5-hydroxy-2-phenyl-7-(4-(piperidin-1-yl)butoxy)-4H-chromen-4-one

• 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: 5-hydroxy-2-phenyl-7-(4-(piperidin-1-yl)butoxy)-4H-chromen-4-one
• 英文别名: 5-hydroxy-2-phenyl-7-(4-piperidin-1-yl-butoxy)-chromen-4-one；5-Hydroxy-2-phenyl-7-(4-piperidin-1-ylbutoxy)chromen-4-one
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: WYFMWLOQWAVSBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-hydroxy-2-phenyl-7-(4-(piperidin-1-yl)butoxy)-4H-chromen-4-one 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 在 碳酸氢钠 作用下， 生成
  参考文献：
  名称：

  白杨素衍生配体半夹心Ru、Rh和Ir配合物的抗癌活性：配体中侧链的强作用和金属的影响

  摘要：

  抗癌化疗领域的一个重要挑战是寻找新物种来克服标准药物的耐药性。一种有趣的方法是将生物活性配体与金属片段连接。在这项工作中，我们合成了一组对-伞花烃-Ru或环戊二烯基-M（M = Rh，Ir）配合物，其中四个白杨素衍生的前配体在环A的7位上具有不同的-OR取代基。白杨素上的哌啶环产生高细胞毒性前配体HL4及其金属配合物L4-M （SW480 和 A549 细胞系，细胞毒性顺序： L4-Ir > L4-Ru ≈ L4-Rh ）。 HL4及其复合物诱导细胞凋亡并可以克服顺铂耐药性。然而，事实证明， HL4在健康细胞中的细胞毒性比在肿瘤细胞中的细胞毒性更大，与其金属络合物相比，HL4 对癌细胞表现出比顺铂更高的选择性。所有L4-M复合物均与双链 DNA 相互作用。尽管如此，金属的影响是显而易见的，因为只有复杂的L4-Ir才会通过产生高活性氧 ( 1 O 2 ) 来导致 DNA 裂解。这一结果支持了

  DOI：

  10.3390/pharmaceutics13101540
• 作为产物：
  描述：

  白杨素 在 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 5-hydroxy-2-phenyl-7-(4-(piperidin-1-yl)butoxy)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel C (7) modified chrysin analogues as antibacterial agents

  摘要：

  The natural product, chrysin (5,7-dihydroxy flavone), obtained from Oroxylum indicum, exhibits numerous biological activities including anticancer, anti-inflammatory, and antiallergic activities. Three series of chrysin analogues were prepared, in which chrysin and heterocyclic moieties are separated by 3-carbon, 4-carbon, and 6-carbon spacers. All the derivatives were screened for antibacterial activity against a panel of susceptible and resistant Gram-positive and Gram-negative organisms. It was observed that most of the derivatives displayed significant activity as compared to their parent compound (chrysin). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.009

文献信息

• [EN] FLAVANOID COMPOUNDS AND PROCESS FOR PREPARATION THEREOF<br/>[FR] COMPOSÉS FLAVANOÏDES ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2010097816A1

  公开（公告）日：2010-09-02

  The present invention relates to flavanoid compounds of general formula (X1) wherein: R1 is selected from a group consisting of morpholinyl, N-methyl piperizinyl, piperidinyl and N,N'-dimethylamino groups, and n ranges from 3 to 6, and process for preparation thereof. The present invention relates to the demonstration of anti Helicobacter pylori activity and gastric antisecretory activity of semisynthetically designed flavonoid compounds, to be used for the prevention and treatment of gastroduodenal disorders in general and peptic ulcer diseases in particular. The present invention also relates to a hetero-dimeric bi-functional molecule that can be used as monotherapy substituting/replacing/overcoming currently used triple/quadruple therapy, thereby implicating/ anticipating/envisaging its commercial applicability.

