2-phenyl-1,8-naphthyridin-4(1H)-one | 907555-02-6

• 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-phenyl-1,8-naphthyridin-4(1H)-one
• 英文别名: 2-Phenyl-1,8-naphthyridin-4-ol；2-phenyl-1H-1,8-naphthyridin-4-one
• CAS: 907555-02-6
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: IPVMHKHKTQYJIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-1,8-naphthyridin-4(1H)-one 、 2-bromo-N-methyl-N-phenylpropanamide 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 19.0h， 以10%的产率得到N-methyl-N-phenyl-2-[(2-phenyl-1,8-naphthyridin-4-yl)oxy]propanamide
  参考文献：
  名称：

  Development of N-Methyl-(2-arylquinolin-4-yl)oxypropanamides as Leads to PET Radioligands for Translocator Protein (18 kDa)

  摘要：

  Translocator protein (18 kDa), known as TSPO, is a recognized biomarker of neuroinflammation. Radioligands with PET accurately quantify TSPO in neuroinflammatory conditions. However, the existence of three human TSPO genotypes that show differential affinity to almost all useful TSPO PET radioligands hampers such studies. There is an unmet need for genotype-insensitive, high-affinity, and moderately lipophilic TSPO ligands that may serve as leads for PET radioligand development. To address this need, we varied the known high-affinity TSPO ligand (l)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide in its aryl scaffold, side chain tether, and pendant substituted amido group while retaining an N-methyl group as a site for labeling with carbon-11. From this effort, oxygen-tethered N-methyl-aryloxypropanamides emerged as new high-affinity TSPO ligands with attenuated lipophilicity, including one example with attractive properties for PET radioligand development, namely N-methyl-N-phenyl-2-{[2-(pyridin-2-yl)quinolin-4-yl]oxy}propanamide (22a; rat K-i = 0.10 nM; human TSPO genotypes K-i = 1.4 nM; clogD = 4.18).

  DOI：

  10.1021/jm5007947
• 作为产物：
  描述：

  2-溴-3-吡啶甲醛 在 copper(l) iodide 、 正丁基锂 、 碳酸氢铵 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 formamide 、 二甲基亚砜 为溶剂， 反应 12.25h， 生成 2-phenyl-1,8-naphthyridin-4(1H)-one
  参考文献：
  名称：

  通过将正交“ NH3”插入邻卤代芳基壬酸酯获得2-烷基/芳基-4-（1H）-喹诺酮类化合物：生物活性假单宁，甲酚，甲酚胺和Waltherione F的全合成。

  摘要：

  提出了一种有效的一锅法合成4-（1H）-喹诺酮的方法，该方法是在Cu（I）存在下，通过串联的迈克尔加成反应和ArCsp2-N偶联作用，使多种邻卤代芳基炔酮与氨进行正交结合。已绘制出此便捷方案的底物范围，其中碳酸铵既可作为原位氨源，又可作为多种2-取代的4-（1H）-喹诺酮类的碱，并且其功效已通过生物活性天然产物的简明全合成进行了验证假单胞菌（IV，VII，VIII和XII），砾石，gravolinine和waltherioneF。

  DOI：

  10.1021/acs.orglett.0c00172

文献信息

• Efficient [5 + 1]-strategy for the assembly of 1,8-naphthyridin-4(1H)-ones by domino amination/conjugate addition reactions of 1-(2-chloropyridin-3-yl)prop-2-yn-1-ones with amines
  作者：Viktor O. Iaroshenko、Ingo Knepper、Muhammad Zahid、Rene Kuzora、Sergii Dudkin、Alexander Villinger、Peter Langer

  DOI：10.1039/c2ob07030h

  日期：——

  A facile synthetic approach for the synthesis of 1,8-naphthyridine-4(1H)-one derivatives via a catalyst free and Pd-supported tandem amination sequence is developed and described. In a case of aliphatic amines reaction proceeds in a catalyst free mode, however anilines demand Pd-supported reaction conditions.

  开发并描述了一种简便的合成方法，通过无催化剂和钯支持的串联胺化反应合成1,8-萘啶-4(1H)-酮衍生物。在脂肪胺的反应中，无催化剂条件下进行，而芳香胺则需要钯支持的反应条件。
• 1-알킬-2-페닐-1,8-나프티리딘-4-온의 신규한 제조방법
  申请人：Duksung Women's University Industry-Academic Cooperation Foundation 덕성여자대학교 산학협력단(220050332221) BRN ▼210-82-08681

  公开号：KR101766414B1

  公开（公告）日：2017-08-08

  본 발명은 2-클로로니코틴산으로부터 1-알킬-2-페닐-1,8-나프티리딘-4-온을 제조하는 신규한 제조방법을 제공한다. 본 발명의 제조방법은 출발물질로서 2-클로로니코틴산을 이용하여 간단한 반응조건 및 간단한 단계를 통해 1-알킬-2-페닐-1,8-나프티리딘-4-온 및 약간의 반응 조건 변경으로 1-알킬-2-페닐-2,3-디하이드로-1,8-나프티리딘-4-온을 고수율로 새롭게 합성할 수 있는 장점이 있다.

