4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde | 154658-30-7

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
• 英文别名: 9,10-Dihydro-4,5-dihydroxy-9,10-dioxoanthracene-2-aldehyde；4,5-dihydroxy-9,10-dioxoanthracene-2-carbaldehyde
• CAS: 154658-30-7
• 化学式: C₁₅H₈O₅
• 分子量: 268.226
• InChiKey: NJCKPHTYGRPUNK-UHFFFAOYSA-N

物化性质

• 熔点：
  216 °C
• 沸点：
  533.4±50.0 °C(Predicted)
• 密度：
  1.600±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 4.5h， 以15.5 g的产率得到大黄酸
  参考文献：
  名称：

  一种适合双醋瑞因工业化的生产方法

  摘要：

  本发明公开了一种适合双醋瑞因工业化的生产方法，原料经二次氧化得到式I，本发明克服了现有文献报道的合成路线制备的成品重金属超标、污染严重、易燃易爆的缺点，本发明使用的试剂成本低，环境污染小，易于操作，适合工业化生产，本发明的产品品质良好，总杂少且单杂全部控制在0.1％以下，成品控制为单一稳定的晶型，符合药用级别原料药的要求。

  公开号：

  CN108218701A
• 作为产物：
  描述：

  diacerein 在 Pd-BaSO₄ 、 xylene 作用下， 生成 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
  参考文献：
  名称：

  Mitter; Banerjee, Journal of the Indian Chemical Society, 1932, vol. 9, p. 375

  摘要：

  DOI：

文献信息

• Pharmaceutical compounds
  申请人：Lilly Industries Limited

  公开号：US05480873A1

  公开（公告）日：1996-01-02

  Pharmaceutical compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, hydroxyl, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acyloxy, --O-glucoside, optionally substituted phenyl or optionally substituted phenyl-C.sub.1-4 alkoxy; R.sup.3 is tetrazolyl, or and R.sup.4 and R.sup.5 are each hydrogen, hydroxy, acyloxy, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halo, optionally substituted phenyl, --SO.sub.3 H or --NR'R" where R' and R" are each hydrogen or C.sub.1-4 alkyl; provided that when R.sup.3 is --CR'R".CHR'"CO.sub.2 H or tetrazolyl, R.sup.1 and R.sup.2 are each hydroxyl, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acyloxy, --O-glucoside, optionally substituted phenyl or optionally substituted phenyl C.sub.1-4 alkoxy; and or a pharmaceutically acceptable salt or ester thereof.

  公式为##STR1##的药物化合物，其中R.sup.1和R.sup.2分别为氢、羟基、卤素、C.sub.1-4烷基、C.sub.1-4烷氧基、酰氧基、-O-葡萄糖苷、可选择取代的苯基或可选择取代的苯基-C.sub.1-4烷氧基；R.sup.3为四唑基，或者R.sup.4和R.sup.5分别为氢、羟基、酰氧基、硝基、C.sub.1-4烷基、C.sub.1-4烷氧基、卤素、可选择取代的苯基、-SO.sub.3 H或-NR'R"，其中R'和R"分别为氢或C.sub.1-4烷基；但是当R.sup.3为--CR'R".CHR'"CO.sub.2 H或四唑基时，R.sup.1和R.sup.2分别为羟基、卤素、C.sub.1-4烷基、C.sub.1-4烷氧基、酰氧基、-O-葡萄糖苷、可选择取代的苯基或可选择取代的苯基-C.sub.1-4烷氧基；或其药学上可接受的盐或酯。
• Synthesis, biological evaluation and molecular modeling of aloe-emodin derivatives as new acetylcholinesterase inhibitors
  作者：Da-Hua Shi、Wei Huang、Chao Li、Ling-Ting Wang、Shi-Fan Wang

  DOI：10.1016/j.bmc.2013.01.015

  日期：2013.3

  A series of aloe-emodin derivatives were designed, synthesized and evaluated as acetylcholinesterase inhibitors. Most of the new prepared compounds showed remarkable acetylcholinesterase inhibitory activities. Among them, the compound 1-((4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl) methyl) pyridin-1-ium chloride (C3) which has a pyridinium substituent possessed the best inhibitory activity

  设计，合成和评估了一系列芦荟大黄素衍生物，作为乙酰胆碱酯酶抑制剂。大多数新制备的化合物显示出显着的乙酰胆碱酯酶抑制活性。其中，具有吡啶鎓取代基的化合物1-（（4,5-二羟基-9,10-二氧杂-9,10-二氢蒽-2-基）甲基）吡啶-1-氯（C3）具有最好的乙酰胆碱酯酶的抑制活性（IC 50  = 0.09μM）。用AUTODOCK进行的对接研究表明C3可以与乙酰胆碱酯酶的催化活性位点（CAS）和外围阴离子位点（PAS）相互作用。
• Design and Synthesis of Sulfanilamide Aminophosphonates as Novel Antibacterial Agents towards <i>Escherichia coli</i>
  作者：Juan Wang、Mohammad Fawad Ansari、Jian‐Mei Lin、Cheng‐He Zhou

