(E)-3-(4-(benzyloxy)phenyl)-1-(2-iodophenyl)prop-2-en-1-one | 1381931-18-5

• 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)-3-(4-(benzyloxy)phenyl)-1-(2-iodophenyl)prop-2-en-1-one
• 英文别名: (E)-1-(2-iodophenyl)-3-(4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 1381931-18-5
• 化学式: C₂₂H₁₇IO₂
• 分子量: 440.28
• InChiKey: SQQRGBADWKAIOU-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 2'-碘苯乙酮 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-3-(4-(benzyloxy)phenyl)-1-(2-iodophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of chalcone derivatives as potential anti-diabetic agents

  摘要：

  Chalcones bearing electron donating or electron withdrawing substitutions were prepared and their glucose uptake activity was evaluated. Chalcone derivatives were synthesized in one step protocol with high purity and yield. Chalcones with chloro, bromo, iodo and hydroxy substitutions at position 2 on A-ring exhibited the highest activity with glucose medium concentration (210 to 236 mg/dl) compared to pioglitazone and rosiglitazone (230 and 263 mg/dl, respectively). Also chalcones with iodo substitution at position 3 on A-ring were comparably active (<= 238 mg/dl). The structure-activity relationship of the tested chalcones was studied and the findings were supported statistically (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.108

文献信息

• [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 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。
• US9085520B2
  申请人：——

  公开号：US9085520B2

  公开（公告）日：2015-07-21
• Synthesis of chalcone derivatives as potential anti-diabetic agents
  作者：Chi-Ting Hsieh、Tusty-Jiuan Hsieh、Mohamed El-Shazly、Da-Wei Chuang、Yi-Hong Tsai、Chiao-Ting Yen、Shou-Fang Wu、Yang-Chang Wu、Fang-Rong Chang

  DOI：10.1016/j.bmcl.2012.04.108

  日期：2012.6

  Chalcones bearing electron donating or electron withdrawing substitutions were prepared and their glucose uptake activity was evaluated. Chalcone derivatives were synthesized in one step protocol with high purity and yield. Chalcones with chloro, bromo, iodo and hydroxy substitutions at position 2 on A-ring exhibited the highest activity with glucose medium concentration (210 to 236 mg/dl) compared to pioglitazone and rosiglitazone (230 and 263 mg/dl, respectively). Also chalcones with iodo substitution at position 3 on A-ring were comparably active (<= 238 mg/dl). The structure-activity relationship of the tested chalcones was studied and the findings were supported statistically (C) 2012 Elsevier Ltd. All rights reserved.