(2E)-1-(4-acetylaminophenyl)-3-(4-methylphenyl)prop-2-enone

• 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: (2E)-1-(4-acetylaminophenyl)-3-(4-methylphenyl)prop-2-enone
• 英文别名: N-{4-[(2E)-3-(4-methylphenyl)prop-2-enoyl]phenyl}acetamide；(E)-1-(4-acetamidophenyl)-3-(4-methylphenyl)-2-propen-1-one；N-[4-[(E)-3-(4-methylphenyl)prop-2-enoyl]phenyl]acetamide
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: DRHSZWYLZYWQPG-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-1-(4-acetylaminophenyl)-3-(4-methylphenyl)prop-2-enone 在 sodium acetate 、 一水合肼 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.0h， 以85%的产率得到3-(4-acetylaminophenyl)-5-(4-methylphenyl)-1H-pyrazoline
  参考文献：
  名称：

  Facile sonochemical synthesis of novel pyrazolyne derivates at ambient conditions

  摘要：

  Claisen-Schmidt condensation reaction of 4-acetamidoacetophenone with aromatic aldehydes under ultrasonic irradiation affords acetylaminochalcones (yields: 71-90%) which also under ultrasonic irradiation and in the presence of sodium acetate and acetic acid aqueous undergo facile and clean cyclocondensation with hydrazine to afford 3-(4-acetamidophenyl)-5-(aryl)-1-H-pyrazolines. The pyrazolines were obtained in good to excellent yields (81-89%), and were characterized by conventional spectral data. The work-up is simple and the results obtained indicate that, unlike classical heating, ultrasonic irradiation results in higher yields, shorter reaction times (1.5-2.3 h) and milder conditions. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2012.11.018
• 作为产物：
  描述：

  4-氨基苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 (2E)-1-(4-acetylaminophenyl)-3-(4-methylphenyl)prop-2-enone
  参考文献：
  名称：

  4'-Acetamidochalcone Derivatives as Potential Antinociceptive Agents

  摘要：

  合成了九种乙酰氨基查尔酮，并使用小鼠扭体试验评估其作为抗伤害药的效果。腹腔内给予所有化合物都比用于比较的两种参考镇痛药物（乙酰水杨酸和对乙酰氨基酚）更有效。 N-{4-[(2E)-3-(4-硝基苯基)丙-2-烯酰基]苯基}乙酰胺(6)是最有效的化合物，因此被选择进行更详细的研究。它在扭体试验中产生了剂量相关的抑制作用，其效力比标准药物强约 32 至 34 倍。在第二阶段的福尔马林试验和辣椒素试验中也有效。这些乙酰氨基查尔酮，特别是化合物6，可能进一步用作模型来获得新的、更有效的镇痛药物。

  DOI：

  10.3390/12040896

文献信息

• 4'-Acetamidochalcone Derivatives as Potential Antinociceptive Agents
  作者：Fátima De Campos-Buzzi、Pâmela Padaratz、Aleandra Meira、Rogério Corrêa、Ricardo Nunes、Valdir Cechinel-Filho

  DOI：10.3390/12040896

  日期：——

  Nine acetamidochalcones were synthesized and evaluated as antinociceptive agents using the mice writhing test. Given intraperitoneally all the compounds were more effective than the two reference analgesic drugs (acetylsalicylic acid and acetaminophen) used for comparison. N-4-[(2E)-3-(4-nitrophenyl)prop-2-enoyl]phenyl}acetamide (6) was the most effective compound and was therefore selected for more detailed studies. It caused dose-related inhibition in the writhing test, being about 32 to 34-fold more potent than the standard drugs. It was also effective in the second phase of the formalin test and the capsaicin test. These acetamidochalcones, especially compound 6, might be further used as models to obtain new and more potent analgesic drugs.

  合成了九种乙酰氨基查尔酮，并使用小鼠扭体试验评估其作为抗伤害药的效果。腹腔内给予所有化合物都比用于比较的两种参考镇痛药物（乙酰水杨酸和对乙酰氨基酚）更有效。 N-4-[(2E)-3-(4-硝基苯基)丙-2-烯酰基]苯基}乙酰胺(6)是最有效的化合物，因此被选择进行更详细的研究。它在扭体试验中产生了剂量相关的抑制作用，其效力比标准药物强约 32 至 34 倍。在第二阶段的福尔马林试验和辣椒素试验中也有效。这些乙酰氨基查尔酮，特别是化合物6，可能进一步用作模型来获得新的、更有效的镇痛药物。
• PYRIDINE DERIVATIVES
  申请人：TAISHO PHARMACEUTICAL CO. LTD

