1-(1,4-dihydroxy-[2]naphthyl)-octan-1-one | 873392-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1,4-dihydroxy-[2]naphthyl)-octan-1-one
• 英文别名: 2-octanoylnaphthohydroquinone；1-(1,4-Dihydroxy-[2]naphthyl)-octan-1-on
• CAS: 873392-81-5
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: HOMIOLOGASMTFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(1,4-dihydroxy-[2]naphthyl)-octan-1-one 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-heptyl)-7H-benzo[g]benzo[4,5]-3-methylthiazolo[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：

  辛酰氯 在 二硫化碳 、 三氯化铝 作用下， 生成 1-(1,4-dihydroxy-[2]naphthyl)-octan-1-one
  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

• 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。
• Synthetic approaches and in vitro cytotoxic evaluation of 2-acyl-3-(3,4,5-trimethoxyanilino)-1,4-naphthoquinones
  作者：Jaime A. Valderrama、Mónica Cabrera、Julio Benites、David Ríos、Ricardo Inostroza-Rivera、Giulio G. Muccioli、Pedro Buc Calderon

  DOI：10.1039/c7ra03238b

  日期：——

  formation of the heterocyclic compounds is discussed in terms of the ring closure of C–C Michael type adduct intermediates through two alternative N–C-bond formations. The propensity of the substrates to undergo preferential C–C instead of C–N bond formation and the further heterocyclization of the C–C Michael type adduct intermediates is rationalized by using product stability parameters assessed by DFT

  2-酰基-1,4-萘醌与3,4,5-三甲氧基苯胺在有氧条件下反应，生成苯并菲啶醌，苯并咔唑和2-酰基-3-（3,4,5-三甲氧基苯胺基）-1,4-萘醌衍生品。关于杂环化合物的形成，将通过两个备选的N-C键形成对C–C Michael型加合物中间体的闭环进行讨论。通过使用DFT计算评估的产品稳定性参数，可以使底物发生优先C–C而不是C–N键形成的倾向以及C–C Michael型加合物中间体的进一步杂环化。初步结果报道了从2-酰基萘醌制备2-酰基-3-（3,4,5-三甲氧基苯胺基）-1,4-萘醌的便利方法及其对癌细胞的细胞毒活性。
• 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。
• 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。
• Light-Driven Carbon–Carbon Coupling of α-sp³–CH of Aliphatic Alcohols with sp²–CH Bond of 1,4-Naphthoquinones
  作者：Raushan Kumar Jha、Aditya Upadhyay、Kanika、Saket Jain、Neena K A、Sangit Kumar

  DOI：10.1021/acs.orglett.2c03066

  日期：2022.10.21

  Here, an α-selective Csp3–H bond functionalization of primary aliphatic alcohols with 1,4-naphthoquinones yielded Csp2–Csp2 coupled products driven by blue-LED light under catalyst, metal, base, and reagent-free conditions. In this transformation, cleavage of three C–H bonds (two sp3–C-H, one sp2–C–H, and one O–H) and four new bonds formed, leading to fluorescent 2-acylated-1,4-naphthohydroquinones

  在这里，在催化剂、金属、碱和无试剂条件下，脂肪伯醇与 1,4-萘醌的 α-选择性 C sp3 -H 键官能化产生了由蓝色 LED 光驱动的 C sp 2 -C sp 2偶联产物. 在该转化过程中，三个 C-H 键（两个 sp 3 -CH、一个 sp 2 -C-H 和一个 O-H）断裂并形成四个新键，从而产生荧光 2-acylated-1,4-naphthohydroquinones .