2-氰基-3-(1H-吲哚-3-基)丙烯酸乙酯 | 6286-56-2

• 物质功能分类: 医药中间体 - 吲哚类化合物
• 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
• 中文名称: 2-氰基-3-(1H-吲哚-3-基)丙烯酸乙酯
• 英文名称: 2-cyano-3-(2,3-dihydro-1H-indol-3-yl)acrilic acid ethyl ester
• 英文别名: 2-cyano-3-(1H-indol-3-yl-methylene)-ethyl acrylate；ethyl 2-cyano-3-(1H-indol-3-yl)acrylate；2-cyano-3-phenyl-acrylic acid ethyl ester；Ethyl (2E)-2-cyano-3-(1H-indol-3-YL)prop-2-enoate；ethyl 2-cyano-3-(1H-indol-3-yl)prop-2-enoate
• CAS: 6286-56-2
• 化学式: C₁₄H₁₂N₂O₂
• mdl: MFCD00192138
• 分子量: 240.261
• InChiKey: XDRLIASMKGKPDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  65.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氰基-3-(1H-吲哚-3-基)丙烯酸乙酯 在 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 3-(pyrrolidin-3-yl)-1H-indole
  参考文献：
  名称：

  Structure-based design of 7-azaindole-pyrrolidine amides as inhibitors of 11β-hydroxysteroid dehydrogenase type I

  摘要：

  Indole-pyrrolidines were identified as inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) by high-throughput screening. Optimisation of the initial hit through structure-based design led to 7-azaindole-derivatives, with the best analogues displaying single digit nanomolar IC(50) potency. The modeling hypotheses were confirmed by solving the X-ray co-crystal structure of one of the lead compounds. These compounds were selective against 11β-hydroxysteroid dehydrogenase type 2 (selectivity ratio >200) and exhibited good inhibition of 11β-HSD1 (IC(50)<1μM) in a cellular model (3T3L1 adipocytes).

  DOI：

  10.1016/j.bmcl.2012.07.070
• 作为产物：
  描述：

  吲哚 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 7.5h， 生成 2-氰基-3-(1H-吲哚-3-基)丙烯酸乙酯
  参考文献：
  名称：

  Structure-based design of 7-azaindole-pyrrolidine amides as inhibitors of 11β-hydroxysteroid dehydrogenase type I

  摘要：

  Indole-pyrrolidines were identified as inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) by high-throughput screening. Optimisation of the initial hit through structure-based design led to 7-azaindole-derivatives, with the best analogues displaying single digit nanomolar IC(50) potency. The modeling hypotheses were confirmed by solving the X-ray co-crystal structure of one of the lead compounds. These compounds were selective against 11β-hydroxysteroid dehydrogenase type 2 (selectivity ratio >200) and exhibited good inhibition of 11β-HSD1 (IC(50)<1μM) in a cellular model (3T3L1 adipocytes).

  DOI：

  10.1016/j.bmcl.2012.07.070

文献信息

• Synthesis, Reactions, and Pharmacological Screening of Heterocyclic Derivatives Using Nicotinic Acid as a Natural Synthon
  作者：Nehad A. Abd El-Latif、Abd El-Galil E. Amr、Alhusain A. Ibrahiem

  DOI：10.1007/s00706-007-0628-z

  日期：2007.6

  acetate to afford 3-β-(3-indolyl)acryloylpyridine oxime and oxazole derivatives. The oxime was treated with ethyl isothiocyanate or toluene-3,5-diisocyanate in refluxing dioxane to give the corresponding ethyl thiosemicarbazide and 3,5-bissemicarbazide derivative. 3-β-(3-Indolyl)acryloylpyridine was condensed with malononitrile in refluxing ethanol in the presence of piperidine as a catalyst to give cyanoaminopyrane

  由3-乙酰基吡啶制备了一系列取代的吡啶衍生物，所述3-乙酰基吡啶由相应的烟酸作为天然原料制备。3-乙酰基吡啶与吲哚-3-甲醛的反应得到相应的3-β-（3-吲哚基）丙烯酰吡啶，在乙酸钠存在下，其与盐酸羟胺在吡啶或乙酸中反应，得到3-β-（3 -吲哚基）丙烯酰基吡啶肟和恶唑衍生物。在回流的二恶烷中用异硫氰酸乙酯或甲苯-3，5-二异氰酸酯处理肟，得到相应的乙基硫代氨基脲和3，5-双氨基脲衍生物。在哌啶为催化剂的情况下，在回流的乙醇中将3-β-（3-吲哚基）丙烯酰基吡啶与丙二腈缩合，得到氰基氨基吡喃，在乙酸铵存在下，将其与氰基乙酸乙酯或丙二腈缩合，得到氰基吡啶酮和氰基氨基吡啶衍生物。丙烯腈吡啶环化 Ó 苯二胺在回流的正丁醇导致形成相应的benzodiazipine 经由 中间 甲 。最后，丙烯酰基吡啶与硫脲的环加成反应得到硫代嘧啶，将其用氯乙酸处理以产生噻唑并嘧啶。通过使噻唑并嘧啶与吲哚-3-羧醛
• Synthesis of Some Novel 3-Substituted Indole Derivatives Using Polyamine Functionalized Heterogeneous Catalyst
  作者：Rupali L. Magar、Prashant B. Thorat、Jagdish L. Waware、Rameshwar R. More、Usha A. Solanke、Bhagwan R. Patil、Rajendra P. Pawar

  DOI：10.1002/jhet.2265

  日期：2015.11

  have described the use of polyamine solid supported GN3 as catalyst in organic transformations using 1H‐indole‐3‐carbaldehyde. To the best of our knowledge, reports for the synthesis of chromen substituted at 3C position of indole are extremely rare in the literature. The polyamine functionalized immobilized silica (GN3) was found to be an excellent catalyst for synthesis of novel 2‐amino‐4‐(1H‐indol‐3‐yl)‐5‐oxo‐4

