3-(3′,5′-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(3′,5′-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• 英文别名: 3-(3,5-Dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: ITYKWBGUHDCECN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3′,5′-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-(3,5-dimethoxyphenyl)chroman-4-one
  参考文献：
  名称：

  3-氨基黄酮类化合物合成的细胞静止缩合O，N-杂环的合成及HPLC-ECD研究

  摘要：

  合成了具有在C-3-C-4键上与吗啉，噻唑或吡咯部分缩合的2-芳基苯并二氢吡喃或2-芳基-2 H-亚甲基亚基的外消旋手性O，N-杂环通过将顺式或反式-3-氨基黄酮类似物环化。3-氨基黄烷酮前体是在黄烷酮的肟甲苯磺酸盐的Neber重排中获得的，这提供了反式非对映异构体作为主要产物，并能够分离顺式和反式非对映异构体。该顺-和反式-氨基黄酮被用于制备5-芳基-铬诺[4,3-b] [ 1,4 ]恶嗪的三种非对映异构体。评估了稠合的杂环和前体的抗增殖活性，针对A2780和WM35癌细胞系。对于3-（N-氯乙酰氨基）-flavan-4-ol衍生物，显示与无环酸神经酰胺酶抑制剂的结构相似性，针对A2780，WM35和HaCat细胞系，测量了0.15μM，3.50μM和6.06μM的IC 50值，并证实了其凋亡机制。噻唑和吡咯缩合的2 H的低微摩尔IC 50值低至2.14μM-色烯衍生物。使用手性固定相通

  DOI：

  10.3390/biom10101462
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 、 2'-羟基苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以55%的产率得到3-(3′,5′-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  查耳酮A环和B环上的取代基对抗寄生虫活性的影响

  摘要：

  查耳酮是一组天然产物，具有许多公认的生物活性，包括抗寄生虫活性。尽管已经合成了许多查耳酮并对其进行了抗寄生虫分析，但已知与这种生物学特性有关的结构特征的数量很少。因此，在本研究中，合成了 21 种查耳酮，以确定 A 和 B 环中的取代基对巴西利什曼原虫、克氏锥虫和恶性疟原虫的活性的影响。这些化合物以结构依赖的方式对巴西乳杆菌有活性。只有一种化合物对 T. cruzi 非常有效，但没有一种化合物具有显着的抗疟原虫活性。B环中的给电子取代基和C-2'与羰基的氢键影响抗寄生虫活性。

  DOI：

  10.1002/ardp.202000157

文献信息

• Silica-Supported Silver as a Green and Sustainable Catalyst for the [3+2]-Cycloaddition Reaction of Azomethine Ylides with 2′-Hydroxychalcone Derivatives
  作者：Suchithra Madhavan、Sentaro Okamoto

  DOI：10.1002/cctc.201702035

  日期：2018.5.9

  A reusable heterogeneous silver nanoparticle catalyst supported on silica was used for the [3+2]‐cycloaddition reaction of azomethine ylides with 2′‐hydroxychalcone derivatives. The green and sustainable catalytic protocol afforded highly functionalized pyrrolidines, indolizidines, and pyrrolizidines in good yields with high regio‐ and diastereoselectivities.

  负载在二氧化硅上的可重复使用的异质银纳米颗粒催化剂用于偶氮甲亚胺与2'-羟基查耳酮衍生物的[3 + 2]-环加成反应。绿色和可持续的催化方案以高收率和高区域选择性和非对映选择性提供了高度官能化的吡咯烷，吲哚并咪唑和吡咯烷。
• Guanidino-Graphene Catalysed Synthesis of Flavones via Aldol-Michael-Oxidation
  作者：Sweta Mishra、Smriti Arora、Ritika Nagpal、Shive Murat Singh Chauhan

  DOI：10.1166/jnn.2017.12644

  日期：2017.4.1

  Guanidino-graphene has been synthesized by the reaction of bromoamine with reduced graphene oxide and characterized by FT-IR, Raman, TGA, powder XRD, TEM, SEM, and zeta potential. It is a cheap, heterogeneous and environmentally benign solid base catalyst used for cascade Aldol-Michael-oxidation in the synthesis of chalcone, flavonoids.

