(E)-1-Naphthalen-2-yl-3-(3-nitro-phenyl)-propenone | 22290-84-2

• 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-Naphthalen-2-yl-3-(3-nitro-phenyl)-propenone
• 英文别名: 1-(Naphthalen-2-yl)-3-(3-nitrophenyl)prop-2-en-1-one；1-naphthalen-2-yl-3-(3-nitrophenyl)prop-2-en-1-one
• CAS: 22290-84-2
• 化学式: C₁₉H₁₃NO₃
• 分子量: 303.317
• InChiKey: IXRSRSAIQNFEBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-Naphthalen-2-yl-3-(3-nitro-phenyl)-propenone 、 溶剂黄146 在 一水合肼 作用下， 反应 3.0h， 生成 1-[4,5-dihydro-3-(naphth-2-yl)-5-(3-nitrophenyl)-1H-pyrazol-1-yl]ethanone
  参考文献：
  名称：

  Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones

  摘要：

  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 .

  DOI：

  10.1007/s00044-011-9824-9
• 作为产物：
  描述：

  1-(2-萘甲酰基 )乙醇 在 potassium tert-butylate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 26.0h， 生成 (E)-1-Naphthalen-2-yl-3-(3-nitro-phenyl)-propenone
  参考文献：
  名称：

  新型含丙二酸查耳酮衍生物的合成、生物活性及作用机理研究

  摘要：

  合成了一系列新型查耳酮丙二酸酯衍生物并评价了它们的抗菌和抗病毒活性。所有目标化合物均通过光谱数据表征。抗菌生物测定结果表明，一种化合物（[3-（萘-2-基）-1-（3-硝基苯基）-3-氧代丙基]丙二酸二乙酯）对米黄单胞菌具有优异的抗菌活性。oryzae (Xoo)，EC50 值为 10.2 μg/mL，明显优于双甲噻唑 (71.7 μg/mL) 和硫二唑铜 (97.8 μg/mL)。同时，通过扫描电子显微镜证实了两种化合物的作用机制。此外，另一种化合物（[3-（萘-2-基）-1-（4-硝基苯基）-3-氧丙基]丙二酸二乙酯）对烟草花叶病毒显示出显着的治疗活性，值为74.3%，优于 53。3%的宁南霉素。微量热泳的结果还表明，两种化合物与烟草花叶病毒外壳蛋白结合的Kd值为0.211和0.166 μmol/L，优于0.596 μmol/L的宁南霉素。同时，两种化合物与烟草花叶病毒外壳蛋白的分子对

  DOI：

  10.1002/cbdv.202000025

文献信息

• 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 .
• Synthesis, Biological Activity and Action Mechanism Study of Novel Chalcone Derivatives Containing Malonate
  作者：Tao Guo、Rongjiao Xia、Tingting Liu、Feng Peng、Xuemei Tang、Qing Zhou、Hui Luo、Wei Xue

  DOI：10.1002/cbdv.202000025

  日期：2020.4

  A series of novel chalcone malonate derivatives were synthesized and their antibacterial and antiviral activities were evaluated. All target compounds were characterized by spectral data. The results of antimicrobial bioassay showed that one compound (diethyl [3‐(naphthalen‐2‐yl)‐1‐(3‐nitrophenyl)‐3‐oxopropyl]propanedioate) showed excellent antibacterial activity against Xanthomonas oryzae pv. oryzae

  合成了一系列新型查耳酮丙二酸酯衍生物并评价了它们的抗菌和抗病毒活性。所有目标化合物均通过光谱数据表征。抗菌生物测定结果表明，一种化合物（[3-（萘-2-基）-1-（3-硝基苯基）-3-氧代丙基]丙二酸二乙酯）对米黄单胞菌具有优异的抗菌活性。oryzae (Xoo)，EC50 值为 10.2 μg/mL，明显优于双甲噻唑 (71.7 μg/mL) 和硫二唑铜 (97.8 μg/mL)。同时，通过扫描电子显微镜证实了两种化合物的作用机制。此外，另一种化合物（[3-（萘-2-基）-1-（4-硝基苯基）-3-氧丙基]丙二酸二乙酯）对烟草花叶病毒显示出显着的治疗活性，值为74.3%，优于 53。3%的宁南霉素。微量热泳的结果还表明，两种化合物与烟草花叶病毒外壳蛋白结合的Kd值为0.211和0.166 μmol/L，优于0.596 μmol/L的宁南霉素。同时，两种化合物与烟草花叶病毒外壳蛋白的分子对