2-benzoylnaphthalene-1,4-dione | 74652-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-benzoylnaphthalene-1,4-dione
• 英文别名: 2-benzoyl-1,4-naphthoquinone；2-benzoyl-[1,4]naphthoquinone；2-Benzoyl-[1,4]naphthochinon
• CAS: 74652-31-6
• 化学式: C₁₇H₁₀O₃
• 分子量: 262.265
• InChiKey: CASWDWHEUUBQQN-UHFFFAOYSA-N

物化性质

• 熔点：
  159-161.5 °C
• 沸点：
  431.2±45.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoylnaphthalene-1,4-dione 在 甲醇 、 硫酸 、 tin(ll) chloride 作用下， 生成 4-甲氧基-2-苯甲酰基-1-萘酚
  参考文献：
  名称：

  Ettlinger, Journal of the American Chemical Society, 1954, vol. 76, p. 2775

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-二甲氧基萘-2-甲醛 在 ammonium cerium (IV) nitrate 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 19.0h， 生成 2-benzoylnaphthalene-1,4-dione
  参考文献：
  名称：

  Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells

  摘要：

  Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, alpha- and beta-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6-11.7 mu M) compared to the current drug of choice cisplatin (IC50 = 16.5 mu M). This study also established that the two new synthetic halogenated compounds 12a and 16a (IC50 = 3.0 and 7.3 mu M) and the previously reported compound 11a (IC50 = 3.9 mu M), were non-toxic to NIH3T3 normal fibroblast cells. Cell death of oesophageal cancer cells by processes involving PARP cleavage caused by 11a was shown to be associated with elevated c-Jun levels, suggesting a role for this pathway in the mechanism of action of this cohort of naphthoquinone compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.048

文献信息

• Total synthesis of redox-active 1.4-naphthoquinones and their metabolites and their therapeutic use as antimalarial and schistomicidal agents
  申请人：Centre National de la Recherche Scientifique

  公开号：EP2505583A1

  公开（公告）日：2012-10-03

  Naphthoquinones, azanaphthoquinones and benxanthones, their process of synthesis and their use as antimalarial or antischistosomal agents.

  萘醌、氮杂萘醌和苯基蒽醌，它们的合成过程及其作为抗疟疾或抗血吸虫药剂的用途。
• [EN] TOTAL SYNTHESIS OF REDOX-ACTIVE 1.4-NAPHTHOQUINONES AND THEIR METABOLITES AND THEIR THERAPEUTIC USE AS ANTIMALARIAL AND SCHISTOMICIDAL AGENTS<br/>[FR] SYNTHÈSE TOTALE DE 1,4-NAPHTOQUINONES PRÉSENTANT UNE ACTIVITÉ D'OXYDO-RÉDUCTION ET DE LEURS MÉTABOLITES ET LEUR UTILISATION THÉRAPEUTIQUE COMME AGENTS ANTIPALUDIQUES ET SCHISTOMICIDES
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2012131010A1

  公开（公告）日：2012-10-04

  Naphthoquinones, azanaphthoquinones and benxanthones, their process of synthesis and their use as antimalarial or antischistosomal agents.

  萘醌、氮杂萘醌和苯基蒽醌，它们的合成过程以及它们作为抗疟疾或抗血吸虫药物的用途。
• 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。
• 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。
• A novel manganese(iii) acetate mediated reaction between 2-benzoyl-1,4-naphthoquinones and 1,3-dicarbonyl compounds
  作者：Chien-Yu Lin、Yu-Chih Cheng、An.-I. Tsai、Che-Ping Chuang

  DOI：10.1039/b516285h

  日期：——

  A manganese(III)-mediated reaction between 2-benzoyl-1,4-naphthoquinones and 1,3-dicarbonyl compounds is described. This reaction provides an effective method for the synthesis of naphtho[2,3-c]furan-4,9-diones and naphthacene-5,12-diones, and it shows fair to high chemoselectivity depending on the electronic effect of the benzoyl group substituent on the reactants. With ethyl benzoylacetate and 1

  描述了2-苯甲酰基-1,4-萘醌与1,3-二羰基化合物之间的锰（III）介导的反应。该反应提供了一种合成萘并[2,3-c]呋喃-4,9-二酮和萘并5,12-二酮的有效方法，并且根据苯甲酰基的电子效应，其显示出中等至高的化学选择性。反应物上的取代基。用苯甲酰乙酸乙酯和1，3-二酮，可以高效，高选择性地生产新型萘并[2,3-c]呋喃-4,9-二酮。