methyl 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetate | 314745-06-7

• 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: methyl 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetate
• 英文别名: methyl [(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]acetate；methyl 2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyacetate
• CAS: 314745-06-7
• 化学式: C₁₈H₁₄O₆
• 分子量: 326.306
• InChiKey: DQFQSWLRJGZJOV-UHFFFAOYSA-N

物化性质

• 沸点：
  536.9±50.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetate 在 甲醇 、 potassium hydroxide 作用下， 生成 2-(5-羟基-4-氧代-2-苯基-4H-色烯-7-基氧基)乙酸
  参考文献：
  名称：

  一种黄酮衍生物类氨肽酶N抑制剂及其制备方法和应用

  摘要：

  本发明属于有机化合物合成与医药应用技术领域，具体涉及一种黄酮衍生物类氨肽酶N抑制剂及其制备方法和应用。本发明所述黄酮衍生物类氨肽酶N抑制剂具有式(I)所示的结构：式(I)。体外抑制氨肽酶N活性试验显示，部分黄酮衍生物类氨肽酶N抑制剂的抑酶活性与阳性药乌苯美司相比，提高了一至两个数量级；个别黄酮衍生物类氨肽酶N抑制剂的抑酶活性达到了纳摩尔水平，解决了非肽类氨肽酶N抑制剂活性较差，结构单一的问题，丰富了氨肽酶N抑制剂的结构多样性。

  公开号：

  CN116655577A
• 作为产物：
  描述：

  白杨素 、 溴乙酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以94%的产率得到methyl 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetate
  参考文献：
  名称：

  新型白杨素-去烯丙基 PAC-1 杂化类似物作为抗癌化合物：设计、合成和生物学评价

  摘要：

  新的 chrysin-De-allyl-Pac-1 杂化类似物与可变杂环系统 (4a-4o) 相连，经过合理设计和合成。在三阴性乳腺癌 (TNBC) 细胞系、MDA-MB-231 和正常人乳腺上皮细胞 (HMEC) 中筛选目标化合物的体外抗增殖功效。两种化合物 4g 和 4i 对 MDA-MB-231 细胞具有最高的功效和选择性，因此通过机械实验进一步评估。结果表明，化合物 4g 和 4i 均通过 (1) 诱导 MDA-MB-231 细胞 G2 期细胞周期停滞和 (2) 以浓度依赖性方式激活内在凋亡途径来诱导细胞凋亡。这些化合物的物理化学特征表明它们可以进一步优化为潜在的 TNBC 细胞抗癌化合物。总体而言，我们的结果表明 4g 和 4i 可能是开发治疗 TNBC 的新型化合物的合适先导物。

  DOI：

  10.3390/molecules25133063

文献信息

• NO供体类化合物、组合物、制备方法和及其应用
  申请人：天津国际生物医药联合研究院

  公开号：CN110396086B

  公开（公告）日：2023-03-24

  本发明的目的在于提供NO供体类化合物、组合物、制备方法和及其应用，这些化合物组合物在体外抗癌活性测试中表现了很高的抗癌活性，尤其对乳腺癌细胞MDA‑MB‑231、SUM159、MCF‑7、SKBR‑3和4T1具有抑制活性，并且有些化合物的抑制活性高达1μM，可作为治疗癌症的药物以及癌症辅助治疗的药物使用。
• <p>Design, synthesis, and biologic evaluation of novel chrysin derivatives as cytotoxic agents and caspase-3/7 activators</p>
  作者：Buthina Abdallah Al-Oudat、Mohammad Ali Alqudah、Suaad Abdallah Audat、Qosay Ali Al-Balas、Tamam El-Elimat、Mohammad Abdelhafeez Hassan、Islam Nawaf Frhat、Marwah Mohammad Azaizeh

