4-Methyl-4'-phenyl-chalkon | 37620-39-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4-Methyl-4'-phenyl-chalkon
• 英文别名: (2E)-1-{[1,1'-biphenyl]-4-yl}-3-(4-methylphenyl)prop-2-en-1-one；3-(4-methylphenyl)-1-(4-phenylphenyl)prop-2-en-1-one
• CAS: 37620-39-6
• 化学式: C₂₂H₁₈O
• 分子量: 298.384
• InChiKey: JTSGWWQKGVNALD-UHFFFAOYSA-N

物化性质

• 沸点：
  479.4±45.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  4-Methyl-4'-phenyl-chalkon 在 盐酸 、 sodium ethanolate 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 生成 [[5-(4-methylphenyl)-3-(4-phenylphenyl)cyclohex-2-en-1-ylidene]amino]urea
  参考文献：
  名称：

  一些5-（4-联苯基）-7-芳基[3,4-d] [1,2,3]-苯并噻二唑的合成及抑菌活性。

  摘要：

  合成了一系列5-（4-联苯基）-7-芳基[3,4-d] [1,2,3]-苯并噻二唑，并通过红外光谱，核磁共振和元素分析进行​​了表征，并评价了对某些化合物的体外抗菌活性。革兰氏阳性和革兰氏阴性细菌。抗菌数据表明，与参考环丙沙星和诺氟沙星相比，化合物7a-j对受试革兰氏阳性生物具有更好的活性。但是，这些化合物对革兰氏阴性菌几乎没有活性。化合物7c和7d是对抗革兰氏阳性细菌最有活性的化合物。

  DOI：

  10.1016/j.ejmech.2005.01.005
• 作为产物：
  描述：

  联苯 在 aluminum (III) chloride 、 sodium hydroxide 作用下， 以 乙醇 、 硝基苯 为溶剂， 反应 0.5h， 生成 4-Methyl-4'-phenyl-chalkon
  参考文献：
  名称：

  An Efficient Synthesis and In Vitro Antimicrobial Screening of 2-Cyanoimino -4-aryl-6-(1,1'-biphenyl-4-yl)-3,4-dihydro-1H-Pyrimidines

  摘要：

  本研究描述了在氢氧化钠存在下，从苯乙烯-4-联苯酮和氰基胍中高效合成 2-氰基亚胺-4-芳基-6-(1,1'-联苯-4-基)-3,4-二氢-1H-嘧啶的方法。氰基胍是构建所需氰基亚氨基嘧啶的 N-C≡N 源。根据质谱、傅立叶变换红外光谱、质子光谱和碳-13 NMR 光谱等光谱，对命名产物进行了结构鉴定。利用计算频率分析确定了更稳定的同分异构形式。经测试，这些化合物在微生物中具有显著的抗菌活性。

  DOI：

  10.13005/ojc/340222

文献信息

• Design, synthesis, and biological evaluation of polyphenols with 4,6-diphenylpyrimidin-2-amine derivatives for inhibition of Aurora kinase A
  作者：Young Han Lee、Jihyun Park、Seunghyun Ahn、Youngshim Lee、Junho Lee、Soon Young Shin、Dongsoo Koh、Yoongho Lim

  DOI：10.1007/s40199-019-00272-5

  日期：2019.6

  cytotoxicities against cancer cells, quantitative structure-activity relationships (QSAR) were calculated. Biological activities were determined by flow cytometry for cell cycle analysis and by immunoblot analysis for the detection of Aurora kinase A (AURKA) activity. Because 2-(2-Amino-6-(2,4-dimethoxyphenyl)pyrimidin-4-yl) phenol (derivative 12) selectively inhibited AURKA activity from the kinome assay

