2-((3-(甲硫基)苯基)氨基)烟酸 | 115891-07-1

• 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-((3-(甲硫基)苯基)氨基)烟酸
• 英文名称: 2-(3-Methylsulfanyl-phenylamino)-nicotinic acid
• 英文别名: 2-(3-methylsulfanylanilino)pyridine-3-carboxylic acid
• CAS: 115891-07-1
• 化学式: C₁₃H₁₂N₂O₂S
• mdl: MFCD11523542
• 分子量: 260.316
• InChiKey: XSJKCCUASQVUSD-UHFFFAOYSA-N

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-((3-(甲硫基)苯基)氨基)烟酸 在 potassium tert-butylate 、 三乙胺 作用下， 以 甲醇 、 丙酮 、 苯 为溶剂， 反应 52.25h， 生成 1-<3-(methylthio)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 、 3-氨基茴香硫醚 以96%的产率得到2-((3-(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

• Pyrido¬2,3-d|pyrimidine derivatives as phosphodiesterase inhibitors
  申请人：Roche Palo Alto LLC

  公开号：EP1770093A1

  公开（公告）日：2007-04-04

  The present invention relates to optionally substituted pyrido-[2,3-d]-pyrimidine-2,4(1H,3H)-diones or optionally substituted pyrido-[2,3-d]-pyrimidine-2(1H,3H)-ones, particularly to 1-(optionally substituted) phenyl-3-(optionally substituted heteroarylalkyl or arylalkyl)-pyrido-[2,3-d]pyrimidine-2,4(1H,3H)-diones and pyrido-[2,3-d]-pyrimidine-2(1H,3H)-ones, useful as anti-inflammatory agents, immunosuppressive agents, anti-allograft rejection agents, anti-graft-vs-host disease agents, anti-allergic agents (e.g., asthma, rhinitis and atopic dermatitis), anti-autoimmune agents or analgetic agents, to their precursors, to their preparation and to pharmaceutical compositions using the compounds of the invention.

  本发明涉及任选取代的吡啶-[2,3-d]-嘧啶-2,4(1H,3H)-二酮或任选取代的吡啶-[2,3-d]-嘧啶-2(1H,3H)-酮，特别是 1-(任选取代的)苯基-3-(任选取代的杂芳基或芳烷基)-吡啶-[2、3-d]嘧啶-2,4(1H,3H)-二酮和吡啶-[2,3-d]嘧啶-2(1H,3H)-酮，可用作抗炎剂、免疫抑制剂、抗移植物排斥剂、抗移植物抗宿主病剂、抗过敏剂（如g.,哮喘、鼻炎和特应性皮炎）、抗自身免疫剂或镇痛剂，以及它们的前体、制备方法和使用本发明化合物的药物组合物。
• URBANSKA H.; SWIRSKA A.; BOGDAL M.; PRZEMYK B.; KRZYWOSINSKI L., ACTA POL. PHARM., 1979, 36, NO 6, 657-665
  作者：URBANSKA H.、 SWIRSKA A.、 BOGDAL M.、 PRZEMYK B.、 KRZYWOSINSKI L.

  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：——
• PYRIDO 2,3-d]PYRIMIDINE DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0631580A1

  公开（公告）日：1995-01-04
• [EN] PYRIDO[2,3-d]PYRIMIDINE DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS
  申请人：SYNTEX (U.S.A.) INC.

  公开号：WO1993019068A1

  公开（公告）日：1993-09-30

  (EN) The present invention relates to optionally substitued pyrido[2,3-d]-pyrimidine-2,4(1H,3H)-diones or optionally substituted pyrido[2,3-d]-pyrimidine-2(1H,3H)-ones, i.e., compounds of Formula (I) wherein: Y is -CH2- or -C(O)-; R1 is hydrogen or -(CH2)n-R7, wherein: R7 is aryl or heteroaryl, and n is 1 or 2, provided that when Y is -C(O)-, R7 is heteroaryl; and R2, R3, R4, R5 and R6 are hydrogen, or one is selected from lower alkyl, halo, carboxy, methoxycarbonyl, carbamoyl, methylcarbamoyl, di-methylcarbamoyl, methylcarbonyl, methylthio, methylsulfinyl, methylsulfonyl, hydroxymethyl, amino, trifluoromethyl, cyano or nitro; or R2, R3, R4 and R5 are independently selected from hydrogen, lower alkyl, nitro, chloro, fluoro, methoxycarbonyl or methylcarbonyl, provided that at least one is hydrogen, and R6 is hydrogen; or a pharmaceutically acceptable ester, ether, N-oxide or salt thereof.(FR) Cette invention concerne des pyrido[2,3-d]-pyrimidine-2,4(1H, 3H)-diones facultativement substituées ou des pyrido[2,3-d]-pyrimidine-2(1H, 3H)-ones facultativement substituées, c'est-à-dire des composés de formule (I). Dans cette formule, Y représente -CH2- ou -C(O)-; R1 représente hydrogène ou -(CH2)n-R7: R7 représentant aryle ou hétéroaryle, et n valant 1 ou 2, à condition que lorsque Y représente -C(O)-, R7 représente hétéroaryle; et R2, R3, R4, R5 et R6 représentent hydrogène ou l'un d'entre eux est sélectionné parmi alkyle inférieur, halo, carboxy, méthoxycarbonyle, carbamoyle, méthylcarbamoyle, di-méthylcarbamoyle, méthylcarbonyle, méthylthio, méthylsulfinyle, méthylsulfonyle, hydroxyméthyle, amino, trifluoromethyle, cyano ou nitro; ou R2, R3, R4 et R5 sont indépendamment sélectionnés parmi hydrogène, alkyle inférieur, nitro, chloro, fluoro, méthoxycarbonyle ou méthylcarbonyle à condition qu'au moins un d'entre eux représente hydrogène, et R6 représente hydrogène. L'invention concerne également un ester, un éther, un oxyde-N ou un sel pharmaceutiquement acceptables de ces composés.