1-(1,4-二羟基-2-萘基)-1-己酮 | 875247-81-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(1,4-二羟基-2-萘基)-1-己酮
• 英文名称: 1-(1,4-dihydroxy-2-naphthyl)-1-hexanone
• 英文别名: 2-hexanoylnaphthohydroquinone；2-hexanoyl-1,4-naphthohydroquinone；1-(1,4-dihydroxynaphthalen-2-yl)hexan-1-one；1-(1,4-dihydroxy-[2]naphthyl)-hexan-1-one；1-(1,4-Dihydroxy-[2]naphthyl)-hexan-1-on；1-(1,4-Dihydroxynaphthalen-2-yl)hexan-1-one
• CAS: 875247-81-7
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: MGIUPWKFUGPNCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1,4-二羟基-2-萘基)-1-己酮 在 magnesium sulfate 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 13-hydroxy-13-(1-pentyl)-7H-benzo[g]benzo[4,5]-3-methoxythiazolo[2,3-b]quinazoline-7,12-quinone
  参考文献：
  名称：

  2-酰基萘醌和2-氨基苯并噻唑之间的异环反应。抗增殖苯并[ g ]苯并噻唑并[2,3 - b ]喹唑啉-7,12-醌的合成新途径

  摘要：

  开发了一种方便的两步法，用于从2-酰基萘氢醌和2-氨基苯并噻唑制备苯并[ g ]苯并噻唑并[2,3 - b ]喹唑啉-7,12-醌。X射线晶体学支持杂环醌的结构。该方案为制备标题化合物提供了一种操作简单的策略，并显示出良好的功能灵活性和易于获得的起始原料。据报道，某些获得的杂环醌对前列腺，膀胱和乳腺人类来源的肿瘤细胞系具有显着的体外抗增殖活性。

  DOI：

  10.1016/j.tetlet.2015.07.034
• 作为产物：
  描述：

  己酰氯 在 二硫化碳 、 三氯化铝 、 苯 作用下， 生成 1-(1,4-二羟基-2-萘基)-1-己酮
  参考文献：
  名称：

  Hase; Nishimura, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 203,205,206

  摘要：

  DOI：

文献信息

• Access to New Cytotoxic Quinone-Amino Acid Conjugates Linked through A Vinylic Spacer from 2-Acylnaphthoquinones and Methyl 3-Aminocrotonate
  作者：Jaime Valderrama、Joel Garrido、Virginia Delgado、Julio Benites、Cristina Theoduloz

  DOI：10.3390/molecules22122281

  日期：——

  bonded through a vinyl spacer in the yields range 40-71%. The presence of not-separable isomers of the naphthoquinone amino acids conjugates in the ¹H- and 13C-NMR spectra is explained by the existence of conformational isomers generated by hindered rotation of the substituent bonded to the quinone double bond. These new naphthoquinone amino acids conjugates were screened in vitro on normal and cancer cell

  2-乙酰基和2-苯甲酰基-1,4-萘醌与（Z）-3-（羟甲基）氨基巴豆酸甲酯的反应通过正式的[3 + 3]过程进行，从而在63中得到相应的1,2-二氢苯并异喹啉喹啉％和72％的收率分别。2-酰基-1，4-萘醌与衍生自不同的1-和d-氨基酸甲基酯的烯胺酮的反应产生了通过乙烯基间隔基键合的相应的萘醌氨基酸共轭物，产率范围为40-71％。在1 H-和13 C-NMR光谱中萘醌氨基酸共轭物的不可分离的异构体的存在是由于存在由于与醌双键结合的取代基的旋转受阻而产生的构象异构体。
• In Vitro Inhibition of Hsp90 Protein by Benzothiazoloquinazolinequinones Is Enhanced in The Presence of Ascorbate. A Preliminary In Vivo Antiproliferative Study
  作者：Jaime A. Valderrama、David Ríos、Giulio G. Muccioli、Pedro Buc Calderon、Julio Benites

  DOI：10.3390/molecules25040953

  日期：——

  A series of benzo[g]benzothiazolo[2,3-b]quinazoline-7,12-quinones were prepared from 2-acylnaphthohydroquinones and 2-aminobenzothiazoles and were evaluated for their in vitro antiproliferative activity. After screening using the MTT reduction assay, their IC50 values were calculated on a panel of cancer cells (T24, DU-145, MCF-7). Current standard anticancer drugs were included as control, and their calculated IC50 values were 7.8 and 23.5 µM for 5-fluorouracil and tamoxifen, respectively. Non-cancer cells (AG1523) were included to assess cancer cell sensitivity and drug selectivity. Four members of the series, with IC50 values from 0.11 to 2.98 µM, were chosen for further assays. The selected quinones were evaluated regarding their effects on cancer cell proliferation (clonogenic assay) and on Hsp90 and poly(ADPribose)polymerase (PARP) protein integrity. The most active compound (i.e., 15) substantially inhibited colony forming unit (CFU) formation at 0.25 µM. In the presence of ascorbate, it induced an oxidative cleavage of Hsp90 but had no effect on PARP protein integrity. In an in vivo animal model, it discreetly increased the mean survival time (m.s.t.) of tumor-bearing mice. In light of these results, compound 15 represents a potential lead-molecule to be further developed.

