(+/-)-2-<4-Dimethylamino-phenyl>-chromanon-(4) | 77038-22-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (+/-)-2-<4-Dimethylamino-phenyl>-chromanon-(4)
• 英文别名: 4H-1-Benzopyran-4-one, 2-[4-(dimethylamino)phenyl]-2,3-dihydro-；2-[4-(dimethylamino)phenyl]-2,3-dihydrochromen-4-one
• CAS: 77038-22-3
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: MDSBXFQOYRGPIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-<4-Dimethylamino-phenyl>-chromanon-(4) 生成 (2e)-3-[4-(二甲氨基)苯基]-1-(2-羟基苯基)-2-酮
  参考文献：
  名称：

  不仅是AIE：4-二甲基氨基-2'-羟基查尔酮的光敏性对4'-二甲基氨基黄酮的高效光化学合成有利

  摘要：

  晶体中的4-二甲基氨基-2'-羟基查耳酮因其在光谱红色区域的聚集诱导发射（AIE）而闻名。但是，我们观察到在液体溶液中，这种染料及其类似物经历了可逆的依赖于波长的光诱导环化为黄烷酮衍生物。因此，当该化合物用于要求高纯度的光电应用时，应格外小心，尤其是通过溶液加工方法。讨论的分子内环化反应在非极性介质中进行得更快，并在质子溶剂存在下或通过在结晶相中形成聚集体而完全淬灭。尽管单个光诱导转变的量子产率不超过1％，连续照射可提供92％的产物，这使其成为之前报道的4'-二甲基氨基黄酮及其衍生物的最有效制备途径。根据实验研究的光谱特征支持的DFT和TDDFT计算，光诱导形成4'-二甲基氨基黄酮的机理涉及几种转化：激发态分子内质子转移（ESIPT），激发态和基态旋转异构化通过基态质子转移，将反式转化为顺式异构体，环化和烯醇-酮互变异构。

  DOI：

  10.1016/j.molliq.2020.113526
• 作为产物：
  描述：

  2'-hydroxy-4-dimethylaminochalcone 在 水 、 三氯氧磷 作用下， 反应 1.5h， 以88%的产率得到(+/-)-2-<4-Dimethylamino-phenyl>-chromanon-(4)
  参考文献：
  名称：

  水介导的磷酸化环化脱氢：黄酮和黄烷酮的有效制备

  摘要：

  摘要 开发了一种利用 POCl3-水将 2'-羟基查耳酮转化为黄烷酮和黄酮的新合成策略。该试剂通过涉及环化和氧化脱氢的黄烷酮有效地促进了 2'-羟基查尔酮向黄酮的一锅法转化。通过改变试剂的化学计量，可以调整反应以生成黄烷酮或黄酮。发现开发的协议适用于各种 2'-羟基查尔酮。图形概要

  DOI：

  10.1080/00397911.2019.1643484

文献信息

• Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis
  作者：Yuanyuan Zheng、Wenchen Pu、Jiao Li、Xianyan Shen、Qiang Zhou、Xin Fan、Sheng-Yong Yang、Yamei Yu、Qiang Chen、Chun Wang、Xin Wu、Yong Peng

  DOI：10.1002/asia.201801461

  日期：2019.1.4

  isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7‐(benzyloxy)‐3,5‐dihydroxy‐2‐(4‐methoxyphenyl)‐8‐(3‐methylbut‐2‐en‐1‐yl)‐4H‐chromen‐4‐one (AF‐39) was identified as a novel Pin1

  肽脯氨酰顺-反异构酶中Pin1在人类癌症的发展至关重要的作用。最近，我们披露了Pin1调节miRNA的生物发生，miRNA在HCC中异常表达并促进HCC进展，表明Pin1在HCC治疗中的治疗作用。在此，7-（苄氧基）-3,5-二羟基-2-（4-甲氧基苯基）-8-（3-甲基丁-2-烯-1-基）-4H-铬-4--1（AF-39）被鉴定为新型的Pin1抑制剂。生化试验表明，AF-39有效抑制中Pin1活性，其IC 50的1.008μ值米，并且还显示中肽基脯氨酰异构酶对中Pin1高选择性。此外，AF‐39以剂量和时间依赖性方式显着抑制HCC细胞的细胞增殖。从机制上讲，AF-39调节XPO5的亚细胞分布并增加HCC细胞中miRNA的生物发生。这项工作为HCC治疗提供了有希望的先导化合物，突出了基于miRNA的疗法对人类癌症的治疗潜力。
• Glycolytic Inhibition and Antidiabetic Activity on Synthesized Flavanone Scaffolds with Computer Aided Drug Designing Tools
  作者：Natarajan Kiruthiga、Govindaraj Saravanan、Chellappa Selvinthanuja、Kulandaivel Srinivasan、Thangavel Sivakumar

