(2E)-1-(3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one | 1164523-33-4

• 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: (2E)-1-(3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
• 英文别名: 1-(3-Nitrophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；(E)-1-(3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1164523-33-4
• 化学式: C₁₈H₁₇NO₆
• 分子量: 343.336
• InChiKey: OYCXONLNNCKOQR-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E)-1-(3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one 在 barium hydroxide 、 一水合肼 作用下， 以 乙二醇 为溶剂， 生成 ethyl 6-(3,4,5-methoxyphenyl)-4-(3-nitrophenyl)-2-oxocyclohex-3-enecarboxylate
  参考文献：
  名称：

  Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents

  摘要：

  A series of chalcones (1-8) were prepared by Claisen-Schmidt condensation of 3-nitroacetophenone with various aldehydes. These chalcones on cyclization with hydrazine hydrate in the presence of glacial acetic acid, hydrazine hydrate in absolute ethanol and ethyl acetoacetate in the presence of barium hydroxide gave corresponding N-acetyl pyrazolines (9-16), N-unsubstituted pyrazolines (17-19) and cyclohexenone derivatives (20-22). All the synthesized compounds were evaluated for their in vitro antibacterial and antifungal activity by using broth microdilution method, and many compounds showed promising activity against various tested bacteria and fungi. Among various tested compounds, 16 and 19 exhibited strongest activities against Streptococcus pyogenes and Pseudomonas aeruginosa; both have MIC value of 25 mu g/mL, which is fourfold greater than the standard drug. Many compounds showed good activity against Candida albican. Analogs 11, 12, 15-17 and 19 displayed two- to fivefold greater activity against C. albican as compared to the standard drug. Results of antitubercular evaluation revealed that compounds 4 and 19 displayed strong antimycobacterial activity against H(37)Rv having MIC of 25 and 62.5 mu g/mL, respectively. All analogs were found to be inactive against Leishmania braziliensis except analogs 4 and 5 which exhibited strong leishmanicidal activity against Leishmania promastigotes with IC50 values of 9.3 and 8.9 mu g/mL, respectively.

  DOI：

  10.1007/s00044-013-0803-1
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 间硝基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以77%的产率得到(2E)-1-(3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents

  摘要：

  A series of chalcones (1-8) were prepared by Claisen-Schmidt condensation of 3-nitroacetophenone with various aldehydes. These chalcones on cyclization with hydrazine hydrate in the presence of glacial acetic acid, hydrazine hydrate in absolute ethanol and ethyl acetoacetate in the presence of barium hydroxide gave corresponding N-acetyl pyrazolines (9-16), N-unsubstituted pyrazolines (17-19) and cyclohexenone derivatives (20-22). All the synthesized compounds were evaluated for their in vitro antibacterial and antifungal activity by using broth microdilution method, and many compounds showed promising activity against various tested bacteria and fungi. Among various tested compounds, 16 and 19 exhibited strongest activities against Streptococcus pyogenes and Pseudomonas aeruginosa; both have MIC value of 25 mu g/mL, which is fourfold greater than the standard drug. Many compounds showed good activity against Candida albican. Analogs 11, 12, 15-17 and 19 displayed two- to fivefold greater activity against C. albican as compared to the standard drug. Results of antitubercular evaluation revealed that compounds 4 and 19 displayed strong antimycobacterial activity against H(37)Rv having MIC of 25 and 62.5 mu g/mL, respectively. All analogs were found to be inactive against Leishmania braziliensis except analogs 4 and 5 which exhibited strong leishmanicidal activity against Leishmania promastigotes with IC50 values of 9.3 and 8.9 mu g/mL, respectively.

  DOI：

  10.1007/s00044-013-0803-1

文献信息

• Modulation of peroxisome proliferator-activated receptors
  申请人：Abgenomics Corporation

  公开号：EP1803809A2

  公开（公告）日：2007-07-04

  A method of treating a peroxisome proliferators-activated receptors related disease by administering to a subject in need thereof an effective amount of a modulator of 15-keto prostaglandin-Δ13-reductase. Also disclosed are methods of identifying a compound for inhibiting activity of the reductase and of lowering blood glucose levels by administering to a subject an effective amount of a reductase inhibitor.

  一种治疗与过氧化物酶体增殖物激活受体有关的疾病的方法，其方法是向有需要的受试者施用有效量的15-酮前列腺素-Δ13-还原酶调节剂。还公开了通过向受试者施用有效量的还原酶抑制剂来鉴定抑制还原酶活性和降低血糖水平的化合物的方法。
• [EN] PROSTAGLANDIN REDUCTASE INHIBITORS<br/>[FR] INHIBITEURS DE PROSTAGLANDINE RÉDUCTASES
  申请人：ABGENOMICS CORP

  公开号：WO2007082178A2

  公开（公告）日：2007-07-19

  [EN] A method of inhibiting 15-keto prostaglandin-?¹³-reductase 2 by contacting 15-keto prostaglandin-?¹³-reductase 2 with an aryl compound of Formula (I), (II), (III), or (IV) shown herein. Also disclosed are methods of treating peroxisome proliferators-activated receptor related diseases and lowering blood glucose levels by administering to a subject in need thereof an effective amount of such an aryl compound.
  [FR] Procédé d'inhibition de la 15-céto-prostaglandine-?¹³-réductase 2 par la mise en contact de la 15-céto-prostaglandine-?¹³-réductase 2 avec un composé aryle de formule (I), (II), (III) ou (IV) illustrée dans la présente invention. La présente invention concerne également des procédés de traitement de maladies liées au récepteur activé par des proliférateurs de peroxysome et d'abaissement des taux de glucose sanguin en administrant une quantité efficace de ce composé d'aryle à un sujet nécessitant un tel traitement.
• Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents
  作者：Vikramdeep Monga、Kamya Goyal、Mario Steindel、Manav Malhotra、Dhanji P. Rajani、Smita D. Rajani

  DOI：10.1007/s00044-013-0803-1

  日期：2014.4

  A series of chalcones (1-8) were prepared by Claisen-Schmidt condensation of 3-nitroacetophenone with various aldehydes. These chalcones on cyclization with hydrazine hydrate in the presence of glacial acetic acid, hydrazine hydrate in absolute ethanol and ethyl acetoacetate in the presence of barium hydroxide gave corresponding N-acetyl pyrazolines (9-16), N-unsubstituted pyrazolines (17-19) and cyclohexenone derivatives (20-22). All the synthesized compounds were evaluated for their in vitro antibacterial and antifungal activity by using broth microdilution method, and many compounds showed promising activity against various tested bacteria and fungi. Among various tested compounds, 16 and 19 exhibited strongest activities against Streptococcus pyogenes and Pseudomonas aeruginosa; both have MIC value of 25 mu g/mL, which is fourfold greater than the standard drug. Many compounds showed good activity against Candida albican. Analogs 11, 12, 15-17 and 19 displayed two- to fivefold greater activity against C. albican as compared to the standard drug. Results of antitubercular evaluation revealed that compounds 4 and 19 displayed strong antimycobacterial activity against H(37)Rv having MIC of 25 and 62.5 mu g/mL, respectively. All analogs were found to be inactive against Leishmania braziliensis except analogs 4 and 5 which exhibited strong leishmanicidal activity against Leishmania promastigotes with IC50 values of 9.3 and 8.9 mu g/mL, respectively.