent-Dependence in the Photoreactions of Purine Nucleosides with Pyrimido[5,4-g]pteridinetetrone N-Oxide: Possible Generatiion of Hydroxyl Radical from the Excited N-Oxide in Alcohols

  摘要：

  Photoreaction of 2',3',5'-tri-O-acetyladenosine (5) with pyrimido[5,4-g]pteridinetetrone N-oxide (1) in acetonitrile gave N6-cyanomethyl-2',3',5'-tri-O-acetyladenosine (6) as a major detectable product via coupling of adenosyl radical with cyanomethyl radical generated by the mediation of 1. Under the analogous conditions, N2-benzoyl-2',3',5'-tri-O-acetylguanosine (8) underwent oxidative degradation of the guanine skeleton by 1. In sharp contrast, photoreactions of 5 and 8 with 1 in tert-butanol resulted in the formation of the corresponding 8-hydroxypurine nucleosides (7) and (9), respectively. These facts and other observations suggest that 1 could generate hydroxyl radical upon irradiation in alcohols.

  DOI：

  10.3987/com-92-s20

文献信息

• CuI Controlled C–C and C–N Bond Formation of Heteroaromatics through C(sp³)–H Activation
  作者：Ran Xia、Hong-Ying Niu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/ol302640e

  日期：2012.11.2

  A new method for C–C and C–N bond formation of heteroaromatics and C(sp3)–H alkanes was developed with high regioselectivity. The reaction occurred on C8 to give 8-cylcoakylpurines by C–C bond formation only promoted by tBuOOtBu, while it occurred on the amino group to give N6-alkylated purines by C–N bond formation when 2 equiv of CuI were added. A reaction mechanism was also proposed based on our

  具有高区域选择性的杂芳烃和C（sp 3）-H烷烃的C–C和C–N键形成的新方法得到了发展。该反应发生在C8上，仅通过t BuOO t Bu促进了通过C–C键形成的8烷基甲酰基嘌呤，而当氨基当上，当2当量的CuI为2时，通过C–N键的形成产生了N 6烷基化的嘌呤。添加。根据我们的初步实验数据，还提出了一种反应机理。
• Regioselective<i>O</i>2′,<i>O</i>3′-Deacetylations of Peracetylated Ribonucleosides by Using Tetra-<i>n</i>-butylammonium Fluoride
  作者：Arun Babu Kumar、Roman Manetsch

  DOI：10.1002/ejoc.201400085

  日期：2014.6

  a single-step route to access O5′-acetyl ribonucleosides, a key intermediate in the synthesis of biomedically important nucleosides and nucleotides. Moreover, it offered the general applicability of a non-enzymatic method for the selective deacetylation of peracetylated 2′-deoxyribonucleosides. Its synthetic utility was further demonstrated by the synthesis of molecules of biomedical interest by using

  通过使用四正丁基氟化铵，在其他乙酸酯官能团存在的情况下，实现了 1,2-二醇二乙酸酯的稳健、温和且高度区域选择性的脱乙酰化。该方法提供了获取 O5'-乙酰核糖核苷的单步途径，O5'-乙酰核糖核苷是合成具有生物医学意义的核苷和核苷酸的关键中间体。此外，它为全乙酰化 2'-脱氧核糖核苷的选择性脱乙酰化提供了非酶促方法的普遍适用性。通过使用这种特殊的脱乙酰反应合成具有生物医学意义的分子，进一步证明了其合成效用。
• Nucleosides and nucleotides. 103. 2-Alkynyladenosines: a novel class of selective adenosine A2 receptor agonists with potent antihypertensive effects
  作者：Akira Matsuda、Misao Shinozaki、Toyofumi Yamaguchi、Hiroshi Homma、Rie Nomoto、Tadashi Miyasaka、Yohko Watanabe、Toichi Abiru

  DOI：10.1021/jm00080a007

  日期：1992.1

  Additionally, we describe how hypotensive activity and heart rate decrease brought on by 5 and some other compounds with spontaneously hypertensive rats are proportional to the order of the potency to both A1 and A2 binding affinities. Thus, 2-alkynyladenosines are interesting and promising as antihypertensive agents that should be considered for further detailed preclinical evaluation.

