2-Hexanoyl-hydrochinon | 4693-18-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Hexanoyl-hydrochinon
• 英文别名: 1-(2,5-dihydroxy-phenyl)-hexan-1-one；1-(2,5-Dihydroxy-phenyl)-hexan-1-on；1-(2,5-Dihydroxyphenyl)-1-hexanone；1-(2,5-dihydroxyphenyl)hexan-1-one
• CAS: 4693-18-9
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: FAGHITZLJQFYNE-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C
• 沸点：
  369.1±27.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  2-Hexanoyl-hydrochinon 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 环己烷 、 乙腈 、 苯 为溶剂， 生成
  参考文献：
  名称：

  2-酰基-1,4-醌的光化学二聚反应

  摘要：

  2-Acyl-1,4-benzoquinones 和 2-acyl-1,4-naphthoquinones 通过光解经历了一种新型的区域专一性和立体专一性环二聚化。反应是一般的，不受...的影响。

  DOI：

  10.1246/bcsj.52.3019
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢溴酸 、 溶剂黄146 作用下， 生成 2-Hexanoyl-hydrochinon
  参考文献：
  名称：

  Ingle et al., Journal of the Indian Chemical Society, 1949, vol. 26, p. 569,572

  摘要：

  DOI：

文献信息

• Half-Wave Potentials and In Vitro Cytotoxic Evaluation of 3-Acylated 2,5-Bis(phenylamino)-1,4-benzoquinones on Cancer Cells
  作者：Julio Benites、Jaime A. Valderrama、Maryan Ramos、Maudy Valenzuela、Angélica Guerrero-Castilla、Giulio G. Muccioli、Pedro Buc Calderon

  DOI：10.3390/molecules24091780

  日期：——

  two one-electron reduction waves to the corresponding radical-anion and dianion, and two quasi-reversible oxidation peaks. The first and second half-wave potential values (E1/2) of the members of the series were sensitive to the push-pull electronic effects of the substituents around the benzoquinone nucleus. The in vitro cytotoxic activities of the 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones against

  合成了广泛的 3-酰基-2,5-双(苯基氨基)-1,4-苯醌，并评估了它们的伏安值以及体外癌细胞的细胞毒性。该系列的成员由酰基苯醌和苯胺以中等至良好的产率（47-74％）通过涉及两个原位区域选择性氧化胺化反应的序列的程序制备。氨基醌的循环伏安图对相应的自由基阴离子和二价阴离子表现出两个单电子还原波，以及两个准可逆氧化峰。该系列成员的第一个和第二个半波电位值 (E1/2) 对苯醌核周围取代基的推挽电子效应敏感。3-酰基-2,5-双(苯基氨基)-1的体外细胞毒活性，使用 MTT 比色法测量 4-苯醌对人癌细胞（膀胱和前列腺）和非肿瘤人胚胎肾细胞的作用。通过甲氧基（给电子效应）或氟（吸电子效应）取代两个苯胺基团，降低了氨基醌的细胞毒性。在未取代的苯氨基系列的成员中，18 种化合物中有两种显示出有趣的抗癌活性。进行了初步分析，寻找所选基因表达的变化。在这种情况下，这两种化合物增加了 TNF 基因表
• Antifungal Activity and In Silico Studies on 2-Acylated Benzo- and Naphthohydroquinones
  作者：David Ríos、Jaime A. Valderrama、Gonzalo Quiroga、Jonathan Michea、Felipe Salas、Eduardo Álvarez Duarte、Edmundo A. Venegas-Casanova、Rafael Jara-Aguilar、Carlos Navarro-Retamal、Pedro Buc Calderon、Julio Benites

