4-(1,2-diphenylbut-1-en-1-yl)aniline

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-(1,2-diphenylbut-1-en-1-yl)aniline
• 英文别名: 4-(1,2-diphenylbut-1-enyl)aniline
• 化学式: C₂₂H₂₁N
• 分子量: 299.415
• InChiKey: SHXXNJZYKCKOER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(1,2-diphenylbut-1-en-1-yl)aniline 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.5h， 生成
  参考文献：
  名称：

  Self-assembled 4-(1,2-diphenylbut-1-en-1-yl)aniline based nanoparticles: podophyllotoxin and aloin as building blocks

  摘要：

  报道了4-(1,2-二苯基丁-1-烯-1-基)苯胺作为自组装诱导剂的能力。

  DOI：

  10.1039/c6ob02591a
• 作为产物：
  描述：

  4-硝基二苯甲酮 、 苯丙酮 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以55%的产率得到4-(1,2-diphenylbut-1-en-1-yl)aniline
  参考文献：
  名称：

  用苯胺或乙酰苯胺基团取代苯酚基团可增强2-二茂铁基-1,1-二苯基-丁-1-烯化合物对乳腺癌细胞的细胞毒性

  摘要：

  先前我们已经证明，共轭二茂铁基对苯酚可能通过氧化醌甲基化物形成，对激素依赖性MCF-7和激素依赖性MDA-MB-231乳腺癌细胞系均表现出强大的细胞毒性作用。现在我们介绍一系列类似的胺和乙酰胺化合物：2-二茂铁基-1-（4-氨基苯基）-1-苯基-丁-1-烯（Z + E - 2），2-二茂铁基-1-（4- N-乙酰氨基苯基）-1-苯基丁-1-烯（Z - 3）及其相应的有机分子1-（4-氨基苯基）-1,2-双苯基丁-1-烯（Z + E - 4）和1-（4- ñ-乙酰氨基苯基）-1，2-双苯基丁-1-烯（Z + E - 5）。所有的化合物对雌激素受体具有足够的相对结合亲和力值。在计算机ER对接实验中，ERα介于2.8％和5.7％之间，ERβ介于0.18％和15.5％之间，以及放热配体结合。化合物2和3对MCF-7细胞系具有双重雌激素/细胞毒活性；它们在低浓度（0.1μM）时具有增生作用，在高浓度

  DOI：

  10.1016/j.jorganchem.2008.11.035

文献信息

• Efficient new constructs against triple negative breast cancer cells: synthesis and preliminary biological study of ferrocifen–SAHA hybrids and related species
  作者：José de Jesús Cázares Marinero、Marion Lapierre、Vincent Cavaillès、Rénette Saint-Fort、Anne Vessières、Siden Top、Gérard Jaouen

  DOI：10.1039/c3dt51917a

  日期：——

  Chemotherapeutic agents combining several active groups within a single molecule can modulate multiple cellular pathways and, thus, exhibit higher efficacy than single-target drugs. In this study, six new hybrid compounds combining tamoxifen (TAM) or ferrocifen (FcTAM) structural motifs with suberoylanilide hydroxamic acid (SAHA) were synthesised and evaluated. Antiproliferative activity was first explored in cancer cell lines. Combining FcTAM and SAHA structural motifs to form the unprecedented FcTAM–SAHA hybrid molecule led to an increased cytotoxicity (IC50 = 0.7 μM) in triple-negative MDA-MB-231 breast cancer cells when compared to FcTAM or SAHA alone (IC50 = 2.6 μM and 3.6 μM, respectively), while the organic hybrid analogue TAM–SAHA was far less cytotoxic (IC50 = 8.6 μM). In hormone-dependent MCF-7 breast cancer cells, FcTAM–SAHA was more active (IC50 = 2.0 μM) than FcTAM (IC50 = 4.4 μM) and TAM–SAHA (IC50 > 10 μM), but less toxic than SAHA (IC50 = 1.0 μM). Surprisingly, FcTAM–PSA, an N1-phenylsuberamide derivative, also possessed strong antiproliferative activity (IC50 = 0.5 μM and 1.8 μM in MDA-MB-231 and MCF-7 cells, respectively). Subsequent biochemical studies indicate that estrogen receptor alpha (ERα) and histone deacetylases (HDAC) are not the main targets of the hybrid compounds for their antiproliferative effect. Interestingly, both organometallic compounds were able to induce p21waf1/cip1 gene expression in MCF-7 breast cancer cells in accordance with their antiproliferative activity.

