2-((4-(甲硫基)苯基)氨基)烟酸 | 115891-08-2

• 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
• 中文名称: 2-((4-(甲硫基)苯基)氨基)烟酸
• 英文名称: 2-(4-Methylsulfanyl-phenylamino)-nicotinic acid
• 英文别名: 2-{[4-(Methylsulfanyl)phenyl]amino}pyridine-3-carboxylic acid；2-(4-methylsulfanylanilino)pyridine-3-carboxylic acid
• CAS: 115891-08-2
• 化学式: C₁₃H₁₂N₂O₂S
• mdl: MFCD11523560
• 分子量: 260.316
• InChiKey: FPDRRLGZXHQOEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C(Solv: acetone (67-64-1))
• 沸点：
  445.0±40.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((4-(甲硫基)苯基)氨基)烟酸 在 potassium tert-butylate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 56.75h， 生成 1-<4-(methylsulfonyl)phenyl>-3-n-butyl-4-acetoxy-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 、 4-氨基茴香硫醚 以70%的产率得到2-((4-(甲硫基)苯基)氨基)烟酸
  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

• TING, PAULINE C.;KAMINSKI, JAMES J.;SHERLOCK, MARGARET H.;TOM, WING C.;LE+, J. MED. CHEM., 33,(1990) N0, C. 2697-2706
  作者：TING, PAULINE C.、KAMINSKI, JAMES J.、SHERLOCK, MARGARET H.、TOM, WING C.、LE+

  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：——
• 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.
• Substituted 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-ones as potential antiinflammatory agents
  作者：Pauline C. Ting、James J. Kaminski、Margaret H. Sherlock、Wing C. Tom、Joe F. Lee、Robert W. Bryant、Arthur S. Watnick、Andrew T. McPhail

  DOI：10.1021/jm00172a004

  日期：1990.10

  A series of analogues based on the 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one ring system have been synthesized and shown to possess oral antiinflammatory activity in both the reverse passive Arthus reaction (RPAR) pleural cavity assay in rats and in the adjuvant-induced arthritic rat model (AAR). Several members of this series additionally exhibit an inhibitory effect on the in vivo production of prostaglandin- and leukotriene-derived products or arachidonic acid metabolism although these compounds exhibit no significant inhibitory activity against the cyclooxygenase and 5-lipoxygenase enzymes in vitro. Structure-activity relationships in this series are discussed.