  本发明涉及一般式为（X1）的黄酮类化合物，其中：R1从包括吗啡啶基、N-甲基哌嗪基、哌啶基和N,N'-二甲基氨基等基团中选择，n的范围为3至6，并涉及其制备方法。本发明涉及半合成设计的黄酮类化合物展示抗幽门螺杆菌活性和胃分泌抑制活性，可用于预防和治疗胃十二指肠疾病，特别是消化性溃疡。本发明还涉及一种异源二聚体双功能分子，可用作单疗法替代/取代/克服目前使用的三联/四联疗法，从而暗示/预期/设想其商业适用性。
• Luminescent cyclometalated platinum compounds with N, P, and O^O ligands: Density‐functional theory studies and analysis of the anticancer potential
  作者：Jorge Leal、Gema Durá、Félix A. Jalón、Elisenda Zafon、Anna Massaguer、José Vicente Cuevas、Lucia Santos、Ana M. Rodríguez、Blanca R. Manzano

  DOI：10.1002/aoc.6983

  日期：2023.3

  different in nature to those of 1–4. Time-dependent DFT (TD-DFT) calculations showed that for 1–4 the excited states S1 and T1 reflect metal-to-ligand charge transfer (MLCT) and ligand-centered (LC) (C^N) contributions while for 5–6 these states are an LC transition centered on L1 or L2. The speciation in DMSO and DMSO/H2O was evaluated. Biological studies showed that [Pt(thpy)Cl(Hthpy)], 1, [Pt(dfppy)Cl(Hdfppy)]

  发光的铂环金属化配合物之所以受到关注，主要是因为它们在光电和生物领域的应用，尤其是在抗癌活性方面。鉴于这种兴趣水平，一系列环金属化（2-[2'-噻吩基]吡啶酸盐，thpy 和 2-[2,4-二氟苯基] 吡啶酸盐，dfppy）铂络合物与 N-供体，PTA（1,3,5 -triaza-7-phosphaadamantane) 或白杨素衍生的配体（掺入哌啶HL1或吗啉HL2片段）被合成。复合物是发光的，发射波长可调。[Pt(dfppy)L1], 5在溶液中观察到聚集. 密度泛函理论 (DFT) 研究描述了最高占据分子轨道 (HOMO) 和最少未占据分子轨道 (LUMO) 特征及其对光物理性质的影响。5 – 6的轨道在性质上与1 – 4的轨道不同。时间相关 DFT (TD-DFT) 计算表明，对于1 – 4，激发态 S 1和 T 1反映了金属到配体电荷转移 (MLCT) 和以配体为中心 (LC) (C^N)
• Flavanoid Compounds and Process for Preparation Thereof
  申请人：Dab Pratap Kumar

  公开号：US20120022062A1

  公开（公告）日：2012-01-26

  The present invention relates to flavanoid compounds of general formula (X 1 ) wherein: R 1 is selected from a group consisting of morpholinyl, N-methyl piperizinyl, piperidinyl and N,N′-dimethylamino groups, and n ranges from 3 to 6, and process for preparation thereof. The present invention relates to the demonstration of anti Helicobacter pylori activity and gastric antisecretory activity of semisynthetically designed flavonoid compounds, to be used for the prevention and treatment of gastroduodenal disorders in general and peptic ulcer diseases in particular. The present invention also relates to a hetero-dimeric bi-functional molecule that can be used as monotherapy substituting/replacing/overcoming currently used triple/quadruple therapy, thereby implicating/anticipating/envisaging its commercial applicability.
• FLAVANOID COMPOUNDS AND PROCESS FOR PREPARATION THEREOF
  申请人：Council of Scientific & Industrial Research

  公开号：US20150174135A1

  公开（公告）日：2015-06-25

  The present invention relates to flavanoid compounds of general formula (X 1 ) wherein: R 1 is selected from a group consisting of morpholinyl, N-methyl piperizinyl, piperidinyl and N,N′-dimethylamino groups, and n ranges from 3 to 6, and process for preparation thereof. The present invention relates to the demonstration of anti Helicobacter pylori activity and gastric antisecretory activity of semisynthetically designed flavonoid compounds, to be used for the prevention and treatment of gastroduodenal disorders in general and peptic ulcer diseases in particular. The present invention also relates to a hetero-dimeric bi-functional molecule that can be used as monotherapy substituting/replacing/overcoming currently used triple/quadruple therapy, thereby implicating/anticipating/envisaging its commercial applicability.
• US8969384B2
  申请人：——

  公开号：US8969384B2

  公开（公告）日：2015-03-03