5-[(2S,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]吡啶-3-甲酰胺 | 107325-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-[(2S,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]吡啶-3-甲酰胺
• 英文名称: 5-(β-D-ribofuranosyl)nicotinamide
• 英文别名: 5-β-D-ribofuranosylnicotinamide；5-Ribofuranosylnicotinamide；5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridine-3-carboxamide
• CAS: 107325-67-7
• 化学式: C₁₁H₁₄N₂O₅
• 分子量: 254.243
• InChiKey: UBWZUUUKBOMAPO-KYXWUPHJSA-N

物化性质

• 沸点：
  579.5±50.0 °C(Predicted)
• 密度：
  1.509±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[(2S,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]吡啶-3-甲酰胺 在 三氯氧磷 作用下， 以 various solvent(s) 为溶剂， 反应 4.0h， 以76 mg的产率得到Phosphoric acid mono-[(2R,3S,4R,5S)-5-(5-carbamoyl-pyridin-3-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester
  参考文献：
  名称：

  NAD analogs. 1. Synthesis of isosteric analogs of nicotinamide adenine dinucleotide containing C-nucleotide of nicotinamide or picolinamide

  摘要：

  Two isosteric analogues of nicotinamide adenine dinucleotide, C-NAD (11) and C-PAD (12), in which the nicotinamide riboside portion is replaced by a C-nucleoside, were synthesized from 5-(beta-D-ribofuranosyl)nicotinamide (7) and 6-(beta-D-ribofuranosyl)picolinamide (8), respectively. Nucleoside 7 was prepared from the 2,3-O-isopropylidene-5-O-(tetrahydropyranyl)-D-ribonolactone (13) and 3-cyano-5-lithiopyridine as reported earlier. Nucleoside 8 was obtained by conversion of the bromo function of the 6-(2,3:4,5-di-O-isopropylidene-D-altro-pentitol-1-yl)-2-bromopyridine (14) into a carboxamido group followed by mesylation of the anomeric hydroxyl group to give derivative 18. Treatment of 18 with CF3COOH/CHCl3 caused deisopropylidenation with simultaneous cyclization into the desired 6-(beta-D-ribofuranosyl)picolinamide (8). NAD analogues, C-NAD (11) and C-PAD (12), were synthesized by imidazole-catalyzed coupling of the corresponding 5'-monophosphates of 7 and 8 with the adenosine-5'-monophosphate. Dinucleotide 11 was found to inhibit the proliferation of L1210 cells (IC50 = 7 muM) and to be a good competitive inhibitor of inosine monophosphate dehydrogenase (IMPDH, ID50 = 20 muM) as well as bovine glutamate dehydrogenase (GDH, K(i) = 15 muM). Interestingly, C-NAD (11) caused extremely potent noncompetitive inhibition of horse liver alcohol dehydrogenase (ADH, K(i) = 1.1 nM), whereas C-PAD (12) was found to be a much less potent competitive inhibitor (K(i) = 20 muM) of ADH.

  DOI：

  10.1021/jm00065a008
• 作为产物：
  描述：

  3,5-二溴吡啶 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 正丁基锂 、 氯甲烷 、 氨 、 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 21.25h， 生成 5-[(2S,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]吡啶-3-甲酰胺
  参考文献：
  名称：

  Nucleosides. 141. Synthesis of 5-.beta.-D-ribofuranosylnicotinamide and its N-methyl derivative. The isosteric and isoelectronic analogs of nicotinamide nucleoside

  摘要：

  The pyridine C-nucleosides 5-beta-D-ribofuranosylnicotinamide and its N-methylpyridinium derivative (1 and 2), which are isosteric and isoelectronic, respectively, to nicotinamide nucleoside were synthesized. Condensation of 3-bromo-5-lithiopyridine with 2,4:3,5-di-O-benzylidene-D-aldehydoribose (7) afforded an allo/altro mixture of the corresponding bromopyridine derivatives, which were converted into nicotinamide C-nucleoside precursors 10. Mesylation of the hydroxyl group of 10 followed by acid hydrolysis of the product afforded the anomeric nicotinamide C-nucleosides. The beta anomer 1 was separated and treated with MeI to give 2.

  DOI：

  10.1021/jm00388a030

文献信息

• Angiogenesis inhibitors
  申请人：THE JOHNS-HOPKINS UNIVERSITY

  公开号：EP2803357A2

  公开（公告）日：2014-11-19

  Described herein are methods of inhibiting angiogenesis, and treating or preventing a disease or disorder (or symptoms thereof) associated with angiogenesis, wherein an anti-angiogenesis compound is administered to a subject.

  本文描述了抑制血管生成和治疗或预防与血管生成有关的疾病或紊乱（或其症状）的方法，其中向受试者施用抗血管生成化合物。
• Inhibiting GS-FDH to modulate NO bioactivity
  申请人：DUKE UNIVERSITY Office of Science and Technology

  公开号：US20020128205A1

  公开（公告）日：2002-09-12

  Patients needing NO donor therapy or inhibition of pathologically proliferating cells or increased NO bioactivity are treated with a therapeutically effective amount of an inhibitor of glutathione-dependent formaldehyde dehydrogenase.

  需要 NO 供体治疗或抑制病理增殖细胞或增加 NO 生物活性的患者，可使用治疗有效量的谷胱甘肽依赖性甲醛脱氢酶抑制剂。
• Antiviral agents for treatment of Flaviviridae infections
  申请人：——

  公开号：US20040266723A1

  公开（公告）日：2004-12-30

  The disclosed invention is a composition for and a method of treating Flaviviridae ( Hepacivirus, Flavivirus, Pestivirus ) infections, including BVDV and HCV, in a host, including animals, and especially humans, using a small molecule or its pharmaceutically acceptable salt or prodrug.

  本发明是一种用于治疗以下疾病的组合物和方法 病毒科 ( 病毒(Hepacivirus, Flavivirus, Pestivirus) )感染的组合物和方法，包括使用小分子或其药学上可接受的盐或原药治疗宿主（包括动物，特别是人类）的BVDV和HCV感染。
• Nucleosides. 151. Efficient synthesis of 5-(.beta.-D-ribofuranosyl)nicotinamide and its .alpha.-isomer
  作者：Krzysztof W. Pankiewicz、Elzbieta Sochacka、Marek M. Kabat、Lech A. Ciszewski、Kyoichi A. Watanabe

  DOI：10.1021/jo00250a013

  日期：1988.7
• PANKIEWICZ, KRZYSZTOF W.;KABAT, MAREK M.;SOCHACKA, ELZBIETA;CISZEWSKI, LE+, NUCLEOSIDES AND NUCLEOTIDES, 7,(1988) N-6, C. 589-593
  作者：PANKIEWICZ, KRZYSZTOF W.、KABAT, MAREK M.、SOCHACKA, ELZBIETA、CISZEWSKI, LE+

  DOI：——

  日期：——