DNPM

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: DNPM
• 英文别名: [3-(dimethylamino)-2-(4-nitrophenyl)prop-2-enylidene]-dimethylazanium;perchlorate
• 化学式: C₁₃H₁₈N₃O₂*ClO₄
• 分子量: 347.755
• InChiKey: FFTVCABYLWLAAT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.92
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  DNPM 在 hydrazine hydrate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.25h， 生成 4-(4-硝基苯基)-1H-吡唑
  参考文献：
  名称：

  Design, synthesis, and biologic evaluation of some novel N-arylpyrazole derivatives as cytotoxic agents

  摘要：

  A novel series of N-arylpyrazole derivatives (5a-5d, 7a-7c) has been designed and synthesized via aromatic substitution reaction of N-nonsubstituted pyrazoles with 4-fluoronitrobenzene in the presence of base. The structures of these compounds were established on the basis of elemental (C, H, and N) and spectral analysis (H-1 NMR, C-13 NMR, HRMS, and FT-IR). All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines: carcinoma (Bel-7402), nasopharyngeal carcinoma (KB), immature granulocyte leukemia (HL-60), and gastrocarcinoma (BGC-823) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The results showed that most of the obtained compounds exhibited promising cytotoxicity against tested carcinoma cell lines with low IC50 values. The bis-pyrazole derivative 7c, bearing alkoxy group on the 5-position of phenyl ring, was the most effective one. It is inhibition of cell growth of Bel-7402 cells was 1.5-fold higher than that found for cisplatin. And, also mono-pyrazole derivatives 5a and 5b, decorated with trifluoromethyl group on the phenyl ring, displayed better cytotoxicity than that of cisplatin against Bel-7402 cell line.

  DOI：

  10.1007/s00044-013-0552-1
• 作为产物：
  描述：

  [(Z)-3-Dimethylamino-2-(4-nitro-phenyl)-allylidene]-dimethyl-ammonium 在 sodium perchlorate 作用下， 生成 DNPM
  参考文献：
  名称：

  New Synthetic Routes to 3-, 5-, and 6-Aryl-2-chloropyridines

  摘要：

  The efficient synthesis of 3-, 5-, and 6-aryl-2-chloropyridines via the facile preparation of 5-(dimethyamino)aryl-substituted pentadienyl nitriles and cyclization with hydro chloric acid is described. This approach allows for the introduction of other electron-withdrawing substituents on the pyridine ring as well as the preparation of the desired unsubstituted arylpyridines. Some differences in the rates of cyclization of the pentadienyl nitriles as well as the yields of chloropyridines were observed that depended on the position and degree of substitution in the aryl substituent. The arylpentadienyl nitriles 5 and 6 could also be converted directly into the corresponding 2-aminopyridines.

  DOI：

  10.1021/jo00117a029

文献信息

• <i>S</i>-<i>Cis</i> Diene Conformation: A New Bathochromic Shift Strategy for Near-Infrared Fluorescence Switchable Dye and the Imaging Applications
  作者：Hsiang-Jung Chen、Chee Ying Chew、En-Hao Chang、Yu-Wei Tu、Li-Yu Wei、Bo-Han Wu、Chien-Hung Chen、Ya-Ting Yang、Su-Chin Huang、Jen-Kun Chen、I-Chia Chen、Kui-Thong Tan

  DOI：10.1021/jacs.8b01159

  日期：2018.4.18

  fluorescence-switchable near-infrared (IR) dye based on merocyanine for target specific imaging. In contrast to the typical bathochromic shift approach by extending π-conjugation, the bathochromic shift of our merocyanine dye to the near-IR region is due to an unusual S- cis diene conformer. This is the first example where a fluorescent dye adopts the stable S- cis conformation. In addition to the novel

  在本文中，我们提出了一种基于部花青的新型无电荷荧光可切换近红外 (IR) 染料，用于目标特异性成像。与通过扩展 π 共轭的典型红移方法相比，我们的部花青染料向近红外区域的红移是由于不寻常的 S-顺式二烯构象异构体。这是荧光染料采用稳定的 S-cis 构象的第一个例子。除了新颖的红移机制外，该染料还表现出响应极性和粘度的荧光可切换特性。通过将蛋白质特异性配体加入染料中，探针（针对 SNAP-tag 和 hCAII 蛋白）在与其靶蛋白结合后表现出显着的荧光增加（高达 300 倍）。大的荧光增强，近红外吸收/发射，和无电荷支架能够在活细胞和体内以最小的背景荧光对目标蛋白进行无清洗和位点特异性成像。我们相信，我们对具有 S-顺式二烯构象的近红外染料的非常规方法可以为近红外染料的设计带来新的策略。
• Synthesis of Oligo(diazaphenyls). Tailor-Made Fluorescent Heteroaromatics and Pathways to Nanostructures
  作者：Rudolf Gompper、Hans-Jürgen Mair、Kurt Polborn

  DOI：10.1055/s-1997-1405

  日期：1997.6

  Oligoaza derivatives of biphenyl, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl, septiphenyl, octiphenyl, noviphenyl, deciphenyl and dodeciphenyl and poly(pyrimidinylenephenylene) can be synthesized from readily accessible vinamidinium salts and amidines or N,N,N'-tris(trimethylsilyl)amidines. The fluorescence of these systems can be tuned over a wide spectral range by varying number and positions of N atoms. Oligo(diazaphenyls) are thermally and photochemically stable, are easier to reduce than oligophenyls, can be dissolved at any rate in strong acids and show strong blue fluorescence in solution as well as in the solid state.

