5-amino-1-β-D-ribofuranosyl-V-triazole-4-carboxaldehyde | 38874-49-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: 5-amino-1-β-D-ribofuranosyl-V-triazole-4-carboxaldehyde
• 英文别名: 5-Amino-4-carbamoyl-1β-D-ribofuranosyl-v-triazol；5-amino-1-β-D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide；5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]triazole-4-carboxamide
• CAS: 38874-49-6
• 化学式: C₈H₁₃N₅O₅
• 分子量: 259.222
• InChiKey: RYGDRPTZZVTRIE-UMMCILCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  170
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5-amino-1-β-D-ribofuranosyl-V-triazole-4-carboxaldehyde 在 吡啶 作用下， 反应 18.0h， 生成 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-v-triazole-4-carboxamide
  参考文献：
  名称：

  Total synthesis of (4R)- and (4S)-5,6-dihydro-1-.beta.-D-ribofuranosyl-4H-pyrazolo[3,4-d][1,3]diazepin-4-ol and (8R)- and (8S)-7,8-dihydro-3-.beta.-D-ribofuranosyl-6H-v-triazolo[4,5-d][1,3]diazepin-8-ol: two heterocyclic analogs of the nucleoside antibiotic coformycin

  摘要：

  DOI：

  10.1021/jo00357a020
• 作为产物：
  描述：

  5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-v-triazole-4-carboxamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 5-amino-1-β-D-ribofuranosyl-V-triazole-4-carboxaldehyde
  参考文献：
  名称：

  5-Ethynyl-1-β-d-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (ETCAR) and its analogues: Synthesis and cytotoxic properties

  摘要：

  Efficient Pd(0)-catalysed synthesis of 5-alkynyl-1-beta-D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide depends on the presence of different protecting groups of the ribose moiety. Peracetylated 5-iodo substrate (15) couples with terminal alkynes or trimethyl-[(tributylstannyl)ethynyl] silane in 50-71% and 72% yield (ETCAR), respectively, although its hydrodehalogenation to 19 is noticeable. On the other hand, hydrodehalogenation of acetonide (16) predominates over coupling with terminal alkyne and slightly decreases a yield of cross-coupling reaction with trimethyl[(tributylstannyl)ethynyl] silane. Alternative conditions of reaction with terminal alkynes, to exclude so far identified hydride sources to produce hydridopalladium species, have been established for acetonide 16 and allowed to achieve 72% of coupling. Fluoromethyl derivative (42) was prepared from its 5-hydroxymethyl precursor by fluorination with DAST. Additionally, X-ray structural analysis of 42 was performed. All 1,2,3-triazolonucleosides and two synthesized cycloSal-pronucleotides were evaluated for cytotoxic activity against K562, HeLa and HUVEC cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.050

文献信息

• Monocyclic L-nucleosides, analogs and uses thereof
  申请人：ICN Pharmaceuticals, Inc.

  公开号：EP1254911A1

  公开（公告）日：2002-11-06

  Novel monocyclic L- nucleoside compounds have general formula (I). Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th 1 and Th 2 response.

  新型单环L-核苷化合物的一般化学式为（I）。这些化合物的实施形式被认为在治疗包括感染、寄生虫感染、肿瘤和自身免疫性疾病在内的各种疾病中是有用的。从机制上看，这些新型化合物的实施形式显示出免疫调节活性，并有望在调节细胞因子模式方面发挥作用，包括调节Th1和Th2反应。
• Branched alkoxy-subsituted 2-aminopyridines
  申请人：——

  公开号：US20020022642A1

  公开（公告）日：2002-02-21

  The present invention relates to 6-phenyl-pyridin-2-ylamine derivatives of the formula 1 wherein R 1 , R 2 , R 3 and R 4 are defined as in the specification, that exhibit activity as nitric oxide synthase (NOS) inhibitors, to pharmaceutical compositions containing them and to their use in the treatment and prevention of central nervous system and other disorders.

  本发明涉及式1中R1、R2、R3和R4如规范中定义的6-苯基吡啶-2-胺衍生物，其具有作为一氧化氮合酶（NOS）抑制剂的活性，以及含有它们的药物组合物，并用于治疗和预防中枢神经系统和其他疾病。
• METHOD AND COMPOUNDS FOR AICA RIBOSIDE DELIVERY AND FOR LOWERING BLOOD GLUCOSE
  申请人：GENSIA, INC.

  公开号：EP0427799B1

  公开（公告）日：1994-11-30
• NEW INHIBITORS OF PLATELET AGGREGATION
  申请人：AstraZeneca AB

  公开号：EP0840740B1

  公开（公告）日：2002-05-02
• BRANCHED ALKOXY-SUBSITUTED 2-AMINOPYRIDINES AS NOS INHIBITORS
  申请人：Pfizer Products Inc.

  公开号：EP1007512B1

  公开（公告）日：2002-04-03