5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxylic acid | 53459-69-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxylic acid
• 英文别名: 5-amino-1-(2,3,5-tris-O-acetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid；5-amino-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)imidazole-4-carboxylic acid；5-amino-1-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]imidazole-4-carboxylic acid
• CAS: 53459-69-1
• 化学式: C₁₅H₁₉N₃O₉
• 分子量: 385.331
• InChiKey: QLRMAZFNEAAGMK-XIDUGBJDSA-N

物化性质

• 沸点：
  625.3±55.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  169
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxylic acid 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 苯甲醚 、 1,2-二氯乙烷 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-氨基-3-beta-D-呋喃核糖基咪唑并(4,5-d)(1,3)恶嗪-7(3H)-酮
  参考文献：
  名称：

  A novel synthesis of oxanosine and 1-thiaguanosine

  摘要：

  A novel total synthesis of oxanosine has been developed. The key heterocycle forming reaction of this synthesis is the carbodiimide mediated dehydration and cyclization of an urea-acid derived from AICA-riboside. The same procedure was also applied to the synthesis of 1-thiaguanosine.

  DOI：

  10.1016/s0040-4039(00)79951-5
• 作为产物：
  描述：

  阿卡地新 在 sodium hydroxide 作用下， 以 吡啶 、 水 为溶剂， 反应 8.0h， 生成 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxylic acid
  参考文献：
  名称：

  Bleasdale, Christine; Ellwood, Simon B.; Golding, Bernard T., Journal of the Chemical Society. Perkin transactions I, 1994, # 19, p. 2859 - 2866

  摘要：

  DOI：

文献信息

• METHODS, COMPOSITIONS, AND FORMULATIONS FOR PREVENTING OR REDUCING ADVERSE EFFECTS IN A PATIENT
  申请人：Stover Richard R.

  公开号：US20080175891A1

  公开（公告）日：2008-07-24

  The present invention provides transdermal administration of AICA riboside, or a prodrugs, analogs, or salts thereof, and/or a blood clotting inhibitor for preventing or reducing adverse side effects in a patient. The type of patient that may benefit includes a patient with decreased left ventricular function, a patient with a prior myocardial infarction, a patient undergoing non-vascular surgery, or a fetus during labor and delivery.

  本发明提供了通过经皮途径给予AICA核糖苷，或其前药、类似物或盐，和/或血液凝块抑制剂以预防或减少患者的不良副作用。可能受益的患者类型包括左心室功能减退的患者、先前发生心肌梗死的患者、接受非血管手术的患者，或分娩期间的胎儿。
• Synthesis of Fluorinated Purine and 1-Deazapurine Glycosides as Potential Inhibitors of Adenosine Deaminase
  作者：Viktor O. Iaroshenko、Dmytro Ostrovskyi、Andranik Petrosyan、Satenik Mkrtchyan、Alexander Villinger、Peter Langer

  DOI：10.1021/jo102579g

  日期：2011.4.15

  The synthesis of 2- and 6-trifluoromethylated purines and 1-deazapurines was performed by formal [3 + 3]-cyclization reactions of 5-aminoimidazoles with a set of trifluoromethyl-substituted 1,3-CCC- and 1,3-CNC-dielectrophiles. The corresponding fluorinated nucleosides were synthesized by glycosylation of 9-unsubstituted purines and 1-deazapurines with peracetylated β-ribose, β-glucose, and rhamnose

  2-和6-三氟甲基化嘌呤和1-deazapurines的合成是通过5-氨基咪唑与一组三氟甲基取代的1,3-CCC-和1,3-CNC-进行正式的[3 + 3]环化反应进行的介电体。相应的氟化核苷是通过9个未取代的嘌呤和1-deazapurines与过乙酰化的β-核糖，β-葡萄糖和鼠李糖进行糖基化合成的，然后进行脱保护。这些支架可以被认为是腺苷脱氨酶（ADA）和肌苷单磷酸脱氢酶（IMPDH）酶的潜在抑制剂。
• AICA riboside analogs
  申请人：Gensia Inc.

  公开号：US05777100A1

  公开（公告）日：1998-07-07

  Analogs of 5-amino-1-beta-D-ribofuranosylimidazole-4-carboxamide (AICA riboside) are provided which are useful in increasing extracellular levels of adenosine.

  提供了增加腺苷外细胞水平的5-氨基-1-beta-D-核糖呋喃基咪唑-4-甲酰胺（AICA核苷）的类似物。
• 1-thiaguanosine and process for preparing oxanosine and 1-thiaguanosine
  申请人：Hoffmann-La Roche Inc.

  公开号：US05243042A1

  公开（公告）日：1993-09-07

  The invention relates to antibacterially active 5-amino-3-(.beta.-D-ribofuranosyl)imidazo[4,5-d][1,3]thiazin-7(3H)-one, also referred to as 1-thiaguanosine, a composition and method comprising the same and processes and intermediates for the preparation of 1-thiaguanosine and 5-amino-3-(.beta.-D-ribofuranosyl)imidazo[4,5-d][1,3]oxazin-7(3H)-one, also referred to as oxanosine, a known compound.

  本发明涉及一种具有抗菌活性的5-氨基-3-（β-D-核糖呋喃基）咪唑[4,5-d][1,3]噻嗪-7（3H）-酮，也称为1-硫鸟苷，以及包含该化合物的组合物和方法，以及制备1-硫鸟苷和5-氨基-3-（β-D-核糖呋喃基）咪唑[4,5-d][1,3]噁唑-7（3H）-酮的过程和中间体，后者是已知化合物。
• Processes for preparing 2'-deoxy-2'-fluorocoformycin and stereoisomers
  申请人：Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

  公开号：US05773607A1

  公开（公告）日：1998-06-30

  2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin are synthesized in this invention through a multi-stage process via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.- and -.beta.-D-ribofuranosyl bromides. Further, according to this invention, 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin are synthesized by a multi-stage process starting from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.-D-arabinofuranosyl bromide. These four 2'-fluoro derivatives of coformycin are novel compounds and have high enzyme-inhibitory activities against adenosine deaminase. In particular, these novel compounds are useful substances which exhibit therapeutic effects on acute lymphocytic leukemias due to their high enzyme-inhibitory activities above-mentioned. In addition, a variety of intermediates are obtained as novel compounds which are useful for the synthesis of the aforesaid novel 2'-fluoro derivatives of coformycin.

  本发明通过经过多阶段的过程，通过3,5-二-O-苯甲酰基-2-脱氧-2-氟-.alpha.-和-.beta.-D-核糖溴化物合成了2'-脱氧-2'-氟可酶霉素和2'-脱氧-8-表-2'-氟可酶霉素。此外，根据本发明，从3,5-二-O-苯甲酰基-2-脱氧-2-氟-.alpha.-D-阿拉伯核糖溴化物开始，通过多阶段过程合成了2'-脱氧-2'-表-2'-氟可酶霉素和2'-脱氧-8,2'-双表-2'-氟可酶霉素。这四种2'-氟可酶霉素衍生物是新化合物，并且对腺苷脱氨酶具有高的酶抑制活性。特别是，这些新化合物是有用的物质，因为它们具有上述高酶抑制活性，对急性淋巴细胞白血病具有治疗作用。此外，还获得了多种中间体作为新化合物，这些中间体对于合成上述新的2'-氟可酶霉素衍生物是有用的。