  DOI：10.2174/1570180817999201209204523

  日期：2021.8.10

  Diabetes mellitus is a challengeable metabolic disorder that leads to a group of complications when the HbA1c level is not maintained. Most of the existing drugs available in the market in long-term use may lead to serious adverse effects. Hence, current research focuses on drug development for the management of diabetes by synthesizing natural mimicking flavonoid analogues.

  This study focused on the synthesis of flavanone derivatives imitating natural flavonoid core and investigated for their antidiabetic and antioxidant activity, which can help in the development of drug discovery targeting diabetic management.

  The novel 2-phenyl-2,3-dihydro-chromen-4-ones were synthesized from 1,3-diphenyl-prop-2-en-1-one derivatives and characterized using UV, IR, ¹HNMR, ¹³CNMR and mass spectroscopic techniques. Drug target site was determined using graph theoretical analysis and screened the characterized title compounds for their in-silico studies by analyzing their physiochemical properties, ADMET studies, and molecular docking analysis. Antidiabetic and free radical scavenging effects were investigated both by in-vitro (alpha-amylase inhibitory assay) and in-vivo models. Streptozotocin (STZ) induced rats were used as in-vivo models.

  The α-amylase inhibitory assay showed flavanones with hydroxyl substitution HFA1- HFA7 had significant IC50 values. The test compounds (HFA3-HFA7) were investigated for their antidiabetic activity on STZ induced rats at 40 mg/kg. The blood glucose level and antioxidant enzymes were significantly restored by title compounds (HFA5, HFA4, and HFA6) with an electron-donating group such as hydroxyl, methoxy and thiophenyl group on ring B compared to glibenclamide.

  These results suggest that naturally mimicking synthesized flavanone have antidiabetic and antioxidant properties, which can aid in the development of drugs towards diabetes management.

  背景：糖尿病是一种具有挑战性的代谢紊乱，当HbA1c水平未得到控制时会导致一系列并发症。市场上现有的大部分长期使用的药物可能会导致严重的不良反应。因此，当前的研究重点在于通过合成天然模拟类黄酮类似物来开发治疗糖尿病的药物。 目标：本研究侧重于合成模拟天然类黄酮核心的黄酮衍生物，并对其抗糖尿病和抗氧化活性进行研究，这有助于开发针对糖尿病管理的药物发现。 材料和方法：从1,3-二苯基-丙-2-烯-1-酮衍生物合成了新型的2-苯基-2,3-二氢-香豆素，并利用紫外线、红外线、核磁共振、质谱等技术对其进行表征。通过图论分析确定了药物靶点位点，并通过对其物理化学性质、ADMET研究和分子对接分析进行了体外研究。通过体外（α-淀粉酶抑制实验）和体内模型研究了抗糖尿病和自由基清除效果。利用链脲霉素（STZ）诱导的大鼠作为体内模型。 结果：α-淀粉酶抑制实验显示，具有羟基取代的黄酮类物质HFA1-HFA7具有显著的IC50值。将试验化合物（HFA3-HFA7）以40 mg/kg剂量用于STZ诱导的大鼠，发现HFA5、HFA4和HFA6等具有电子给予基团（如羟基、甲氧基和硫苯基）的化合物明显恢复了血糖水平和抗氧化酶活性，与格列本脲相比。 结论：这些结果表明，天然模拟合成的黄酮类物质具有抗糖尿病和抗氧化性能，有助于开发针对糖尿病管理的药物。
• Synthesis and kinetic study for the interconversion process of some 2'–hydroxychalcones to their corresponding flavanones
  作者：Zainab Majed、Said Said、Omar Shareef

  DOI：10.21608/ejchem.2020.22974.2363

  日期：2020.4.10

  were interpreted by a four-step mechanism which considered the existence of phenoxide ion as the key intermediate. The main reaction was achieved as a pseudo first order reaction in which the rate of the studied compounds followed the sequence 1>2>3>4>5, and the activation energy had the same sequence for these compounds. The reaction rate was affected by the electronic behavior of the different substituents