  公开号：EP0795545A1

  公开（公告）日：1997-09-17

  A pyridine derivative represented by the following formula: , where R1 is a methyl group or a functional group represented by any one of the following formulae:         ―CONHCH2CH2N(CH3)2         ―CONHCH2CH2CH2N(CH3)2         ―COOCH2CH2N(CH3)2         ―COOCH2CH2N(CH2CH3)2         ―NHCOCH2N(CH3)2         ―NHCOCH2N(CH2CH3)2 and R2 is a hydrogen atom, an amino group or a functional group represented by any one of the following formulae:         ―CONHCH2CH2N(CH3)2         ―COOCH2CH2N(CH3)2         ―NHCOCH2N(CH3)2         ―NHCOCH2N(CH2CH3)2 or a salt thereof directly or indirectly acts on neuronal cells in vivo and is expected to show an effect on amelioration and curing of nerve disorders due to neuronal degeneration, with application as a drug for ameliorating and curing, for example, traumatic symptoms and maladies, those induced by drugs such as alcohol, antineoplastic agents, etc., inflammatory ones, metabolic ones as observed in diabetes, etc., and furthermore those due to idiopathic degeneration of peripheral nerves, and also with application as drugs for ameliorating and curing symptoms and maladies due to degeneration of central nerves, for example, Alzheimer's disease and cerebrovascular ischemia, Down syndrome, Parkinson's disease, Huntington chorea, diseases secondary to cerebral ischemia, cerebral infarction, intracerebral bleeding, head injuries, etc., amnesia, spinal neuropathy, etc.

  下式所代表的吡啶衍生物： 其中 R1 是甲基或下式中任何一种所代表的官能团： -conhch2ch2n(ch3)2 -conhch2ch2ch2n（ch3）2 -cooch2ch2n(ch3)2 -cooch2ch2n(ch2ch3)2 -NHCOCH2N(CH3)2 -NHCOCH2N（CH2CH3）2 而 R2 是氢原子、氨基或由下式中任一式代表的官能团： -conhch2ch2n(ch3)2 -cooch2ch2n(ch3)2 -NHCOCH2N（CH3）2 -NHCOCH2N（CH2CH3）2 或其盐在体内直接或间接作用于神经元细胞，并有望显示出改善和治疗因神经元变性引起的神经紊乱的效果，可用作改善和治疗创伤性症状和弊病、酒精等药物引起的症状和弊病、抗肿瘤药物等引起的症状和弊病、炎症性症状和弊病、糖尿病等引起的代谢性症状和弊病的药物、此外，还可用于改善和治疗中枢神经退化引起的症状和疾病，如阿尔茨海默病和脑血管缺血、唐氏综合症、帕金森病、亨廷顿舞蹈症、继发于脑缺血、脑梗塞、脑出血、头部损伤等的疾病、健忘症、脊髓神经病等。
• <i>N</i>-(4-((E)-3-Arylacryloyl)phenyl)acetamide Derivatives and their Antileishmanial Activity
  作者：Dency J. Pacheco、Jorge Trilleras、Jairo Quiroga、Jennifer Gutiérrez、Luis Prent、Tobinson Coavas、Juan C. Marín、Gabriela Delgado

  DOI：10.5935/0103-5053.20130203

  日期：——

  The antileishmanial activity of a series of enonic derivatives (chalcones) synthesized via Claisen-Schmidt condensation reactions assisted by ultrasonic radiation was characterized by analyzing their cytotoxicity against Leishmania (Viannia) panamensis promastigotes, a species responsible for over 90% of Leishmania cases in Colombia. Two compounds were active against Leishmania with selectivity indexes of LC50 EC50-1 (lethal concentration 50 and effective concentration 50) higher than 27 and 3, respectively. These results suggest that a substitution on one of the two chalcone rings (aromatic ring A) with oxygen is convenient. Compound 3g should be further investigated for its antileishmanial activity, especially for being easy to obtain in high yields, making it possible to produce drugs for the treatment of cutaneous leishmaniasis.
• US5922743A
  申请人：——

  公开号：US5922743A

  公开（公告）日：1999-07-13
• Antimicrobial and Cytotoxicity Potential of Acetamido, Amino and Nitrochalcones
  作者：T. Tristão、F. Campos-Buzzi、R. Corrêa、R.C Cruz、V. Cechinel Filho、A. Bella Cruz

  DOI：10.1055/s-0032-1327610

  日期：——

  Background: Chalcones constitute one of the major classes of natural products belonging to the flavonoid family, and they have been reported as having a range of important therapeutic activities, including some chalcones are effective as antimicrobial agents. Currently, the search for new structures with antimicrobial activity has been intensified due to the emergence of many strains resistant to antibiotics currently used to treat infectious diseases.Method: 3 chalcone series (amino, acetamido and nitrochalcones) were prepared (23 compounds) and evaluated for their antimicrobial and cytotoxic potential. The effects of substituents on their respective activities also was evaluated.Results & Conclusion: The results showed that 4 aminochalcones (2, 4, 8, 9), 3 acetoamidochalcones (10, 14, 18) and 3 nitrochalcones (20, 22, 23), exhibited antifungal effects. The aminochalcones were more toxic than the acetamidochalcones, while the nitrochalcones did not present any toxic effect. It was verified that there seems to be structure-activity correlation in some electron-donating and withdrawing substituents groups in rings A and B of the synthetized chalcone analogues and its antifungal and cytotoxic activity.