  将多个活性基团结合于单一分子中的化疗药物能够调控多条细胞信号通路，因此其疗效高于单一靶点药物。在本研究中，我们合成并评估了6种新型混合化合物，它们结合了他莫昔芬（TAM）或铁西他莫（FcTAM）结构基团与辛二酰苯胺异羟肟酸（SAHA）。首先在癌细胞系中探索它们的抗增殖活性。将FcTAM与SAHA结构基团结合起来形成前所未有的FcTAM-SAHA混合分子，与单独的FcTAM或SAHA相比（分别为IC50 = 2.6 μM和3.6 μM），在三阴性乳腺癌细胞MDA-MB-231中显示出增加的细胞毒性（IC50 = 0.7 μM），而有机混合类似物TAM-SAHA的细胞毒性则低得多（IC50 = 8.6 μM）。在激素依赖性乳腺癌细胞MCF-7中，FcTAM-SAHA的活性比FcTAM（IC50 = 4.4 μM）和TAM-SAHA（IC50 > 10 μM）更高（IC50 = 2.0 μM），但毒性比SAHA（IC50 = 1.0 μM）低。令人惊讶的是，N1-苯基辛二酰胺衍生物FcTAM-PSA也显示出强大的抗增殖活性（在MDA-MB-231和MCF-7细胞中分别为IC50 = 0.5 μM和1.8 μM）。后续的生化研究表明，雌激素受体α（ERα）和组蛋白去乙酰化酶（HDAC）并不是这些混合化合物抗增殖作用的主要靶点。有趣的是，这两种有机金属化合物都能根据其抗增殖活性诱导MCF-7乳腺癌细胞中的p21waf1/cip1基因表达。
• Folic acid functionalization for targeting self-assembled paclitaxel-based nanoparticles
  作者：Eleonora Colombo、Davide Andrea Coppini、Simone Maculan、Pierfausto Seneci、Benedetta Santini、Filippo Testa、Lucia Salvioni、Giovanni Maria Vanacore、Miriam Colombo、Daniele Passarella

  DOI：10.1039/d2ra06306a

  日期：——

  Hetero-nanoparticles self-assembled from a conjugate bearing folic acid as the targeting agent, and another bearing paclitaxel as the active agent are reported. Hetero-nanoparticles containing varying percentages of folic acid conjugates are characterised, and their biological activity is determined.

  报道了由以叶酸为靶向剂的缀合物和另一种以紫杉醇为活性剂的缀合物自组装的杂纳米颗粒。表征了含有不同百分比的叶酸缀合物的杂纳米颗粒，并确定了它们的生物活性。
• Design and synthesis of (Z)-1,2-diphenyl-1-(4-methanesulfonamidophenyl)alk-1-enes and (Z)-1-(4-azidophenyl)-1,2-diphenylalk-1-enes: novel inhibitors of cyclooxygenase-2 (COX-2) with anti-inflammatory and analgesic activity
  作者：Md. Jashim Uddin、P.N. Praveen Rao、Edward E. Knaus

