3-(4-methoxyphenyl)-1-(1-naphthyl)-2-propen-1-one | 36203-45-9

• 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: 3-(4-methoxyphenyl)-1-(1-naphthyl)-2-propen-1-one
• 英文别名: p-Methoxybenzylidenmethyl-(1)-naphthyl-keton；1-<4-Methoxy-cinnamoyl>-naphthalin；3-(4-methoxyphenyl)-1-naphthalen-1-ylprop-2-en-1-one
• CAS: 36203-45-9
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: GGXMINHUYKSEJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  485.9±37.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-1-(1-naphthyl)-2-propen-1-one 在 四溴化碳 、 Ru(dtbbpy)₃(PF₆)₂ 、 sodium hydride 、 lithium bromide 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙腈 为溶剂， 反应 7.83h， 生成 2-(4-methoxyphenyl)-5-naphylfuran
  参考文献：
  名称：

  可见光诱导的环丙基酮直接合成多取代呋喃

  摘要：

  在本文中，提出了一种光氧化还原方案，用于通过环丙基酮与酮氧原子原位生成的烯烃的氧化偶联来合成呋喃。此外，在化学计量过量的氧化剂存在下，呋喃的溴化反应具有很高的区域选择性。

  DOI：

  10.1021/acs.joc.6b00436
• 作为产物：
  描述：

  萘 在 sodium hydroxide 、 三氯化铝 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 2.5h， 生成 3-(4-methoxyphenyl)-1-(1-naphthyl)-2-propen-1-one
  参考文献：
  名称：

  Synthesis, in vitro antibacterial and antifungal evaluations of 2-amino-4-(1-naphthyl)-6-arylpyrimidines

  摘要：

  A series of 2-amino-4-(1 -naphthyl)-6-arylpyrimidines have been synthesized and characterized by IR, NMR, MS, elemental analyses and evaluated for in vitro antibacterial and antifungal activities. Some of the compounds were found to be active against a limited panel of bacteria and fungi. In particular, compounds 4b and 4e were found to be the most effective analogs against the tested bacterial and fungal strains. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.09.012

文献信息

• Synthesis and Cytotoxicity Evaluation of New 3-substituted 4-(4-methyloxy phenyl)-1<i>H</i>-Pyrrole Derivatives
  作者：Xiaoping Zhan、Lan Lan、Yuankui Zhang、Jian Chen、Kai Zhao、Shuai Wang、Yuxuan Xin、Zhenmin Mao

  DOI：10.1002/bkcs.10653

  日期：2016.2

  A new series of 3‐substituted 4‐(4‐methyloxy phenyl)‐1H‐pyrrole derivatives were synthesized and biologically evaluated for potential anticancer activity. Fifteen targeted compounds showed high selectivity toward normal cells and cancer cells: that is, all targeted compounds had no obvious cytotoxicity toward normal human cells (HUVEC and NIH/3T3), but some compounds exhibited broad‐spectrum proliferation

  合成了一系列新的3-取代的4-（4-甲氧基苯基）-1 H-吡咯衍生物，并对其生物学潜力进行了评估。15种靶向化合物对正常细胞和癌细胞具有高选择性：也就是说，所有靶向化合物对正常人细胞（HUVEC和NIH / 3T3）都没有明显的细胞毒性，但有些化合物对筛选出的癌细胞具有广谱增殖抑制活性线。在这些吡咯衍生物中，化合物3b和3o对MG-63细胞系显示出有效的抗癌活性，IC 50值分别为14.9和12.7μM。其他吡咯衍生物也显示出有希望的增殖抑制活性，包括针对A375的3d（IC 50 = 18.6μM ），针对MGC80-3的化合物3f和3j（IC 50 = 19.9μM ）和针对MGC80-3的化合物3o（IC 50 = 11.9μM ）。由于已开发的吡咯衍生物显示出强大的抗癌活性和高选择性，因此这一新系列的吡咯衍生物可以被视为进一步开发有效和安全的抗癌药物的有前途的先导化合物。
• Naphthalene-triazolopyrimidine hybrid compounds as potential multifunctional anti-Alzheimer’s agents
  作者：Tarana Umar、Siddharth Gusain、Md Kausar Raza、Shruti Shalini、Jitendra Kumar、Manisha Tiwari、Nasimul Hoda

