1-(4-methoxy-2-(prop-2-yn-1-yloxy)phenyl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-methoxy-2-(prop-2-yn-1-yloxy)phenyl)ethanone
• 英文别名: 1-(4-methoxy-2-(prop-2-yn-1-yloxy)phenyl)ethan-1-one；1-(4-Methoxy-2-prop-2-ynoxyphenyl)ethanone；1-(4-methoxy-2-prop-2-ynoxyphenyl)ethanone
• 化学式: C₁₂H₁₂O₃
• mdl: MFCD23713679
• 分子量: 204.225
• InChiKey: PYQAPRXIKPKNOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxy-2-(prop-2-yn-1-yloxy)phenyl)ethanone 在 叔丁基过氧化氢 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 14.0h， 生成 (Z)-4-((E)-benzylidene)-8-methoxy-3-(tosylmethylene)-3,4-dihydrobenzo[b]oxepin-5(2H)-one
  参考文献：
  名称：

  炔丙基查尔酮自由基环化/磺化反应：苯并[b]oxepin-5(2H)-one 和铬烷衍生物的高效合成

  摘要：

  在实验室条件下，炔丙基查耳酮与芳基磺酰氯通过自由基级联环化/磺化反应，报道了一种用于合成磺化苯并[ b ]氧杂萜酮和色烷衍生物的新型简便方法。易得的炔丙基查尔酮、商品化的芳基磺酰氯和简单的反应条件使这种六（七）元含氧杂环的合成策略更具吸引力并具有重要的应用价值。

  DOI：

  10.1021/acs.joc.2c00361
• 作为产物：
  描述：

  丹皮酚 、 3-溴丙炔 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以23%的产率得到1-(4-methoxy-2-(prop-2-yn-1-yloxy)phenyl)ethanone
  参考文献：
  名称：

  Design, Synthesis and Antifungal Activity of Novel Paeonol Derivatives Linked with 1,2,3-Triazole Moiety by the Click Reaction

  摘要：

  为了获得具有显著抗真菌活性的新型生物活性化合物，我们设计并以 Cu(OAc)2-H2O/sodium ascorbate 为催化剂，在温和条件下通过点击反应合成了一系列与 1,2,3 三唑分子相连的新型芍药酚衍生物。体外评估了所有目标化合物对两种植物病原真菌（Colletotrichum capsici 和Rhizoctonia cerealis）的抗真菌活性。而 1-(2-{[1-(2-氟苯基)-1H-1,2,3-三唑-4-基]甲氧基}-4-甲氧基苯基)乙酮和 1-(4-甲氧基-2-{[1-(邻甲苯基)-1H-1,2,3-三唑-4-基]甲氧基}苯基)乙酮对测试的两种真菌具有更好的抗真菌活性。所有合成的化合物都通过红外光谱、HR MS 和 NMR 光谱进行了测定。

  DOI：

  10.3184/174751915x14284938334623

文献信息

• Tryptamine–Triazole Hybrid Compounds for Selective Butyrylcholinesterase Inhibition
  作者：Minky Son、Haneul Lee、Cheolmin Jeon、Yujung Kang、Chanin Park、Keun Woo Lee、Jeong Ho Park

  DOI：10.1002/bkcs.11729

  日期：2019.6

  Tryptamine–triazole hybrid compounds (11–18) were synthesized via click reaction between tryptamine azide and propargylated natural compounds. Their cholinesterase inhibitory activity was evaluated. Among the eight compounds, compound 11 showed the most potent inhibitory activity [IC50 = 0.42 ± 0.29 μM for equine butyrylcholinesterase (BuChE) and 1.96 ± 0.15 μM for human BuChE]. From the molecular

  色胺三唑杂化化合物（11 - 18）经色胺叠氮化物和propargylated天然化合物之间点击反应合成。评价了它们对胆碱酯酶的抑制活性。在这八种化合物中，化合物11表现出最强的抑制活性[ 对马的丁酰胆碱酯酶（BuChE）的IC 50 = 0.42±0.29μM，对人的BuChE的IC 50 = 1.96±0.15μM]。通过分子建模研究，化合物11通过形成发夹或U形结构与人或马BuChE的催化阴离子部位，阴离子亚部位，外围阴离子亚部位，酰基结合袋和氧阴离子孔结合。化合物11的Lineweaver-Burk图 针对BuChE的抗性暗示了一种混合的抑制类型，与分子模型研究非常吻合。
• Design, Synthesis and Antifungal Activity of Novel Paeonol Derivatives Linked with 1,2,3-Triazole Moiety by the Click Reaction
  作者：Yuqin Jiang、Baoqi Ren、Xiaomeng Lv、Weiwei Zhang、Wei Li、Guiqing Xu

