1β-(6-(carbamoyl)pyridin-3-yl)-1-deoxy-D-ribofuranose | 125211-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1β-(6-(carbamoyl)pyridin-3-yl)-1-deoxy-D-ribofuranose
• 英文别名: 5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridine-2-carboxamide
• CAS: 125211-33-8
• 化学式: C₁₁H₁₄N₂O₅
• 分子量: 254.243
• InChiKey: KEHGEOXHJNPODU-KYXWUPHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 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

• 作为产物：
  描述：

  2,3,5-tri-O-tert-butyldimethylsilyl-D-ribono-1,4-lactone 在 三乙基硅烷 、 potassium phosphate 、 正丁基锂 、 氨 、 palladium diacetate 、 triethylamine tris(hydrogen fluoride) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， -78.0~80.0 ℃ 、101.33 kPa 条件下， 反应 48.93h， 生成 1β-(6-(carbamoyl)pyridin-3-yl)-1-deoxy-D-ribofuranose
  参考文献：
  名称：

  General and Modular Synthesis of Isomeric 5-Substituted Pyridin-2-yl and 6-Substituted Pyridin-3-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Hetaryl, Amino, Carbamoyl, and Hydroxy Groups

  摘要：

  A general modular and practical methodology for preparation of diverse 5-substituted pyriclin-2-yl and 6-substituted pyridin-3-yl C-ribonucleosides was developed. Regioselective lithiation of 2,5-dibromopyridine proceeded at position 5 or 2 depending on the solvent, and the resulting bromopyridyl lithium species underwent additions to TBS-protected ribonolactone and follow-up transformations to corresponding acetylated hemiketal intermediates 7 and 10 that were diastereoselectively reduced to give either 5-bromopyridin-2-yl or 6-bromopyridin3-yl silyl-protected C-ribonucleosides 8 or 11 in 68% and 77% overall yields as pure beta-anomers. These bromopyridyl C-nucleoside intermediates were then subjected to a series of palladium-catalyzed cross-coupling reactions, aminations, aminocarbonylations, and hydroxylations to give a series of protected 1 beta-(5-alkyl-, 5-aryl-, 5-amino-, 5-carbamoyl-, and 5-hydroxypyridin-2-yl)-C-ribonucleosides 13a-i and beta-(6-alkyl-, 6-aryl-, 6-amino-, 6-carbamoyl-, and 6-hydroxypyridin-3-yl)-C-ribonucleosides 15a-i. Deprotection of silylated nucleosides by Et3N center dot 3HF, TBAF, or TFA gave a series of free C-nucleosides 14a-i and 16a-i.

  DOI：

  10.1021/jo200949c

文献信息

• Aldehyde functional monoterpenoids for the treatment of coronavirus infection
  申请人：Coe William B.

  公开号：US10993958B1

  公开（公告）日：2021-05-04

  Compositions comprising aldehyde functional monoterpenoids in combination with 3,3′,4′,7-tetrahydroxyflavone, zinc, and a 5-beta-D-Ribofuranosylpicolineamide adenine-dinucleotide molecule are provided for treating viral infections, e.g., coronavirus infections such as COVID-19.

  提供了包含醛功能单萜与 3,3′,4′,7-四羟基黄酮、锌和 5-beta-D-Ribofuranosylpicolineamide 腺嘌呤-二核苷酸分子的组合物，用于治疗病毒感染，例如冠状病毒感染，如 COVID-19。
• 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。
• ALDERWEIRELDT, F. C.;VRIJENS, I.;ESMANS, E. L.;WOTRING, L. L.;TOWNSEND, L+, NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N-6, C. 891-894
  作者：ALDERWEIRELDT, F. C.、VRIJENS, I.、ESMANS, E. L.、WOTRING, L. L.、TOWNSEND, L+

  DOI：——

  日期：——
• ANTIVIRAL AGENTS FOR TREATMENT OF FLAVIVIRIDAE INFECTIONS
  申请人：Pharmasset Limited

  公开号：EP1366055A2

  公开（公告）日：2003-12-03
• ALDEHYDE FUNCTIONAL MONOTERPENOIDS FOR THE TREATMENT OF CORONAVIRUS INFECTION
  申请人：Coe William B.

  公开号：US20210283162A1

  公开（公告）日：2021-09-16

  Compositions comprising aldehyde functional monoterpenoids in combination with 3,3′,4′,7-tetrahydroxyflavone, zinc, and a 5-beta-D-Ribofuranosylpicolineamide adenine-dinucleotide molecule are provided for treating viral infections, e.g., coronavirus infections such as COVID-19.