1-(4-hydroxy-3-methylphenyl)-3-phenyl-2-propen-1-one | 2910-76-1

• 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: 1-(4-hydroxy-3-methylphenyl)-3-phenyl-2-propen-1-one
• 英文别名: 4'-hydroxy-3'-methyl-trans-chalcone；4'-Hydroxy-3'-methyl-trans-chalkon；(E)-1-(4-hydroxy-3-methylphenyl)-3-phenylprop-2-en-1-one
• CAS: 2910-76-1
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: SHPMQNTYESNIQW-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxy-3-methylphenyl)-3-phenyl-2-propen-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 5-phenyl-3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-1H-1-pyrazolyl-2-toluidinomethanethione
  参考文献：
  名称：

  新型吡唑啉衍生物的合成及其对人肺肿瘤细胞系 (A549) 的细胞毒活性

  摘要：

  在本研究中，一系列 5-(-4-(取代)苯基)-3-(4-羟基-3-甲基苯基)-4,5-二氢-1H-1-吡唑基-2-甲苯胺基甲硫酮和合成了 5-(取代)苯基-3-(4-羟基-3-甲基苯基)-4,5-二氢-1H-1-吡唑基-2-甲氧基苯胺基甲硫酮，并针对人肺肿瘤细胞系 (A549 ) 在体外使用 MTT 测定系统。在这些测试中，5-(4-氟苯基)-3-(4-羟基-3-甲基苯基)-4,5-二氢-1H-1-吡唑基-2-甲苯胺基甲硫酮和5-(4-氯苯基)- 3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-1H-1-pyrazolyl-2-methoxy anilino methane thione 对人肺肿瘤细胞系 (A549) 的细胞毒性比其他合成化合物更强。

  DOI：

  10.1002/jccs.200700014
• 作为产物：
  描述：

  trans-cinnamic acid o-tolyl ester 在 三氯化铝 、 硝基苯 作用下， 生成 1-(4-hydroxy-3-methylphenyl)-3-phenyl-2-propen-1-one
  参考文献：
  名称：

  Christian; Amin, Journal of the Indian Chemical Society, 1959, vol. 36, p. 715,718

  摘要：

  DOI：

文献信息

• Pyrimidinones as Casein Kinase II (CK2) Modulators
  申请人：Rice Kenneth D.

  公开号：US20090215803A1

  公开（公告）日：2009-08-27

  A compound having Formula (I) or a pharmaceutically acceptable salt thereof, wherein X, R 1 and R 2 are defined in the specification; pharmaceutical compositions thereof; and methods of use thereof.

  具有化学式（I）或其药用可接受的盐的化合物，其中X、R1和R2在规范中定义；其药物组成；以及使用方法。
• Synthesis and antimycobacterial activity of novel 4-[5-(substituted phenyl)-1-phenyl-4,5-dihydro-1H-3-pyrazolyl]-2-methylphenol derivatives
  作者：Mohamed Ashraf Ali、Mohammad Shahar Yar

  DOI：10.1007/s00044-007-9000-4

  日期：2007.12

  hydrazide in glacial acetic acid, which led to the formation of novel 4-[5-(substituted phenyl)-1-phenyl-4,5-dihydro-1 H -3-pyrazolyl]-2-methylphenol derivatives. All newly synthesized compounds were evaluated for their antimycobacterial activities against isoniazid-resistant Mycobacterium tuberculosis using agar dilution. 4-[5-(4-Fluoro phenyl)-1-phenyl-4,5-dihydro-1 H -3-pyrazolyl]-2-methylphenol

  在目前的研究中，4-羟基-3-甲基苯乙酮与适当的醛在氢氧化钾甲醇溶液中缩合，生成相应的查耳酮（CI -XI）。这些相应的查耳酮在冰醋酸中与酰肼反应，导致形成新的4- [5-（取代的苯基）-1-苯基-4,5-二氢-1 H -3-吡唑基] -2-甲基苯酚衍生物。使用琼脂稀释液评估所有新合成的化合物对耐异烟肼 结核分枝杆菌的抗分枝 杆菌活性 。4- [5-（4-氟苯基）-1-苯基-4,5-二氢-1 H -3-吡唑基] -2-甲基苯酚显示出良好的抗分枝杆菌活性，最低抑制浓度为0.62μg/ ml。
• Synthesis and in vitro antimycobacterial activity of N1-nicotinoyl-3-(4′-hydroxy-3′-methyl phenyl)-5-[(sub)phenyl]-2-pyrazolines
  作者：Mohammad Shaharyar、Anees Ahamed Siddiqui、Mohamed Ashraf Ali、Dharmarajan Sriram、Perumal Yogeeswari

  DOI：10.1016/j.bmcl.2006.05.024

  日期：2006.8

  A series of N1-nicotinoyl-3- (4'-hydroxy-3'-methyl phenyl)-5-(substituted phenyl)-2-pyrazolines were synthesized by the reaction between isoniazid (INH) and chalcones and were tested for their antimycobacterial activity in vitro against Mycobacterium tuberculosis H37Rv (MTB) and INH-resistant M. tuberculosis (INHR-MTB) using the agar dilution method. Among the synthesized compounds, compound (i) N

  通过异烟肼（INH）与查耳酮的反应合成了一系列N1-烟酰基-3-（4'-羟基-3'-甲基苯基）-5-（取代的苯基）-2-吡唑啉，并测试了它们的抗分枝杆菌作用琼脂稀释法在体外对结核分枝杆菌H37Rv（MTB）和耐INH结核分枝杆菌（INHR-MTB）具有体外活性。在合成的化合物中，发现化合物（i）N1-烟酰基-3-（4'-羟基-3'-甲基苯基）-5-（1''-氯苯基）-2-吡唑啉是最有效的抗MTB和INHR-MTB，最低抑菌浓度为0.26微米。当与INH化合物比较时，我发现其对MTB和INHR-MTB的活性分别高2.8倍和43.7倍。
• Ali, Mohamed A.; Yar, Mohammad Shahar; Siddiqui, Anees A., Acta poloniae pharmaceutica, 2007, vol. 64, # 5, p. 435 - 439
  作者：Ali, Mohamed A.、Yar, Mohammad Shahar、Siddiqui, Anees A.、Husain, Asif、Abdullah, Mustaqeem

  DOI：——

  日期：——
• Synthesis, structural activity relationship and anti-tubercular activity of novel pyrazoline derivatives
  作者：Mohamed Ashraf Ali、Mohammad Shaharyar、Anees Ahamed Siddiqui

  DOI：10.1016/j.ejmech.2006.08.004

  日期：2007.2

  In the present investigation, a series of 5+4-(substituted) phenyl)-3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-IH-1-pyrazolyl-2-toluidino methane thione and 5-(substituted) phenyl-3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-1H-1-pyrazolyl-2-methoxyanilino methane thione were synthesized by the reaction between hydrazine hydrate and chalcones (3a-k) followed by condensation with appropriate aryl isothiocyanate which yielded N-substituted pyrazoline derivatives. Newly synthesized compounds were tested for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the synthesized compounds, compound anilino-3-(4-hydroxy-3-methylphenyl)-5-(2,6-dichlorophenyl)-4,5-dihydro-1H-1-pyrazolylmethanethione (6i) was found to be more active agent against M. tuberculosis H37Rv with minimum inhibitory concentration of 0.0034 mu M. (c) 2006 Elsevier Masson SAS. All rights reserved.