1-(2-(dimethylamino)-5-methylphenyl)naphthalen-2-ol | 1346854-94-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-(dimethylamino)-5-methylphenyl)naphthalen-2-ol
• 英文别名: 1-(2-(Dimethylamino)-4-methylphenyl)naphthalen-2-ol；1-[2-(dimethylamino)-5-methylphenyl]naphthalen-2-ol
• CAS: 1346854-94-1
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: OUHMGQWRGZQSIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-萘酚 、 N,N-二甲基对甲苯胺 在 双氧水 、 silver nitrate 作用下， 以 水 、 甲苯 为溶剂， 反应 6.0h， 以65.3%的产率得到1-(2-(dimethylamino)-5-methylphenyl)naphthalen-2-ol
  参考文献：
  名称：

  银（I）介导的苯酚和苯胺衍生物的区域选择性氧化交叉偶联，产生2'-氨基联苯-2-醇

  摘要：

  已经开发了在AgNO 3和H 2 O 2存在下导致2'-氨基联苯-2-醇的酚和苯胺衍生物的广泛和有效的区域选择性好氧氧化交叉偶联。该反应对在各个起始原料中的胺和羟基官能团的邻位产生新的C C键具有选择性。尽管已经报道了酚和苯胺的氧化交叉偶联导致2'-氨基联苯-2-醇衍生物，但是这些反应主要限于2-萘酚和1-萘酚。这是罕见的报道之一，其中这种类型的交叉偶联反应扩展到简单的苯酚衍生物。

  DOI：

  10.1016/j.tetlet.2016.02.111

文献信息

• Iron-Catalyzed Regioselective Direct Oxidative Aryl–Aryl Cross-Coupling
  作者：Malapaka Chandrasekharam、Barreddi Chiranjeevi、Kankatala S. V. Gupta、B. Sridhar

  DOI：10.1021/jo202152b

  日期：2011.12.16

  Regioselective iron-catalyzed cross-dehydrogenative coupling (CDC) of two aromatic compounds using tert-BuOOH as oxidant under mild conditions has been reported. The direct oxidative coupling reaction is selective toward creation of a carbon–carbon bond at the position ortho to the functional groups of the substrates, completely preventing the homocoupled products. The C–C bond-forming reaction makes

  据报道，在温和条件下，使用叔-BuOOH作为氧化剂的两种芳香族化合物的区域选择性铁催化的交叉脱氢偶联（CDC）。直接的氧化偶联反应对在基质功能基团邻位的碳-碳键产生选择性，从而完全阻止了均相偶联的产物。C–C键形成反应使该方法变得通用，从而导致功能化的2,2'-二取代联芳基。
• Aerobic Catalyzed Oxidative Cross-Coupling of <i>N</i>,<i>N</i>-Disubstituted Anilines and Aminonaphthalenes with Phenols and Naphthols
  作者：Thomas J. Paniak、Marisa C. Kozlowski

  DOI：10.1021/acs.orglett.0c00046

  日期：2020.3.6

  N-dialkyl aniline and aminonaphthalenes with phenols and naphthols using a Cr-salen catalyst under aerobic conditions was developed. Notably, air serves as an effective oxidant affording products in high selectivity. Initial mechanistic studies suggest an outer-sphere oxidation of the aniline/aminonaphthalene partner, followed by nucleophilic attack of the phenol/naphthol. Single products were observed

  开发了在好氧条件下使用Cr-salen催化剂将N，N-二烷基苯胺和氨基萘与酚和萘交叉偶联的方法。值得注意的是，空气以有效的氧化剂提供了高选择性的产物。最初的机理研究表明，苯胺/氨基萘伴侣会发生外层氧化，然后苯酚/萘酚会发生亲核攻击。在大多数情况下，观察到单一产物，而CC和CO偶联产物的混合物是由涉及氨基萘和空间上不受阻碍的苯酚的反应产生的。
• Iron‐Catalyzed Oxidative C−C Cross‐Coupling Reaction of Tertiary Anilines with Hydroxyarenes by Using Air as Sole Oxidant
  作者：Alexander Purtsas、Olga Kataeva、Hans‐Joachim Knölker

  DOI：10.1002/chem.201905595

  日期：2020.2.21

  A mild procedure for the oxidative C-C cross-coupling of tertiary anilines with phenols is described which provides the products generally in high yields and with excellent selectivity. The reaction is catalyzed by the hexadecafluorinated iron-phthalocyanine complex FePcF16 in the presence of substoichiometric amounts of methanesulfonic acid and ambient air as sole oxidant.