  苯并、联苯、四苯、五苯、六苯、七苯、八苯、九苯、十苯和十二苯的寡氮杂衍生物以及聚(嘧啶亚苯基亚苯)可以从易得的乙烯胺盐和胺或N,N,N'-三(三甲基硅基)胺合成。通过改变N原子的数量和位置，这些体系的荧光可以在广泛的光谱范围内调节。寡(二氮苯)在热和光化学上是稳定的，比寡苯更容易还原，在强酸中可以以任意速率溶解，并且在溶液中以及固态中显示强烈的蓝色荧光。
• Diazepines. Part 25. Preparation and properties of 6-aryl-2,3-dihydro-1,4-diazepinium salts. Electronic interaction between the rings and steric inhibition thereof
  作者：Douglas Lloyd、Kanwaljit S. Tucker、Donald R. Marshall

  DOI：10.1039/p19810000726

  日期：——

  substitution in the 6-phenyl ring. Solution in deuteriosulphuric acid generates a stable radical species. Nucleophiles (monoamines, diamines, sodium hydroxide) attack the 5-and 7-positions of the diazepine ring. The 13C n.m.r. and mass spectra of these compounds are discussed.

  已经制备了多种6-芳基二氢二氮杂吡啶鎓盐（还包括6-联苯基-4-基，6-α-萘基和6- N-吡啶基），主要是通过1,2-二胺与3-芳基-1的反应来制备的。 ，5-二氮杂戊二烯鎓盐。富电子的二氢二氮杂pin鎓阳离子活化6-芳基取代基，使其趋于亲电子攻击，并且卤化和硝化在对位发生。六元或七元环中靠近环结的取代基可能会阻止两个环的共面性，从而抑制这种反应性。这些药物取代的化合物的13 C nmr光谱也显示出环之间的电子相互作用降低。NN “和2,2-二苯基NN′-二苄基取代基也抑制6-苯环中的亲电取代。氘代硫酸溶液中产生稳定的自由基。亲核试剂（单胺，二胺，氢氧化钠）攻击二氮杂环的5位和7位。讨论了这些化合物的13 C nmr和质谱。
• Synthetic Utility of Vilsmeier Reagents: Formation of Vinamidinium Salts from Acyl Ureas
  作者：Srinivasan Selvi、Paramasivan T Perumal

  DOI：10.1016/s0040-4039(97)01403-2

  日期：1997.9

  Attempted synthesis of uracil derivatives (2) from acyl ureas (1) resulted in the formation of vinamidinium salts (3) which can be hydrolysed to give dialdehydes. © 1997 Published by Elsevier Science Ltd.

  尝试从酰基脲（1）合成尿嘧啶衍生物（2）导致形成乙烯基ami盐（3），可以将其水解生成二醛。©1997由Elsevier Science Ltd发布。
• Design, synthesis and biological evaluation of some novel N-arylpyrazole derivatives bearing the sulfonamide moiety as cytotoxic agents
  作者：Xiaobo Duan、Yingxing Wang、Weipei Feng、Yaxing Yang、Hongyan Li、Shenghui Li、Xiaobing Yang、Jinchao Zhang、Shuxiang Wang、Guoqiang Zhou、Chuanqi Zhou

  DOI：10.1007/s11164-016-2620-x

  日期：2017.1

  A series of novel N-arylpyrazole derivatives (4a–4l) bearing the sulfonamide moiety were synthesized by the condensation reaction of 1,3-dicarbonyl compounds with 4-hydrazinylbenzenesulfonamide. The structures of the obtained compounds were established on the basis of elemental (C, H, and N) and spectral analysis (1H NMR, 13C NMR, ESIMS, and FT-IR). These compounds were tested for their in vitro cytotoxic

  通过1，3-二羰基化合物与4-肼基苯磺酰胺的缩合反应，合成了一系列带有磺酰胺基团的新型N-芳基吡唑衍生物（4a-4l）。根据元素（碳，氢和氮）和光谱分析（1 H NMR，13 C NMR，ESIMS和FT-IR）建立所得化合物的结构。测试了这些化合物对三种人类肿瘤细胞系MCF-7，Hela和A549的体外细胞毒性活性。结果表明，大多数获得的化合物对IC 50值较低的被测细胞系均显示出有希望的细胞毒性。吡唑衍生物4k最有效的一种是在苯环的3位和4位带有两个甲氧基的化合物。它对MCF-7细胞的细胞生长抑制作用优于塞来昔布和顺铂。