2-(3-pyridinylamino)-3-pyridine carboxylic acid, methyl ester | 115891-33-3

• 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
• 英文名称: 2-(3-pyridinylamino)-3-pyridine carboxylic acid, methyl ester
• 英文别名: Methyl 2-(pyridin-3-ylamino)pyridine-3-carboxylate
• CAS: 115891-33-3
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: KAGLUHNDYIIDES-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  369.6±32.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  正己酸乙酯 、 2-(3-pyridinylamino)-3-pyridine carboxylic acid, methyl ester 在 potassium tert-butylate 作用下， 以15%的产率得到3-(n-BUTYL)-4-HYDROXY-1-(3-PYRIDINYL)-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 2-(3-pyridinylamino)-3-pyridine carboxylic acid, methyl ester
  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

• Naphthyridine and pyridopyrazine compounds and pharmaceutical usage thereof
  申请人：SCHERING CORPORATION

  公开号：EP0267740A1

  公开（公告）日：1988-05-18

  Certain substituted 1,8-naphthyridines and 1,5,8-azanaphthyridines of formula I are disclosed which are useful for treating allergy or inflammation in mammals. A preferred use is the treatment of chronic obstructive lung disease in mammals. The compounds have the formula wherein X is CH or N;     R¹ represents alkenyl, alkynyl, cycloalkyl, cycloalkenyl, 2-, 3- or 4- pyridinyl, 2-, 4- or 5- pyrimidinyl, 2- or 3- thienyl, 2- or 3-furanyl, alkyl carbonyl, phenyl carbonyl or alkyl, each of which may be substituted with -COOH, hydroxy, halogen, alkoxy phenyl, 2-, 3-, or 4- pyridinyl, 2-, 4- or 5-pyrimidinyl, 2- or 3-thienyl, 2- or 3- furanyl, alkyl carbonyl, phenyl carbonyl, cycloalkyl, formyloxy, alkyl carbonyloxy, or phenyl carbonyloxy;     R² represents hydrogen, hydroxyalkyl, dihydroxyalkyl, hydroxyalkoxyalkyl, a cation, alkenyl having, R aR bN(CH₂) n-(wherein R a and R b are hydrogen or alkyl and n is an integer from 2 to 6), alkynyl or a group of the general formula: where Z = 0 or 1; p is an integer of 0 to 5, R³ and R⁴ are each alkyl or R³ and R⁴ together form a cycloalkyl up to 6 carbon atoms, and M is H or where Y¹, Y² and Y³ represent hydrogen, hydroxy, halogen, alkyl, alkoxy, halogenated alkyl; and     A is 2-, 3- or 4-biphenyl, 1- or 2-naphthylenyl, 4- or 5-indenyl, 4- or 5- indanyl, 2-, 3-, 4-, 5-, 6-, 7-or 8-quinolinyl, 1-, 3-, 4-, 5-, 6-, 7- or 8-isoquinolinyl, 2-, 3- or 4-pyridinyl, 2-, 4- or 5-pyrimidinyl, 2-pyrazinyl, 3- or 4-pyridazinyl, 3-, 5- or 6-(1,2,4-triazinyl), 2- or 3-furanyl, 2- or 3-thienyl, 2-, 3-, 4-, 5-, 6- or 7-benzofuranyl, 3- 4- or 5-pyrazolyl, 3- or 5-(1,2,4-triazolyl) each of which may be substituted with one or more of hydroxy, alkyl, halogen, nitro, alkoxy, trifluoromethyl or cyano.

  公开了一些具有以下式I的1,8-萘啶和1,5,8-氮杂萘啶的替代物，这些替代物对于治疗哺乳动物的过敏或炎症很有用。首选用途是治疗哺乳动物慢性阻塞性肺病。这些化合物具有以下式，其中X为CH或N；R¹代表烯基、炔基、环烷基、环烯基、2-、3-或4-吡啶基、2-、4-或5-嘧啶基、2-或3-噻吩基、2-或3-呋喃基、烷基羰基、苯基羰基或烷基，每个基可能被取代为-COOH、羟基、卤素、烷氧基苯基、2-、3-或4-吡啶基、2-、4-或5-嘧啶基、2-或3-噻吩基、2-或3-呋喃基、烷基羰基、苯基羰基、环烷基、甲酰氧基、烷基羰氧基或苯基羰氧基；R²代表氢、羟基烷基、二羟基烷基、羟基烷氧基烷基、阳离子、具有的烯基，R aR bN(CH₂) n-（其中R a和R b为氢或烷基，n为2至6的整数）、炔基或具有以下一般式的基团：其中Z = 0或1；p为0至5的整数，R³和R⁴分别为烷基或R³和R⁴一起形成含有最多6个碳原子的环烷基，M为H或其中Y¹、Y²和Y³代表氢、羟基、卤素、烷基、烷氧基、卤代烷基；A为2-、3-或4-联苯基、1-或2-萘基、4-或5-茚基、4-或5-茚基、2-、3-、4-、5-、6-、7-或8-喹啉基、1-、3-、4-、5-、6-、7-或8-异喹啉基、2-、3-或4-吡啶基、2-、4-或5-嘧啶基、2-吡啶基、3-或4-吡啶基、3-、5-或6-（1,2,4-三唑基）、2-或3-呋喃基、2-或3-噻吩基、2-、3-、4-、5-、6-或7-苯并呋喃基、3-、4-或5-吡唑基、3-或5-（1,2,4-三唑基）其中每个基可能被一个或多个羟基、烷基、卤素、硝基、烷氧基、三氟甲基或氰基取代。
• 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：——
• Antiallergy agents. 1. Substituted 1,8-naphthyridin-2(1H)-ones as inhibitors of SRS-A release
  作者：Margaret H. Sherlock、James J. Kaminski、Wing C. Tom、Joe F. Lee、Shing Chun Wong、William Kreutner、Robert W. Bryant、Andrew T. McPhail

  DOI：10.1021/jm00119a010

  日期：1988.11

  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.