6-benzylamino-8-bromo-9-(β-D-ribofuranosyl)purine | 1427459-39-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-benzylamino-8-bromo-9-(β-D-ribofuranosyl)purine
• 英文别名: N⁶-benzyl-8-bromoadenosine；6-benzylamino-8-bromopurine 9-riboside；6-Benzylamino-8-bromo-9-(beta-D-ribofuranosyl)purine；(2R,3R,4S,5R)-2-[6-(benzylamino)-8-bromopurin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 1427459-39-9
• 化学式: C₁₇H₁₈BrN₅O₄
• 分子量: 436.265
• InChiKey: IPDCFAPSYVBWKL-XNIJJKJLSA-N

物化性质

• 沸点：
  729.0±70.0 °C(Predicted)
• 密度：
  1.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-benzylamino-8-bromo-9-(β-D-ribofuranosyl)purine 在 potassium permanganate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.75h， 生成 6-benzylamino-8-cyano-9-(β-D-ribofuranosyl)purine
  参考文献：
  名称：

  6,8-DISUBSTITUTED PURINE COMPOSITIONS

  摘要：

  提供可用于药物和化妆品组合物和/或应用的6,8-二取代嘌呤。这些6,8-二取代嘌呤具有广泛的生物活性，例如抗炎、抗衰老等，以及其他在制药和化妆品应用中特别有用的活性。含有这些6,8-二取代嘌呤的化合物和组合物提供生长调节、分化、抗衰老和抗衰老特性，具有比迄今为止已知的类似物更好的选择性和效率，以及较低的毒性。

  公开号：

  US20130072506A1
• 作为产物：
  描述：

  6-氯嘌呤核苷 在 溴 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 6-benzylamino-8-bromo-9-(β-D-ribofuranosyl)purine
  参考文献：
  名称：

  α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5′-Nucleotidase (CD73) Inhibitors

  摘要：

  ecto-5'-Nucleotidase (eN, CD73) catalyzes the hydrolysis of extracellular AMP to adenosine. eN inhibitors have potential for use as cancer therapeutics. The eN inhibitor alpha,beta-methylene-ADP (AOPCP, adenosine-5'-O-[(phosphonomethyl)phosphonic acid]) was used as a lead structure, and derivatives modified in various positions were prepared. Products were tested at rat recombinant eN. 6-(Ar)alkylamino substitution led to the largest improvement in potency. N-6-Monosubstitution was superior to symmetrical N-6,N-6-disubstitution. The most potent inhibitors were N-6-(4chlorobenzyl)-(10l, PSB-12441, K-i 7.23 n.M), N-6-phenylethyl(10h, PSB-12425, K-i 8.04 nM), and N-6-benzyl-adenosine-5'-O[(phosphonomethyl)phosphonic acid] (10g, PSB-12379, K-i 9.03 nM). Replacement of the 6-NH group in 10g by 0 (10q, PSB-12431) or S (10r, PSB-12553) yielded equally potent inhibitors (10q, 9.20 nM; 10r, 9.50 aM). Selected compounds investigated at the human enzyme did not show species differences; they displayed high selectivity versus other ecto-nudeotidases and ADP-activated P2Y receptors. Moreover, high metabolic stability was observed. These compounds represent the most potent eN inhibitors described to date.

  DOI：

  10.1021/acs.jmedchem.5b00802

文献信息

• Synthesis of a Cytokinin Linked by a Spacer to Dexamethasone and Biotin: Conjugates to Detect Cytokinin-Binding Proteins
  作者：You Wang、David Letham、Peter John、Ren Zhang

  DOI：10.3390/molecules21050576

  日期：——

  (e.g., dexamethasone) linked to a cytokinin via a spacer. In the yeast nucleus, this ligand by binding connects two fusion proteins leading to a reporter gene activation and detection and characterisation of cytokinin binding proteins. Herein is reported the first synthesis of dexamethasone-cytokinin ligands with a spacer linkage. This was attached to the purine ring of 6-benzylaminopurine (BAP) at positions