  DOI：10.3184/174751915x14284938334623

  日期：2015.4

  For obtaining novel bioactive compounds with significant antifungal activities, a series of novel paeonol derivatives linked with a 1,2,3-triazole moiety have been designed and synthesised by a click reaction under mild conditions using Cu(OAc)₂·H₂O/sodium ascorbate as a catalyst. The antifungal activities of all the target compounds were evaluated in vitro against two plant pathogenic fungi, Colletotrichum capsici and Rhizoctonia cerealis. Preliminary results indicated that 1-(4-methoxy-2-[1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl]-methoxy}phenyl)ethanone showed the best antifungal activities against C. capsici, while 1-(2-[1-(2-fuorophenyl)-1H-1,2,3-triazol-4-yl]methoxy}-4-methoxyphenyl)ethanone and 1-(4-methoxy-2-[1-(o-tolyl)-1H-1,2,3-triazol-4-yl]methoxy}phenyl)ethanone were found to have better antifungal activities against the tested two fungi. All the synthesised compounds have been determined by IR, HR MS and NMR spectra.

  为了获得具有显著抗真菌活性的新型生物活性化合物，我们设计并以 Cu(OAc)2-H2O/sodium ascorbate 为催化剂，在温和条件下通过点击反应合成了一系列与 1,2,3 三唑分子相连的新型芍药酚衍生物。体外评估了所有目标化合物对两种植物病原真菌（Colletotrichum capsici 和Rhizoctonia cerealis）的抗真菌活性。而 1-(2-[1-(2-氟苯基)-1H-1,2,3-三唑-4-基]甲氧基}-4-甲氧基苯基)乙酮和 1-(4-甲氧基-2-[1-(邻甲苯基)-1H-1,2,3-三唑-4-基]甲氧基}苯基)乙酮对测试的两种真菌具有更好的抗真菌活性。所有合成的化合物都通过红外光谱、HR MS 和 NMR 光谱进行了测定。
• 신규한 트립타민 컨쥬게이트 화합물 및 그의 용도
  申请人：Hanbat National University Industry-Academic Cooperation Foundation 한밭대학교 산학협력단(220040246965) BRN ▼314-82-09226

  公开号：KR20160046450A

  公开（公告）日：2016-04-29

  본 발명은 트립타민 유도체와 항산화제 유도체를 클릭 반응을 통해 컨쥬게이트시킨 신규 트립타민 컨쥬게이트(conjugated) 화합물 및 이를 함유하는 퇴행성 질환의 예방 또는 치료용 약제학적 조성물 및 건강보조식품 조성물에 관한 것이다. 본 발명에 따른 트립타민 컨쥬게이트(conjugated) 화합물은 아세틸콜린에스터라제(AChE; acetylcholinesterase) 및 부티릴콜린에스터라제(BuChE; butyrylcholinesterase)의 콜린에스터라제(ChE; cholinesterase)에 대한 저해 활성을 나타내어 퇴행성 질환의 예방 또는 치료에 있어 효과적인 물질이다. 특히, 본 발명의 트립타민 컨쥬게이트 화합물은 콜린에스터라제(ChE) 형태 중 선택적으로 부티릴콜린에스터라제(BuChE) 저해활성 특성을 갖는다. 본 발명의 약제학적 조성물은 콜린에스터라제(ChE)의 활성을 저해하는 트립타민 컨쥬게이트(conjugated) 화합물을 유효성분으로 함유하여 알츠하이머병 또는 퇴행성 질환의 예방 및 치료에 사용할 수 있을 뿐만 아니라, 퇴행성 질환을 개선시키거나 학습능력 및 기억력을 개선시키는 건강보조식품으로도 활용 가능하다.

