(E)-1-(3,4-dichlorophenyl)-3-(furan-2-yl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(3,4-dichlorophenyl)-3-(furan-2-yl)prop-2-en-1-one
• 英文别名: (2E)-1-(3,4-Dichlorophenyl)-3-(furan-2-yl)prop-2-en-1-one
• 化学式: C₁₃H₈Cl₂O₂
• 分子量: 267.111
• InChiKey: JRNHEVUNNACLIL-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(3,4-dichlorophenyl)-3-(furan-2-yl)prop-2-en-1-one 以 乙醇 为溶剂， 反应 10.0h， 生成 2-(3-(3,4-dichlorophenyl)-5-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-methoxyphenyl)thiazole
  参考文献：
  名称：

  Discovery and modification of sulfur-containing heterocyclic pyrazoline derivatives as potential novel class of β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors

  摘要：

  A series of sulfur-containing heterocyclic pyrazoline derivatives (C1-C18; D1-D9) have been synthesized and purified (all are new except one) to be screened for FabH inhibitory activity. Compound C14 showed the most potent biological activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis (MIC values: 1.56-3.13 mu g/mL), being comparable with the positive control, while D6 performed the best in the thiazolidinone series (MIC values: 3.13-6.25 mu g/mL). They also demonstrated strong broad-spectrum antimicrobial activity. Compounds C14 and D6 exhibited the most potent E. coli FabH inhibitory activity with IC50 of 4.6 and 8.4 mu M, respectively, comparable with the positive control DDCP (IC50 = 2.8 mu M). Docking simulation was performed to position compound C14 and D6 into the E. coli FabH structure active site to determine the probable binding model. The structurally modification of previous compounds and the attempt in innovative target have brought a positive progress. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.05.091
• 作为产物：
  描述：

  糠醛 、 3,4-二氯苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以55%的产率得到(E)-1-(3,4-dichlorophenyl)-3-(furan-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Design, Facile Synthesis and Characterization of Dichloro Substituted Chalcones and Dihydropyrazole Derivatives for Their Antifungal, Antitubercular and Antiproliferative Activities

  摘要：

  真菌和分枝杆菌引起的传染病对人类构成重要问题。同样，癌症是全球死亡的主要原因之一。因此，迫切需要开发新型药物来对抗癌症、结核病以及真菌感染等致命问题。因此，在本研究中，我们设计、合成和表征了30种化合物，包括15种香豆素（2-16）和15种二氢吡唑（17-31），含有二氯苯基团，并对这些化合物进行了抗真菌、抗结核和抗增殖活性的筛选。在这些化合物中，二氢吡唑表现出优异的抗真菌和抗结核活性，而香豆素表现出有希望的抗增殖活性。在二氢吡唑中，含有2-噻吩基团的31号化合物显示出有希望的抗真菌活性（MIC为5.35 µM），而含有2,4-二氟苯基和4-三氟甲基骨架的22号和24号化合物分别显示出显著的抗结核活性，MIC分别为3.96和3.67 µM。在香豆素系列中，含有2-噻吩基团的16号化合物显示出最高的抗增殖活性，IC50值为17 ± 1 µM。通过本研究确定的最活性化合物可能被视为具有潜在抗真菌、抗结核和抗增殖活性药物开发的起点。

  DOI：

  10.3390/molecules25143188

文献信息

• MODIFIED CHALCONE COMPOUNDS AS ANTIMITOTIC AGENTS
  申请人：ROSE Seth D.

  公开号：US20070265317A1

  公开（公告）日：2007-11-15

  Antimitotic agents comprising a modified chalcone or modified chalcone derivative are disclosed. The modified chalcone or modified chalcone derivative compounds are of the general formula CHAL-LIN—COV, wherein CHAL is a chalcone or chalcone derivative portion, LIN is an optional linker portion, and COV is a covalent bonding portion (e.g., an α,β-unsaturated thiol ester group). The modified chalcone or modified chalcone derivative compounds provide an improved method of interference with tubulin polymerization, for example by covalent (and essentially irreversible) bonding between tubulin and the covalent bonding portion, potentially resulting in a decrease in tumor size and/or disappearance of the cancer, to the benefit of cancer patients.

