2-amino-4-(2,5-dimethoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2-amino-4-(2,5-dimethoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile
• 化学式: C₂₂H₁₈N₂O₃
• 分子量: 358.397
• InChiKey: IXJUELOQZXGJFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(2,5-dimethoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile 在 溶剂黄146 作用下， 生成 7-(2,5-dimethoxyphenyl)-N-(2-fluorophenyl)-7H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-amine
  参考文献：
  名称：

  Facile synthesis and antiproliferative activity of 7H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-amines

  摘要：

  A series of 7H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-amines 6a-t were synthesized as new potential antiproliferative agents. The in vitro antiproliferative activity evaluation of title compounds using MU assay revealed that most compounds showed significant activity against tested cancer cell lines (A549, MOLT-4, and HeLa). The 2-fluoro-aniline derivatives 6e and 61 were the most active compounds against A549 and MOLT-4 cells, respectively. The benzylamine analog 6h showed superior activity against HeLa cells. However, compound 61 with IC50 values of 5.2-6.9 mu M had the best profile of activity against all tested cell lines. The morphological and flow cytometric analyses showed that compound 61 can induce apoptosis in the MOLT-4 cells. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.12.037
• 作为产物：
  描述：

  萘酚 、 2,5-二甲氧基苯甲醛 、 丙二腈 在 Fe₃O₄ supported sulfonated graphene oxide nanoparticles 作用下， 以 乙醇 、 水 为溶剂， 反应 0.22h， 以90%的产率得到2-amino-4-(2,5-dimethoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile
  参考文献：
  名称：

  Fe3O4 负载的磺化氧化石墨烯作为绿色和磁性可分离纳米催化剂用于合成 2-氨基-3-氰基-4H-色烯衍生物及其计算机研究

  摘要：

  摘要 在超声照射下，通过脂肪/芳香/杂环醛、丙二腈和α-萘酚/β-的一锅三组分多米诺 Knoevenagel-Michael 缩合反应制备了 17 个 2-Amino-3-cyano-4H-chromene 衍生物。萘酚/间苯二酚在 Fe 3 O 4负载的磺化氧化石墨烯存在下作为 H 2中的绿色磁性可分离纳米催化剂O: EtOH (1:1) 溶剂系统。FT-IR、TGA、SEM和XRD用于评估催化剂。目前的协议具有吸引力，因为原子经济性高（95%）、产率高（88-95%）、反应时间短、无废物条件、成本效益高、使用无毒溶剂、无需高温回流, 产品的非色谱纯化, 催化剂的可回收性等。对选定的蛋白质 DNA 旋转酶 (1KZN) 和 CYP51 (4WMZ) 进行了计算机研究, 以研究最高对接分数4h (-8.8 kcal/mol ) 的对接相互作用) 和4e (-10.1 kcal/mol)。还进行了对接化合物和参考药物的

  DOI：

  10.1080/00397911.2022.2120404

文献信息

• Serendipitous Observation of Liquid-Phase Size Selectivity inside a Mesoporous Silica Nanoreactor in the Reaction of Chromene with Formic Acid
  作者：Paramita Das、Suman Ray、Piyali Bhanja、Asim Bhaumik、Chhanda Mukhopadhyay

  DOI：10.1002/cctc.201701975

  日期：2018.5.24

  product switches from pyrimidine to enol lactones and δ‐keto acids inside the nanoreactor. The shape/size selectivity in the liquid phase is a highly desired phenomenon in organic synthesis. We prepared four different varieties of porous silica materials to obtain this product selectivity. Very high yields of these biologically relevant compounds surpass that achieved by existing methodologies. Again

  在液相色谱中，作为纳米反应器的MCM-41内，在色烯与甲酸的水解/脱羧反应序列中，观察到了前所未有的产品形状/尺寸选择性。预计烯会在与HCOOH的反应中形成嘧啶。然而，在此偶然地，产物从嘧啶变为烯醇内酯和δ纳米反应器内部的酮酸。液相中的形状/尺寸选择性是有机合成中非常需要的现象。我们准备了四种不同的多孔二氧化硅材料，以获得这种产品的选择性。这些生物学上相关的化合物的非常高的产率超过了现有方法所获得的产率。再次，尽管很少有香豆素融合的烯醇内酯的报道，但是这种方法可以轻松合成萘融合的烯醇内酯。此外，这是在许多水解/脱羧/开环/互变异构/脱羧步骤之后的第一个δ-酮酸的一般合成方法。
• Aegle marmelos in heterocyclization: greener, highly efficient, one-pot three-component protocol for the synthesis of highly functionalized 4H-benzochromenes and 4H-chromenes
  作者：Sachin Shinde、Shashikant Damate、Smita Morbale、Megha Patil、Suresh S. Patil

  DOI：10.1039/c6ra28779d

  日期：——

  A facile, one-pot three-component protocol for the synthesis of 2-amino-4H-chromene derivatives has been demonstrated using Bael Fruit Extract (BFE) as a natural catalyst in a green reaction medium. This method offers a mild, efficient and highly economical protocol since the reaction proceeds in natural BFE-catalyst at room temperature under aerobic conditions with a very short reaction time (30 min)

  使用Bael水果提取物（BFE）作为绿色反应介质中的天然催化剂，已经证明了用于合成2-氨基-4 H-色烯衍生物的一种简便的一锅三组分方案。该方法提供了温和，有效和高度经济的方案，因为该反应在需氧条件下于室温下在天然BFE催化剂中进行，在配体/外部催化剂/无外部助催化剂的条件下，反应时间非常短（30分钟），因此，它是现有协议的绿色环保选择。通过热处理，然后水提取Aegle marmelos（bael）果皮的外皮得到催化剂。还发现它是清洁的，高产率的并且具有大规模合成的能力。
• Iodine mediated synthesis of coumarins from chromenes
  作者：Himanshu Sharma、Mohini Mourya、Lokesh K. Soni、Debanjan Guin、Yogesh C. Joshi、Mahaveer P. Dobhal、Ashok K. Basak

  DOI：10.1016/j.tetlet.2015.11.019

  日期：2015.12

  Iodine mediated rapid conversion of 2-amino-3-cyano-4-aryl-4H chromenes to the corresponding coumarins in the presence of water is described. Several chromenes are obtained in high yields without chromatographic purification. Under anhydrous conditions, 2-iminochromenes are obtained as major products. (C) 2015 Elsevier Ltd. All rights reserved.
• Facile synthesis and antiproliferative activity of 7H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-amines
  作者：Hamidreza Akrami、Maliheh Safavi、Bibi Fatemeh Mirjalili、Mahmood Dehghani Ashkezari、Farhang Dadfar、Najme Mohaghegh、Saeed Emami、Fahimeh Salehi、Hamid Nadri、Sussan K. Ardestani、Loghman Firoozpour、Mehdi Khoobi、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2016.12.037

  日期：2017.2

  A series of 7H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-amines 6a-t were synthesized as new potential antiproliferative agents. The in vitro antiproliferative activity evaluation of title compounds using MU assay revealed that most compounds showed significant activity against tested cancer cell lines (A549, MOLT-4, and HeLa). The 2-fluoro-aniline derivatives 6e and 61 were the most active compounds against A549 and MOLT-4 cells, respectively. The benzylamine analog 6h showed superior activity against HeLa cells. However, compound 61 with IC50 values of 5.2-6.9 mu M had the best profile of activity against all tested cell lines. The morphological and flow cytometric analyses showed that compound 61 can induce apoptosis in the MOLT-4 cells. (C) 2016 Elsevier Masson SAS. All rights reserved.