(2E)-1-(2-naphthyl)-3-(2-chlorophenyl)-2-propen-1-one | 183164-47-8

• 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-(2-naphthyl)-3-(2-chlorophenyl)-2-propen-1-one
• 英文别名: 3-(2-chlorophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one；3-(2-chlorophenyl)-1-(2-naphthyl)-2-propen-1-one；3-(2-Chlorophenyl)-1-(2-naphthyl)prop-2-en-1-one；(E)-3-(2-chlorophenyl)-1-naphthalen-2-ylprop-2-en-1-one
• CAS: 183164-47-8
• 化学式: C₁₉H₁₃ClO
• 分子量: 292.765
• InChiKey: ZXDUIUQFWPZFRC-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E)-1-(2-naphthyl)-3-(2-chlorophenyl)-2-propen-1-one 在 三乙烯二胺 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 二甲基亚砜 为溶剂， 生成 4-(2-chlorophenyl)-6-naphthalen-2-yl-2-oxo-1H-pyridine-3-carbonitrile
  参考文献：
  名称：

  硫促进查耳酮与未取代的氰基乙酰胺在 DMSO 中的氧化缩合：获得 3-氰基吡啶-2-酮

  摘要：

  人们发现元素硫和 DABCO 是一种极好的组合，可促进查尔酮和未取代的氰基乙酰胺在 DMSO 中缩合氧化环化的一锅级联，从而提供 3-氰基吡啶-2-酮。

  DOI：

  10.1021/acs.joc.3c01207
• 作为产物：
  描述：

  2-氯苯甲醛 、 2-萘乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (2E)-1-(2-naphthyl)-3-(2-chlorophenyl)-2-propen-1-one
  参考文献：
  名称：

  硫促进查耳酮与未取代的氰基乙酰胺在 DMSO 中的氧化缩合：获得 3-氰基吡啶-2-酮

  摘要：

  人们发现元素硫和 DABCO 是一种极好的组合，可促进查尔酮和未取代的氰基乙酰胺在 DMSO 中缩合氧化环化的一锅级联，从而提供 3-氰基吡啶-2-酮。

  DOI：

  10.1021/acs.joc.3c01207

文献信息

• Inhibitory potential of some chalcones on cathepsins B, H and L
  作者：Shweta Garg、Neera Raghav

  DOI：10.1039/c5ra12856k

  日期：——

  Cathepsins, intracellular proteases, are known to be involved in a number of physiological processes such as degradation of extracellular proteins, prohormone processing, progressions of atherosclerosis etc.

  卡特普辛是细胞内蛋白酶，已知参与多种生理过程，如降解细胞外蛋白、前激素加工、动脉粥样硬化进展等。
• Synthesis, in vitro and in silico Studies of Naphthalene Pyrazoline Prop-2-en-1-one Derivatives
  作者：B. Prabha、C. Raja、S. Nathiya、M.R. Ezhilarasi

  DOI：10.14233/ajchem.2020.22654

  日期：——

  The synthesized new naphthalene pyrazoline prop-2-en-1-one derivatives (NDPP 1-8) were obtained by the Michael addition reaction of ethyl propanoate, hydrazine hydrate with NPD as a multicomponent scaffold. (E)-1-(naphthalen-3-yl)-3-phenylprop-2-en-1-one (NPD) was formed from 2-acetyl naphthalene and substituted aldehyde via Claisen-Schmidt condensation reaction. The NDPP skeleton structures were confirmed by infrared, 1H & 13C NMR spectral data and elemental analysis. The structure of NDPP compounds was subjected to molecular docking and ADME studies. The result of ADME prediction, compound NDPP 2, which contains electron withdrawing -Cl group has high drug-likeness value 4.21 than the compounds NDPP 4 and 7 which had electron donating CH3 and OCH3 group shows the drug-likeness value 2.62. The NDPP 2 also has high drug score 0.63 than NDPP 4 and NDPP 7 have drug score 0.60 and 0.69, respectively. Docking studies shows that compound NDPP 5 which also contain electron withdrawing NO2 group has good binding affinity value -8.8 Kcal/mol were docked with 1UAG protein. These compounds showed good drug-likeness value 2.25 and drug score 0.65. in vitro Studies have a high inhibition value for the same NO2 substituted derivative. All the compounds have higher binding affinity value than standards binding affinity value.

