(E)-1-(4-chlorophenyl)-3-(3-methoxyphenyl)prop-2-en-1-one | 196866-09-8

• 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: (E)-1-(4-chlorophenyl)-3-(3-methoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-1-(4-chlorophenyl)-3-(3-methoxyphenyl)prop-2-en-1-one
• CAS: 196866-09-8
• 化学式: C₁₆H₁₃ClO₂
• 分子量: 272.731
• InChiKey: WOIWMJZWHCQKEE-BJMVGYQFSA-N

物化性质

• 沸点：
  425.1±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-chlorophenyl)-3-(3-methoxyphenyl)prop-2-en-1-one 在 氰化钠 、 ammonium acetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-[5-(4-Chloro-phenyl)-3-(3-methoxy-phenyl)-1H-pyrrol-2-yl]-pyridine
  参考文献：
  名称：

  Potent, orally absorbed glucagon receptor antagonists

  摘要：

  The SAR of 2-pyridyl-3,5-diaryl pyrroles, ligands of the human glucagon receptor and inhibitors of p38 kinase, were investigated. This effort resulted in the identification of 2-(4-pyridyl)-5-(4-chlorophenyl)-3-(5-bromo-2-propyloxyphenyl)pyrrole 49 (L-168,049), a potent (Kb = 25 nM), selective antagonist of glucagon. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00081-5
• 作为产物：
  描述：

  对氯苯乙酮 、 3-甲氧基苯甲醛 在 montmorillonite KSF 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以78%的产率得到(E)-1-(4-chlorophenyl)-3-(3-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  蒙脱石粘土促进的无溶剂交叉羟醛缩合在聚焦微波辐照下

  摘要：

  为合成芳基和杂芳基反式查耳酮开发了一种环境友好、清洁和通用的协议。该方法涉及在粘土基催化剂存在下在微波辐射下的无溶剂反应条件，并以良好的收率和较短的反应时间提供目标​​化合物。此外，相同的条件允许从芳香醛和酮合成对称的二芳基亚甲基-α,β-不饱和酮。

  DOI：

  10.3390/molecules19067317

文献信息

• Montmorillonite Clay-Promoted, Solvent-Free Cross-Aldol Condensations under Focused Microwave Irradiation
  作者：Damiano Rocchi、Juan González、J. Menéndez

  DOI：10.3390/molecules19067317

  日期：——

  An environmentally benign, clean and general protocol was developed for the synthesis of aryl and heteroaryl trans-chalcones. This method involved solvent-free reaction conditions under microwave irradiation in the presence of a clay-based catalyst, and afforded the target compounds in good yields and short reaction times. Furthermore, the same conditions allowed the synthesis of symmetrical, diarylmethylene-α

  为合成芳基和杂芳基反式查耳酮开发了一种环境友好、清洁和通用的协议。该方法涉及在粘土基催化剂存在下在微波辐射下的无溶剂反应条件，并以良好的收率和较短的反应时间提供目标​​化合物。此外，相同的条件允许从芳香醛和酮合成对称的二芳基亚甲基-α,β-不饱和酮。
• Study on the substituents' effects of a series of synthetic chalcones against the yeast Candida albicans
  作者：D. Batovska、St. Parushev、A. Slavova、V. Bankova、I. Tsvetkova、M. Ninova、H. Najdenski

  DOI：10.1016/j.ejmech.2006.08.012

  日期：2007.1

  A large series of chalcones were synthesized and studied for activity against Candida albicans. The SAR analysis showed that the antifungal activity was highly dependent on the substitution pattern of the aryl rings and correlated to a large extent with the ability of compounds to interact with sulfhydryl groups. The most active were the hydroxylated chalcones as their activity related to the location

  合成了大量查耳酮，并研究了其对白色念珠菌的活性。SAR分析表明，抗真菌活性高度依赖于芳基环的取代方式，并在很大程度上与化合物与巯基相互作用的能力有关。最具活性的是羟基化查耳酮，因为它们的活性与芳基环B中酚基的位置有关，如下所示：o-OH> p-OH约为3,4-di-OH> m-OH。获得的这些相关性和其他相关性极大地有助于设计抗候选查耳酮。
• [EN] COMPOSITION FOR TREATING DIABETES AND METABOLIC DISEASES AND A PREPARATION METHOD THEREOF<br/>[FR] COMPOSITION POUR LE TRAITEMENT DU DIABÈTE ET DE MALADIES MÉTABOLIQUES, ET SON PROCÉDÉ DE PRÉPARATION
  申请人：UNIV KAOHSIUNG MEDICAL

