N-phenyl-3-(phenylsulfanylmethyl)pyridin-2-amine | 128271-32-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-phenyl-3-(phenylsulfanylmethyl)pyridin-2-amine
• CAS: 128271-32-9
• 化学式: C₁₈H₁₆N₂S
• 分子量: 292.404
• InChiKey: FEFWYJXHHJSCFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenyl-3-(phenylsulfanylmethyl)pyridin-2-amine 在 三甲基氯硅烷 、 sodium hydride 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.5h， 生成 1,3-二氢-3-甲基-1-苯基-2H-吡咯并[2,3-b]吡啶-2-酮
  参考文献：
  名称：

  Substituted 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-ones as potential antiinflammatory agents

  摘要：

  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.

  DOI：

  10.1021/jm00172a004
• 作为产物：
  描述：

  2-苯胺烟酸 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 56.0h， 生成 N-phenyl-3-(phenylsulfanylmethyl)pyridin-2-amine
  参考文献：
  名称：

  Substituted 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-ones as potential antiinflammatory agents

  摘要：

  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.

  DOI：

  10.1021/jm00172a004

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：——
• US5023265A
  申请人：——

  公开号：US5023265A

  公开（公告）日：1991-06-11
• [EN] SUBSTITUTED 1-H-PYRROLO(2,3-B)PYRIDINE-3-CARBOXAMIDES
  申请人：SCHERING CORPORATION

  公开号：WO1991018902A1

  公开（公告）日：1991-12-12

  (EN) Substituted 1-H-pyrrolo[2,3-b]pyridine-3-carboxamides of formula (I) and their use in pharmaceutical compositions and in treating inflammation are disclosed. In formula (I) ring A represents a fused pyridine ring; X is oxygen or sulfur; and R represents hydrogen, alkyl, aryl, aralkyl, or a heterocyclic aromatic group. R1 represents alkyl, aryl, aralkyl, or a heterocyclic aromatic group. Another embodiment of the invention is directed to compounds of formula (II), wherein R is as defined above.(FR) On décrit des 1-H-pyrrolo[2,3-b]pyrridine-3-carboxamides substitués répondant à la formule (I), ainsi que leur utilisation dans des compositions pharmaceutiques et pour le traitement des inflammations. Dans ladite formule (I), l'anneau A représente une combinaison cyclique condensée de pyridine; X représente oxygène ou soufre; R représente hydrogène, alkyle, aryle, aralkyle, ou un groupe aromatique hétérocyclique. R1 représente alkyle, aryle, aralkyle, ou un groupe aromatique hétérocyclique. Un autre mode de réalisation concerne des composés répondant la formule (II), dans laquelle R est tel que défini ci-dessus.
• 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.