  背景技术几种4，6-二芳基嘧啶-2-胺衍生物显示出抗癌特性。但是，它们的作用方式尚未完全表征。为了开发有效的抗癌化学治疗剂，我们设计并合成了25个含有胍基部分的4,6-二苯基嘧啶-2-胺衍生物。方法进行了长期克隆存活试验以筛选抗癌化合物。为了得出对癌细胞具有良好细胞毒性的结构条件，计算了定量构效关系（QSAR）。通过流式细胞术测定生物活性以进行细胞周期分析，并通过免疫印迹分析测定Aurora激酶A（AURKA）活性。由于2-（2-氨基-6-（2,4-二甲氧基苯基）嘧啶-4-基）苯酚（衍生物12）通过kinome分析选择性抑制AURKA活性，在计算机对接实验中进行了阐明衍生物12和AURKA之间的分子结合模式。结果药效基团是基于QSAR计算得出的。衍生物12抑制了HCT116人结肠癌细胞在Thr283处的AURKA活性并降低了AURKA的磷酸化。衍生物12引起细胞周期G2 / M期的积累，并
• Synthesis and Characterization of 2-Pyrazoline Derivatives and their in silico and in vitro Studies on Antimicrobial and Anticancer Activities
  作者：S. Rathinamanivannan、K. Megha、Raja Chinnamanayakar、Ashok Kumar、M.R. Ezhilarasi

  DOI：10.14233/ajchem.2019.22082

  日期：2019.9.10

  The new series of 1-(4,5-dihydro-5-phenyl-3-diphenylpyrazol-1-yl)butan-1-one derivatives were synthesized by cyclization method using biphenyl chalcone with n-butyric acid and hydrazine hydrate. The synthesized 1-(4,5-dihydro-5-phenyl-3-diphenylpyrazol-1-yl)butan-1-one derivatives chemical structures were confirmed from spectral data such as FT-IR, 1H and 13C NMR. 2-Pyrazoline derivatives were docked with bacterial (1UAG) and breast cancer (1OQA) protein. Based on high binding affinity score, the best compound was subjected to in vitro anticancer activity by MTT assay. Also, antimicrobial activity were studied for synthesized 2-pyrazoline derivatives.

  新系列的1-(4,5-二氢-5-苯基-3-二苯基吡唑-1-基)丁酮衍生物通过使用联苯酮与丁酸和水合肼的环化方法合成。合成的1-(4,5-二氢-5-苯基-3-二苯基吡唑-1-基)丁酮衍生物的化学结构通过FT-IR、1H和13C NMR等光谱数据得到确认。2-吡唑衍生物与细菌蛋白(1UAG)和乳腺癌蛋白(1OQA)进行了对接。基于高结合亲和力分数，最佳化合物经过MTT分析进行了体外抗癌活性测试。此外，合成的2-吡唑衍生物的抗菌活性也进行了研究。
• SOCl<sub>2</sub> catalyzed cyclization of chalcones: Synthesis and spectral studies of some bio-potent <sup>1</sup><i>H</i> pyrazoles
  作者：K. Ranganathan、R. Suresh、G. Vanangamudi、K. Thirumurthy、P. Mayavel、G. Thirunarayanan

  DOI：10.4314/bcse.v28i2.11

  日期：——

  Some aryl-aryl 1H pyrazoles have been synthesised by cyclization of aryl chalcones and hydrazine hydrate in the presence of SOCl2. The yields of the pyrazoles are more than 85%. These pyrazoles are characterized by their physical constants and spectral data. The infrared, NMR spectral group frequencies of these pyrazolines have been correlated with Hammett substituent constants, F and R parameters. From the results of statistical analyses the effects of substituent on the spectral frequencies have been studied. The antimicrobial activities of all synthesised pyrazolines have been studied using Bauer-Kirby method.

