Methyl 2-(p-anisidino)-nicotinic acid | 51947-86-5

• 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-(p-anisidino)-nicotinic acid
• 英文别名: methyl 2-((4-methoxyphenyl)amino)nicotinate；Methyl 2-(p-anisidino)-nicotinate；methyl 2-(4-methoxyanilino)pyridine-3-carboxylate
• CAS: 51947-86-5
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: MVIZDTFUMGEVDC-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C(Solv: ethanol (64-17-5))
• 沸点：
  381.7±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-(p-anisidino)-nicotinic acid 在 potassium tert-butylate 作用下， 以 xylene 为溶剂， 反应 24.0h， 生成 4-hydroxy-1-(4-methoxyphenyl)-1,8-naphthyridin-2(1H)-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-(p-anisidino)-nicotinic acid
  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

• New bronchodilators. 3. Imidazo[4,5-c][1,8]naphthyridin-4(5H)-ones
  作者：Fumio Suzuki、Takeshi Kuroda、Takashi Kawakita、Haruhiko Manabe、Shigeto Kitamura、Kenji Ohmori、Michio Ichimura、Hiroshi Kase、Shunji Ichikawa

  DOI：10.1021/jm00104a013

  日期：1992.12

  imidazol[4,5-c][1,8]naphthyridin-4(5H)-ones 5 were designed and synthesized. Some of these new heterocycles exhibited more potent bronchodilator activity in vitro and in vivo than theophylline. With respect to modification at the 5-position, both phenyl and n-butyl substitution produced potent activity. Though bulk tolerance at N-3 is observed with short and small lipophilic groups, any substitution at the

  为了开发新的口服支气管扩张剂，设计并合成了一系列新型的咪唑[4,5-c] [1,8]萘啶-4（5H）-ones 5。这些新杂环中的一些在体外和体内比茶碱表现出更强的支气管扩张活性。关于在5-位的修饰，苯基和正丁基取代均产生有效的活性。尽管在短和小的亲脂基团上观察到了在N-3处的体积耐受性，但亲本骨架的其他位置的任何取代和转化都消除了活性。因此，选择了满足这些条件的5-苯基-1H-咪唑并[4,5-c] [1,8]萘啶-4（5H）-一（23）（KF17625）进行进一步研究（抗原吸入诱导支气管痉挛模型；最小有效剂量（MED）= 1 mg / kg，口服；抗原诱导的气管收缩（Schultz-Dale反应），IC50 = 2.2 microM）。在豚鼠分离的气管制剂中，化合物23抑制了卡巴胆碱，组胺或白三烯D4诱导的收缩和松弛的自发音调，其效力比氨茶碱高4至16倍。因此，它似乎直接放松了气道平滑肌。23对10
• 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。
• Synthesis and biological activity of 2-arylaminonicotinic acid hydrazide derivatives
  作者：A. I. Mikhalev、L. B. Falaleeva、N. I. Shramm、L. M. Polukhina、V. S. Zalesov、G. N. Pershin

  DOI：10.1007/bf00765715

  日期：1981.1
• CHESNOKOV V. P.; KONSHIN M. E., NAUCH. TR. PERM. FARMATSEVT. IN-TA <TRFI-AR>, 1975, VYP. 8, 29-31
  作者：CHESNOKOV V. P.、 KONSHIN M. E.

  DOI：——

  日期：——
• MIXALEV A. I.; KUDRYASHOVA V. K.; ZALESOV V. S.; CHESNOKOV V. P.; KONSHIN+, XIM.-FARMATSEVT. ZH., 1977, 11, HO 11, 78-81
  作者：MIXALEV A. I.、 KUDRYASHOVA V. K.、 ZALESOV V. S.、 CHESNOKOV V. P.、 KONSHIN+

  DOI：——

  日期：——