  在这项工作中，使用克莱森-施密特缩合法制备了五个取代的2'-羟基查耳酮，它们随后通过碱催化的异构化反应用作取代黄烷酮的合成酮。为了确定速率常数，已经对后一个过程进行了动力学研究。这些实验是使用HPLC技术在（8：2）（CH3CN：CH3OH）介质中于不同温度（298 K-318 K）下进行的。通过四步机理解释了获得的结果，该机理将酚盐离子的存在作为关键中间体。主要反应以拟一级反应完成，其中所研究化合物的速率遵循顺序1> 2> 3> 4> 5，并且这些化合物的活化能具有相同的序列。
• Synthesis, Biological Evaluation and In Silico Metabolic and Toxicity Prediction of Some Flavanone Derivatives
  作者：Narayana Subbiah Hari Narayana Moorthy、Rahul Jitendra Singh、Hemendra Pratap Singh、Sayan Dutta Gupta

  DOI：10.1248/cpb.54.1384

  日期：——

  flavone) possess various pharmacological activities and due to its xanthine-oxidase enzyme inhibitory effect it also has superoxide-scavenging activities. A series of 2-phenyl-2,3-dihydrochromon-4-one derivatives (flavanone derivatives) were synthesized from chalcones by cyclization method and their activities were evaluated against some gram positive and gram-negative bacteria. IR, NMR and CHN analysis

  黄酮化学上是花青素，以游离态或与单宁有关的糖苷（类黄酮）存在。类黄酮（黄酮的衍生物）具有多种药理活性，并且由于其具有黄嘌呤氧化酶抑制作用，因此还具有超氧化物清除活性。通过环化法从查耳酮合成了一系列的2-苯基-2,3-二氢色子-4-酮衍生物（黄酮衍生物），并评估了它们对某些革兰氏阳性和革兰氏阴性细菌的活性。IR，NMR和CHN分析证实了合成化合物的结构。抗菌研究的结果表明，化合物2b，2e，2f和2h具有对抗许多细菌菌株的活性。其中，化合物（2h）对所有菌株viz具有显着的活性。对金黄色葡萄球菌，S。sonnei，大肠杆菌，鼠伤寒沙门氏菌和霍乱弧菌的抑制浓度为25微克/毫升。化合物2f对大肠杆菌和鼠伤寒沙门氏菌的最低抑菌浓度为200微克/毫升，对S. sonnei，痢疾链球菌和霍乱弧菌的最小抑菌浓度为25微克/毫升。在计算机上对合成的化合物进行代谢和毒性研究，预测结果表明具有羟基官能团的化合
• 3-Methylene flavanones and 3-methylene chromanones, antimicrobial composition containing same and method of inhibiting the growth of microorganisms
  申请人：MILES LABORATORIES, INC.

  公开号：EP0025161A1

  公开（公告）日：1981-03-18

  Compounds which are 3-methylene flavanones and 3-methylene chromanones having activity against microorganisms are disclosed. The compounds are represented by the general structural formula: wherein: R' is a member selected from the group consisting of hydrogen, Br, CH3 and OCH3; R2 is selected from the group consisting of hydrogen and wherein R4 is a member selected from the group consisting of hydrogen, Br, Cl, CH3, OCH3, NO2, N/CH3)2, C(CH3)3 and CN; R' is selected from the group consisting of hydrogen and Cl, with the proviso that when R5 is Cl, R' is hydrogen or Cl; and R3 is selected from the group consisting of hydrogen, phenyl, 2-thienyl, 4-pyridyl and naphthyl, with the proviso that when R3 is naphthyl, R1 and R2 are hydrogen.

  本发明公开了具有抗微生物活性的 3-亚甲基黄烷酮和 3-亚甲基色满酮化合物。这些化合物由一般结构式表示： 其中R'选自由氢、Br、CH3 和 O 组成的组 其中 R4 选自由氢、Br、Cl、 、O 、NO2、N/ )2、C( )3 和 CN 组成的组；R'选自由氢和 Cl 组成的组，但当 R5 为 Cl 时，R'为氢或 Cl；以及 R3 选自由氢、苯基、2-噻吩基、4-吡啶基和萘基组成的组，但当 R3 为萘基时，R1 和 R2 为氢。