  在目前的工作中，我们已经描述了使用多胺固体负载的GN3作为催化剂使用1 H-吲哚-3-甲醛进行有机转化。据我们所知，在文献中极少见有吲哚的3C位取代的铬烯合成报告。发现多胺官能化的固定化二氧化硅（GN3）是合成新型2-氨基-4-（（1 H-吲哚-3-基）-5-氧代-4,5-二氢吡喃[3,2- c ]色烯-3-腈衍生物和Knoevenagel缩合。催化剂GN3能够为多种产品提供出色的产量。此外，该催化剂可重复使用并重复使用几次，而不会损失其催化活性。
• SYNTHESIS AND ANTI-INFLAMMATORY ACTIVITY OF NEW THIAZOLIDINE-2,4-DIONES, 4-THIOXOTHIAZOLIDINONES AND 2-THIOXOIMIDAZOLIDINONES
  作者：L.C. SANTOS、F.T. UCHŌA、A.R.P.A. CANAS、I.A. SOUSA、R.O. MOURA、M.C.A. LIMA、S.L. GALDINO、I.R. PITTA、J. BARBE

  DOI：10.1515/hc.2005.11.2.121

  日期：2005.1

  compounds. In particular thiazolidines are known to show anti-inflammatory activity. With reference to this, synthesis of some 5-benzylidene-thioxoimidazolidinones and thioxothiazolidinones substituted at the position 3 by a benzyl (or phenacyl) group, were reported in previous papers [3-5]. Synthesis and physicochemical data of new 5-benzylidene-3-(4-chlorobenzyl)thiazolidine-2,4-diones 8-10 or 5-(l//

  新的亚苄基咪唑烷和噻唑烷衍生物是通过在氰基丙烯酸酯上由取代的硫代咪唑烷酮、噻唑烷二酮和硫代噻唑烷酮亲核加成而制备的。通过角叉菜胶诱导的爪水肿试验评价合成的噻唑烷的抗炎活性。简介 由于它们的药理特性 [1,2]，咪唑烷二酮和噻唑烷二酮是被广泛研究的化合物。特别是已知噻唑烷显示抗炎活性。与此相关，一些5-亚苄基-硫代咪唑烷酮和3位被苄基（或苯甲酰基）取代的硫代噻唑烷酮的合成在以前的论文中有所报道[3-5]。新型5-benzylidene-3-(4-chlorobenzyl)thiazolidine-2的合成及理化数据，4-二酮 8-10 或 5-(l//-indol-3-yl-methylene)-3-(4-chlorobenzyl)-4-thioxo-thiazolidin2-one 11（图 1）如下所示。这些化合物是从 3-(4-chlorobenzyl)thiazolidine-2,4-dione
• Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles
  作者：Ana M. F. Oliveira-Campos、Abdellatif M. Salaheldin、Filipe A. Almeida Paz、Ligia M. Rodrigues

  DOI：10.3998/ark.5550190.0012.b11

  日期：——

  The reaction of indole derivatives with cyanoacetic acid followed by treatment with DMFDMA gave the intermediate indolyl enaminonitriles 3. Further reaction with aminoguanidine yielded 5´-cyanomeridianin analogues 4. The same intermediate reacted with p-methoxyphenylhydrazine to give the pyrazolyl derivative 8. Treatment of (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate 3a with hydroxylamine hydrochloride

  吲哚衍生物与氰基乙酸反应，然后用 DMFDMA 处理得到中间体吲哚烯氨基腈 3。与氨基胍进一步反应产生 5'-氰基花青素类似物 4。相同的中间体与对甲氧基苯肼反应得到吡唑基衍生物 8. ( 2E)-3-二甲氨基-2-(1H-吲哚-3-基)-丙烯酸酯3a与盐酸羟胺在碱性介质中得到(5-氨基-异恶唑-4-基)-(1H-吲哚-3-基)-分别在短时间或长时间加热后得到甲酮 5 和丙烯酸衍生物 6。后一种化合物的明确结构说明是通过单晶 X 射线衍射研究实现的。
• Metal-organic framework (ZIF-8) for Knoevenagel condensation and multi-components Biginelli Reaction
  作者：Mostafa Sayed、Ahmed Soliman、Hani Nasser Abdelhamid

  DOI：10.1016/j.jssc.2023.124534

  日期：2024.4

  numerous advantages in the realm of organic synthesis, particularly in the construction of physiologically active organic blocks. This study utilized zeolitic imidazolate framework-8 (ZIF-8) as a heterogeneous catalyst in the Knoevenagel condensation and Biginelli reaction. ZIF-8 was synthesized under varying conditions, both in the presence and absence of guest molecules such as benzoic acid, terephthalic

  金属有机框架（MOF）是一种多相催化剂，在有机合成领域，特别是在构建生理活性有机嵌段方面具有众多优势。本研究利用咪唑骨架沸石 8 (ZIF-8) 作为 Knoevenagel 缩合和 Biginelli 反应中的多相催化剂。ZIF-8 是在不同条件下合成的，包括存在和不存在客体分子（例如苯甲酸、对苯二甲酸和碳酸盐）。研究了通过使用不同的醛与丙二腈或氰基乙酸乙酯组合来合成各种α,β-不饱和腈或酯。研究了 ZIF-8 对反应产率的影响，并评估了广泛的底物范围。此外，ZIF-8在Biginelli反应中的应用在多种二氢嘧啶酮/硫酮的合成中表现出显着的催化功效。ZIF-8 材料的产率高于 99%。在五个周期内检查了催化剂的可回收性，结果表明催化剂的反应活性没有显着下降。