2-amino-5,10-dihydro-5,10-dioxo-4-(thiophen-2-yl)-4H-benzo[g]chromene-3-carbonitrile | 415942-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-amino-5,10-dihydro-5,10-dioxo-4-(thiophen-2-yl)-4H-benzo[g]chromene-3-carbonitrile
• 英文别名: 2-amino-5,10-dioxo-4-(thiophen-2-yl)-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile；2-amino-5,10-dioxo-4-thiophen-2-yl-4H-benzo[g]chromene-3-carbonitrile
• CAS: 415942-74-4
• 化学式: C₁₈H₁₀N₂O₃S
• 分子量: 334.355
• InChiKey: JANLCICVIXGIPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-5,10-dihydro-5,10-dioxo-4-(thiophen-2-yl)-4H-benzo[g]chromene-3-carbonitrile 、 环己酮 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 14-amino-13-(thiophen-2-yl)-2,3,4,13-tetrahydro-1H-benzo[6,7]chromeno[2,3-b]quinoline-7,12-dione
  参考文献：
  名称：

  Cu-metal organic frameworks (Cu-MOF) as an environment-friendly and economical catalyst for one pot synthesis of tacrine derivatives

  摘要：

  本研究描述了Cu-MOF的催化活性，用于在AlCl₃存在下通过2-羟基萘酮-1,4-二酮、醛、丙二腈和环酮的四组分反应一步合成Tacrine衍生物。

  DOI：

  10.1039/c9ra10111j
• 作为产物：
  描述：

  2-噻吩甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 2-amino-5,10-dihydro-5,10-dioxo-4-(thiophen-2-yl)-4H-benzo[g]chromene-3-carbonitrile
  参考文献：
  名称：

  Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-Pyrano-[2,3-b]naphthoquinones with anticancer activity

  摘要：

  4H-Pyrano-[2,3-b]naphthoquinone is a structural motif commonly found in natural products manifesting anticancer activities. As part of a program aimed at structural simplification of bioactive natural products utilizing multicomponent synthetic processes, we developed a compound library based on this heterocyclic scaffold. We found that several library members displayed low micromolar antiproliferative activity and induced apoptosis in human cancer cells. Selected compounds showed promising activity against cancer cell lines resistant to proapoptotic stimuli, demonstrating their potential in treating cancers with dismal prognoses. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.073

文献信息

• Zn(<scp>L</scp>-proline)₂as a powerful and reusable organometallic catalyst for the very fast synthesis of 2-amino-4<i>H</i>-benzo[<i>g</i>]chromene derivatives under solvent-free conditions
  作者：Behrooz Maleki、Saeed Babaee、Reza Tayebee

  DOI：10.1002/aoc.3306

  日期：2015.6

  An efficient route for the synthesis of 2‐amino‐4H‐benzo[g]chromenes via a three‐component coupling reaction of aldehydes, malononitrile and 2‐hydroxy‐1,4‐naphthaquinone in the presence of Zn( L‐proline)2 is reported. High yields, short reaction times, non‐toxicity and recyclability of the catalyst, and easy work‐up are the main merits of this protocol. Copyright © 2015 John Wiley & Sons, Ltd.

  在锌（L-脯氨酸）存在下，醛，丙二腈和2-羟基-1,4-萘醌的三组分偶联反应合成2-氨基-4 H-苯并[ g ]色烯的有效途径报告2。该方案的主要优点是高收率，较短的反应时间，催化剂的无毒性和可回收性以及易于后处理。版权所有©2015 John Wiley＆Sons，Ltd.
• Catalytic application of a nano-molten salt catalyst in the synthesis of biological naphthoquinone-based compounds
  作者：Meysam Yarie、Mohammad Ali Zolfigol、Saeed Babaee、Saeed Baghery、Diego A. Alonso、Abbas Khoshnood

  DOI：10.1007/s11164-018-3264-9

  日期：2018.4

  Abstract In this investigation, a new application of 1 H -imidazol-3-ium tricyanomethanide catalyst was explored. The catalyst presented a robust catalytic applicability for the preparation of naphthoquinone-based compounds under mild and green reaction conditions. A wide range of aromatic aldehydes were able to react with 2-hydroxynaphthalene-1,4-dione and 3-methyl-1-phenyl-1 H -pyrazol-5(4 H )-one

