2-(丁基氨基)-3-甲基-1,4-萘醌 | 18690-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(丁基氨基)-3-甲基-1,4-萘醌
• 英文名称: 2-Methyl-3-butylamino-naphthochinon-1,4
• 英文别名: 3-Butylamino-2-methyl-1,4-naphthochinon；2-(Butylamino)-3-methylnaphthalene-1,4-dione
• CAS: 18690-80-7
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: NFFLYRHGZUIVAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922399090

反应信息

• 作为反应物：
  描述：

  2-(丁基氨基)-3-甲基-1,4-萘醌 在 sodium 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  维生素 K3 的正烷基氨基类似物：其氧化形式和一种电子还原形式的电化学、DFT 和抗癌活性

  摘要：

  摘要 进行了还原形式的维生素 K3 正烷基氨基类似物（1Na 至 8Na）的合成、表征和抗癌活性。2-乙基氨基-3-甲基-1,4-萘醌(2)和2-己氨基-3-甲基-1,4-萘醌(6)氧化形式的分子结构和分子缔合研究了单晶X射线分析。2 在单斜 C2/c 中结晶，6 在 P21 空间群中结晶。使用钠金属作为还原剂在 0 °C 的甲醇中合成了 8 种 2-(n-烷基氨基)-3-甲基-1,4-萘醌 (1Na 至 8Na) 同系物的还原形式。从它们的 EPR 光谱证实了 1 到 6 中萘半醌自由基的形成。1 至 6 的多晶粉末 X 带 EPR 光谱在 133 K 下显示信号 ~2.0020 ± 0.0026。2-(n-烷基氨基)-3-methyl-1 的抗癌活性，

  DOI：

  10.1016/j.molstruc.2018.11.024
• 作为产物：
  描述：

  甲萘醌 、 正丁胺 以 甲醇 为溶剂， 反应 24.0h， 以52.6%的产率得到2-(丁基氨基)-3-甲基-1,4-萘醌
  参考文献：
  名称：

  Photo-Oxidation of 2-Methylamino-3-(1-piperidinylmethyl)-1,4-naphthoquinone.

  摘要：

  2-甲基氨基-3-(1-哌啶基甲基)-1, 4-萘醌 (7) 由 2-甲基-1, 4-萘醌（维生素 K3, 3）通过几个步骤制备。醌(7)被光化学氧化成2-甲基氨基-3-(1-哌啶基羰基)-1, 4-萘醌(8)和/或2-烷氧基羰基-3-甲基氨基-1, 4-萘醌(9)，具体取决于与所使用的溶剂有关。

  DOI：

  10.1248/cpb.42.2360

文献信息

• Synthesis and Macrofilaricidal Activity of Substituted 2-Hydroxy/5-Hydroxy/2-Methyl-1,4-Naphthoquinones
  作者：Twinkle Karunan、Nisha Mathew、Lakshmy Srinivasan、Kalyanasundaram Muthuswamy

  DOI：10.1002/ddr.21065

  日期：2013.5

  Preclinical Research

  临床前研究
• One-Step Synthesis of 1,2,3,4-Tetrahydrobenzo(g)quinazoline-5,10-dione Derivatives from Vitamin K3.
  作者：Shunsaku OHTA、Yasunari HINATA、Masayuki YAMASHITA、Ikuo KAWASAKI、Yoko JINDA、Shinobu HORIE

  DOI：10.1248/cpb.42.1730

  日期：——

  The reactions of 2-halogenonaphthoquinones (5, 13, 14 and 15) and 2-methyl-1, 4-naphthoquinone (20; vitamin K3) with primary and secondary amines were examined. 1, 3-Dialkyl-1, 2, 3, 4-tetrahydrobenzo[g]quinazoline-5, 10-diones (9) were obtained in moderate yields by treating 20 with formaldehyde in primary amines. A plausible reaction path-way is also presented.

  对2-卤代萘醌（5、13、14和15）和2-甲基-1,4-萘醌（20；维生素K3）与一级和二级胺的反应进行了研究。通过在一级胺中用甲醛处理20，获得了1,3-二烷基-1,2,3,4-四氢苯并[g]喹唑啉-5,10-二酮（9），产率适中。同时也提出了一个合理的反应路径。
• Blue Light Irradiated Metal-, Oxidant-, and Base-Free Cross-Dehydrogenative Coupling of C(<i>sp</i>²)–H and N–H Bonds: Amination of Naphthoquinones with Amines
  作者：Raushan Kumar Jha、Monojit Batabyal、Sangit Kumar