  一些芳基-芳基1H吡唑通过在SOCl2存在下对芳香醛和水合肼进行环化合成。吡唑的得率超过85%。这些吡唑通过其物理常数和谱学数据进行了表征。这些吡唑频率的红外和核磁共振（NMR）光谱组频率与Hammett取代基常数、F和R参数相关联。通过统计分析结果，研究了取代基对光谱频率的影响。所有合成的吡唑的抗微生物活性通过Bauer-Kirby方法进行了研究。
• 피리미딘-2-아민 유도체, 이의 제조방법 및 이를 포함하는 항암제
  申请人：Konkuk University Industrial Cooperation Corp 건국대학교 산학협력단(220040157648) BRN ▼206-82-07325

  公开号：KR20190106839A

  公开（公告）日：2019-09-18

  본 발명은 피리미딘-2-아민 유도체, 이의 제조방법 및 이를 포함하는 항암제에 관한 것으로, 본 발명에 따른 화학식 1로 표시되는 피리미딘-2-아민 유도체는 오로라 A 키나아제 활성을 저해하는 효과가 우수하므로, 항암제로 유용할 수 있다.

  本发明涉及嘧啶-2-胺衍生物、其制备方法和包含它们的抗癌药物，根据本发明，用化学式1表示的嘧啶-2-胺衍生物具有优越的抑制Aurora A激酶活性的效果，因此可以作为抗癌药物有用。
• Synthesis and Characterization of 2-Phenylpyrazoline Derivatives and Evaluation of their Activities against Antimicrobial and Breast Cancer Cell Line in vitro and in silico Studies
  作者：RAJA CHINNAMANAYAKAR、M.R. EZHILARASI

  DOI：10.14233/ajchem.2019.21915

  日期：2019.5.25

  The new series of 2-phenylpyrazoline derivatives (2a-j) were synthesized and evaluated for their antimicrobial, in silico and in vitro anticancer activity was performed by MTT assay using MDA-MB-231 (human breast adenocarcinoma) cell line. The 2-phenylpyrazoline derivatives (2a-j) were obtained by the cyclization of chalcones with phenylhydrazine hydrochloride. Synthesized compounds were confirmed using FT-IR, 1H NMR and 13C NMR spectral data. Molecular docking studies were carried out using Auto Dock Tool version 1.5.6 and Auto dock version 4.2.5.1 docking program. in silico Docking study, compound 2d showed good binding score and good binding interaction with selected bacterial proteins and breast cancer protein. Based on this result, compound 2d was performed the anticancer activity by MTT assay method. From this result, compound 2d shown the LC50 value is 185.30 ± 1. 469 μg/mL. From the antibacterial activity compound 2i (2,3-dichloro substituted 2-pyrazoline derivative) showed a good zone of inhibition at high concentration (100 mg/mL) as compared to other derivatives (2a-j) and compound 2c (fluoro substituted 2-phenylpyrazoline derivative) showed a good zone of inhibition at low concentration (25 mg/mL) compared to other derivative (2a-j).

  新系列的2-苯基吡唑啉衍生物（2a-j）被合成并评估其抗菌、体外和体内抗癌活性，通过MTT测定法使用MDA-MB-231（人类乳腺腺癌）细胞系进行了评估。2-苯基吡唑啉衍生物（2a-j）是通过香豆素与盐酸苯基肼的环化得到的。合成的化合物通过FT-IR、1H NMR和13C NMR光谱数据进行了确认。分子对接研究使用Auto Dock工具版本1.5.6和Auto dock版本4.2.5.1对接程序进行。体外对接研究中，化合物2d显示出良好的结合得分和与选定的细菌蛋白和乳腺癌蛋白的良好结合相互作用。基于这个结果，化合物2d通过MTT测定法进行了抗癌活性评估。根据这个结果，化合物2d的LC50值为185.30 ± 1.469 μg/mL。从抗菌活性方面，化合物2i（2,3-二氯取代的2-吡唑啉衍生物）在高浓度（100 mg/mL）下显示出较好的抑菌区域，相比其他衍生物（2a-j），而化合物2c（氟取代的2-苯基吡唑啉衍生物）在低浓度（25 mg/mL）下显示出较好的抑菌区域，相比其他衍生物（2a-j）。