(2E)-1-(3'-nitrophenyl)-3-(2-naphthyl)-2-propen-1-one | 1098176-66-9

• 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-(2-naphthyl)-2-propen-1-one
• 英文别名: (2E)-1-(3-nitrophenyl)-3-(2-naphthyl)-2-propen-1-one；[3-[(E)-3-(2-naphthyl)prop-2-enoyl]phenyl]azinic acid；(E)-3-naphthalen-2-yl-1-(3-nitrophenyl)prop-2-en-1-one
• CAS: 1098176-66-9
• 化学式: C₁₉H₁₃NO₃
• 分子量: 303.317
• InChiKey: JHJNVIAWPMWSNR-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-1-(3'-nitrophenyl)-3-(2-naphthyl)-2-propen-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 以62%的产率得到4,5-dihydro-5-(naphthalen-2-yl)-3-(3-nitrophenyl)-1H-pyrazole
  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：

  2-萘甲醛 、 间硝基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以62%的产率得到(2E)-1-(3'-nitrophenyl)-3-(2-naphthyl)-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

• Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA
  作者：Louise Domeneghini Chiaradia、Alessandra Mascarello、Marcela Purificação、Javier Vernal、Marlon Norberto Sechini Cordeiro、María Emilia Zenteno、Andréa Villarino、Ricardo José Nunes、Rosendo Augusto Yunes、Hernán Terenzi

  DOI：10.1016/j.bmcl.2008.09.105

  日期：2008.12

  In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were obtained by aldolic condensation between aldehydes and acetophenones, under basic conditions. Five compounds presented moderate or good activity. The structure - activity analysis reveals that the predominant factor for the activity is the molecule planarity/hydrophobicity and the nature of the substituents. (C) 2008 Elsevier Ltd. All rights reserved.
• Antihyperglycemic activity of naphthylchalcones
  作者：Rosangela Guollo Damazio、Ana Paula Zanatta、Luisa Helena Cazarolli、Louise Domeneghini Chiaradia、Alessandra Mascarello、Ricardo José Nunes、Rosendo Augusto Yunes、Fátima Regina Mena Barreto Silva

  DOI：10.1016/j.ejmech.2009.12.017

  日期：2010.4

  The purpose of the present work was to investigate, following previous works, naphthylchalcones as antihyperglycemic agent in glucose loaded animal model, insulin secretion as well as the action of these compounds on glucose uptake in a target tissue of insulin. The naphthylchalcones were found to have an acute serum glucose-lowering effect in hyperglycemic normal rats. In addition, chalcones 2 and 4 stimulated significantly the insulin secretion induced by glucose. These results suggest that the presence of nitro group and their position in the phenyl rings are responsible for the antihyperglycemic activity of chalcones. Additionally, the effect of chalcones on serum glucose-lowering seems to be a consequence of insulin secretion and these chalcones represent potential compounds with strong antihyperglycemic properties. (C) 2009 Elsevier Masson SAS. All rights reserved.
• 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.
• Synthetic compounds from an <i>in house</i> library as inhibitors of falcipain-2 from <i>Plasmodium falciparum</i>
  作者：Jean Borges Bertoldo、Louise Domeneghini Chiaradia-Delatorre、Alessandra Mascarello、Paulo César Leal、Marlon Norberto Sechini Cordeiro、Ricardo José Nunes、Emir Salas Sarduy、Philip Jon Rosenthal、Hernán Terenzi

  DOI：10.3109/14756366.2014.920839

  日期：2015.3.4

  Falcipain-2 (FP-2) is a key cysteine protease from the malaria parasite Plasmodium falciparum. Many previous studies have identified FP-2 inhibitors; however, none has yet met the criteria for an antimalarial drug candidate. In this work, we assayed an in-house library of non-peptidic organic compounds, including (E)-chalcones, (E)-N'-benzylidene-benzohydrazides and alkylesters of gallic acid, and assessed the activity toward FP-2 and their mechanisms of inhibition. The (E)-chalcones 48, 54 and 66 showed the lowest IC50 values (8.5 +/- 0.8 mu M, 9.5 +/- 0.2 mu M and 4.9 +/- 1.3 mu M, respectively). The best inhibitor (compound 66) demonstrated non-competitive inhibition, and using mass spectrometry and fluorescence spectroscopy assays, we suggest a potential allosteric site for the interaction of this compound, located between the catalytic site and the hemoglobin binding arm in FP-2. We combined structural biology tools and mass spectrometry to characterize the inhibition mechanisms of novel compounds targeting FP-2.