  一系列苯并[g]苯并噻唑[2,3-b]喹唑啉-7,12-醌类化合物是通过2-酰基萘羟喹醌和2-氨基苯并噻唑反应制备的，并对它们的体外抗增殖活性进行了评估。通过MTT还原实验筛选后，在一系列癌细胞（T24、DU-145、MCF-7）中计算了它们的IC50值。当前标准的抗癌药物被包括为对照，5-氟尿嘧啶和他莫昔芬的计算IC50值分别为7.8和23.5微米。非癌细胞（AG1523）被包括以评估癌细胞的敏感性和药物选择性。系列中的四个成员，其IC50值从0.11到2.98微米不等，被选定进行进一步的实验。选定的醌类化合物被评估其对癌细胞增殖（克隆形成实验）以及对Hsp90和聚(ADP核糖)聚合酶（PARP）蛋白完整性的影响。最活性的化合物（即15号）在0.25微米下显著抑制了克隆形成单位（CFU）的形成。在抗坏血酸存在的情况下，它诱导了Hsp90的氧化裂解，但对PARP蛋白的完整性没有影响。在体内动物模型中，它轻微增加了携带肿瘤的小鼠的平均存活时间（m.s.t.）。鉴于这些结果，化合物15代表了一个有潜力进一步开发的先导分子。
• An Improved Procedure for the Photoacylation of 1,4-Naphthoquinone with Aliphatic Aldehydes
  作者：Michael Oelgemöller、Ferdinand Friedrichs、Brian Murphy、Delphine Nayrat、Torsten Ahner、Mario Funke、Michael Ryan、Johann Lex、Jochen Mattay

  DOI：10.1055/s-0028-1087272

  日期：——

  Irradiation of 1,4-naphthoquinone at 300±25 nm in benzene and in the presence of aliphatic aldehydes readily yields acylated hydroquinones in good to high yields. The developed protocol represents a significant improvement over the original procedure using medium-pressure mercury lamps. Subsequent oxidation gives the corresponding acylated quinones.

  1,4-萘醌在苯中和脂肪醛存在下以 300±25 nm 进行辐照，很容易以良好到高产率产生酰化氢醌。开发的协议代表了对使用中压汞灯的原始程序的重大改进。随后的氧化得到相应的酰化醌。
• Solar photochemistry: optimisation of the photo Friedel–Crafts acylation of naphthoquinones
  作者：Lorna J. Mitchell、William Lewis、Christopher J. Moody

  DOI：10.1039/c3gc41477a

  日期：——

  A practical and robust photo Friedel–Crafts acylation of naphthoquinones is described. Although the reaction proceeds slowly in sunlight, the optimised conditions offer a substantial improvement to those already reported, by the utilisation of a more reliable and practical ‘sun-mimicking’ light source, a less hazardous solvent system (trifluorotoluene) and faster reaction times. Using these conditions, the reaction scope has been expanded to include functionalised aldehyde and naphthoquinone substrates, affording the desired photo-products in acceptable to excellent yields (17–81%). Factors influencing the regiochemistry of the photo Friedel–Crafts reaction on unsymmetrical naphthoquinones have also been investigated.

  本文介绍了一种实用而可靠的萘醌光弗里德酰化反应。虽然该反应在阳光下进行得很慢，但优化后的条件与已报道的条件相比有了很大改进，因为它利用了更可靠、更实用的 "模拟太阳 "光源、危害更小的溶剂系统（三氟甲苯）以及更快的反应时间。利用这些条件，反应范围扩大到包括官能化醛和萘醌底物，以可接受到极好的收率（17%-81%）获得所需的光反应产物。此外，还研究了影响不对称萘醌的光弗里德卡夫斯反应的区域化学性质的因素。
• Green photochemistry: photo-Friedel–Crafts acylations of 1,4-naphthoquinone in room temperature ionic liquids
  作者：Brian Murphy、Peter Goodrich、Christopher Hardacre、Michael Oelgemöller

  DOI：10.1039/b913252j

  日期：——

  The photo-Friedel–Crafts acylation of 1,4-naphthoquinone with various aldehydes was investigated in a series of room temperature ionic liquids. High conversions and selectivities were achieved in [C2mim]+-based ionic liquids with the highest isolated yields found in [C2mim][NTf2]. The developed procedure allowed for a replacement of hazardous solvents such as benzene and acetonitrile which are commonly used for this transformation.

  在一系列室温离子液体中研究了 1,4-萘醌与各种醛的光-弗里德尔-卡夫酰化反应。在[C2mim]+基离子液体中实现了高转化率和高选择性，其中[C2mim][NTf2]的分离产率最高。所开发的程序可以替代苯和乙腈等危险溶剂，这些溶剂通常用于这种转化。