  本发明涉及一种包含改性查尔酮或改性查尔酮衍生物的抗有丝分裂剂。改性查尔酮或改性查尔酮衍生物化合物的一般式为CHAL-LIN-COV，其中，CHAL是查尔酮或查尔酮衍生物部分，LIN是可选的连接部分，COV是共价键合部分（例如α，β-不饱和硫酯酯基）。改性查尔酮或改性查尔酮衍生物化合物提供了一种改进的干扰微管聚合的方法，例如通过微管和共价键合部分之间的共价键合（基本上是不可逆的），可能导致肿瘤大小减小和/或癌症消失，从而使癌症患者受益。
• Modified chalcone compounds as antimitotic agents
  申请人：Arizona Biomedical Research Commission

  公开号：EP2447248A2

  公开（公告）日：2012-05-02

  Antimitotic agents comprising a modified chalcone or modified chalcone derivative are disclosed. The modified chalcone or modified chalcone derivative compounds are of the general formula CHAL-LIN-COV, wherein CHAL is a chalcone or chalcone derivative portion, LIN is an optional linker portion, and COV is a covalent bonding portion (e.g., an a,ss-unsaturated thiol ester group). The modified chalcone or modified chalcone derivative compounds provide an improved method of interference with tubulin polymerization, for example by covalent (and essentially irreversible) bonding between tubulin and the covalent bonding portion, potentially resulting in a decrease in tumor size and/or disappearance of the cancer, to the benefit of cancer patients.

  本发明公开了包含改性查尔酮或改性查尔酮衍生物的抗硝化剂。改性查尔酮或改性查尔酮衍生物化合物的通式为 CHAL-LIN-COV，其中 CHAL 为查尔酮或查尔酮衍生物部分，LIN 为任选连接部分，COV 为共价键部分（例如，a,s-不饱和硫醇酯基）。改性查尔酮或改性查尔酮衍生物化合物提供了一种改进的干扰小管蛋白聚合的方法，例如通过小管蛋白与共价键部分之间的共价键（且基本上不可逆），可能导致肿瘤体积减小和/或癌症消失，从而使癌症患者受益。
• Synthesis and anti-inflammatory activity of chalcone derivatives
  作者：Felipe Herencia、M.Luisa Ferrándiz、Amalia Ubeda、JoséN. Domínguez、Jaime E. Charris、Gricela M. Lobo、M.José Alcaraz

  DOI：10.1016/s0960-894x(98)00179-6

  日期：1998.5

  Chalcones and their derivatives were synthesized and evaluated for their anti-inflammatory activity. In vitro, chalcones 2, 4, 8, 10 and 13 inhibited degranulation and 5-lipoxygenase in human neutrophils, whereas 11 behaved as scavenger of superoxide. Only four compounds (4-7) inhibited cyclo-oxygenase-2 activity. The majority of these samples showed anti-inflammatory effects in the mouse air pouch model. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Modified Chalcone Compounds as Antimitotic Agents
  申请人：Rose Seth D.

  公开号：US20100222380A1

  公开（公告）日：2010-09-02

  Antimitotic agents comprising a modified chalcone or modified chalcone derivative are disclosed. The modified chalcone or modified chalcone derivative compounds are of the general formula CHAL-LIN-COV, wherein CHAL is a chalcone or chalcone derivative portion, LIN is an optional linker portion, and COV is a covalent bonding portion (e.g., an α,β-unsaturated thiol ester group). The modified chalcone or modified chalcone derivative compounds provide an improved method of interference with tubulin polymerization, for example by covalent (and essentially irreversible) bonding between tubulin and the covalent bonding portion, potentially resulting in a decrease in tumor size and/or disappearance of the cancer, to the benefit of cancer patients.
• US7714025B2
  申请人：——

  公开号：US7714025B2

  公开（公告）日：2010-05-11