  DOI：10.2147/dddt.s189476

  日期：——

  Background: Chrysin (5,7-dihydroxyflavone) is a widely distributed natural flavonoid found in many plant extracts, honey and propolis. Several studies revealed that chrysin possesses multiple biological activities including anti-cancer effects. It has been established that activation of apoptosis is the key molecular mechanism responsible for the cytotoxic potential of chrysin. The objective of this study was to design and synthesize potent chrysin analogues as potential cytotoxic agents.Methods: A series of chrysin derivatives (3a-m) bearing N'-alkylidene/arylideneacetohydrazide moiety were designed, synthesized, and evaluated for their antiproliferative activity against two human breast cancer cell lines, MDA-MB-231 and MCF-7 by applying the MTT colorimetric assay. Selected compounds were tested for their ability to induce apoptosis through caspase 3/7 activation in MDA-MB-231 cells only since MCF-7 cells lack procaspase 3.Results: Compounds (3a-m) were obtained as geometrical isomers (E/Z isomers) in good yields upon treatment of hydrazide 5 with different aliphatic and aromatic aldehydes. Most of the synthesized compounds demonstrated moderate-to-good activity against both cell lines. The cytotoxicity results revealed the importance of lipophilic moieties at C-4 position of ring D in imparting the cytotoxic activities to the compounds. Compound 3e with 4-benzyloxy substituent was found to be the most active among the synthesized compounds with IC50 3.3 mu M against MDA-MB-231 and 4.2 mu M against MCF-7 cell lines. The cytotoxic potential of compound 3e is comparable to that of the well-known anti-cancer agent doxorubicin. In addition, compounds substituted with fluoro (3b), nitro (3h), and dimethylamino (3j) exhibited good cytotoxicity with IC50<6.5 mu M against MDA-MB-231 and <12 mu M against MCF-7. Selected compounds were able to induce apoptosis in MDA-MB-231 cells as indicated by caspase-3 and/or -7 activation.Conclusion: Our results show that the newly designed chrysin derivatives exert anticancer activity in human breast cancer cell lines, MDA-MB-231 and MCF-7. Therefore, they can be considered as leads for further development of more potent and selective cytotoxic agents.
• Structure-based design of flavone-based inhibitors of wild-type and T315I mutant of ABL
  作者：Hyeonjeong Choe、Jieun Kim、Sungwoo Hong

  DOI：10.1016/j.bmcl.2013.05.095

  日期：2013.8

  The existence of drug resistance caused by mutations in the break-point cluster region-Abelson (BCR-ABL) tyrosine kinase domain remains a clinical challenge due to limited treatment options for effective CML therapies. Here, we report a series of flavone-based common inhibitors equipotent for the wild type and the most drug-resistant T315I mutant of BCR-ABL. The original hit 1 was extensively modified through a structure-based drug design strategy, especially by varying the C7 acetamide appendage of the scaffold to exploit extended interactions with P-loop residues. Structural features relevant to the stabilization of the newly identified inhibitors in the ATP-binding site of ABL are discussed in detail. (C) 2013 Elsevier Ltd. All rights reserved.
• Evaluation and molecular docking study of two flavonoids from Oroxylum indicum (L.) Kurz and their semi-synthetic derivatives as histone deacetylase inhibitors
  作者：La-or Somsakeesit、Thanaset Senawong、Gulsiri Senawong、Pakit Kumboonma、Arunta Samankul、Narissara Namwan、Chavi Yenjai、Chanokbhorn Phaosiri

  DOI：10.1007/s11418-023-01758-y

  日期：2024.1
• [EN] ANTI-ULCER ACTIVITY OF FLAVONE ANALOGS<br/>[FR] ACTIVITÉ ANTI-ULCÈRE D'ANALOGUES DE LA FLAVONE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2009110008A1

  公开（公告）日：2009-09-11

  The present invention relates to the use of a compound of general formula (1), useful for anti- ulcer activity. The compounds comprising substituted chrysin or substituted 7-hydroxy flavone analogs of the formula (1) wherein R' is selected from the group consisting of alkyl, alkenyl, alkoyl,benzoyl, hydrogen, carboxymethyl, acetamjde and R" is selected from the group consisting of H, OH, alkoxy, acetoxy and propenyl. More particularly, the present invention provides the use of analogs of 7-hydroxy flavone, to provide anti-ulcer against aspirin induced ulceration, pylorus ligation induced ulceration, ethanol induced ulceration and stress induced ulceration at a dose ranging between.1 -25mg/kg body weight.