1-methyl-4-hydroxyoxindole | 20870-81-9

• 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-methyl-4-hydroxyoxindole
• 英文别名: 4-hydroxy-1-methyloxindole；4-hydroxy-1-methyl-indolin-2-one；4-Hydroxy-1-methyl-indolin-2-on；4-hydroxy-1-methyl-1,3-dihydro-2H-indol-2-one；4-Hydroxy-N-methyl-oxindol；4-Hydroxy-1-methylindolin-2-one；4-hydroxy-1-methyl-3H-indol-2-one
• CAS: 20870-81-9
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: ANIZZDHCSZULKA-UHFFFAOYSA-N

物化性质

• 熔点：
  230-232 °C
• 沸点：
  431.3±45.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-4-hydroxyoxindole 在 吡啶 、 tetraphosphorus decasulfide 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 Acetic acid 1-methyl-2-thioxo-2,3-dihydro-1H-indol-4-yl ester
  参考文献：
  名称：

  Tyrosine Kinase Inhibitors. 3. Structure-Activity Relationships for Inhibition of Protein Tyrosine Kinases by Nuclear-Substituted Derivatives of 2,2'-Dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)

  摘要：

  A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3-dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity, While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20-fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC(50)s in the range 2-25 mu M, the most active being 4-substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF-mediated phosphorylation.

  DOI：

  10.1021/jm00039a016
• 作为产物：
  描述：

  2-甲氧基-N-甲基苯胺 在 三氯化铝 作用下， 生成 1-methyl-4-hydroxyoxindole
  参考文献：
  名称：

  2：3-Dihydro-3-oxobenz-1：4-恶嗪

  摘要：

  DOI：

  10.1039/jr9550000739

文献信息

• Über die Synthese eines physostigminähnlichen Körpers
  作者：E. Kretz、J. M. Müller、E. Schlittler

  DOI：10.1002/hlca.19520350218

  日期：1952.2.1

  Zum Studium des Verhältnisses von chemischer Konstitution und physostigminähnlicher Wirkung wurde das 1-Methyl-3-spiro-(N-methyl-piperidin-4)-5-N-methylcarbamoxy-indolin aufgebaut. Die Synthese des entsprechenden Urethans in 6-Stellung wurde bis zur Äthoxy-indolin-Stufe, diejenige des Analogons in 7-Stellung bis zur Oxyoxindol-Stufe durchgeführt.

  为了研究化学组成与毒扁豆碱样作用之间的关系，建立了1-甲基-3-螺-（N-甲基-哌啶-4）-5-N-甲基氨基甲酰二氢吲哚。在6-位直至乙氧基-二氢吲哚阶段进行相应的氨基甲酸酯的合成，在7-位直至羟氧吲哚阶段的类似物的合成。
• FUSED HETEROCYCLIC COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2103620A1

  公开（公告）日：2009-09-23

  The present invention provides a fused heterocyclic compound having a tyrosine kinase inhibitory action, which is represented by the formula: wherein R1 is a hydrogen atom, a halogen atom, or an optionally substituted group bonded via a carbon atom, a nitrogen atom or an oxygen atom; R2 is a hydrogen atom, or an optionally substituted group bonded via a carbon atom or a sulfur atom, or R1 and R2, or R2 and R3 are optionally bonded to each other to form an optionally substituted ring structure; R3 is a hydrogen atom or an optionally substituted aliphatic hydrocarbon group, or R3 is optionally bonded to the carbon atom on ring A to form an optionally substituted ring structure; ring A is an optionally substituted benzene ring; and ring B is (i) an optionally substituted fused ring, or (ii) a pyridine ring having optionally substituted carbamoyl (the pyridine ring is optionally further substituted).

  本发明提供了一种具有酪氨酸激酶抑制作用的融合杂环化合物，其化学式如下： 其中 R1是氢原子、卤素原子或通过碳原子、氮原子或氧原子键合的可选择取代基； R2是氢原子，或通过碳原子或硫原子键合的可选择取代基，或 R1和R2，或R2和R3可选择键合在一起形成可选择取代的环结构； R3是氢原子或可选择取代的脂肪烃基，或 R3可选择键合到环A上的碳原子上形成可选择取代的环结构； 环A是可选择取代的苯环；环B是 (i) 可选择取代的融合环，或 (ii) 具有可选择取代的氨基甲酰基的吡啶环（吡啶环可进一步取代）。
• Photochemical 1,3-Migration of the Hydroxyl Group in 1-Alkyl-3-hydroxyoxindoles
  作者：Jiro Tatsugi、Kenji Ikuma、Yasuji Izawa

  DOI：10.1016/0040-4039(95)01854-b

  日期：1995.11

  Irradiation of 1-alkyl-3-hydroxyoxindoles in degassed solutions afforded 1-alkyl-4-hydroxyoxindolcs via 1,3-migration of the hydroxyl group together with 1-alkyloxindoles.

  在脱气溶液中辐照1-烷基-3-羟基羟吲哚通过羟基与1-烷基氧吲哚的1，3-迁移而得到1-烷基-4-羟基氧吲哚。
• Synthesis and biological evaluation of benzoxepinoindol‐1‐one analogs as <scp>Brd4</scp> bromodomain inhibitors
  作者：Goni Jung、Joo‐Youn Lee、Chi Hoon Park、Eunyoung Yoon、Jung‐Nyoung Heo

  DOI：10.1002/bkcs.12656

  日期：2023.3

  A novel series of benzo[6,7]oxepino[4,3,2-cd]indol-1(2H)-one derivatives were synthesized via a one-pot aldol condensation and SNAr reaction by coupling indolin-2-ones with 2-fluorobenzaldehydes. In addition, molecular docking studies of the designed compound 2 revealed strong hydrogen bonds in the hot binding pocket of Brd4. All compounds were evaluated for their enzymatic activity in Brd4 bromodomain

  一系列新型苯并[6,7]oxepino[4,3,2- cd ]indol-1(2 H )-one 衍生物通过一锅醇醛缩合和 S N Ar 反应通过偶联 indolin-2- 合成含有 2-氟苯甲醛的物质。此外，设计的化合物2的分子对接研究揭示了 Brd4 的热结合口袋中的强氢键。评估了所有化合物在 Brd4 溴结构域抑制中的酶活性。
• Selective Photo-Reduction of 1-Alkylisatins in Degassed Alcoholic Solutions
  作者：Jiro Tatsugi、Kenji Ikuma、Yasuji Izawa

  DOI：10.3987/com-95-7272

  日期：——

  Irradiation of 1-alkylisatins (1) in degassed alcohols afforded 1-alkyl-3-hydroxyoxindoles (2) and 1-alkyloxindoles (3) as chemoselective photoproducts.