  DOI：10.1016/j.bmc.2019.06.004

  日期：2019.7

  anti-Alzheimer's agents Naphthalene-triazolopyrimidine hybrids were synthesized and screened in vitro against the two cholinesterases (ChE)s, amyloid β aggregation and for antioxidation activity. Single-crystal X-ray crystallography was utilized for crystal structure determination of one of the compounds. In vitro study of compounds revealed that most of the compounds are capable of inhibiting acetylcholinesterase

  为了构建潜在的抗阿尔茨海默氏病药物，合成了萘-三唑并嘧啶杂合物，并针对两种胆碱酯酶（ChE），淀粉样β聚集和抗氧化活性进行了体外筛选。单晶X射线晶体学用于确定一种化合物的晶体结构。化合物的体外研究表明，大多数化合物都能抑制乙酰胆碱酯酶和丁酰胆碱酯酶的活性。尤其是，化合物4e和4d对AChE的IC50值比标准药物多奈哌齐（IC50 49 nM）低，为8.6至14 nM。化合物4e的最佳结果为IC50为8.6 nM（对于AChE）和150 nM（对于BuChE）。在4a，4c和4h观察到高达多奈哌齐的选择性，甚至更高。通过电子显微镜检查 透射电子显微镜和ThT荧光测定揭示了这样的事实，即合成的杂种表现出淀粉样β自聚集抑制作用。化合物4i和4j在50μM时显示出最高的抑制潜力，分别为85.46％和72.77％。高于标准Aβ崩解剂姜黄素。还分析了它们的抗氧化特性。DPPH自由基清除测定法和ORAC
• A rational approach for the design and synthesis of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles as a new class of potential non-purine xanthine oxidase inhibitors
  作者：Kunal Nepali、Gurinderdeep Singh、Anil Turan、Amit Agarwal、Sameer Sapra、Raj Kumar、Uttam C. Banerjee、Prabhakar K. Verma、Naresh K. Satti、Manish K. Gupta、Om P. Suri、K.L. Dhar

  DOI：10.1016/j.bmc.2011.01.058

  日期：2011.3

  Xanthine oxidase is a complex molybdoflavoprotein that catalyses the hydroxylation of xanthine to uric acid. Fifty three analogues of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles were rationally designed and synthesized and evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Some notions about structure activity relationships are presented. Six compounds 41, 42, 44, 46,

  黄嘌呤氧化酶是一种复杂的钼黄素蛋白，可催化黄嘌呤羟化为尿酸。合理设计和合成了1-乙酰基3,5-二芳基-4,5-二氢（1 H）吡唑的53种类似物，并首次评估了其体外黄嘌呤氧化酶抑制活性。提出了有关结构活动关系的一些概念。六种化合物41，42，44，46，55和59被认为是最有效对抗XO带IC 50范围为5.3μM至15.2μM。化合物59成为最有效的XO抑制剂（IC 50 = 5.3μM）。通过分子模拟已经确定了59与XO活性位点氨基酸残基的一些重要相互作用。
• Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones
  作者：Kunal Nepali、Kanika Kadian、Ritu Ojha、Rajni Dhiman、Atul Garg、Gagandip Singh、Abhishek Buddhiraja、Preet Mohinder Singh Bedi、Kanaya Lal Dhar

  DOI：10.1007/s00044-011-9824-9

  日期：2012.10

  Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C-6-C-3-C-6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines.All the synthesized compounds were evaluated for in vitro cytotoxicity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Compound 68 was found to be the most potent showing broad spectrum of cytotoxicity against all the cell lines .
• SOLID SiO2-H3PO4 IS AN EFFICIENT CATALYST FOR CYCLIZATION OF ENONES UNDER SOLVENT-FREE CONDITION: SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF SOME OXAZINE DERIVATIVES
  作者：GANESAMOORTHY THIRUNARAYAN、VELAYUTHAM RENUKA

  DOI：10.4067/s0717-97072014000300011

  日期：——

  A series of some 1, 3-oxazine amine derivatives including 4-(1-naphthyl)-5,6-dihydro-6-(substituted phenyl)-oxazine-2-amines has been synthesised by lsolid SiO2-H3PO4 catalyzed solvent-free cyclization of aryl chalcones and urea under microwave irradiation. The yields of the oxazines were more than 80%. The synthesised oxazine amines were characterized by their physical constants, analytical and spectroscopic data. The antimicrobial activities of these oxazine derivatives have been studied using Bauer-Kirby method.