annoquinone-A | 30684-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: annoquinone-A
• 英文别名: 3-methoxy-phenanthrene-1,4-dione；3-Methoxy-phenanthren-1,4-dion；3-Methoxyphenanthren-1,4-chinon；Annoquinone A；3-methoxyphenanthrene-1,4-dione
• CAS: 30684-16-3
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: BTIQIBXDCYXMBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  annoquinone-A 在 乙酸酐 、 溶剂黄146 、 锌 作用下， 生成 1,4-diacetoxy-3-methoxy-phenanthrene
  参考文献：
  名称：

  Lora-Tamayo et al., Anales de la Real Sociedad Espanola de Fisica y Quimica, 1957, vol. 53, p. 63,68

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴香兰素 在 ammonium peroxydisulfate 、 iron(III) chloride hexahydrate 、 双氧水 、 palladium diacetate 、 sodium carbonate 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 29.5h， 生成 annoquinone-A 、
  参考文献：
  名称：

  评估合成的丹参酮I和异丹参酮I类似物在斑马鱼中的抗炎作用。

  摘要：

  在炎症过程中，嗜中性粒细胞行为失调可能在一系列慢性炎症疾病中起主要作用，对于这些疾病，许多目前的治疗方法通常无效。最近，通过在体内靶向嗜中性粒细胞，特定的天然丹参酮已显示出令人鼓舞的抗炎作用，然而，就合成和生物学效应而言，此类丹参酮以及其异构体异丹参酮对应物在很大程度上仍未得到充分开发。为了探索异丹参酮和更广泛的丹参酮的抗炎作用，合成了一系列取代的丹参酮和异丹参酮类似物，以及其他结构相似的分子。使用嗜中性炎症的转基因斑马鱼模型对这些化合物的评估显示了体内不同的抗炎特性，许多化合物显示出令人鼓舞的效果。几种化合物减少嗜中性白细胞的初始募集和/或促进嗜中性白细胞炎症的消退，其中两种还导致人嗜中性白细胞的凋亡增加。特别是，甲氧基取代的丹参酮39可以在不影响嗜中性粒细胞募集到炎症部位的情况下，特别地加速炎症的消退，这使其成为潜在的促分辨率治疗剂特别有吸引力的候选物，以及功能化丹参酮的未来开发的潜在

  DOI：

  10.1371/journal.pone.0240231

文献信息

• Some results obtained in the utilisation of quinones as philodiene
  作者：M. Lora-Tamayo

  DOI：10.1016/0040-4020(58)88002-3

  日期：1958.1

  In the course of a study of new applications of the Diels-Alder reaction, the addition of p-benzoquinone and substituted quinones to ethylene-aromatic dienes and heteroconjugations containing nitrogen, has been investigated.

  在的Diels-Alder反应的新应用的研究的过程中，的添加p苯醌和取代的苯醌为乙烯芳族二烯和含氮heteroconjugations，进行了研究。
• Facile construction of 3-hydroxyphenanthrene-1,4-diones: key intermediates to tanshinone I and its A-ring-modified analogue
  作者：Mingkun Jiao、Chunyong Ding、Ao Zhang

  DOI：10.1016/j.tet.2014.03.019

  日期：2014.5

  key precursor for total synthesis of tanshinone I. This tandem process includes decarboxylative radical alkylation, intramolecular C–H arylation and one-pot O-demethylation and aromatization. Variously substituted phenylpropanoic acids were well tolerated in this approach, and synthesis of tanshinone I (1) was finally successful in six straight steps in 19% overall yields from commercially available

  建立了温和的合成方法，可以方便地构建丹参酮I全合成的关键前体三环羟基菲蒽醌。该串联过程包括脱羧自由基烷基化，分子内C–H芳基化和一锅O-脱甲基化和芳构化。在这种方法中，各种取代的苯基丙酸均具有良好的耐受性，丹参酮I（1）的合成终于成功地以连续6个步骤成功完成，从商业上可获得的5-溴香兰素的总产率为19％。
• Annoquinone-A, an antimicrobial and cytotoxic principle from Annona montana
  作者：Tian-Shung Wu、Ting-Ting Jong、Hsien-Ju Tien、Chang-Sheng Kuoh、Hiroshi Furukawa、Kuo-Hsiung Lee

  DOI：10.1016/s0031-9422(00)82257-8

  日期：1987.1

  new naturally occurring phenanthrene-1,4-quinone, annoquinone-A, along with parietin (physcion) and β-sitostenone were isolated from the stem bark of Annona montana . The structure of annoquinone-A was elucidated by spectral methods and synthesis. Annoquinone-A demonstrated potent antimicrobial activity against Bacillus subtilis and Micrococcus luteus as well as cytotoxicity in the KB ( ED 50 = 0.16

  摘要 从番荔枝的茎皮中分离到了一种新的天然存在的菲-1,4-醌，苯醌-A，以及parietin (physcion) 和β-sitostenone。苯醌-A的结构通过光谱方法和合成阐明。Annoquinone-A 在 KB (ED 50 = 0.16 μg/ml) 组织培养试验中显示出对枯草芽孢杆菌和藤黄微球菌的有效抗菌活性以及细胞毒性。β-Sitostenone 也显示出显着的细胞毒性。
• Lora-Tamayo et al., Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica, 1957, vol. 53, p. 63,66
  作者：Lora-Tamayo et al.

  DOI：——

  日期：——
• Mentally disordered parricide and stranger killers admitted to high-security care. 1: A descriptive comparison
  作者：Helen Baxter、Conor Duggan、Emmet Larkin、Christopher Cordess、Kim Page

  DOI：10.1080/09585180122057

  日期：2001.1

  Parricide is an uncommon crime, so that many of the descriptive studies suffer from methodological shortcomings of small sample sizes and a non-representative ascertainment. We describe a consecutive series of mentally disordered offenders convicted of parricide who were admitted to high-security care and we compare their index characteristics with a group convicted of killing one or more strangers. The main findings were that the parricides were more likely to suffer from schizophrenia but less likely to have had a disrupted childhood and criminal history, as compared with those who had killed a stranger. Those in the parricide group had made a previous attack on their victim in 40% of cases. Overall, the study confirmed some of the differences that one might expect between these two groups of homicides, which had entirely different relationships to their victims.

表征谱图