3-(naphth-1-yl)-1-(4-chloro)phenylprop-2-en-1-one | 56412-56-7

• 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-(naphth-1-yl)-1-(4-chloro)phenylprop-2-en-1-one
• 英文别名: 1-(4-chlorophenyl)-3-(naphthalen-1-yl)-2-propen-1-one；1-(4-chlorophenyl)-3-naphthylprop-2-en-1-one；1-(4-chlorophenyl)-3-(naphth-1-yl)prop-2-en-1-one；1-(4-chlorophenyl)-3-(1-naphthalenyl)prop-2-en-1-one；1-(4-chlorophenyl)-3-naphthalen-1-ylprop-2-en-1-one
• CAS: 56412-56-7
• 化学式: C₁₉H₁₃ClO
• 分子量: 292.765
• InChiKey: XPHQJOOQZCMEMB-UHFFFAOYSA-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：

  3-(naphth-1-yl)-1-(4-chloro)phenylprop-2-en-1-one 在 sodium acetate 、 乙酸酐 、 potassium hydroxide 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 2-(3-(4-chlorophenyl)-5-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazole
  参考文献：
  名称：

  Synthesis and biological evaluation of compounds which contain pyrazole, thiazole and naphthalene ring as antitumor agents

  摘要：

  A series of compounds which contain pyrazole, thiazole and naphthalene ring (1a-7a, 1b-7b, 1c-7c, 1d-7d) were firstly synthesized and their anti-proliferative activity, EGFR inhibitory activity, cytotoxicity and inhibition to Hela cell migration were evaluated. Compound 2-(3-(3,4-dimethylphenyl)-5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl) thiazol-4(5H)-one (7d) displayed the most potent inhibitory activity (IC50 = 0.86 mu M for Hela and IC50 = 0.12 mu M for EGFR). Structure-activity relationship (SAR) analysis showed that the anti-proliferative activity was affected by A-ring-substituent (-OCH3 > -CH3 > -H > -Br > -Cl > -F). Docking simulation of compound 7d into EGFR active site showed that naphthalene ring of 7d with LYS721 formed two p-pi bonds, which enhanced antitumor activity. Therefore, compound 7d may be developed as a potential antitumor agent. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.072
• 作为产物：
  描述：

  对氯苯乙酮 、 1-萘甲醛 在 Zn(L-proline)₂ 作用下， 以 乙醇 、 水 为溶剂， 反应 0.08h， 生成 3-(naphth-1-yl)-1-(4-chloro)phenylprop-2-en-1-one
  参考文献：
  名称：

  提高锌连接氨基酸配合物的催化性能，在水性介质中合成新型嘧啶具有生态友好性

  摘要：

  锌连接的氨基酸配合物Zn（l-脯氨酸）2被认为是合成新型嘧啶衍生物5a-q的绿色催化剂。嘧啶5a-q是通过两种途径制备的：第一种是胍3a -c与芳族醛1和苯乙酮2的单锅反应。第二个是胍3 a–c与不同查耳酮4 a–j的反应在水性介质中。该协议的主要优点是操作简单，反应时间短，效率高（97％）。此外，通过检查Zn（l-脯氨酸）2配合物在五个连续循环中的可重复使用性，而没有明显降低催化活性，对该合成方案的绿色方面进行了进一步研究。该新方法在不使用任何有机溶剂的情况下，在安全性，简便性，稳定性，温和条件，较短的反应时间，优异的收率和高纯度方面显示出显着的优势。

  DOI：

  10.1002/aoc.6197

文献信息

• Synthesis and biological effects of naphthalene-chalcone derivatives
  作者：Qing-Hao Jin、Hong-Hai Chen、Wen-Bo Chen、Zhi-Yang Fu、Li-Ping Guan、Hai-Ying Jiang

  DOI：10.1007/s00044-020-02525-4

  日期：2020.5

  In this paper, 21 naphthalene-chalcone derivatives were synthesized and their biological effects were evaluated. The results showed that compounds 2a–2u displayed clear antidepressant activity at 30 mg/kg in the forced swimming test. Compounds 2h, 2o, 2t, and 2u exhibited a good antidepressant effect in the forced swimming test and tail suspension test at 30 mg/kg. Compounds 2h, 2o, 2t, and 2u but

  本文合成了21种萘-查耳酮衍生物，并对其生物学效果进行了评价。结果表明，在强制游泳试验中，化合物2a–2u在30 mg / kg时显示出明显的抗抑郁活性。化合物2h，2o，2t和2u在30 mg / kg的强迫游泳试验和尾部悬吊试验中表现出良好的抗抑郁作用。化合物2h，2o，2t和2u在小鼠的野外试验中对运动能力没有影响。此外，化合物2o的最抗抑郁活性可能是由中枢神经系统中5-羟色胺和去甲肾上腺素水平升高介导的。化合物2a–2u在30 mg / kg时也显示出镇痛和抗炎作用。
• Synthesis and Pharmacochemistry of New Pleiotropic Pyrrolyl Derivatives
  作者：Markella Konstantinidou、Alice Gkermani、Dimitra Hadjipavlou-Litina

  DOI：10.3390/molecules200916354

  日期：——

  Within the framework of our attempts to synthesize pleiotropic anti-inflammatory agents, we have synthesized some chalcones and their corresponding 3,4-pyrrolyl derivatives. Chalcones constitute a class of compounds with high biological impact. They are known for a number of biological activities, including anti-inflammatory and free radical scavenging activities. They inhibit several enzymes implicated in the inflammatory process, such as lipoxygenase, cyclooxygenase (COX) and lysozymes. The synthesized pyrroles have been studied for: (1) their in vitro inhibition of lipoxygenase; (2) their in vitro inhibition of COX; (3) their in vitro inhibition of lipid peroxidation; (4) their interaction with the stable, N-centered, free radical, 2,2-diphenyl-1-picrylhydrazyl (DPPH); (5) their inhibition on interleukin-6 (IL-6); (6) their anti-proteolytic activity; and (7) their in vivo anti-inflammatory activity using carrageenan-induced rat paw edema. Their physicochemical properties were determined to explain the biological results. Lipophilicity was experimentally determined. 2i and 2v were found to be promising multifunctional molecules with high antiproteolytic and anti-inflammatory activities in combination with anti-interleukin-6 activity.