  摘要 在本研究中，探索了1 H- 咪唑-3-三氰基氨基甲烷催化剂的新应用 。该催化剂在温和和绿色的反应条件下，对于制备基于萘醌的化合物具有很强的催化适用性。多种芳族醛能够与2-羟基萘-1,4-二酮和3-甲基-1-苯基-1 H- 吡唑-5（4 H ）-一或丙二腈反应，得到所需的萘醌基分子在短时间内以高至优异的产率。 图形摘要 用2-羟基萘-1,4-二酮（henna）和3-甲基-1-苯基-1 H- 吡唑-5（4 H ）处理了各种芳香醛 或丙二腈可在短反应时间内提供所需的基于指甲花的目标分子，并具有良好或极好的收率。
• CeO₂/CuO@N‐GQDs@NH₂nanocomposite as a high‐performance catalyst for the synthesis of benzo[g]chromenes
  作者：Javad Safaei‐Ghomi、Fatemeh‐Sadat Bateni、Pouria Babaei

  DOI：10.1002/aoc.5657

  日期：2020.7

  A three‐component reaction of aromatic aldehydes, malononitrile or ethyl cyanoacetate and 2‐hydroxy‐1,4‐naphthaquinone has been achieved in the presence of an amino‐functionalized CeO2/CuO@ nitrogen graphene quantum dot nanocomposite as a highly effective heterogeneous catalyst to produce benzo[g]chromenes. The catalyst has been characterized by X‐ray diffraction, scanning electron microscopy, transmission

  在氨基官能化的CeO 2 / CuO @氮石墨烯量子点纳米复合物作为高效多相催化剂的存在下，已实现了芳族醛，丙二腈或氰基乙酸乙酯与2-羟基-1,4-萘醌的三组分反应。生产苯并[g]色烯。该催化剂的特征在于X射线衍射，扫描电子显微镜，透射电子显微镜，傅立叶变换红外光谱，能量色散X射线光谱，热重分析，X射线光电子光谱，Brunauer-Emmett-Teller（BET）和振动样品磁力计。该新催化剂已被证明在制备苯并[g]二甲基苯酮中非常有效。
• A facile route to the synthesis of 1,4-pyranonaphthoquinone derivatives under microwave irradiation without catalyst
  作者：Xing-Han Wang、Xiao-Hong Zhang、Shu-Jiang Tu、Feng Shi、Xiang Zou、Shu Yan、Zheng-Guo Han、Wen-Juan Hao、Xu-Dong Cao、Shan-Shan Wu

  DOI：10.1002/jhet.153

  日期：2009.9

  A series of 1,4-pyranonaphthoquinone derivatives were synthesized via the reaction of arylidenemalononitrile and 2-hydroxynaphthalene-1,4-dione in the mixed solvent of N,N-dimethylformamide and glacial acetic acid (HOAc) under microwave irradiation without catalyst. This protocol has the notable advantages of short reaction time, high yield, and convenient operation. J. Heterocyclic Chem., (2009).

  通过芳基丙二腈与苯并丙二腈反应合成了一系列1,4-吡喃萘醌衍生物。混合溶剂中的2-羟基萘-1,4-二酮N，N-二甲基甲酰胺和冰醋酸（HOAc）在无催化剂的微波辐射下。该方案的显着优点是反应时间短，收率高，操作方便。J.杂环化​​学，（2009）。
• Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-Pyrano-[2,3-b]naphthoquinones with anticancer activity
  作者：Igor V. Magedov、Artem S. Kireev、Aaron R. Jenkins、Nikolai M. Evdokimov、Dustin T. Lima、Paul Tongwa、Jeff Altig、Wim F. A. Steelant、Severine Van slambrouck、Mikhail Yu. Antipin、Alexander Kornienko

  DOI：10.1016/j.bmcl.2012.06.073

  日期：2012.8

  4H-Pyrano-[2,3-b]naphthoquinone is a structural motif commonly found in natural products manifesting anticancer activities. As part of a program aimed at structural simplification of bioactive natural products utilizing multicomponent synthetic processes, we developed a compound library based on this heterocyclic scaffold. We found that several library members displayed low micromolar antiproliferative activity and induced apoptosis in human cancer cells. Selected compounds showed promising activity against cancer cell lines resistant to proapoptotic stimuli, demonstrating their potential in treating cancers with dismal prognoses. (c) 2012 Elsevier Ltd. All rights reserved.