  公开号：WO2013022951A1

  公开（公告）日：2013-02-14

  Disclosed is a chalcone composition for treating diabetes and metabolic syndromes. In particular, the chalcone compound bound with 2-halogen in ring A significantly decreases the blood glucose level in the in vitro anti-diabetic effect experiment. In the in vivo animal model, the leading chalcone compound can prevent the progression of diabetes and control the blood glucose level, and there is no significant difference in the gains in body weight. Throughout the seven-week administration, there are no hepatic or renal toxicity observed.

  揭示了一种用于治疗糖尿病和代谢综合征的茚素组合物。具体来说，在环A中与2-卤素结合的茚素化合物在体外抗糖尿病效应实验中显着降低了血糖水平。在体内动物模型中，主要的茚素化合物可以预防糖尿病的进展并控制血糖水平，体重增加方面没有显著差异。在为期七周的给药过程中，没有观察到肝脏或肾脏毒性。
• COMPOSITION FOR TREATING ATHEROSCLEROSIS AND A PREPARATION METHOD THEREOF
  申请人：WU YANG-CHANG

  公开号：US20130040996A1

  公开（公告）日：2013-02-14

  Disclosed are a composition for preventing and treating atherosclerosis which includes chalcone compound. In particular, the chalcone compound bound with 2-hydroxyl in ring A and 4′-methyoxy in ring B has versatile therapeutic potentials on anti-atherosclerosis by acting as PPARγ inducer, p44/42 MAPK inhibitor and cell cycle blocker and does not show toxicity to human aortic smooth muscle cells (HASMCs). In addition, the chalcone compound exhibits synergistic effect with the PPARγ ligand (rosiglitazone) to inhibit cell proliferation and the upregulation of cyclin D1, cyclin D3, interleukin-1β (IL-1β) and interleukin-6 (IL-6) induced by oxidized low density lipoprotein (Ox-LDL).

  本发明涉及一种用于预防和治疗动脉粥样硬化的组合物，其中包括查尔酮化合物。特别地，环A中与2-羟基结合，环B中与4'-甲氧基结合的查尔酮化合物具有多种治疗潜力，可作为PPARγ诱导剂、p44/42 MAPK抑制剂和细胞周期阻滞剂，且不对人体主动脉平滑肌细胞（HASMCs）显示毒性。此外，查尔酮化合物与PPARγ配体（罗格列酮）表现出协同作用，可抑制由氧化低密度脂蛋白（Ox-LDL）诱导的细胞增殖和cyclin D1、cyclin D3、白细胞介素-1β（IL-1β）和白细胞介素-6（IL-6）上调。
• COMPOSITION FOR TREATING DIABETES AND METABOLIC DISEASES AND A PREPARATION METHOD THEREOF
  申请人：Wu Yang-Chang

  公开号：US20140350304A1

  公开（公告）日：2014-11-27

  Disclosed is a chalcone composition for treating diabetes and metabolic syndromes. In particular, the chalcone compound bound with 2-halogen in ring A significantly decreases the blood glucose level in the in vitro anti-diabetic effect experiment. In the in vivo animal model, the leading chalcone compound can prevent the progression of diabetes and control the blood glucose level, and there is no significant difference in the gains in body weight. Throughout the seven-week administration, there are no hepatic or renal toxicity observed.

  本发明公开了一种治疗糖尿病和代谢综合症的查尔酮组合物。特别是，环A中结合有2-卤素的查尔酮化合物在体外抗糖尿病实验中显著降低血糖水平。在体内动物模型中，主要的查尔酮化合物可以预防糖尿病的进展并控制血糖水平，体重增加也没有显著差异。在七周的给药过程中，没有观察到肝脏或肾脏毒性。