  DOI：10.1021/acs.joc.3c00666

  日期：2023.6.2

  reaction proceeds by radical pathway in which naphthoquinone forms a highly oxidizing naphthoquinonyl biradical upon irradiation of blue light (457 nm). Consequently, electron transfer from electron-rich amine to an oxidizing naphthoquinonyl biradical leads to a naphthoquinonyl radical anion and aminyl radical cation, followed by proton transfer and delocalization leading to a carbon-centered naphthoquinonyl

  在此，我们报道了蓝光驱动的萘醌和醌的 C( sp 2 )–H 键与伯胺和仲胺的 N–H 键的胺化反应，用于合成 2-氨基萘醌和 2-氨基醌. 萘醌与各种具有给电子（-CH 3、-OCH 3、-SCH 3）、撤电子（-F、-Cl、-Br、-I）的脂肪族胺、芳香族胺、手性胺、伯胺和仲胺的偶联), 和 CO 2 H, -OH, -NH 2在蓝光照射下，无需使用任何额外的试剂、添加剂和氧化剂，选择性地发生具有酸性质子的基团，以 60-99% 的收率提供 C-N 偶联的 2-氨基-萘醌和氢气作为甲醇溶剂中的副产物。通过 DFT 计算、受控实验、动力学同位素效应和底物的替代效应的机理洞察表明，反应通过自由基途径进行，其中萘醌在蓝光 (457 nm) 照射下形成高度氧化的萘醌基双自由基。因此，从富电子胺到氧化性萘醌基双自由基的电子转移导致萘醌基阴离子和氨基自由基阳离子，随后质子转移和离域导致以碳为中心的萘醌基。
• Synthesis and characterization of n-alkylamino derivatives of vitamin K3: Molecular structure of 2-propylamino-3-methyl-1,4-naphthoquinone and antibacterial activities
  作者：Dattatray Chadar、Maria Camilles、Rishikesh Patil、Ayesha Khan、Thomas Weyhermüller、Sunita Salunke-Gawali

  DOI：10.1016/j.molstruc.2015.01.029

  日期：2015.4

  We would like to introduce eight analogues of n-alkylamino derivatives of vitamin K3 (2-methyl-1,4-naphthoquinone) viz, 2-(n-alkylamino)-3-methyl-1,4-naphthoquinone (where n-alkyl is methyl; LM-1, ethyl; LM-2, propyl; LM-3, butyl; LM-4, pentyl; LM-5, hexyl; LM-6, heptyl; LM-7, octyl; LM-8). All the above analogues have been successfully synthesized from vitamin K3 and characterized using different analytical techniques. Furthermore, in order to understand the mechanistic aspects of formation of LM-1 to LM-8 compounds, we could propose the mechanism. The FT-IR analysis of LM-1 to LM-8 indicate the presence of characteristic band of N-H group similar to 3287-3364 cm(-1), the variation was attributed to extensive intramolecular hydrogen bonding interaction. The molecular structure of LM-3 compound has been confirmed by single crystal X-ray diffraction analysis. LM-3 compound crystallises in triclinic space group P1. There were four independent molecules in asymmetric unit cell and their molecular interactions observed via N-H...O , C-H...O and pi-pi stacking of quinonoid rings. Pharmacological potential of all compounds has been evaluated in terms of their antibacterial activities against Pseudomonas aeruginosa and Staphylococcus aureus. All the compounds were active against both the strains while LM-2 was found to be more effective with a minimum inhibition concentration of 0.3125 mu g/mL and 0.156 mu g/mL respectively. (C) 2015 Elsevier B.V. All rights reserved.
• Design, synthesis, and biological evaluation of novel naphthoquinone derivatives with CDC25 phosphatase inhibitory activity
  作者：Marie-Priscille Brun、Emmanuelle Braud、Delphine Angotti、Odile Mondésert、Muriel Quaranta、Matthieu Montes、Maria Miteva、Nohad Gresh、Bernard Ducommun、Christiane Garbay

  DOI：10.1016/j.bmc.2005.05.005

  日期：2005.8

  CDC25 dual-specificity phosphatases are essential key regulators of eukaryotic cell cycle progression and the CDC25A and B isoforms are over-expressed in different tumors and related cancer cell lines. CDC25s are now considered to be interesting targets in the search for novel anticancer agents. We describe new compounds derived from vitamin K-3 that inhibit CDC25B activity with IC50 values in the low micromolar range. These naphthoquinone derivatives also display antiproliferative activity on HeLa cells as expected for CDC25 inhibitors and inhibit cell growth in a clonogenic assay at submicromolar concentrations. They increase inhibitory tyrosine 15 phosphorylation of CDK and induce the cleavage of PARP, a hallmark of apoptosis. (c) 2005 Elsevier Ltd. All rights reserved.