(E)-1-(2,4-dihydroxyphenyl)-3-(4-(piperidin-1-yl)phenyl)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: (E)-1-(2,4-dihydroxyphenyl)-3-(4-(piperidin-1-yl)phenyl)prop-2-en-1-one
• 英文别名: (E)-1-(2,4-dihydroxyphenyl)-3-[4-(1-piperidyl)phenyl]prop-2-en-1-one；(E)-1-(2,4-dihydroxyphenyl)-3-(4-piperidin-1-ylphenyl)prop-2-en-1-one
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: BXGOTHAOKFSQJG-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(2,4-dihydroxyphenyl)-3-(4-(piperidin-1-yl)phenyl)prop-2-en-1-one 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以57%的产率得到7-hydroxy-2-(4-(piperidin-1-yl)phenyl)chroman-4-one
  参考文献：
  名称：

  Synthesis, Structure–Activity Relationship Studies, and Antibacterial Evaluation of 4-Chromanones and Chalcones, as Well as Olympicin A and Derivatives

  摘要：

  On the basis of recently reported abyssinone II and olympicin A, a series of chemically modified flavonoid phytochemicals were synthesized and evaluated against Mycobacterium tuberculosis and a panel of Gram-positive and -negative bacterial pathogens. Some of the synthesized compounds exhibited good antibacterial activities against Gram-positive pathogens including methicillin resistant Staphylococcus aureus with minimum inhibitory concentration as low as 0.39 mu g/mL. SAR analysis revealed that the 2-hydrophobic substituent and the 4-hydrogen bond donor/acceptor of the 4-chromanone scaffold together with the hydroxy groups at 5- and 7-positions enhanced antibacterial activities; the 2',4'-dihydroxylated A ring and the lipophilic substituted B ring of chalcone derivatives were pharmacophoric elements for antibacterial activities. Mode of action studies performed on selected compounds revealed that they dissipated the bacterial membrane potential, resulting in the inhibition of macromolecular biosynthesis; further studies showed that selected compounds inhibited DNA topoisomerase IV, suggesting complex mechanisms of actions for compounds in this series.

  DOI：

  10.1021/jm500853v
• 作为产物：
  描述：

  1-[2-羟基-4-(甲氧基甲氧基)苯基]乙酮 在 盐酸 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 60.0h， 生成 (E)-1-(2,4-dihydroxyphenyl)-3-(4-(piperidin-1-yl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, Structure–Activity Relationship Studies, and Antibacterial Evaluation of 4-Chromanones and Chalcones, as Well as Olympicin A and Derivatives

  摘要：

  On the basis of recently reported abyssinone II and olympicin A, a series of chemically modified flavonoid phytochemicals were synthesized and evaluated against Mycobacterium tuberculosis and a panel of Gram-positive and -negative bacterial pathogens. Some of the synthesized compounds exhibited good antibacterial activities against Gram-positive pathogens including methicillin resistant Staphylococcus aureus with minimum inhibitory concentration as low as 0.39 mu g/mL. SAR analysis revealed that the 2-hydrophobic substituent and the 4-hydrogen bond donor/acceptor of the 4-chromanone scaffold together with the hydroxy groups at 5- and 7-positions enhanced antibacterial activities; the 2',4'-dihydroxylated A ring and the lipophilic substituted B ring of chalcone derivatives were pharmacophoric elements for antibacterial activities. Mode of action studies performed on selected compounds revealed that they dissipated the bacterial membrane potential, resulting in the inhibition of macromolecular biosynthesis; further studies showed that selected compounds inhibited DNA topoisomerase IV, suggesting complex mechanisms of actions for compounds in this series.

