1,3-dihydro-3-(4-pyridinylmethylene)-1-phenyl-2H-indole-2-one | 33546-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,3-dihydro-3-(4-pyridinylmethylene)-1-phenyl-2H-indole-2-one
• 英文别名: 1-phenyl-3-(4-pyridinylmethylene)-2-oxindole；1-Phenyl-3-[(pyridin-4-yl)methylidene]-1,3-dihydro-2H-indol-2-one；1-phenyl-3-(pyridin-4-ylmethylidene)indol-2-one
• CAS: 33546-08-6
• 化学式: C₂₀H₁₄N₂O
• 分子量: 298.344
• InChiKey: HMXDQCMVHFYIDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dihydro-3-(4-pyridinylmethylene)-1-phenyl-2H-indole-2-one 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 42.0h， 生成 1,3-二氢-3-羟基-1-苯基-3-(吡啶基甲基)-2H-吲哚-2-酮
  参考文献：
  名称：

  3-Substituted 3-(4-pyridinylmethyl)-1,3-dihydro-1-phenyl-2H-indol-2-ones as acetylcholine release enhancers: synthesis and SAR

  摘要：

  A series of 3-substituted, 3-(4-pyridinylmethyl)-1,3-dihydro-1-phenyl-2H-indol-2-ones was synthesized and found to enhance the stimulus-induced release of neurotransmitter acetylcholine (AcCh), and by doing so, might be useful in treating cognitive disorders where the level of this neurotransmitter may be diminished in the brain, as in Alzheimer's disease. An attempt has been made to correlate the structure of the 3-substitution with the ability of the compounds to enhance the release of AcCh from the striatum region of rat brain preparations.

  DOI：

  10.1021/jm00072a009
• 作为产物：
  描述：

  以70的产率得到1,3-dihydro-3-(4-pyridinylmethylene)-1-phenyl-2H-indole-2-one
  参考文献：
  名称：

  Synthetic Communications 1993, 23, 1617-1625

  摘要：

  DOI：

文献信息

• .alpha.,.alpha.-disubstituted aromatics and heteroaromatics as cognition
  申请人：The DuPont Merck Pharmaceutical Co.

  公开号：US05173489A1

  公开（公告）日：1992-12-22

  Cognitive defeciencies or neurological dysfunction in mammals are treated with .alpha.,.alpha.-disubstituted aromatic or heteroaromatic compounds. The compounds have the formula: ##STR1## or a salt thereof wherein X and Y are taken together to form a saturated or unsaturated carbocyclic or heterocyclic first ring and the shown carbon in said ring is .alpha. to at least one additional aromatic ring or heteroaromatic ring fused to the first ring; one of Het.sup.1 is 2, 3 or 4-pyridyl or 2, 4, or 5-pyrimidinyl and the other is selected from (a) 2, 3, or 4-pyridyl, (b) 2, 4, or 5-pyrimidinyl, (c) 2-pyrazinyl, (d) 3, or 4-pyridazinyl, (e) 3, or 4-pyrazolyl, (f) 2, or 3-tetrahydrofuranyl, and (g) 3-thienyl.

  哺乳动物中的认知缺陷或神经功能障碍可使用α，α-二取代芳香或杂芳香化合物进行治疗。该化合物的结构式为：##STR1## 或其盐，其中X和Y结合形成饱和或不饱和的碳环或杂环第一环，所示的碳在该环中为α，至少与一个额外的芳香环或杂芳香环融合在一起；Het.sup.1中的一个是2、3或4-吡啶基或2、4或5-嘧啶基，另一个选择自(a)2、3或4-吡啶基，(b)2、4或5-嘧啶基，(c)2-吡嗪基，(d)3或4-吡啶嗪基，(e)3或4-吡唑基，(f)2或3-四氢呋喃基，和(g)3-噻吩基。
• Process for preparing 3,3-disubstituted indolines
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04806651A1

  公开（公告）日：1989-02-21

  Processes for preparing 3,3-disubstituted indolines, particularly 3,3-dipyridine substituted indolines useful to treat cognitive or neurological dysfunction in a mammal, are provided.

  本发明提供了制备3,3-二取代吲哚啉的方法，特别是3,3-二吡啶取代的吲哚啉，用于治疗哺乳动物的认知或神经功能障碍。
• .alpha., .alpha.-disubstituted aromatics and heteroaromatics as
  申请人：The Du Pont Merck Pharmaceutical Company

  公开号：US05300642A1

  公开（公告）日：1994-04-05

  Cognitive defeciencies or neurological dysfunction in mammals are treated with .alpha.,.alpha.-disubstituted aromatic or heteroaromatic compounds. The compounds have the formula: ##STR1## or a salt thereof wherein X and Y are taken together to form a saturated or unsaturated carbocyclic or heterocyclic first ring and the shown carbon in said ring is .alpha. to at least one additional aromatic ring or heteroaromatic ring fused to the first ring; one of Het.sup.1 or Het.sup.2 is 2, 3, or 4-pyridyl or 2, 4, or 5-pyrimidinyl and the other is selected from (a) 2, 3, or 4-pyridyl, (b) 2, 4, or 5-pyrimidinyl, (c) 2-pyrazinyl, (d) 3, or 4-pyridazinyl, (e) 3, or 4-pyrazolyl, (f) 2, or 3-tetrahydrofuranyl, and (g) 3-thienyl.

  哺乳动物中的认知缺陷或神经功能障碍可用.alpha.，.alpha.-二取代芳香族或杂芳香族化合物进行治疗。该化合物的化学式为：##STR1## 或其盐，其中X和Y共同形成饱和或不饱和的碳环或杂环的第一个环，所示的碳原子在该环中是.alpha.至少一个与第一个环融合的芳香环或杂芳香环；Het.sup.1或Het.sup.2中的一个是2，3或4-吡啶基或2，4或5-嘧啶基，另一个选择自(a)2，3或4-吡啶基，(b)2，4或5-嘧啶基，(c)2-吡嗪基，(d)3或4-吡嗪啉基，(e)3或4-嘧唑基，(f)2或3-四氢呋喃基和(g)3-噻吩基。
• Pierce, Michael E.; Huhn, George F.; Jensen, James H., Journal of Heterocyclic Chemistry, 1994, vol. 31, # 1, p. 17 - 24
  作者：Pierce, Michael E.、Huhn, George F.、Jensen, James H.、Sigvardson, Ken W.、Islam, Qamrul、Xing, Yide

  DOI：——

  日期：——
• 3-Substituted 3-(4-pyridinylmethyl)-1,3-dihydro-1-phenyl-2H-indol-2-ones as acetylcholine release enhancers: synthesis and SAR
  作者：Wendell W. Wilkerson、Ahmed A. Kergaye、S. William Tam

  DOI：10.1021/jm00072a009

  日期：1993.10

  A series of 3-substituted, 3-(4-pyridinylmethyl)-1,3-dihydro-1-phenyl-2H-indol-2-ones was synthesized and found to enhance the stimulus-induced release of neurotransmitter acetylcholine (AcCh), and by doing so, might be useful in treating cognitive disorders where the level of this neurotransmitter may be diminished in the brain, as in Alzheimer's disease. An attempt has been made to correlate the structure of the 3-substitution with the ability of the compounds to enhance the release of AcCh from the striatum region of rat brain preparations.