2-carboxy-3,4-di(benzyloxy)pyridine | 349141-25-9

• 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
• 英文名称: 2-carboxy-3,4-di(benzyloxy)pyridine
• 英文别名: 2-carboxy-3,4-dibenzyloxypyridine；3,4-Bis(benzyloxy)picolinic acid；3,4-bis(phenylmethoxy)pyridine-2-carboxylic acid
• CAS: 349141-25-9
• 化学式: C₂₀H₁₇NO₄
• 分子量: 335.359
• InChiKey: VJZWUWLZBIGVEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C (decomp)
• 沸点：
  534.0±45.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-carboxy-3,4-di(benzyloxy)pyridine 在 4-二甲氨基吡啶 、 氨 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 3,4-dibenzyloxypyridine-2-carboxyamide hydrochloride
  参考文献：
  名称：

  2-（1'-羟烷基）-和2-酰胺基-3-羟基吡啶-4-酮的新颖合成方法

  摘要：

  已经开发出用于合成高pFe 3+铁螯合剂2-（1'-羟烷基）-和2-酰胺基-3-羟基吡啶-4--4-酮的新方法。产物通过N-氧化物中间体从麦芽酚或乙基麦芽酚获得。

  DOI：

  10.1016/s0040-4020(01)00222-8
• 作为产物：
  描述：

  麦芽醇 在 sodium hydroxide 、 氨基磺酸 、 氨 、 三氧化硫吡啶 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 、 sodium chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 9.0h， 生成 2-carboxy-3,4-di(benzyloxy)pyridine
  参考文献：
  名称：

  2-（1'-羟烷基）-和2-酰胺基-3-羟基吡啶-4-酮的新颖合成方法

  摘要：

  已经开发出用于合成高pFe 3+铁螯合剂2-（1'-羟烷基）-和2-酰胺基-3-羟基吡啶-4--4-酮的新方法。产物通过N-氧化物中间体从麦芽酚或乙基麦芽酚获得。

  DOI：

  10.1016/s0040-4020(01)00222-8

文献信息

• 3-Acylamino-1-[[[(substituted sulfonyl)amino]carbonyl]amino]2-azetidinones
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0336369A1

  公开（公告）日：1989-10-11

  Compounds having the formula and pharmaceutically acceptable salts thereof, exhibit antibacterial activity. R is

  具有以下化学式的化合物及其药用盐具有抗菌活性。R 是
• Iron Modulators
  申请人：Hider Robert Charles

  公开号：US20080200520A1

  公开（公告）日：2008-08-21

  Iron modulator compounds of formula (I) are provided for treating amyloidoses wherein R 1 is selected from H, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 hydroxyalkyl, C 1-6 hydroxyalkenyl, R 2 is selected from H, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 hydroxyalkyl, C 1-6 hydroxyalkenyl and C 6-10 aralykyl in which the aryl group of the aralkyl group is optionally substituted by hydroxy, halo or C1-4 alkyl R 3 is selected from H, C 1-6 alkyl, C 1-6 alkenyl and C 1-12 acyl; R 4 is selected from H and C 1-3 alkyl R 5 , R 6 and R 7 are independently selected from H, C 1-6 alkyl, C 3-7 aryl, and C 1-10 aralkyl; the alkyl, aryl and aralkyl groups being optionally substituted by one or more halo, hydroxy and nitro groups or R 5 and R 7 together with the nitrogen atom to which they are bonded form a heterocyclic ring optionally substituted by one or more hydroxyl groups or a pharmaceutically acceptable tautomer, ester or addition salt thereof.

