4-dimethylaminostyryl 3-nitrophenyl ketone

• 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: 4-dimethylaminostyryl 3-nitrophenyl ketone
• 英文别名: 4-dimethylamino-3'-nitrochalcone；4-Dimethylamino-3'-nitro-chalkon；3-Nitro-ω-(4-dimethylamino-benzal)-acetophenon；3-[4-(Dimethylamino)phenyl]-1-(3-nitrophenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₆N₂O₃
• 分子量: 296.326
• InChiKey: MAUZGQVCAOWWHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-dimethylaminostyryl 3-nitrophenyl ketone 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N,N-dimethyl-4-(3-(3-nitrophenyl)-4,5-dihydroisoxazol-5-yl)benzenamine
  参考文献：
  名称：

  Synthesis, Characterization and Biological Evaluation of Some New Isoxazoline Derivatives

  摘要：

  异噁唑啉是一类独特的含氮和含氧的五元杂环化合物，这类化合物在生物化学中具有重要意义。异噁唑啉被认为是最有效的抗菌化合物之一。研究发现，异噁唑啉衍生物对结核分枝杆菌具有显著的抗结核活性。由于结核药物耐药性事件的增加，抗结核药物发现的目标变得更加具有挑战性。本研究旨在合成高效的抗结核异噁唑啉衍生物。通过在羟胺 hydrochloride 存在下对取代的查尔酮衍生物进行环化，合成了不同取代的异噁唑啉衍生物。合成的衍生物通过熔点、薄层色谱 (TLC)、傅里叶变换红外光谱 (FT-IR)、质子核磁共振 (1H NMR) 和质谱 (MS) 进行表征。合成的化合物在体外抗结核活性方面与异烟肼进行了比较，获得了相似的抗结核活性。

  DOI：

  10.14233/ajchem.2013.12899
• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 间硝基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-dimethylaminostyryl 3-nitrophenyl ketone
  参考文献：
  名称：

  4-二烷基氨基查耳酮的荧光特性表征及查耳酮的细胞毒性机制研究

  摘要：

  了解负责查耳酮的各种生物活动的机制，特别是直接的细胞靶点，是一个未解决的挑战。在这里，我们制备了一系列荧光查耳酮衍生物作为化学探针，用于其机理研究。通过系统的物理化学表征，我们探索了它们阐明查耳酮细胞毒性作用模式的潜力。发现查耳酮的荧光对结构和环境因素高度敏感。在结构上，B 环上的 4-二烷基氨基、A 环取代基的合适电子性质以及查耳酮核心结构的平面构象对于最佳荧光至关重要。影响荧光的环境因素包括溶剂极性、pH、以及查耳酮与蛋白质和洗涤剂的相互作用。发现 18 种查耳酮在 DMSO 中的荧光亮度大于 6000 M-1 cm-1。然而，水显着地淬灭了荧光，尽管它可以在 BSA 或去污剂的存在下部分恢复。正如预期的那样，这些荧光查耳酮在其细胞细胞毒性方面表现出明显的构效关系，从而导致鉴定出结构相似的细胞毒性和非细胞毒性荧光查耳酮作为化学探针。共聚焦显微镜结果揭示了细胞毒性探针 C8 和微管蛋白在

  DOI：

  10.1002/ardp.201500434

文献信息

• Synthetic Approaches and Electronic Spectra of some New Butamethine Asycyanine Colorants
  作者：BHUPENDRA NARAYAN、MOBASHSHIR HASAN KHAN、IMTIAZ ALI、M. WAYZUL HAQUE、A.S. ANSARI

  DOI：10.13005/ojc/280234

  日期：2012.6.18

  and ethanolic DMF as solvent. These colorants were synthesized with the object to study the impact of various functional groups and chain enhancement and shortage of prime chain on visible electronic spectra. All the colorants showed increase in electronic spectra whether electron withdrawing or donating. These colorants led to red shifts of the electronic spectra w.r.t. the previously reported styryl

  通过（i）4-二甲基氨基苯乙烯基苯基酮的催化缩合反应，已经合成了十五种新的发色链的β-取代的丁胺基丁菁（CCBSBA）着色剂。（ii）4-二甲基氨基苯乙烯基-3'-硝基苯基酮和（iii）4-二甲基氨基苯乙烯基-3'-甲基苯基酮与2-甲基-3-（1-甲基乙基）苯并噻唑鎓碘化物和2-甲基-6-取代的-3- （1甲基乙基）苯并噻唑鎓碘化物，以哌啶为碱性催化剂，以乙醇DMF为溶剂。合成这些着色剂的目的是研究各种官能团以及链增强和主链短缺对可见电子光谱的影响。无论是吸电子还是供电子，所有着色剂均显示出电子光谱的增加。这些着色剂导致电子光谱发生红移
• Synthesis, cyclooxygenase inhibition and anti-inflammatory evaluation of new 1,3,5-triaryl-4,5-dihydro-1<i>H</i>-pyrazole derivatives possessing methanesulphonyl pharmacophore
  作者：Khaled R. A. Abdellatif、Mohammed T. Elsaady、Salah A. Abdel-Aziz、Ahmed H. A. Abusabaa