  通过溴胺与还原氧化石墨烯的反应合成了胍基石墨烯，并通过傅立叶变换红外光谱、拉曼光谱、热重分析、粉末 XRD、TEM、SEM 和 ZETA 电位对其进行了表征。它是一种廉价、异构和无害环境的固体基础催化剂，可用于合成查尔酮和黄酮类化合物的级联醛-迈克尔氧化反应。
• Access to Chromenopyrrole via Tandem [3 + 2] Cycloaddition and Intramolecular C–O Coupling
  作者：Bubul Das、Nikita Chakraborty、Hirendra Nath Dhara、Pratip Bhattacharyya、Bhisma K. Patel

  DOI：10.1021/acs.joc.3c02479

  日期：2024.1.19

  A mild and concise method for the synthesis of chromenopyrrole from 2′-hydroxychalcone is devised. The reaction proceeds via an initial [3 + 2] cycloaddition on the C═C bond of 2′-hydroxychalcone and 1,3-dipolarophile, generated in situ by the reaction of ethyl isocyanoacetate and AgOAc. This is then followed by an intramolecular C–O bond formation with the −OH group and C5–H of the in situ generated

  设计了一种温和、简洁的从 2'-羟基查尔酮合成色吡咯的方法。该反应通过 2'-羟基查耳酮和 1,3-亲偶极试剂的 C=C 键上的初始 [3 + 2] 环加成进行，该键是由异氰基乙酸乙酯和 AgOAc 反应原位生成的。然后与原位生成的吡咯的 -OH 基团和 C5-H 形成分子内 C-O 键，形成色并吡咯。
• Synthesis and biological evaluation of novel flavonols as potential anti-prostate cancer agents
  作者：Robert G. Britton、Emma Horner-Glister、Odette A. Pomenya、Ewan E. Smith、Roanne Denton、Paul R. Jenkins、William P. Steward、Karen Brown、Andreas Gescher、Stewart Sale

  DOI：10.1016/j.ejmech.2012.06.031

  日期：2012.8

  A library of flavonol analogues was synthesised and evaluated as potential anticancer agents against a human prostate cancer cell line, 22rv1. Compounds 3, 8 and 11 (IC50 2.6, 3.3 and 4.0 mu M respectively) showed potent cancer cell growth inhibition, comparable to the lead compound 3',4',5'-trimethoxyflavonol (1) (IC50 3.1 mu M) and superior to the naturally occurring flavonols quercetin (16) and fisetin (22) (both >15 mu M). Results indicate that the 3',4',5'- arrangement of either hydroxy (OH) or methoxy (OMe) residues is important for growth arrest of these cells and that the OMe analogues may be superior to their OH counterparts. Compounds 1, 3, 8 and 11 warrant further investigation as potential agents for the management of prostate cancer. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Aspergillus niger catalyzes the synthesis of flavonoids from chalcones
  作者：Julio Alarcón、Joel Alderete、Carlos Escobar、Ramiro Araya、Carlos L. Cespedes

  DOI：10.3109/10242422.2013.813489

  日期：2013.8

  Flavonoids, which have many biological activities and have been widely used in nature, can be artificially synthesized. However, regioselective cyclization of chalcones is difficult by chemical methods. In this study, we demonstrated that Aspergillus niger is capable of cyclizing chalcones to flavanones, affording a mimic of plant biosynthetic processes. Chalcones 1-6 were biotransformated to the modified chalcones 8-14 and to the flavanones 15-27. The biotransformation showed that enzymatic cyclization and demethylation occurred during the first days of biotransformation; in contrast, hydroxylation is a later process. With a longer culturing time, it is possible to obtain more hydroxylated flavanones with excellent yields.