  合成的新萘吡唑丙烯酮衍生物（NDPP 1-8）是通过乙酸乙酯、水合肼与NPD的Michael加成反应得到的，NPD作为多组分支架。 （E）-1-（萘-3-基）-3-苯基丙烯酮（NPD）是通过2-乙酰基萘和取代醛经过Claisen-Schmidt缩合反应形成的。 通过红外、1H和13C NMR光谱数据以及元素分析确认了NDPP骨架结构。 NDPP化合物的结构经过了分子对接和ADME研究。 ADME预测结果显示，含有电子吸引性-Cl基团的化合物NDPP 2具有较高的药物相似性值4.21，而含有电子供体CH3和O 基团的化合物NDPP 4和7显示的药物相似性值为2.62。 NDPP 2的药物评分也较高，为0.63，而NDPP 4和NDPP 7的药物评分分别为0.60和0.69。 对接研究表明，含有电子吸引性NO2基团的化合物NDPP 5与1UAG蛋白对接具有良好的结合亲和力值-8.8Kcal/mol。 这些化合物显示出良好的药物相似性值2.25和药物评分0.65。 体外研究显示具有相同 取代衍生物的高抑制值。 所有化合物的结合亲和力值均高于标准结合亲和力值。
• Silica-supported synthesis of some 1,3,5-trisubstituted 2-pyrazolines under solvent-free and microwave irradiation conditions
  作者：Davood Azarifar、Behrooz Maleki

  DOI：10.1002/jhet.5570420125

  日期：2005.1

  A simple method for the synthesis of 2-pyrazolines is described which occurs on silica surface under solvent-free conditions within 110-180 sec using microwave irradiation. The results obtained indicate that the use of silica gel as a support in pyrazoline formation reactions can have a profound effect on reaction rates and yields and cause cleaner reaction conditions.

  描述了一种合成2-吡唑啉的简单方法，该方法在无溶剂条件下，在二氧化硅表面上使用微波辐射在110-180秒内发生。所得结果表明，在吡唑啉形成反应中使用硅胶作为载体可对反应速率和产率产生深远影响，并产生更清洁的反应条件。
• Scaffold hopping for designing of potent and selective CYP1B1 inhibitors to overcome docetaxel resistance: synthesis and evaluation
  作者：Baddipadige Raju、Gera Narendra、Himanshu Verma、Manoj Kumar、Bharti Sapra、Gurleen Kaur、Subheet Kumar Jain、Padakanti Sandeep Chary、Neelesh Kumar Mehra、Om Silakari

  DOI：10.1080/07391102.2024.2310770

  日期：——

  Cytochrome P450 1B1, a tumor-specific overexpressed enzyme, significantly impairs the pharmacokinetics of several commonly used anticancer drugs including docetaxel, paclitaxel and cisplatin, leadi...

  细胞色素 P450 1B1 是一种肿瘤特异性过表达酶，会显着损害多种常用抗癌药物的药代动力学，包括多西他赛、紫杉醇和顺铂、铅等。
• Naphthylchalcones induce apoptosis and caspase activation in a leukemia cell line: The relationship between mitochondrial damage, oxidative stress, and cell death
  作者：Evelyn Winter、Louise Domeneghini Chiaradia、Clarissa A.S. de Cordova、Ricardo José Nunes、Rosendo Augusto Yunes、Tânia Beatriz Creczynski-Pasa

  DOI：10.1016/j.bmc.2010.09.025

  日期：2010.11

  In this study, we investigated the effects of 24 chalcone derivatives from 2-naphthylacetophenone toward a lymphoblastic leukemia cell line (L1210). Three compounds, called R7, R13, and R15, presented concentration- and time-dependent cytotoxicity and induced cellular death by apoptosis via mitochondrial injury and oxidative stress. The effects of these compounds appear to occur through different mechanisms because R13 and R7 induced a greater disturbance of mitochondrial potential, and all compounds induced disturbances of cellular ATP content and increased caspase-3 activity before cellular death. These compounds also interfered with antioxidant enzymes activities and GSH content through different mechanisms. (C) 2010 Elsevier Ltd. All rights reserved.