  在我们合成多效抗炎剂的框架内，我们合成了一些查尔酮及其相应的3,4-吡咯衍生物。查尔酮是一类具有高生物影响的化合物。它们因多种生物活性而知名，包括抗炎和清除自由基的活性。它们能够抑制几种与炎症过程相关的酶，如脂氧化酶、环氧合酶（COX）和溶菌酶。合成的吡咯类化合物已被研究以下方面：(1) 其对脂氧化酶的体外抑制；(2) 其对COX的体外抑制；(3) 其对脂质过氧化的体外抑制；(4) 其与稳定的N中心自由基2,2-二苯基-1-苦味肼（DPPH）的相互作用；(5) 对白细胞介素-6 (IL-6) 的抑制；(6) 其抗蛋白酶活性；(7) 通过卡拉胶诱导的大鼠足部水肿进行的体内抗炎活性。为了解释生物结果，测定了它们的物理化学性质。脂溶性是通过实验确定的。2i和2v被发现是有前景的多功能分子，具有很高的抗蛋白酶和抗炎活性，同时还具备抗白细胞介素-6的活性。
• β-Carbon activation of saturated carboxylic esters through N-heterocyclic carbene organocatalysis
  作者：Zhenqian Fu、Jianfeng Xu、Tingshun Zhu、Wendy Wen Yi Leong、Yonggui Robin Chi

  DOI：10.1038/nchem.1710

  日期：2013.10

  The activation of the α-carbons of carboxylic esters and related carbonyl compounds to generate enolate equivalents as nucleophiles is one of the most powerful strategies in organic synthesis. We reasoned that the horizons of chemical synthesis could be greatly expanded if the typically inert β-carbons of saturated esters could be used as nucleophiles. However, despite the rather significant fundamental

  活化羧酸酯和相关羰基化合物的 α-碳以生成烯醇等价物作为亲核试剂是有机合成中最有效的策略之一。我们推断，如果饱和酯的典型惰性 β-碳可以用作亲核试剂，则化学合成的范围可以大大扩展。然而，尽管具有相当重要的基本和实用价值，但直接使用饱和羰基化合物的 β-碳作为亲核试剂仍然难以捉摸。在这里，我们报告了使用N催化活化作为亲核试剂的简单饱和酯 β-碳（β-碳活化）-杂环卡宾有机催化剂。催化产生的亲核β-碳与亲电子试剂如烯酮和亚胺发生对映选择性反应。鉴于已证明酯 α-碳具有丰富的化学性质，我们预计这种饱和酯 β-碳的催化活化模式将为新的有用反应和合成策略开辟一个有价值的新领域。
• Allosteric protein kinase modulators
  申请人：Engel Matthias

  公开号：US08912186B2

  公开（公告）日：2014-12-16

  The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

  本发明提供了一种特定的小分子化合物，可以变构地调节AGC蛋白激酶和Aurora家族蛋白激酶的活性或调节它们之间的蛋白质相互作用，以及制备它们的方法、包含它们的制药组合物，以及它们用于制备治疗与AGC蛋白激酶或Aurora家族蛋白激酶异常活性相关的疾病的药物。
• 2,4-Diaryl-pyrimido[1,2-a]benzimidazole derivatives as novel anticancer agents endowed with potent anti-leukemia activity: Synthesis, biological evaluation and kinase profiling
  作者：Moataz A. Shaldam、Denisa Hendrychová、Radwan El-Haggar、Veronika Vojáčková、Taghreed A. Majrashi、Eslam B. Elkaeed、Nicolas Masurier、Vladimír Kryštof、Haytham O. Tawfik、Wagdy M. Eldehna

  DOI：10.1016/j.ejmech.2023.115610

  日期：2023.10

  superior sub-micromolar activity towards leukemia. Furthermore, pyrimido[1,2-a]benzimidazoles 5e-l were tested on a panel ofhuman acute leukemia cell lines, namely HL60, MOLM-13, MV4-11, CCRF-CEM and THP-1, where 5e-h reached single-digit micromolar GI50 values for all the tested cell lines. All prepared compounds were first tested for inhibitory action against the leukemia-associated mutant FLT3-ITD

  急性髓系白血病 (AML) 是最具侵袭性的人类癌症之一，发展迅速，因此需要立即治疗。在目前的研究中，报道了作为潜在抗 AML 药物的新型嘧啶并[1,2- a ]苯并咪唑 ( 5a-p )衍生物的开发。在NCI-DTP中检查制备的化合物5a-p的体外抗肿瘤活性，随后选择5h进行全组五剂量筛选以评估其TGI、LC 50和GI 50值。化合物5h在低微摩尔浓度下对所有测试的人类癌细胞系均表现出有效的抗肿瘤活性，GI 50范围为 0.35 至 9.43 μM，对白血病具有优异的亚微摩尔浓度。此外，在一组人急性白血病细胞系（即 HL60、MOLM-13、MV4-11、CCRF-CEM 和 THP-1）上测试了嘧啶并[1,2- a ]苯并咪唑5e-l ，其中5e-h达到了单次所有测试细胞系的数字微摩尔 GI 50值。首先测试所有制备的化合物对白血病相关突变体 FLT3-ITD 以及 ABL、CDK2 和