methyl 2-(o-methoxyanilino)nicotinate | 114501-07-4

• 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: methyl 2-(o-methoxyanilino)nicotinate
• 英文别名: methyl 2-((2-methoxyphenyl)amino)nicotinate；Methyl 2-(2-methoxyanilino)pyridine-3-carboxylate
• CAS: 114501-07-4
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: VQVKGSQAHSFVSQ-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C(Solv: methanol (67-56-1))
• 沸点：
  365.7±37.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(o-methoxyanilino)nicotinate 在 potassium tert-butylate 作用下， 以 xylene 为溶剂， 反应 24.0h， 生成 4-Hydroxy-1-(2-methoxy-phenyl)-1H-[1,8]naphthyridin-2-one
  参考文献：
  名称：

  Antiallergy agents. 1. Substituted 1,8-naphthyridin-2(1H)-ones as inhibitors of SRS-A release

  摘要：

  A novel class of antiallergy agents, the substituted 1,8-naphthyridin-2(1H)-ones, is described. The present compounds are orally active, potent inhibitors of allergic and nonallergic bronchospasm in animal models. Structure-activity studies of the lead compound in this series, 1-phenyl-3-n-butyl-4-hydroxynaphthyridin-2(1H)-one (11), identified three compounds of interest, 1-phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one (12), 1-(3'-chlorophenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H )-one (87), and 1-(3'-methoxyphenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1 H)-one (89). The mechanism of antiallergy activity may involve inhibition of the release of the sulfidopeptide leukotrienes. 1-Phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one, Sch 33303 (12), was selected for preclinical development as an antiallergy agent.

  DOI：

  10.1021/jm00119a010
• 作为产物：
  描述：

  2-氯烟酸 在 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 24.0h， 生成 methyl 2-(o-methoxyanilino)nicotinate
  参考文献：
  名称：

  Antiallergy agents. 1. Substituted 1,8-naphthyridin-2(1H)-ones as inhibitors of SRS-A release

  摘要：

  A novel class of antiallergy agents, the substituted 1,8-naphthyridin-2(1H)-ones, is described. The present compounds are orally active, potent inhibitors of allergic and nonallergic bronchospasm in animal models. Structure-activity studies of the lead compound in this series, 1-phenyl-3-n-butyl-4-hydroxynaphthyridin-2(1H)-one (11), identified three compounds of interest, 1-phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one (12), 1-(3'-chlorophenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H )-one (87), and 1-(3'-methoxyphenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1 H)-one (89). The mechanism of antiallergy activity may involve inhibition of the release of the sulfidopeptide leukotrienes. 1-Phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one, Sch 33303 (12), was selected for preclinical development as an antiallergy agent.

  DOI：

  10.1021/jm00119a010

文献信息

• Photoinitiated Rearrangement of Aromatic Azides to 2-Aminonicotinates
  作者：Denis A. Davydov、Marina A. Giricheva、Yulia B. Malysheva、Georgy K. Fukin、Andrei V. Budruev

  DOI：10.1021/acs.joc.3c01453

  日期：2023.11.3

  This study describes a one-pot photoinduced method for azepine synthesis and their subsequent rearrangement into pyridines. The rearrangement of the azepine, formed during photolysis, occurs due to both thermal and photochemical activation of the reaction. This requires an electron-donating substituent at the second position of the azepine and an electron-withdrawing substituent at the third position

  这项研究描述了一种用于氮杂卓合成及其随后重排为吡啶的一锅光诱导方法。光解过程中形成的氮杂卓的重排是由于反应的热活化和光化学活化而发生的。这需要在氮杂的第二个位置上有一个给电子取代基，并且在氮杂的第三个位置上有一个吸电子取代基。已经提出了一种反应机制来解释水的作用和氮杂取代基的性质。
• GHONEIM, K. M.;BADRAN, M. M.;BOTROS, S.;GAWAD, M. ABDEL, EGYPT. J. PHARM. SCI., 28,(1987) N 1-4, 9-16
  作者：GHONEIM, K. M.、BADRAN, M. M.、BOTROS, S.、GAWAD, M. ABDEL

  DOI：——

  日期：——
• SHERLOCK, MARGARET H.;KAMINSKI, JAMES J.;TOM, WING C.;LEE, JOE F.;WONG, S+, J. MED. CHEM., 31,(1988) N 11, C. 2108-2121
  作者：SHERLOCK, MARGARET H.、KAMINSKI, JAMES J.、TOM, WING C.、LEE, JOE F.、WONG, S+

  DOI：——

  日期：——
• Imidazonaphthyridine derivatives
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0459505B1

  公开（公告）日：1996-10-02
• US5364859A
  申请人：——

  公开号：US5364859A

  公开（公告）日：1994-11-15