  描述了一系列2-炔基腺苷在A1和A2腺苷受体上的合成和受体结合活性。在含三乙胺的N，N-二甲基甲酰胺中，在双（三苯基膦）二氯化钯和碘化亚铜的存在下，钯催化的2-碘腺苷（4a）与各种末端炔的交叉偶联反应生成2-炔基腺苷（5a-r）。一种经济的合成方法，用于制备9a（2,3,5-三-O-乙酰基-1-β-D-呋喃呋喃糖基）-6-氯-2-碘代嘌呤++ +（2），这是4a的前体，也包括在内。2-（1-辛炔-1-基）腺苷（5e）和2-（1-乙炔-1-基）腺苷（9）的几种转化反应以及6-氯嘌呤衍生物11和8的相似交叉偶联反应还报道了带有1-辛炔的-溴腺苷（13）。在大鼠脑中针对A1和A2腺苷受体结合活性进行测试的许多这类2-炔基腺苷对A2腺苷受体具有选择性。其中，2-（1-己炔-1-基）腺苷（5c）对A1和A2受体的亲和力最高，Ki值分别为126.5和2.8 nM。讨论了这一系列化合物的结构活性关系，包
• [EN] NOVEL ANTIBACTERIAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIBACTÉRIENS
  申请人：PASTEUR INSTITUT

  公开号：WO2012090136A1

  公开（公告）日：2012-07-05

  The present invention relates to compounds of formula (I): wherein Rj, R2, R3, R4, Xi, X2, X3 and Z are as defined in claim 1. The compounds are useful in the prevention and/or treatment of bacterial infections.

  本发明涉及以下化合物的公式(I)：其中R1、R2、R3、R4、X1、X2、X3和Z的定义如权利要求1所述。这些化合物在预防和/或治疗细菌感染方面具有用途。
• Selective C8-Metalation of Purine Nucleosides via Oxidative Addition
  作者：Florian Kampert、Dirk Brackemeyer、Tristan Tsai Yuan Tan、F. Ekkehardt Hahn

  DOI：10.1021/acs.organomet.8b00685

  日期：2018.11.26

  the type trans-[PdL2(PPh3)2] (2JPP = 442 Hz for [7]). In addition, two complex molecules of [7] form a trans-Watson–Crick/Hoogsteen AA base pair in the solid state. N7-protonation of the guanosine-derived complexes [5] and [6] with HBF4·Et2O and of adenosine-derived complexes [7] and [8] using lutidinium triflate yields complexes [9]BF4 and [10]BF4 and complexes [11]OTf and [12]OTf bearing protic NH

  8-溴-2'-脱氧-3'，5'-二-O-乙酰鸟嘌呤（1），8-溴-2'，3'，5'-三-O-乙酰鸟嘌呤（2），8-溴- 2′-脱氧-3′，5′-二-O-乙酰腺苷（3）和8-溴-2′，3′，5′-三-O-乙酰腺苷（4）与[Pd（PPh 3）反应4 ]通过C8-Br氧化加成反应生成C8 palpalated的氮杂络合物[ 5 ]-[ 8 ]，其特征是未质子化的N7环氮原子。该配合物具有非对位转位的三苯基膦配体，可测定2 J PP反式-[PdL 2（PPh 3）2 ]类型的络合物（[ 7 ]的2 J PP = 442 Hz ）。此外，[ 7 ]的两个复杂分子以固态形式形成反式Watson-Crick / Hoogsteen AA碱基对。用三氟甲磺酸lut啶鎓对鸟嘌呤衍生的复合物[ 5 ]和[ 6 ]与HBF 4 ·Et 2 O和腺苷衍生的复合物[ 7 ]和[ 8 ]进行N7质子化反应，生成复合物[