  DOI：

  10.1021/jm500853v

文献信息

• Design, synthesis and biological evaluation of 4′-aminochalcone-rivastigmine hybrids as multifunctional agents for the treatment of Alzheimer's disease
  作者：Ganyuan Xiao、Yan Li、Xiaoming Qiang、Rui Xu、Yunxiaozhu Zheng、Zhongcheng Cao、Li Luo、Xia Yang、Zhipei Sang、Fu Su、Yong Deng

  DOI：10.1016/j.bmc.2016.12.013

  日期：2017.2

  A series of 4′-aminochalcone-revastigmine hybrids were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer’s disease. The results showed that most of these compounds exhibited good multifunctional activities. In particular, compound 6c displayed the best inhibitory potency on acetylcholinesterase (IC50 = 4.91 μM), and significant antioxidative activity with

  设计，合成和评估了一系列4'-氨基查尔酮-雷伐他明杂种，作为治疗阿尔茨海默氏病的多功能药物。结果表明，大多数这些化合物表现出良好的多功能活性。特别地，化合物6c对乙酰胆碱酯酶表现出最佳的抑制效能（IC 50  = 4.91μM），并且具有显着的抗氧化活性，其值为Trolox的2.83倍。AChE抑制的动力学分析表明，6c显示出混合型抑制，同时与AChE的催化活性位点和外围阴离子位点结合。此外，6C抑制自感应的β 1-42聚集和Cu 2+诱导的阿β 1-42聚合由89.5％，并在25μM分别79.7％，以及充当选择性单胺氧化酶B抑制剂（IC 50  = 0.29μM）和选择性biometal螯合剂。此外，6c可以在体外穿过血脑屏障。根据这些结果，化合物6c可以被认为是阿尔茨海默氏病非常有前途的先导化合物。
• COMPOSITION FOR PREVENTION, AMELIORATION, OR TREATMENT OF CANCER
  申请人：Ewha University-Industry Collaboration Foundation

  公开号：EP3977988A1

  公开（公告）日：2022-04-06

  A composition according to the present disclosure may be very effectively used not only to prevent, ameliorate or treat cancer, but also to inhibit metastasis of cancer, by inhibiting the growth of cancer cells and very effectively inhibiting the metastasis of cancer cells to other tissues.

  根据本公开的说明，一种组合物不仅可非常有效地用于预防、改善或治疗癌症，还可通过抑制癌细胞的生长和非常有效地抑制癌细胞向其他组织的转移来抑制癌症的转移。
• NOVEL COMPOUND AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS ACTIVE INGREDIENT
  申请人：Industry-Academic Cooperation Foundation, Yonsei University

  公开号：EP3626703A1

  公开（公告）日：2020-03-25

  The present invention relates to a novel compound and a pharmaceutical composition comprising the same as an active ingredient. The novel compound, which is obtained by means of carrying out chemical modification in a mother structure showing excellent AMP-activated protein kinase (AMPK) activation efficacy and in silico binding capacity, enables effective prevention or treatment of degenerative neurological disorders by means of effectively inducing AMP-activated protein kinase enzyme activation.

  本发明涉及一种新型化合物和以其为活性成分的药物组合物。这种新型化合物是通过对母体结构进行化学修饰而获得的，母体结构具有优异的 AMP 活化蛋白激酶（AMPK）激活功效和硅结合能力，通过有效诱导 AMP 活化蛋白激酶酶活化，可有效预防或治疗神经系统退行性疾病。
• Composition for Prevention, Amelioration, or Treatment of Cancer
  申请人：EWHA UNIVERSITY -INDUSTRY COLLABORATION FOUNDATION

  公开号：US20220226263A1

  公开（公告）日：2022-07-21

  A composition according to the present disclosure may be very effectively used not only to prevent, ameliorate or treat cancer, but also to inhibit metastasis of cancer, by inhibiting the growth of cancer cells and very effectively inhibiting the metastasis of cancer cells to other tissues.
• [EN] COMPOSITION FOR PREVENTING, ALLEVIATING OR TREATING METABOLIC DISEASES<br/>[FR] COMPOSITION POUR PRÉVENIR, ATTÉNUER OU TRAITER DES MALADIES MÉTABOLIQUES<br/>[KO] 대사성 질환의 예방, 개선 또는 치료용 조성물
  申请人：UNIV YONSEI IACF

  公开号：WO2020184998A1

  公开（公告）日：2020-09-17

  본 발명은 대사성 질환의 예방 또는 치료용 약학 조성물에 관한 것으로서, 상기 본 발명에 따른 조성물은 대사성 질환을 겪고 있는 개체에 투여되는 경우 매우 효과적으로 혈당을 낮춰, 대사성 질환의 예방, 개선 또는 치료에 매우 적절하게 사용될 수 있다.