  DOI：10.1016/j.bmc.2004.10.017

  日期：2005.1

  A group of novel (Z)-1,2-diphenyl-1-9(4-methanesulfonamidophenyl)alk-1-enes was designed for evaluation as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1/COX-2 enzyme inhibition studies identified (Z)-1,2-dipheny1-1-(4-methanesulfonamidophenyl)oct-1-ene(8d) as a highly potent (IC50=0.03 muM), and an extremely selective [COX-2 SI (selectivity index)> 3,333], COX-2 inhibitor that showed good anti-inflammatory (AI) activity (ID50 = 2.8 mg/kg). A molecular modeling (docking) study showed that the p-MeSO2NH group present in (Z)-8d inserts deep inside the 2degrees-pocket of the COX-2 binding site, it undergoes a hydrophobic interaction with Ala(516) and Gly(519), and one of the O-atoms of the MeSO2 group participates in a weak hydrogen bonding interaction with the NH2 of Arg(513) (distance = 3.85 Angstrom). Similar in vitro COX-1/COX-2 enzyme inhibition studies showed that the azido compound 1-(4-azidophenyl)-1,2-diphenyloct-1-ene (9c) is also a potent and selective COX-2 inhibitor (COX-2 IC50 = 0.11 muM: SI > 909) that exhibits good AI activity (ID50 = 5.0 mg/kg). A docking experiment to determine the orientation of (Z)-9c within the COX-2 binding site showed that the linear p-N-3 group inserts into the COX-2 2degrees-pocket, where it undergoes an ion-ion (electrostatic) interaction with Arg(513). Structure-activity data acquired indicate that an olefin having either a C-1 p-MeSO2NH-phenyl, or a p-N-3-phenyl, substituent, that is, cis to a C-2 unsubstituted phenyl substituent, in conjunction with C-1 unsubstituted phenyl and C-2 alkyl substituents, provides a novel template to design acyclic olefinic COX-2 inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.
• The replacement of a phenol group by an aniline or acetanilide group enhances the cytotoxicity of 2-ferrocenyl-1,1-diphenyl-but-l-ene compounds against breast cancer cells
  作者：Pascal Pigeon、Siden Top、Ouardia Zekri、Elizabeth A. Hillard、Anne Vessières、Marie-Aude Plamont、Olivier Buriez、Eric Labbé、Michel Huché、Sultana Boutamine、Christian Amatore、Gérard Jaouen

  DOI：10.1016/j.jorganchem.2008.11.035

  日期：2009.3

  We have previously shown that conjugated ferrocenyl p-phenols show strong cytotoxic effects against both the hormone-dependent MCF-7 and hormone-independent MDA-MB-231 breast cancer cell lines, possibly via oxidative quinone methide formation. We now present a series of analogous amine and acetamide compounds: 2-ferrocenyl-1-(4-aminophenyl)-1-phenyl-but-1-ene (Z+E-2), 2-ferrocenyl-1-(4-N-acetylami

  先前我们已经证明，共轭二茂铁基对苯酚可能通过氧化醌甲基化物形成，对激素依赖性MCF-7和激素依赖性MDA-MB-231乳腺癌细胞系均表现出强大的细胞毒性作用。现在我们介绍一系列类似的胺和乙酰胺化合物：2-二茂铁基-1-（4-氨基苯基）-1-苯基-丁-1-烯（Z + E - 2），2-二茂铁基-1-（4- N-乙酰氨基苯基）-1-苯基丁-1-烯（Z - 3）及其相应的有机分子1-（4-氨基苯基）-1,2-双苯基丁-1-烯（Z + E - 4）和1-（4- ñ-乙酰氨基苯基）-1，2-双苯基丁-1-烯（Z + E - 5）。所有的化合物对雌激素受体具有足够的相对结合亲和力值。在计算机ER对接实验中，ERα介于2.8％和5.7％之间，ERβ介于0.18％和15.5％之间，以及放热配体结合。化合物2和3对MCF-7细胞系具有双重雌激素/细胞毒活性；它们在低浓度（0.1μM）时具有增生作用，在高浓度
• Self-assembled 4-(1,2-diphenylbut-1-en-1-yl)aniline based nanoparticles: podophyllotoxin and aloin as building blocks
  作者：Gaia Fumagalli、Michael S. Christodoulou、Benedetta Riva、Inigo Revuelta、Cristina Marucci、Veronica Collico、Davide Prosperi、Sergio Riva、Dario Perdicchia、Ivan Bassanini、Aida García-Argáez、Lisa Dalla Via、Daniele Passarella

  DOI：10.1039/c6ob02591a

  日期：——

  The ability of 4-(1,2-diphenylbut-1-en-1-yl)aniline as a self-assembly inducer is reported.

  报道了4-(1,2-二苯基丁-1-烯-1-基)苯胺作为自组装诱导剂的能力。