  DOI：10.3109/14756366.2016.1158168

  日期：2016.11.1

  5-triaryl-4,5-dihydro-1H-pyrazole derivatives 13a-p were synthesized via aldol condensation of 3/4-nitroacetophenones with appropriately substituted aldehydes followed by cyclization of the formed chalcones with 4-methanesulfonylphenylhydrazine hydrochloride. All the synthesized compounds were evaluated for their cyclooxygenase (COX) inhibition, anti-inflammatory activity and ulcerogenic liability

  通过将3 / 4-硝基苯乙酮与适当取代的醛进行醛醇缩合，然后将所形成的查耳酮与4-环化，合成了一系列新的1,3,5-三芳基-4,5-二氢-1H-吡唑衍生物13a-p系列。甲磺酰苯肼盐酸盐。对所有合成的化合物的环氧合酶（COX）抑制作用，抗炎活性和致溃疡性进行了评估。与COX-1相比，所有化合物均是更有效的COX-2抑制剂。尽管大多数化合物具有良好的抗炎活性，但与塞来昔布（ED50 = 68.1μmol/ kg）相比，化合物13d，13f，13k和13o是最有效的衍生物（ED50 = 66.5、73.4、79.8和70.5μmol/ kg）。 ）。化合物13d，13f，13k和13o（溃疡指数= 3.89、4.86、4.96和3.92，分别比阿司匹林（溃疡指数= 22.75）少4-6倍的致溃疡性，显示出与塞来昔布相似的溃疡作用（溃疡指数= 3.35）。此外，对在COX-2活性位点内的化合物1
• Rational design, synthesis and in vitro evaluation of allylidene hydrazinecarboximidamide derivatives as BACE-1 inhibitors
  作者：Priti Jain、Pankaj K. Wadhwa、Shilpa Rohilla、Hemant R. Jadhav

  DOI：10.1016/j.bmcl.2015.11.044

  日期：2016.1

  BACE-1 (beta-secretase) is considered to be one of the promising targets for treatment of Alzheimer's disease as it catalyzes the rate limiting step of A beta-42 production. Herein, we report a novel class of allylidene hydrazinecarboximidamide derivatives as moderately potent BACE-1 inhibitors, having aminoguanidine substitution on allyl linker with two aromatic groups on either side. A library of derivatives was designed based on the docking studies, synthesized and evaluated for BACE-1 inhibition in vitro. The designed ligands displayed interactions with the catalytic aspartate dyad through guanidinium functionality. Further, the aromatic rings placed on either side of the linker occupied S1 and S3 active site regions contributing to the activity. These ligands were also predicted to follow Lipinski rule and cross blood brain barrier. Compound 2.21, having high docking score, was found to be most active with IC50 of 6.423 mu M indicating good correlation with docking prediction. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis, antioxidant evaluation, and quantitative structure–activity relationship studies of chalcones
  作者：P. M. Sivakumar、P. K. Prabhakar、M. Doble

  DOI：10.1007/s00044-010-9342-1

  日期：2011.5

  Synthesis, antioxidant activity, and quantitative structure-activity relationship (QSAR) of 25 of chalcone derivatives is reported here. They were synthesized by Claisen-Schmidt reaction and were characterized by FTIR, NMR, and mass spectroscopy. Antioxidant activity is evaluated through four different methods namely, superoxide radical-scavenging, hydrogen peroxide scavenging, reducing power, and DPPH radical-scavenging assays. Generally, compounds with -SCH3 and -OCH3 in the para position of the A-ring and -OH in the B-ring were more active than others. In few cases some of the compounds were more active than ascorbic acid or butylated hydroxytoluene. QSAR was developed correlating the antioxidant activity with the structural features of the compounds and the predictive capability of the models was estimated using internal and external validation methods. All the predictions were within the 99% confidence level. Spatial, structural, and lipophilic properties of the compounds determine their antioxidant properties.
• Rupe; Wasserzug, Chemische Berichte, 1901, vol. 34, p. 3530
  作者：Rupe、Wasserzug

  DOI：——

  日期：——