  描述了用于叔苯胺与酚的氧化CC交叉偶联的温和方法，该方法通常以高收率和优异的选择性提供产物。在亚化学计量量的甲磺酸和环境空气作为唯一氧化剂存在下，通过十六氟化铁-酞菁配合物FePcF16催化该反应。
• Multifaceted approach toward mapping out the anticancer properties of small molecules via in vitro evaluation on melanoma and nonmelanoma skin cancer cells, and in silico target fishing
  作者：Samuel T. Boateng、Tithi Roy、Mercy E. Agbo、Md Ashiq Mahmud、Sergette Banang‐Mbeumi、Roxane‐Cherille N. Chamcheu、Rajesh K. Yadav、Marion Bramwell、Long K. Pham、Danny D. Dang、Keith E. Jackson、Bolni Marius Nagalo、Ronald A. Hill、Tatiana Efimova、Jean Fotie、Jean Christopher Chamcheu

  DOI：10.1111/cbdd.14418

  日期：2024.1

  Melanoma and nonmelanoma skin cancers are among the most prevalent and most lethal forms of skin cancers. To identify new lead compounds with potential anticancer properties for further optimization, in vitro assays combined with in‐silico target fishing and docking have been used to identify and further map out the antiproliferative and potential mode of action of molecules from a small library of compounds previously prepared in our laboratory. From screening these compounds in vitro against A375, SK‐MEL‐28, A431, and SCC‐12 skin cancer cell lines, 35 displayed antiproliferative activities at the micromolar level, with the majority being primarily potent against the A431 and SCC‐12 squamous carcinoma cell lines. The most active compounds 11 (A431: IC₅₀ = 5.0 μM, SCC‐12: IC₅₀ = 2.9 μM, SKMEL‐28: IC₅₀ = 4.9 μM, A375: IC₅₀ = 6.7 μM) and 13 (A431: IC₅₀ = 5.0 μM, SCC‐12: IC₅₀ = 3.3 μM, SKMEL‐28: IC₅₀ = 13.8 μM, A375: IC₅₀ = 17.1 μM), significantly and dose‐dependently induced apoptosis of SCC‐12 and SK‐MEL‐28 cells, as evidenced by the suppression of Bcl‐2 and upregulation of Bax, cleaved caspase‐3, caspase‐9, and PARP protein expression levels. Both agents significantly reduced scratch wound healing, colony formation, and expression levels of deregulated cancer molecular targets including RSK/Akt/ERK1/2 and S6K1. In silico target prediction and docking studies using the SwissTargetPrediction web‐based tool suggested that CDK8, CLK4, nuclear receptor ROR, tyrosine protein‐kinase Fyn/LCK, ROCK1/2, and PARP, all of which are dysregulated in skin cancers, might be prospective targets for the two most active compounds. Further validation of these targets by western blot analyses, revealed that ROCK/Fyn and its associated Hedgehog (Hh) pathways were downregulated or modulated by the two lead compounds. In aggregate, these results provide a strong framework for further validation of the observed activities and the development of a more comprehensive structure–activity relationship through the preparation and biological evaluation of analogs.

  摘要 黑色素瘤和非黑色素瘤皮肤癌是发病率最高、致死率最高的皮肤癌之一。为了鉴定具有潜在抗癌特性的新先导化合物并进行进一步优化，我们采用体外试验结合体内靶标捕获和对接的方法，从我们实验室以前制备的小型化合物库中鉴定并进一步绘制出分子的抗增殖作用和潜在作用模式图。通过对 A375、SK-MEL-28、A431 和 SCC-12 皮肤癌细胞系进行体外筛选，35 个化合物显示出微摩水平的抗增殖活性，其中大多数化合物主要对 A431 和 SCC-12 鳞癌细胞系有效。活性最强的化合物 11（A431：IC50 = 5.0 μM；SCC-12：IC50 = 2.9 μM；SKMEL-28：IC50 = 4.9 μM；A375：IC50 = 6.7 μM）和 13（A431：IC50 = 5.0 μM，SCC-12：IC50 = 3.3 μM，SKMEL-28：IC50 = 13.8 μM，A375：两种药物都能显著诱导 SCC-12 和 SK-MEL-28 细胞凋亡，且呈剂量依赖性，表现为抑制 Bcl-2，上调 Bax、裂解的 caspase-3、caspase-9 和 PARP 蛋白表达水平。这两种制剂都能明显降低划痕伤口愈合、集落形成以及包括 RSK/Akt/ERK1/2 和 S6K1 在内的失调癌症分子靶点的表达水平。利用 SwissTargetPrediction 网络工具进行的硅学靶点预测和对接研究表明，CDK8、CLK4、核受体 ROR、酪氨酸蛋白激酶 Fyn/LCK、ROCK1/2 和 PARP（所有这些靶点在皮肤癌中都失调）可能是这两种活性最强的化合物的潜在靶点。通过西部印迹分析对这些靶点的进一步验证表明，ROCK/Fyn 及其相关的刺猬（Hh）通路受到这两种先导化合物的下调或调节。总之，这些结果为进一步验证观察到的活性以及通过制备和生物评估类似物来发展更全面的结构-活性关系提供了一个强有力的框架。
• Cerium-containing MCM-41 catalyst for selective oxidative arene cross-dehydrogenative coupling reactions
  作者：Adinarayana Murthy Akondi、Rajiv Trivedi、Bojja Sreedhar、Mannepalli Lakshmi Kantam、Suresh Bhargava

  DOI：10.1016/j.cattod.2012.05.029

  日期：2012.12

  Cerium (IV)-mediated intermolecular direct biaryl coupling of aromatic tertiary amines and naphthol via dual C-H bond activation has been reported. The new C-C bond is formed regioselectively ortho to the amino and hydroxyl substituents under oxidative conditions to give substituted bifunctional amino naphthols. We report here the use of Ce-MCM-41 catalyst for the synthesis of these unsymmetrical biaryls via oxidative cross coupling under mild conditions. The catalyst was recovered by simple filtration and reused for several cycles with consistent activity. (C) 2012 Elsevier B. V. All rights reserved.