  本发明涉及通过点击反应将三甲胺衍生物和抗氧化剂衍生物结合成新的三甲胺结合物，以及包含该结合物的用于预防或治疗退行性疾病的药学组合物和保健食品组合物。根据本发明，三甲胺结合物表现出对乙酰胆碱酯酶（AChE; acetylcholinesterase）和丁酰胆碱酯酶（BuChE; butyrylcholinesterase）的胆碱酯酶（ChE; cholinesterase）的抑制活性，是一种在预防或治疗退行性疾病方面具有有效作用的物质。特别是，本发明的三甲胺结合物具有选择性抑制丁酰胆碱酯酶（BuChE）的活性特性。本发明的药学组合物包含抑制胆碱酯酶（ChE）活性的三甲胺结合物作为有效成分，可用于阿尔茨海默病或退行性疾病的预防和治疗，同时也可用作改善退行性疾病或提高学习能力和记忆力的保健食品。
• 신규한 코직산 컨쥬게이트 화합물 및 그의 용도
  申请人：Hanbat National University Industry-Academic Cooperation Foundation 한밭대학교 산학협력단(220040246965) BRN ▼314-82-09226

  公开号：KR20160046136A

  公开（公告）日：2016-04-28

  본 발명은 코직산과 항산화제 유도체를 클릭 반응을 통해 컨쥬게이트시킨 신규 코직산 컨쥬게이트(conjugated) 화합물 및 이를 함유하는 항산화용 건강보조식품 및 피부의 미백, 항산화, 항노화 효과를 갖는 피부외용제 조성물에 관한 것이다. 본 발명에 따른 코직산 컨쥬게이트(conjugated) 화합물은 티로시나아제를 효과적으로 저해하므로 항산화용 건강보조식품 조성물 및 항산화, 노화방지 및 미백 기능을 가진 피부외용제 조성물의 유효성분으로 활용 가능하다.

  本发明涉及通过点击反应使辅酶A和抗氧化剂诱导体共轭的新型辅酶A共轭化合物，以及含有该化合物的抗氧化健康辅助食品和具有美白、抗氧化和抗衰老效果的皮肤外用制剂组合物。根据本发明，辅酶A共轭化合物有效地抑制酪氨酸酶，因此可用作抗氧化健康辅助食品组合物和具有抗氧化、抗衰老和美白功能的皮肤外用制剂的有效成分。
• Synthesis and in vitro Assay of New Triazole Linked Decursinol Derivatives Showing Inhibitory Activity against Cholinesterase for Alzheimer’s Disease Therapeutics
  作者：Jung-Youl Park、Sujeong Shin、Kyoung Chan Park、Eunju Jeong、Jeong Ho Park

  DOI：10.5012/jkcs.2016.60.2.125

  日期：2016.4.20

  With the goal of developing Alzheimer’s disease therapeutics, we have designed and synthesized new triazole linked decursinol derivatives having potency inhibitory activities against cholinesterase [acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE)]. Since inhibition of cholinesterase (ChE) is still considered to be one of the most effective targets to treat AD patients, many new classes of ChE inhibitors have been synthesized. In an effort of identifying new type of cholinergic drug, decursinol derivatives 11-17 have been synthesized between decursinol and other biological interesting compounds such as lipoic acid, polyphenols, etc by using the click reaction and then evaluated their biological activities. Compound 12 (IC₅₀ = 5.89 ± 0.31 mM against BuChE) showed more effective inhibitory activity against BuChE than galantamine (IC₅₀ = 9.4 ± 2.5 mM). Decursinol derivatives can be considered a new class inhibitor for BuChE and can be applied to be a novel drug candidate to treat AD patients.

  为了开发阿尔茨海默病治疗药物，我们设计并合成了新的三唑类癸二醇衍生物，它们对胆碱酯酶[乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）]具有强效抑制活性。由于抑制胆碱酯酶（ChE）仍被认为是治疗注意力缺失症患者最有效的靶点之一，因此人们合成了许多新型的胆碱酯酶抑制剂。为了寻找新型胆碱能药物，研究人员利用点击反应，将去甲熊果醇与其他具有生物活性的化合物（如硫辛酸、多酚等）合成了去甲熊果醇衍生物 11-17，并对其生物活性进行了评估。化合物 12（对 BuChE 的 IC₅₀ = 5.89 ± 0.31 mM）比加兰他敏（IC₅₀ = 9.4 ± 2.5 mM）对 BuChE 具有更有效的抑制活性。Decursinol衍生物被认为是一种新的BuChE抑制剂，可作为治疗AD患者的新型候选药物。