  表达cDNA文库的酵母细胞提供了两种新方法，以促进进一步鉴定细胞分裂素结合蛋白和受体。这些是酵母三杂交（Y3H）系统和荧光激活细胞分选（FACS）。Y3H系统需要合成的杂合配体，该杂合的配体包含通过间隔子与细胞分裂素连接的“锚”部分（例如地塞米松）。在酵母核中，该配体通过结合连接两个融合蛋白，从而导致报告基因激活以及细胞分裂素结合蛋白的检测和表征。本文报道了具有间隔键的地塞米松-细胞分裂素配体的首次合成。将其连接至6，苄基氨基嘌呤（BAP）的嘌呤环的2、8或9位。要实现这一点，地塞米松通过高碘酸盐氧化进行修饰，产生用于通过酰胺形成与间隔基缀合的羧基。用于FACS的细胞分裂素的生物素衍生物包括通过生物素的活化酯与BAP的8-（10-氨基-癸基氨基）衍生物和BAP 9-核糖苷反应合成的那些。简要讨论了结合物的性质和一些可能适用的生物学情况。
• 6, 8- DISUBSTITUTED PURINE COMPOSITIONS AND THEIR PHARMACEUTICAL AND COSMETIC USE
  申请人：Univerzita Palackého v Olomouci

  公开号：EP2755977A1

  公开（公告）日：2014-07-23
• 6,8-DISUBSTITUTED PURINE COMPOSITIONS AND THEIR PHARMACEUTICAL AND COSMETIC USE
  申请人：Univerzita Palackého v Olomouci

  公开号：EP2755977B1

  公开（公告）日：2016-11-02
• [EN] 6, 8- DISUBSTITUTED PURINE COMPOSITIONS AND THEIR PHARMACEUTICAL AND COSMETIC USE<br/>[FR] COMPOSITIONS DE PURINES 6,8-DISUBSTITUÉES ET LEUR UTILISATION PHARMACEUTIQUE ET COSMÉTIQUE
  申请人：UNIV PALACKEHO

  公开号：WO2013037333A1

  公开（公告）日：2013-03-21

  6,8-Disubstituted purines which can be used in drug and cosmetic compositions and/or applications are provided. These 6,8-disubstituted purines have a wide range of biological activities, including for example anti-inflammatory, anti-senescent, as well as well as other activities which are especially useful in pharmaceutical and cosmetic applications. The 6,8-disubstituted purine compounds and compositions containing such 6,8- disubstituted purines provide growth-regulatory, differentiating, antisenescent and antiaging properties with improved selectivities and efficiencies and lower toxicities than analogues known heretofore.
• α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective <i>ecto</i>-5′-Nucleotidase (CD73) Inhibitors
  作者：Sanjay Bhattarai、Marianne Freundlieb、Jan Pippel、Anne Meyer、Aliaa Abdelrahman、Amelie Fiene、Sang-Yong Lee、Herbert Zimmermann、Gennady G. Yegutkin、Norbert Sträter、Ali El-Tayeb、Christa E. Müller

  DOI：10.1021/acs.jmedchem.5b00802

  日期：2015.8.13

  ecto-5'-Nucleotidase (eN, CD73) catalyzes the hydrolysis of extracellular AMP to adenosine. eN inhibitors have potential for use as cancer therapeutics. The eN inhibitor alpha,beta-methylene-ADP (AOPCP, adenosine-5'-O-[(phosphonomethyl)phosphonic acid]) was used as a lead structure, and derivatives modified in various positions were prepared. Products were tested at rat recombinant eN. 6-(Ar)alkylamino substitution led to the largest improvement in potency. N-6-Monosubstitution was superior to symmetrical N-6,N-6-disubstitution. The most potent inhibitors were N-6-(4chlorobenzyl)-(10l, PSB-12441, K-i 7.23 n.M), N-6-phenylethyl(10h, PSB-12425, K-i 8.04 nM), and N-6-benzyl-adenosine-5'-O[(phosphonomethyl)phosphonic acid] (10g, PSB-12379, K-i 9.03 nM). Replacement of the 6-NH group in 10g by 0 (10q, PSB-12431) or S (10r, PSB-12553) yielded equally potent inhibitors (10q, 9.20 nM; 10r, 9.50 aM). Selected compounds investigated at the human enzyme did not show species differences; they displayed high selectivity versus other ecto-nudeotidases and ADP-activated P2Y receptors. Moreover, high metabolic stability was observed. These compounds represent the most potent eN inhibitors described to date.