  DOI：10.3390/molecules27093035

  日期：——

  The high rates of morbidity and mortality due to fungal infections are associated with a limited antifungal arsenal and the high toxicity of drugs. Therefore, the identification of novel drug targets is challenging due to the several resemblances between fungal and human cells. Here, we report the in vitro antifungal evaluation of two acylphenols series, namely 2-acyl-1,4-benzo- and 2-acyl-1,4-naphthohydroquinones. The antifungal properties were assessed on diverse Candida and filamentous fungi strains through the halo of inhibition (HOI) and minimal inhibitory concentration (MIC). The antifungal activities of 2-acyl-1,4-benzohydroquinone derivatives were higher than those of the 2-acyl-1,4-naphthohydroquinone analogues. The evaluation indicates that 2-octanoylbenzohydroquinone 4 is the most active member of the 2-acylbenzohydroquinone series, with MIC values ranging from 2 to 16 μg/mL. In some fungal strains (i.e., Candida krusei and Rhizopus oryzae), such MIC values of compound 4 (2 and 4 μg/mL) were comparable to that obtained by amphotericin B (1 μg/mL). The compound 4 was evaluated for its antioxidant activity by means of FRAP, ABTS and DPPH assays, showing moderate activity as compared to standard antioxidants. Molecular docking studies of compound 4 and ADMET predictions make this compound a potential candidate for topical pharmacological use. The results obtained using the most active acylbenzohydroquinones are promising because some evaluated Candida strains are known to have decreased sensitivity to standard antifungal treatments.

  由于抗真菌药物的数量有限且毒性高，导致真菌感染的发病率和死亡率很高。因此，由于真菌细胞和人类细胞之间存在多种相似之处，寻找新的药物靶点是具有挑战性的。本文报道了两种酰基苯酚系列化合物，即2-酰基-1,4-苯醌和2-酰基-1,4-萘醌羟醌的体外抗真菌评估。通过抑菌圈直径（HOI）和最小抑菌浓度（MIC）来评估多种念珠菌和丝状真菌菌株的抗真菌特性。2-酰基-1,4-苯醌羟醌衍生物的抗真菌活性高于2-酰基-1,4-萘醌羟醌类似物。评估表明，2-辛酰基苯醌羟醌4是2-酰基苯醌羟醌系列中最活跃的成员，MIC值范围为2至16μg/mL。在某些真菌菌株（即克鲁氏念珠菌和米曲霉），化合物4的MIC值（2和4μg/mL）与两性霉素B（1μg/mL）相当。通过FRAP、ABTS和DPPH测定，评估了化合物4的抗氧化活性，显示出与标准抗氧化剂相比的中等活性。化合物4的分子对接研究和ADMET预测使其成为局部药物治疗的潜在候选药物。使用最活跃的酰基苯醌羟醌类化合物获得的结果是有希望的，因为一些评估的念珠菌菌株已知对标准抗真菌治疗的敏感性降低。
• Analogs of platelet activating factor. 6. Mono- and bis-aryl phosphate antagonists of platelet activating factor
  作者：A. Wissner、M. L. Carroll、K. E. Green、S. S. Kerwar、W. C. Pickett、R. E. Schaub、L. W. Torley、S. Wrenn、C. A. Kohler

  DOI：10.1021/jm00087a023

  日期：1992.5

  A series of aryl phosphoglyceride (3, 19-6 1) and bis-aryl phosphate (67-135) antagonists of platelet activating factor (PAF) were prepared. A group of four bifunctional phosphorus reagents (5a-c and 7) were developed that allowed the preparation of these aryl phosphates in which the position of aromatic substitution can be varied. These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets. Selected compounds were also evaluated for their ability to displace [H-3]PAF from its receptor on rabbit platelets. These in vitro data were compared to similar data obtained for a number of known PAF antagonists. The compounds were evaluated in vivo, in both the mouse and rabbit, for their ability to prevent death induced by a lethal challenge of PAF. The relationships between the biological activity and the nature, lipophilicity, and position of substituents of the aromatic rings were studied. Compound 105 (CL 184005) has been selected to undergo further development as a potential therapeutic agent for the treatment of septic shock in man.
• Über die Darstellung von Ketonen 2-wertiger Phenole mittels Carbonsäuren und Borfluorid
  作者：Herbert Oelschläger

  DOI：10.1002/ardp.19552880303

  日期：——
• Vandenberghe,A.; Willems,J.F., Bulletin des Societes Chimiques Belges, 1965, vol. 74, p. 397 - 406
  作者：Vandenberghe,A.、Willems,J.F.

  DOI：——

  日期：——