5-amino-1-(β-D-ribofuranosyl)-4-imidazolecarboxylic acid | 6001-15-6

• 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-(β-D-ribofuranosyl)-4-imidazolecarboxylic acid
• 英文别名: N¹-(β-D-ribofuranosyl)-5-carboxy-5-aminoimidazole；4-carboxy-5-amino-1H-imidazol-1-yl riboside；CAIRs；5-Amino-1-(1β-D-ribofuranosyl)-imidazol-carbonsaeure-(4)；5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxylic acid；5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxylic acid
• CAS: 6001-15-6
• 化学式: C₉H₁₃N₃O₆
• 分子量: 259.219
• InChiKey: GCEYZZWMVRITSE-ZIYNGMLESA-N

物化性质

• 沸点：
  748.4±60.0 °C(Predicted)
• 密度：
  2.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3,5-三嗪 、 5-amino-1-(β-D-ribofuranosyl)-4-imidazolecarboxylic acid 以 二甲基亚砜 为溶剂， 以40%的产率得到9 - (Β-D -呋喃核糖)嘌呤
  参考文献：
  名称：

  Efficient Synthesis of Purines and Purine Nucleosides via an Inverse Electron Demand Diels−Alder Reaction

  摘要：

  DOI：

  10.1021/ja9842316
• 作为产物：
  描述：

  阿卡地新 在 sodium hydroxide 作用下， 反应 24.0h， 生成 5-amino-1-(β-D-ribofuranosyl)-4-imidazolecarboxylic acid
  参考文献：
  名称：

  Synthesis and Mass Spectrometric Fragmentation Characteristics of Imidazole Ribosides–Analogs of Intermediates of Purine De Novo Synthetic Pathway

  摘要：

  Two inherited deficiencies have been described in purine de novo synthesis pathway. Both the defects are diagnosed by detecting ribosides - dephosphorylated substrates of the enzymes - in patient's urine. We describe here a synthesis and mass spectrometric fragmentation of ribosides potentially of diagnostic importance for defects in the second part of the pathway. All the species, except 5-amino-4-imidazolesuccinocarboxamideriboside can be synthesized from the commercially available 5-amino-4-imidazolecarboxamideriboside by chemical methods. Fragmentation spectra of the compounds were obtained by the ion trap mass spectrometry. During fragmentation an opening of the imidazole ring was not observed for any of the compounds but loss of its substituents in the form of small molecules ( NH3, CO2, CO) is the major route of fragmentation. The ribose moiety cleaves off molecule( s) of water, undergoes a cross-ring cleavage or breaks away as a whole.

  DOI：

  10.1080/15257770600894691

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。
• Methods, compositions, and formulations for preventing or reducing adverse effects in a patient
  申请人：Pericor Therapeutics, Inc.

  公开号：EP2594273A1

  公开（公告）日：2013-05-22

  The present invention provides methods, compositions, formulations, and kits related to acadesine, or a prodrug, analog, or salt 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.

  本发明提供了与阿卡替辛或其原药、类似物或盐和/或凝血抑制剂有关的方法、组合物、制剂和试剂盒，用于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、既往患有心肌梗塞的患者、接受非血管手术的患者或分娩期间的胎儿。
• Alenin, V. V.; Domkin, V. D., Journal of general chemistry of the USSR, 1984, vol. 54, # 10, p. 2114 - 2120
  作者：Alenin, V. V.、Domkin, V. D.

  DOI：——

  日期：——
• The Thiamine Biosynthetic Enzyme ThiC Catalyzes Multiple Turnovers and Is Inhibited by S-Adenosylmethionine (AdoMet) Metabolites
  作者：Lauren D. Palmer、Diana M. Downs

  DOI：10.1074/jbc.m113.500280

  日期：2013.10

  ThiC (4-amino-5-hydroxymethyl-2-methylpyrimidine phosphate synthase; EC 4.1.99.17) is a radical S-adenosylmethionine (AdoMet) enzyme that uses a [4Fe-4S](+) cluster to reductively cleave AdoMet to methionine and a 5-deoxyadenosyl radical that initiates catalysis. In plants and bacteria, ThiC converts the purine intermediate 5-aminoimidazole ribotide to 4-amino-5-hydroxymethyl-2-methylpyrimidine phosphate, an intermediate of thiamine pyrophosphate (coenzyme B1) biosynthesis. In this study, assay conditions were implemented that consistently generated 5-fold molar excess of HMP, demonstrating that ThiC undergoes multiple turnovers. ThiC activity was improved by in situ removal of product 5-deoxyadenosine. The activity was inhibited by AdoMet metabolites S-adenosylhomocysteine, adenosine, 5-deoxyadenosine, S-methyl-5-thioadenosine, methionine, and homocysteine. Neither adenosine nor S-methyl-5-thioadenosine had been shown to inhibit radical AdoMet enzymes, suggesting that ThiC is distinct from other family members. The parameters for improved ThiC activity and turnover described here will facilitate kinetic and mechanistic analyses of ThiC.
• AICA RIBOSIDE ANALOGS
  申请人：Metabasis Therapeutics Inc.

  公开号：EP0495091B1

  公开（公告）日：1999-11-24