  本发明提供了一种从2-氯烟酸制备1-烷基-2-苯基-1,8-萘酰基-4-酮的新型制备方法。该制备方法利用2-氯烟酸作为起始原料，通过简单的反应条件和简单的步骤，具有可以高收率地合成1-烷基-2-苯基-1,8-萘酰基-4-酮和稍微调整反应条件即可合成1-烷基-2-苯基-2,3-二酮-1,8-萘酰基-4-酮的优点。
• [EN] 2-ARYLNAPHTHYRIDIN-4-ONES AS POTENT ANTITUMOR AGENTS TARGETING TUMORIGENIC CELL LINES<br/>[FR] 2-ARYLNAPHTYRIDIN-4-ONES EN TANT QU'AGENTS ANTITUMORAUX PUISSANTS CIBLANT DES LIGNÉES CELLULAIRES TUMORIGÈNES
  申请人：KUO SHENG-CHU

  公开号：WO2014179401A1

  公开（公告）日：2014-11-06

  In order to search for new antitumor drug candidates from 2-arylnaphthyridin-4-ones (ANs), we have designed and synthesized a series of 3 '-hydroxy or 6-hydroxy derivatives of ANs. Following the antitumor activity screening, most of these compounds were found to exhibit significant activity. Among them, 2-(3-hydroxyphenyl)-5-methyl-1,8-naphthyridin-4(1H)-one (67) was the most promising. In a preliminary action mechanism study, the treatment of Hep3B hepatoma cells with compound (67) reveals that its mechanism of action is affect on microtubule and metastasis-related proteins. Then, the corresponding phosphate prodrug (86) of compound (67) was tested against Hep3B xenograft nude mice model for antitumor activity.

  为了从2-芳基萘啉并酮（ANs）中寻找新的抗肿瘤药物候选物，我们设计并合成了一系列ANs的3'-羟基或6-羟基衍生物。经过抗肿瘤活性筛选，发现其中大多数化合物表现出显著的活性。其中，2-(3-羟基苯基)-5-甲基-1,8-萘啉-4(1H)-酮（67）是最有前途的。在初步的作用机制研究中，用化合物（67）处理Hep3B肝癌细胞表明其作用机制影响微管和与转移相关的蛋白质。然后，化合物（67）的相应磷酸酯前药（86）被用于对Hep3B异种移植裸鼠模型进行抗肿瘤活性测试。
• A Novel Class of Highly Potent and Selective A₁ Adenosine Antagonists:  Structure−Affinity Profile of a Series of 1,8-Naphthyridine Derivatives
  作者：Pier Luigi Ferrarini、Claudio Mori、Clementina Manera、Adriano Martinelli、Filippo Mori、Giuseppe Saccomanni、Pier Luigi Barili、Laura Betti、Gino Giannaccini、Letizia Trincavelli、Antonio Lucacchini

  DOI：10.1021/jm990321p

  日期：2000.7.1

  A series of 1,8-naphthyridine derivatives (12-36), bearing a phenyl group in position 2 and various substituents in positions 4 and 7, were synthesized in an attempt to obtain potent, selective antagonists for the A1 adenosine receptor subtype. The compounds were tested to evaluate their affinity for A1 compared with A2A and A3 adenosine receptor subtypes. In binding studies in bovine brain cortical

  合成了一系列在位置2带有苯基，在位置4和7带有多个取代基的1,8-萘啶衍生物（12-36），试图获得有效的，选择性的A1腺苷受体亚型拮抗剂。测试了这些化合物以评估它们与A2A和A3腺苷受体亚型相比对A1的亲和力。在牛脑皮质膜的结合研究中，大多数化合物显示出对低纳摩尔范围内的A1受体具有亲和力，而在亚纳摩尔范围内的两个对A1受体具有亲和力，并且具有相对于A2A和A3选择性的有趣程度。对4-取代的衍生物的比较表明，具有4-喹啉结构的4-OH取代引起A1和A2A亲和力的增加，并且通常还引起A1选择性的增加。7位上的取代类型可以极大地调节亲和力：在这个位置上最有趣的取代基似乎是吸电子基团。特别是7-氯萘啶25d表现出显着的选择性（A2A / A1比为670，A3 / A1比为14,000）与更高的A1亲和力（Ki = 0.15 nM）相关。对这些化合物12-36的NMR研究表明，被4-OH取代的化
• Novel therapeutic agents for macromolecular structures
  申请人：——

  公开号：US20030060663A1

  公开（公告）日：2003-03-27

  Disclosed are novel multibinding compounds (agents) which bind macromolecular structures including cellular, extracellular, and microbial components derived from vectors, viruses, fungi, yeasts, bacteria, and the like. The compounds of this invention comprise a plurality of ligands each of which can bind to such macromolecular structures thereby modulating the biological processes/functions thereof. Each of the ligands is covalently attached to a linker (framework) to provide for the multibinding compound. The linker is selected such that the multibinding compound so constructed demonstrates increased modulation or disruption of the biological processes/functions of cell as compared to the aggregate of the individual units of the ligand.

  本发明公开了一种新型的多结合化合物（药剂），其能够结合向量、病毒、真菌、酵母、细菌等细胞、细胞外和微生物成分的大分子结构。本发明的化合物包括多种配体，每种配体均能结合此类大分子结构，从而调节其生物过程/功能。每个配体都与连接体（框架）共价连接，以形成多结合化合物。所选择的连接体使得构建的多结合化合物相对于配体的单个单位的聚集体表现出增加的细胞生物过程/功能调节或干扰。