  提供公式（I）的铁调节剂化合物，用于治疗淀粉样病，其中R1选择自H，C1-6烷基，C1-6烯基，C1-6羟基烷基，C1-6羟基烯基，R2选择自H，C1-6烷基，C1-6烯基，C1-6羟基烷基，C1-6羟基烯基和C6-10芳基烷基，其中芳基烷基的芳基基团可选择性地被羟基，卤素或C1-4烷基取代，R3选择自H，C1-6烷基，C1-6烯基和C1-12酰基; R4选择自H和C1-3烷基，R5，R6和R7独立选择自H，C1-6烷基，C3-7芳基和C1-10芳基烷基; 烷基，芳基和芳基烷基可以选择性地被一个或多个卤素，羟基和硝基基团取代，或者R5和R7与它们连接的氮原子共同形成一个杂环环，该杂环环可以选择性地被一个或多个羟基取代，或其药学上可接受的互变异构体，酯或加成盐。
• 2-Oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0321928A2

  公开（公告）日：1989-06-28

  Antibacterial activity is exhibited by 2-azetidinones having a 3-acylamino substituent and having an activating group in the 1-position of the formula wherein R4 is

  具有 3-酰氨基取代基并在式中 1 位具有活化基团的 2-氮杂环丁酮具有抗菌活性。 其中 R4 是
• Pyridone-Conjugated Monobactam Antibiotics with Gram-Negative Activity
  作者：Matthew F. Brown、Mark J. Mitton-Fry、Joel T. Arcari、Rose Barham、Jeffrey Casavant、Brian S. Gerstenberger、Seungil Han、Joel R. Hardink、Thomas M. Harris、Thuy Hoang、Michael D. Huband、Manjinder S. Lall、M. Megan Lemmon、Chao Li、Jian Lin、Sandra P. McCurdy、Eric McElroy、Craig McPherson、Eric S. Marr、John P. Mueller、Lisa Mullins、Antonia A. Nikitenko、Mark C. Noe、Joseph Penzien、Mark S. Plummer、Brandon P. Schuff、Veerabahu Shanmugasundaram、Jeremy T. Starr、Jianmin Sun、Andrew Tomaras、Jennifer A. Young、Richard P. Zaniewski

  DOI：10.1021/jm400560z

  日期：2013.7.11

  Herein we describe the structure-aided design and synthesis of a series of pyridone-conjugated monohactam analogues with in vitro, antibacterial activity against clinically relevant Grain-negative species including Pseuedomonas aeruginosa, Klebsiella pneumoniae, and Escherichia coli. Rat pharmacokinetic studies with,compound 17 demonstrate low clearance and low plasma protein binding. In addition evidence is provided for a number of analogues suggesting that the siderophore receptors PiuA and PirA play a role in drug uptake in P. aeruginosa strain PAO1.
• Synthesis, physical–chemical characterisation and biological evaluation of novel 2-amido-3-hydroxypyridin-4(1H)-ones: Iron chelators with the potential for treating Alzheimer’s disease
  作者：Alessandra Gaeta、Francisco Molina-Holgado、Xiao L. Kong、Sarah Salvage、Sarah Fakih、Paul T. Francis、Robert J. Williams、Robert C. Hider

  DOI：10.1016/j.bmc.2010.12.007

  日期：2011.2

  A novel class of 2-amido-3-hydroxypyridin-4-one iron chelators is described. These compounds have been designed to behave as suitable molecular probes which will improve our knowledge of the role of iron in neurodegenerative conditions. Neurodegenerative disorders, such as Alzheimer's disease (AD) and Parkinson disease (PD), can be considered as diverse pathological conditions sharing critical metabolic processes such as protein aggregation and oxidative stress. Interestingly, both these metabolic alterations seem to be associated with the involvement of metal ions, including iron. Iron chelation is therefore a potential therapeutic approach. The physico-chemical (pK(a) pFe(3+) and log P) and biological properties (inhibition of iron-containing enzymes) of these chelators have been investigated in order to obtain a suitable profile for the treatment of neurodegenerative conditions. Studies with neuronal cell cultures confirm that the new iron chelators are neuroprotective against beta-amyloid-induced toxicity. (C) 2010 Elsevier Ltd. All rights reserved.