3-(4-chlorophenyl)-2-(1H-indole-3-carbonyl)acrylonitrile | 1013237-89-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4-chlorophenyl)-2-(1H-indole-3-carbonyl)acrylonitrile
• 英文别名: 3-(4-chlorophenyl)-2-(1H-indole-3-carbonyl)prop-2-enenitrile
• CAS: 1013237-89-2
• 化学式: C₁₈H₁₁ClN₂O
• 分子量: 306.751
• InChiKey: QBJDKFVHZFNPBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-2-(1H-indole-3-carbonyl)acrylonitrile 、 cyanomethyltriphenylarsonium bromide 在 potassium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.5h， 以85%的产率得到
  参考文献：
  名称：

  吲哚基和and基内酯的立体选择性合成环丙基吲哚基酮

  摘要：

  实现了从烯烃和ar烯立体选择性合成环丙基吲哚基酮的有效方法。它的优点是条件温和，产率高和良好的立体选择性。此外，还研究了烯烃与溴化物和三苯基ar的一锅法环丙烷化反应。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.432
• 作为产物：
  描述：

  4-氯苯甲醛 、 3-(1H-吲哚-3-基)-3-氧丙腈 以 乙二醇 为溶剂， 反应 0.17h， 以95%的产率得到3-(4-chlorophenyl)-2-(1H-indole-3-carbonyl)acrylonitrile
  参考文献：
  名称：

  微波辐射下合成3'-吲哚基取代杂环的多组分反应

  摘要：

  通过醛，3-氰基乙酰基吲哚与5-甲基苯的一锅多组分反应，合成了一系列多取代的（3'-吲哚基）吡唑并[3,4- b ]吡啶和（3'-吲哚基）苯并[ h ]喹啉衍生物。微波辐射下的氨基吡唑或萘胺。该方法特别有价值的特征包括高产量的产品，广泛的底物范围，较短的反应时间和简单的操作步骤。

  DOI：

  10.1016/j.tetlet.2008.02.101

文献信息

• InCl3 mediated one-pot synthesis of indol-3-yl pyridine and 2,2′-bipyridine derivatives through multi-component reaction
  作者：Prakasam Thirumurugan、Paramasivan T. Perumal

  DOI：10.1016/j.tet.2009.06.097

  日期：2009.9

  6-methoxy-4-aryl-2,2′-bipyridine-5-carbonitrile derivatives has been achieved through one-pot multi-component reaction under reflux condition. Particularly valuable features of this method include high yields of products in short reaction time and broad substrate scope. It is an efficient and promising synthetic strategy to build indol-3-yl pyridine and 2,2′-bipyridine skeletons.

  有效制备2-（1 H-吲哚-3-基）-6-甲氧基-4-芳基吡啶-3,5-二甲腈和6-甲氧基-4-芳基-2,2'-联吡啶的简单方案通过一锅多组分反应在回流条件下获得了-5腈衍生物。该方法的特别有价值的特征包括在短的反应时间内高产率的产品和广泛的底物范围。建立吲哚-3-基吡啶和2,2'-联吡啶骨架是一种有效而有前途的合成策略。
• Multicomponent reactions for the synthesis of new 3′-indolyl substituted heterocycles under microwave irradiation
  作者：Song-Lei Zhu、Shun-Jun Ji、Kai Zhao、Yu Liu

  DOI：10.1016/j.tetlet.2008.02.101

  日期：2008.4

  (3′-indolyl)benzo[h]quinoline derivatives were synthesized via one-pot multicomponent reactions of aldehydes, 3-cyanoacetyl indoles with 5-aminopyrazol or naphthylamine under microwave irradiation. Particularly valuable features of this method include high yields of products, broad substrate scope, short reaction time and straightforward procedure.

  通过醛，3-氰基乙酰基吲哚与5-甲基苯的一锅多组分反应，合成了一系列多取代的（3'-吲哚基）吡唑并[3,4- b ]吡啶和（3'-吲哚基）苯并[ h ]喹啉衍生物。微波辐射下的氨基吡唑或萘胺。该方法特别有价值的特征包括高产量的产品，广泛的底物范围，较短的反应时间和简单的操作步骤。
• Regioselective Three-Component Synthesis of Indolylpyrazolo[3,4- b]pyridines Induced by Microwave and under Solvent-Free Conditions
  作者：Jairo Quiroga、Jorge Trilleras、Ana Sanchez、Braulio Insuasty、Rodrigo Abonia、Manuel Nogueras、Justo Cobo

  DOI：10.2174/157017809788681284

  日期：2009.7.1

  New 4-(1H-indol-3-yl)-6-arylpyrazolo[3,4-b]pyridines 7 have been prepared in a solvent-free three-component reaction induced by microwave from 5-aminopyrazole 1, benzaldehydes 2 and 3-indolyl-3-oxopropanenitrile 5. These compounds were also obtained by means of the reaction of aminopyrazole 1 with benzylidene-derivatives of 3-(1H-indol- 3-yl)-3-oxopropanenitrile 6, prepared in the reaction of 3-(1H-indol-3-yl)-3-oxopropanenitrile and aldehydes.

