N⁶-benzoyl-1,3-dideazaadenine | 855526-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N⁶-benzoyl-1,3-dideazaadenine
• 英文别名: 4-(benzoylamino)benzimidazole；N⁶-benzoyladenine；N-(1H-benzimidazol-4-yl)benzamide
• CAS: 855526-29-3
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: FCRAWCCBBMXULK-UHFFFAOYSA-N

物化性质

• 沸点：
  422.5±18.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N⁶-benzoyl-1,3-dideazaadenine 在 三甲基氯硅烷 、 氨 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 1,3-二去氮杂腺苷
  参考文献：
  名称：

  Synthesis and Antiviral Properties of Arabino and Ribonucleosides of 1,3‐Dideazaadenine, 4‐Nitro‐1, 3‐dideazaadenine and Diketopiperazine

  摘要：

  Different arabinosides and ribosides, viz. Ara-DDA or 9(1-beta-(D)-arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-beta-D-arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or I(1-beta-D-arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-beta-D-ribofuranosyl) 1,3-dideazaadenine (9) and Ribo-NDDP or 9(1-beta-D-ribofuranosyl) 4-nitro-1,3-dideazapurine (10) have been synthesized as probable antiviral agents. The arabinosides have been synthesized using the catalyst TDA-1 that causes stereospecific formation of beta-nucleosides while a one-pot synthesis procedure was adopted for the synthesis of the ribonucleosides where beta-anomers were obtained in higher yields. All the five nucleoside analogs have been screened for antiviral property against HIV-1 ((IIIB)), HSV-1 and 2, parainfluenza-3, reovirus-1 and many others. It was observed that arabinosides had greater inhibitory action than ribosides. The compound 7 or Ara-NDDP has shown maximum inhibition of HIV-1 replication than the rest of the molecules with an IC50 of 79.4 mug/mL.

  DOI：

  10.1081/ncn-200040614
• 作为产物：
  描述：

  4-氨基苯并咪唑 、 苯甲酰氯 生成 N⁶-benzoyl-1,3-dideazaadenine
  参考文献：
  名称：

  Synthesis and Antiviral Properties of Arabino and Ribonucleosides of 1,3‐Dideazaadenine, 4‐Nitro‐1, 3‐dideazaadenine and Diketopiperazine

  摘要：

  Different arabinosides and ribosides, viz. Ara-DDA or 9(1-beta-(D)-arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-beta-D-arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or I(1-beta-D-arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-beta-D-ribofuranosyl) 1,3-dideazaadenine (9) and Ribo-NDDP or 9(1-beta-D-ribofuranosyl) 4-nitro-1,3-dideazapurine (10) have been synthesized as probable antiviral agents. The arabinosides have been synthesized using the catalyst TDA-1 that causes stereospecific formation of beta-nucleosides while a one-pot synthesis procedure was adopted for the synthesis of the ribonucleosides where beta-anomers were obtained in higher yields. All the five nucleoside analogs have been screened for antiviral property against HIV-1 ((IIIB)), HSV-1 and 2, parainfluenza-3, reovirus-1 and many others. It was observed that arabinosides had greater inhibitory action than ribosides. The compound 7 or Ara-NDDP has shown maximum inhibition of HIV-1 replication than the rest of the molecules with an IC50 of 79.4 mug/mL.

  DOI：

  10.1081/ncn-200040614

文献信息

• Discovery and structure–activity relationship studies of N6-benzoyladenine derivatives as novel BRD4 inhibitors
  作者：Tomomi Noguchi-Yachide、Taki Sakai、Yuichi Hashimoto、Takao Yamaguchi

  DOI：10.1016/j.bmc.2015.01.022

  日期：2015.3

  Bromodomain and extra-terminal domain (BET) proteins are epigenetic readers that bind to acetylated lysines in histones. Among them, BRD4 is a candidate target molecule of therapeutic agents for diverse diseases, including cancer and inflammatory disease. As a part of our continuing structural development studies of thalidomide to obtain a broad spectrum of biological modifiers based on the ‘multi-template’

  溴结构域和末端外结构域（BET）蛋白是表观遗传阅读器，可与组蛋白中的乙酰化赖氨酸结合。其中，BRD4是用于多种疾病（包括癌症和炎性疾病）的治疗剂的候选靶分子。作为我们对沙利度胺进行结构开发的持续研究的一部分，该研究基于“多模板”方法获得了广泛的生物改性剂，在这项工作中，我们着重于BRD4抑制活性，并发现N 6-苯甲酰腺嘌呤衍生物显示出这种活性。活动。结构与活性之间的关系研究导致了N 6-（2,4,5-三甲氧基苯甲酰基）腺嘌呤（29），其表现出强大的BRD4 bromodomain1抑制活性，IC 50值为0.427μM 。ñ6-苄基腺嘌呤似乎是开发BRD4抑制剂的新化学支架。
• Synthesis of Well-Defined Adenosine Diphosphate Ribose Oligomers
  作者：Hans A. V. Kistemaker、Lucien N. Lameijer、Nico J. Meeuwenoord、Herman S. Overkleeft、Gijsbert A. van der Marel、Dmitri V. Filippov

  DOI：10.1002/anie.201412283

  日期：2015.4.13

  elucidation of the biology of ADPr, the availability of well‐defined fragments of poly(ADP‐ribose) is essential. Herein we report a solid‐phase synthetic approach for the preparation of ADP‐ribose oligomers of exactly defined length. The methodology is exemplified by the first reported synthesis of an ADP‐ribose dimer and trimer.

  翻译后的蛋白质修饰称为二磷酸腺苷核糖基化（ADPr），可调节多种重要的生物学过程，例如DNA损伤修复和细胞代谢。该修饰也参与致癌作用和衰老过程。因此，更好地了解ADP核糖基化的功能对于开发新型疗法至关重要。为了便于阐明ADPr的生物学特性，必须使用定义明确的聚（ADP-核糖）片段。本文中，我们报告了一种固相合成方法，用于制备长度精确确定的ADP-核糖低聚物。该方法以首次报道的ADP核糖二聚体和三聚体的合成为例。
• Synthesis and Antiviral Properties of Arabino and Ribonucleosides of 1,3‐Dideazaadenine, 4‐Nitro‐1, 3‐dideazaadenine and Diketopiperazine
  作者：Sarika Sinha、Richa Srivastava、Erik De Clercq、Ramendra K. Singh

  DOI：10.1081/ncn-200040614

  日期：2004.1.12

  Different arabinosides and ribosides, viz. Ara-DDA or 9(1-beta-(D)-arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-beta-D-arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or I(1-beta-D-arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-beta-D-ribofuranosyl) 1,3-dideazaadenine (9) and Ribo-NDDP or 9(1-beta-D-ribofuranosyl) 4-nitro-1,3-dideazapurine (10) have been synthesized as probable antiviral agents. The arabinosides have been synthesized using the catalyst TDA-1 that causes stereospecific formation of beta-nucleosides while a one-pot synthesis procedure was adopted for the synthesis of the ribonucleosides where beta-anomers were obtained in higher yields. All the five nucleoside analogs have been screened for antiviral property against HIV-1 ((IIIB)), HSV-1 and 2, parainfluenza-3, reovirus-1 and many others. It was observed that arabinosides had greater inhibitory action than ribosides. The compound 7 or Ara-NDDP has shown maximum inhibition of HIV-1 replication than the rest of the molecules with an IC50 of 79.4 mug/mL.