(5-吡啶-3-基吡啶-3-基)甲醇 | 484673-70-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: (5-吡啶-3-基吡啶-3-基)甲醇
• 英文名称: [3,3']-bipyridinyl-5-ylmethanol
• 英文别名: (5-pyridin-3-ylpyridin-3-yl)methanol；[3,3'-Bipyridin]-5-ylmethanol
• CAS: 484673-70-3
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: QRZOSIMWVFKMKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  (5-吡啶-3-基吡啶-3-基)甲醇 在 甲醇 、 草酰氯 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 肼 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 79.0h， 生成 (3aS,4R,7R,9R,10R,11S,13R,15R,15aR)-1-{2-[(3,3'-bipyridin-5-ylmethyl)(methyl)amino]ethyl}-4-ethyl-11-methoxy-7,9,11,13,15-pentamethyl-2,6,8,14-tetraoxo-3a-vinyltetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl-3,4,6-trideoxy-3-(dimethylamino)-D-xylo-hexopyranoside
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Novel C₁₂ Vinyl Ketolides

  摘要：

  A novel series Of C-12 vinyl erythromycin derivatives have been discovered which exhibit in vitro and in vivo potency against key respiratory pathogens. The C-12 modification involves replacing the natural C-12 methyl group in the erythromycin core with a vinyl group via chemical synthesis. From the C-12 vinyl macrolide core, a series Of C-12 vinyl ketolides was prepared. Several compounds were found to be potent against macrolide-sensitive and -resistant bacteria. The C-12 vinyl ketolides 6j and 6k showed a similar antimicrobial spectrum and comparable activity to the commercial ketolide telithromycin. However, the pharmacokinetic profiles Of C-12 vinyl ketolides 6j and 6k in rats differ from that of telithromycin by having higher lung-to-plasma ratios, larger volumes of distribution, and longer half-lives. These pharmacokinetic differences have a pharmacodynamic effect as both 6j and 6k exhibited better in vivo efficacy than telithromycin in rat lung infection models against Streptococcus pneumoniae and Haemophilus influenzae.

  DOI：

  10.1021/jm051157a
• 作为产物：
  描述：

  二乙基(3-吡啶基)-硼烷 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 61.0h， 生成 (5-吡啶-3-基吡啶-3-基)甲醇
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Novel C₁₂ Vinyl Ketolides

  摘要：

  A novel series Of C-12 vinyl erythromycin derivatives have been discovered which exhibit in vitro and in vivo potency against key respiratory pathogens. The C-12 modification involves replacing the natural C-12 methyl group in the erythromycin core with a vinyl group via chemical synthesis. From the C-12 vinyl macrolide core, a series Of C-12 vinyl ketolides was prepared. Several compounds were found to be potent against macrolide-sensitive and -resistant bacteria. The C-12 vinyl ketolides 6j and 6k showed a similar antimicrobial spectrum and comparable activity to the commercial ketolide telithromycin. However, the pharmacokinetic profiles Of C-12 vinyl ketolides 6j and 6k in rats differ from that of telithromycin by having higher lung-to-plasma ratios, larger volumes of distribution, and longer half-lives. These pharmacokinetic differences have a pharmacodynamic effect as both 6j and 6k exhibited better in vivo efficacy than telithromycin in rat lung infection models against Streptococcus pneumoniae and Haemophilus influenzae.

  DOI：

  10.1021/jm051157a

文献信息

• C12 Modified erythromycin macrolides and ketolides having antibacterial activity
  申请人：——

  公开号：US20030125266A1

  公开（公告）日：2003-07-03

  Antimicrobial macrolide compounds are provided having formulas II: 1 as well as pharmaceutically acceptable salts, esters or prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.

  提供具有II:1式的抗微生物大环内酯化合物，以及其药用盐、酯或前药；包含这类化合物的药物组合物；通过给予这类化合物治疗细菌感染的方法；以及这类化合物的制备方法。
• 一种二酰亚胺基大环化合物的合成方法
  申请人：北京理工大学

  公开号：CN109438457B

  公开（公告）日：2020-08-04

  本申请属于超分子化学技术领域，具体为一种二酰亚胺基大环化合物的合成方法，其结构通式如下：其中R1为吡啶基或苯基；R2为直链或具有支链的烷烃；R3为1,4,5,8‑萘四甲酸二酐或1,6,7,12‑四氯‑3,4,9,10‑四甲酸二酐；R4为3,3‑联吡啶,3,5‑双(吡啶‑3‑基)吡啶,(5‑吡啶‑3‑基吡啶‑3‑基)甲醇,1,4‑二(溴甲基)苯,2,6‑双(溴甲基)萘或1,4‑二(溴甲基)苯中一种。
• Atropisomer-based construction of macrocyclic hosts that selectively recognize tryptophan from standard amino acids
  作者：Fei Yang、Caiping Liu、Di Yin、Yanqing Xu、Mingyan Wu、Wei Wei

  DOI：10.1039/c9cc07646h

  日期：——

  to construct a type of trapezoid-shape macrocycle, namely ‘trapezoid’ molecular boxes (TBox). As supramolecular hosts, TBox can bind electron-rich guests and selectively recognize free tryptophan and tryptophanyl residues from 20 standard amino acids.

  甲顺式萘二酰亚胺作为高预组织前体-atropisomer用于构建一个类型梯形形状大环的，即“梯形”分子盒（TBOX）。作为超分子宿主，TBox可以结合富电子的来宾并选择性地识别来自20个标准氨基酸的游离色氨酸和色氨酸残基。
• Pyridyl substituted ketolide antibiotics
  申请人：Burger T. Matthew

  公开号：US20050009764A1

  公开（公告）日：2005-01-13

  Antimicrobial macrolide and ketolide compounds are provided having formulas XII: as well as pharmaceutically acceptable salts, esters or prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.

  提供具有XII式的抗微生物大环内酯和酮内酯化合物，以及其药学上可接受的盐、酯或前药；包含这些化合物的药物组合物；通过给予这些化合物的途径治疗细菌感染的方法；以及制备这些化合物的过程。
• C12 modified erythromycin macrolides and ketolides having antibacterial activity
  申请人：Chiron Corporation

  公开号：US06756359B2

  公开（公告）日：2004-06-29

  Antimicrobial macrolide compounds are provided having formulas II: as well as pharmaceutically acceptable salts, esters or prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.

  本发明提供具有II式的抗微生物大环内酯化合物，以及其药学上可接受的盐、酯或前药；包含这些化合物的药物组合物；通过给予这些化合物的途径治疗细菌感染的方法；以及制备这些化合物的过程。