  DOI：10.1002/cjoc.202100165

  日期：2021.8

  microbes was synthesized by one-pot three-component reaction. Noticeably, fluorobenzyl derivative 5d (MIC = 2 μg/mL) was active against drug resistant E. coli infection and exerted no obvious toxicity towards human mammalian cells. Compound 5d also displayed good anti-biofilm activity and low possibility to induce drug resistance. Mechanism investigation elucidated that molecule 5d could disrupt E. coli

  传统抗生素治疗耐药细菌的能力有限，需要新的治疗选择。通过一锅三组分反应合成了一类独特的磺胺氨基膦酸盐作为新的潜在抗微生物剂。值得注意的是，氟苄基衍生物 5d (MIC = 2 μg/mL) 对耐药性大肠杆菌感染有活性，对人类哺乳动物细胞没有明显的毒性。化合物5d还表现出良好的抗生物膜活性，诱导耐药性的可能性很小。机制研究阐明分子 5d 可以破坏大肠杆菌膜通过产生活性氧 (ROS) 然后嵌入脱氧核糖核酸 (DNA) 形成稳定的 5d-DNA 复合物，从而导致细菌死亡。这些结果表明磺胺氨基膦酸盐将有助于开发新的潜在抗菌剂。
• An efficient approach for the synthesis of novel methyl sulfones in acetic acid medium and evaluation of antimicrobial activity
  作者：Gollapudi RAVI KUMAR、Chandra Rao DASIREDDY、Ravi VARALA、Vijay KOTRA、Hari Babu BOLLIKOLLA

  DOI：10.3906/kim-2003-10

  日期：——

  A series of nine methyl sulphones (3a–3i) starting from the aldehydes (1a–1i) were synthesized in two consecutive steps. In the first step, preparation of allyl alcohols (2a–2i) from their corresponding aldehydes by the reaction of sodium borohydride in methanol at room temperature is reported. Finally, methyl sulphones are synthesized by condensing sodium methyl sulfinates with allyl alcohols in the presence of BF3.Et2O in acetic acid medium at room temperature for about 2–3 h. The reaction conditions are simple, yields are high (85%–95%), and the products were obtained with good purity. All the synthesized compounds were characterized by their 1H, 13C NMR, and mass spectral analysis. All the title compounds were screened for antimicrobial activity. Among the compounds tested, the compound 3f has inhibited both Gram positive and Gram negative bacteria effectively and compound 3i has shown potent antifungal activity. These promising components may help to develop more potent drugs in the near future for the treatment of bacterial and fungal infections.

  以醛（1a-1i）为起点，通过两个连续步骤合成了一系列九种甲基砜（3a-3i）。第一步，在室温下通过硼氢化钠在甲醇中的反应从相应的醛制备烯丙基醇（2a-2i）。最后，在醋酸介质中，BF3.Et2O 存在下，室温下冷凝甲基亚磺酸钠与烯丙基醇，约 2-3 小时，合成甲基砜。反应条件简单，收率高（85%-95%），产物纯度好。所有合成化合物均通过 1H、13C NMR 和质谱分析进行了表征。对所有标题化合物进行了抗菌活性筛选。在测试的化合物中，化合物 3f 对革兰氏阳性菌和革兰氏阴性菌都有有效的抑制作用，而化合物 3i 则显示出强大的抗真菌活性。这些有前景的成分可能有助于在不久的将来开发出更多治疗细菌和真菌感染的特效药物。
• Design, synthesis, and biological evaluation of pyrazole-linked aloe emodin derivatives as potential anticancer agents
  作者：Guddeti Dileep Kumar、Bandi Siva、Sravanthi Vadlamudi、Surendar Reddy Bathula、Hashnu Dutta、K. Suresh Babu

  DOI：10.1039/d0md00315h

  日期：——

  continuous efforts to generate new derivatives from lead compounds isolated from traditional medicinal plants, a series of aloe-emodin derivatives (6a–6e) were synthesized and assessed for their potential anticancer activity against a panel of cancer cell lines. The results showed that most of the derivatives are more active than the aloe-emodin and particularly, 6b and 6e manifested potent activity with

  在我们不断努力从从传统药用植物中分离出来的先导化合物中生成新衍生物的过程中，我们合成了一系列芦荟大黄素衍生物 ( 6a-6e )，并评估了它们对一组癌细胞系的潜在抗癌活性。结果表明，大多数衍生物比芦荟大黄素更具活性，特别是6b和6e对MDA-MB-231和MCF-7细胞的IC 50值分别为1.32和1.6 μM和0.99和2.68 μM。 ， 分别。此外，6b和6e在 MDA-MB-231 细胞中诱导早期和晚期细胞凋亡以及将细胞周期阻滞在 G2/M 期。总之，结果证实芦荟大黄素衍生物可能是更好治疗乳腺癌的潜在候选药物。