(2E)-1-(3'-nitrophenyl)-3-(1,3-benzodioxol-5-yl)-2-propen-1-one | 1058712-24-5

• 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: (2E)-1-(3'-nitrophenyl)-3-(1,3-benzodioxol-5-yl)-2-propen-1-one
• 英文别名: (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(3-nitrophenyl)prop-2-en-1-one；3-(1,3-Benzodioxol-5-yl)-1-(3-nitrophenyl)prop-2-en-1-one；(E)-3-(1,3-benzodioxol-5-yl)-1-(3-nitrophenyl)prop-2-en-1-one
• CAS: 1058712-24-5
• 化学式: C₁₆H₁₁NO₅
• 分子量: 297.267
• InChiKey: MALGARLLWBWYQV-GQCTYLIASA-N

物化性质

• 沸点：
  485.3±45.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-1-(3'-nitrophenyl)-3-(1,3-benzodioxol-5-yl)-2-propen-1-one 在 barium hydroxide 、 一水合肼 作用下， 以 乙醇 、 乙二醇 为溶剂， 生成 ethyl 6-(benzo[d][1,3]dioxol-5-yl)-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：

  胡椒醇 在 manganese(IV) oxide 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (2E)-1-(3'-nitrophenyl)-3-(1,3-benzodioxol-5-yl)-2-propen-1-one
  参考文献：
  名称：

  胡椒碱和胡椒碱启发的天然产物支架的合成和光谱分析及其与 IL-1β 和 NF-κB 蛋白的分子对接

  摘要：

  受天然产物胡椒碱和胡椒长明所表现出的非凡生物活性的启发，我们合成了八种受天然产物启发的类似物，以进一步研究它们的结构。我们首次确认了关键环化二氢吡唑碳硫酰胺胡椒碱类似物的结构，包括使用基于二维 (2D) 15N 的光谱核磁共振 (NMR) 光谱。先前的研究表明，这些支架在通过下调 IL-1β 和 NF-κB 通路抑制炎症反应方面取得了有希望的结果。然而，这些分子与其蛋白质靶标的分子相互作用仍然未知。从头算计算揭示了分子的电子密度函数图，显示了电子结构中结构修饰的影响。最后，实现了合成分子与蛋白质 IL-1β 和 NF-κB 之间的分子相互作用。对接结果表明，与天然产物相比，所有类似物在NF-κB的DNA结合位点以更高的亲和力相互作用，除9a和9b外，对IL-1β结合位点的亲和力高于天然产物. 确定了通过阳离子-π 相互作用对 3a、3c 和 9b 与 IL-1β 的分子识别的特异性。这些结果表明

  DOI：

  10.3390/molecules25122841

文献信息

• Biocatalytic green alternative to existing hazardous reaction media: synthesis of chalcone and flavone derivatives <i>via</i> the Claisen–Schmidt reaction at room temperature
  作者：Kashyap J. Tamuli、Ranjan K. Sahoo、Manobjyoti Bordoloi

  DOI：10.1039/d0nj03839c

  日期：——

  Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon–carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly

  由于全球废料数量的增加，将废料或次级副产品转化为用于各种应用的增值产品引起了人们的极大兴趣。在此，两种新颖的农业食品废品Musa sp。``马尔堡''果皮灰（MMPA）和Musa Champa霍特 前钩。F.果皮灰（MCPA）用作催化剂，可促进在室温下无溶剂条件下廉价，高效且生态友好的碳-碳键形成交叉羟醛反应。此外，在氧气气氛中使所得产物与这些促进剂反应，并导致形成新的黄酮衍生物。此外，使用不同的复杂分析技术，例如傅立叶变换红外光谱（FT-IR），X射线衍射法（XRD），Brunauer-Emmett-Teller分析（BET），拉曼光谱，扫描电子显微镜，对用过的催化剂进行了适当的表征。能量色散X射线光谱（SEM-EDS），过渡电子显微镜（TEM），X射线光电子能谱（XPS）和热重分析（TGA）以及使用原子吸收光谱和离子色谱法的元素检测。这两种方法均不含金属，并且不含任何额外的添加剂，助催
• A novel and efficient direct aldol condensation from ketones and aromatic aldehydes catalyzed by proline–TEA through a new pathway
  作者：Jun-feng Wang、Meng Lei、Qin Li、Ze-mei Ge、Xin Wang、Run-tao Li

  DOI：10.1016/j.tet.2009.04.052

  日期：2009.6

  aldol condensation from various ketones and a wide range of aldehydes was catalyzed by l-proline–TEA (triethylamine) in MeOH at room temperature, affording the corresponding (E)-α,β-unsaturated ketones in excellent yields. By using the method, some complicated (E)-α,β-unsaturated ketone C-glycosides were obtained from unmodified ketone C-glycosides and aldehydes. This reaction proceeds through a new

  在室温下于甲醇中，通过1-脯氨酸-TEA（三乙胺）催化从各种酮和多种醛中合成的新颖高效的直接羟醛缩合反应，从而以优异的收率得到相应的（E）-α，β-不饱和酮。通过使用该方法，从未改性的酮C-糖苷和醛中获得了一些复杂的（E）-α，β-不饱和酮C-糖苷。该反应通过新的途径进行，其中捕获并鉴定了特定的中间体。
• 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.
• 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.
• HETEROCYCLIC DERIVATIVES AND THEIR USE AS INTEGRIN INHIBITORS
  申请人：AstraZeneca AB

  公开号：EP1133484A2

  公开（公告）日：2001-09-19