  新型 4-(1H-吲哚-3-基)-6-芳基吡唑并[3,4-b]吡啶 7 是由 5-氨基吡唑 1、苯甲醛 2 和 3-吲哚基-3-氧代丙腈 5 通过微波诱导的无溶剂三组分反应制备的。这些化合物也是通过氨基吡唑 1 与 3-(1H-吲哚-3-基)-3-氧代丙腈和醛反应制备的 3-(1H-吲哚-3-基)-3-氧代丙腈 6 的亚苄基衍生物反应得到的。
• Domino reactions in water: diastereoselective synthesis of densely functionalized indolyldihydrofuran derivatives
  作者：Pethaiah Gunasekaran、Kamaraj Balamurugan、Sathiyamoorthi Sivakumar、Subbu Perumal、J. Carlos Menéndez、Abdulrahman I. Almansour

  DOI：10.1039/c2gc16517a

  日期：——

  A library of trans-5-aroyl-2-(indol-3-yl)-4-aryl-4,5-dihydrofuran-3-carbonitriles was diastereoselectively synthesized in excellent yields from the reaction of 2-(3-indolylcarbonyl)-3-aryl-2-propenenitriles with (2-aryl-2-oxoethyl)pyridinium bromides in the presence of triethylamine via a simple, user-friendly domino process carried out in water. Extraction and chromatographic steps were avoided, since the final products could be simply filtered from the aqueous reaction medium and recrystallized. This one-pot transformation generates one C–C and one C–O bond and presumably proceeds by a domino sequence involving the generation of a pyridinium ylide, a Michael addition and a final annulation via intramolecular nucleophilic substitution.

  反式-5-芳酰基-2-(吲哚-3-基)-4-芳基-4,5-二氢呋喃-3-甲腈化合物库是由 2-(3-吲哚羰基)-3-芳基-2-丙烯腈与(2-芳基-2-氧代乙基)溴化吡啶鎓在三乙胺存在下通过一个简单、易操作的多米诺过程在水中非对映选择性合成的，产量极佳。由于只需从水性反应介质中过滤并重结晶最终产物，因此避免了萃取和色谱步骤。这种一锅转化生成了一个 C-C 键和一个 C-O 键，并可能通过多米诺顺序进行，包括生成吡啶鎓酰亚胺、迈克尔加成和通过分子内亲核取代最终环化。
• Indole acrylonitriles as potential anti-hyperglycemic agents: Synthesis, α-glucosidase inhibitory activity and molecular docking studies
  作者：Mehwish Solangi、Kanwal、Khalid Mohammed Khan、Faiza Saleem、Shehryar Hameed、Jamshed Iqbal、Zainab Shafique、Urooj Qureshi、Zaheer Ul-Haq、Muhammad Taha、Shahnaz Perveen

  DOI：10.1016/j.bmc.2020.115605

  日期：2020.11

  One of the most prevailing metabolic disorder diabetes mellitus has become the global health issue that has to be addressed and cured. Different marketed drugs have been made available for the treatment of diabetes but there is still a need of introducing new therapeutic agents that are economical and have lesser or no side effects. The current study deals with the synthesis of indole acrylonitriles (3-23) and the evaluation of these compounds for their potential for alpha-glucosidase inhibition. The structures of these synthetic molecules were deduced by using different spectroscopic techniques. Acarbose (IC50 = 2.91 +/- 0.02 mu M) was used as standard in this study and the synthetic molecules (3-23) have shown promising alpha-glucosidase inhibitory activity. Compounds 4, 8, 10, 11, 14, 18, and 21 displayed superior inhibition of alpha-glucosidase enzyme in the range of (IC50 = 0.53 +/- 0.01-1.36 +/- 0.04 mu M) as compared to the standard acarbose. Compound 10 (IC50 = 0.53 +/- 0.01 mu M) was the most effective inhibitor of this library and displayed many folds enhanced activity in contrast to the standard. Molecular docking of synthetic compounds was performed to verify the binding interactions of ligand with the active site of enzyme. This study had identified a number of potential alpha-glucosidase inhibitors that can be used for further research to identify a potent therapeutic agent against diabetes.