1,4-Dihydroxy-2-(1-hydroxybutyl)anthracene-9,10-dione | 69960-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-Dihydroxy-2-(1-hydroxybutyl)anthracene-9,10-dione
• CAS: 69960-27-6
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: QVPSRXJPGZCFRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-Dihydroxy-2-(1-hydroxybutyl)anthracene-9,10-dione 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  通过生物等排线法设计和合成新型羟基蒽醌氮芥子油衍生物作为潜在的抗癌药

  摘要：

  通过生物等排方法合成了一系列在1'-位具有烷基化N-芥子碱药效基团的羟基蒽醌，以评估其对四种肿瘤细胞系（MDA-MB-231，HeLa，MCF-7和A549）的细胞毒性。这些化合物对MDA-MB-231和MCF-7细胞显示出显着的体外细胞毒性，反映了对人乳腺癌的出色选择性。其中，化合物5k具有最大的细胞毒性，IC 50值为0.263 nM， 在抑制MCF-7细胞生长方面比DXR（IC 50 = 0.294 nM）更有效。化合物5k的优异的细胞毒性和良好的选择性 提示它可能是抗癌药进一步设计和开发的有前途的线索，尤其是对于乳腺癌。

  DOI：

  10.1016/j.ejmech.2015.08.006
• 作为产物：
  描述：

  1,4-二羟基蒽醌 、 正丁醛 在 sodium dithionite 、 sodium hydroxide 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 3.34h， 以61%的产率得到1,4-Dihydroxy-2-(1-hydroxybutyl)anthracene-9,10-dione
  参考文献：
  名称：

  通过改良的马沙克反应将羟基烷基轻松安装到羟基蒽醌和氨基蒽醌中

  摘要：

  1,4-二羟基蒽醌广泛存在于众多天然产品和药物中。能够通过简单而有效的转化使 1,4-二羟基蒽醌骨架功能化非常重要，这可能对药物发现过程有用。我们在此描述了一种通过使用改进的 Marschalk 反应衍生 1,4-二羟基蒽醌的简单有效的方法。与通常需要保护和脱除 OH 基团的传统方法相比，该方法具有明显的优势。我们还证明了该反应对其他羟基蒽醌和氨基蒽醌的适用性。

  DOI：

  10.1002/ejoc.201300891

文献信息

• Esters of 2-(1-hydroxyalkyl)-1,4-dihydroxy-9,10-anthraquinones with melphalan as multifunctional anticancer agents
  作者：Guang-Zhu Jin、Young-Jae You、Byung-Zun Ahn

  DOI：10.1016/s0960-894x(01)00260-8

  日期：2001.6

  Eight esters of 2-(1-hydroxyalkyl)-1,4-dihydroxy-9,10-anthraquinone with melphalan were prepared and tested for their antitumor activity (S-180) and cytotoxicity. 2-[1-[4-(p-Bis(2-chloroethyl)-aminophenyl)-butanoyloxy]methyl]-1,4-dihydroxy-9,10-anthraquinone and 2-[1-[4-(p-bis(2-chloroethyl)-aminophenyl)-butanoyloxy]ethyl]-1,4-dihydroxy-9,10-anthraquinone showed remarkable antitumor activity (T/C,

  制备了2-（1-羟烷基）-1，4-二羟基-9，10-蒽醌与马法兰的八种酯，并测试了它们的抗肿瘤活性（S-180）和细胞毒性。2- [1- [4-（对-双（2-氯乙基）-氨基苯基）-丁酰氧基]甲基] -1,4-二羟基-9,10-蒽醌和2- [1- [4-（p-bis） （2-氯乙基）-氨基苯基）-丁酰氧基]乙基] -1，4-二羟基-9，10-蒽醌显示出显着的抗肿瘤活性（T / C，265和272％）。
• Anthracene-1,4,9,10-tetraone Derivatives: Synthesis and Antitumor Activity
  作者：Guang-Zhu Jin、Yong Kim、Jin-Ho Chung、Dai-Eun Sok、Byung-Zun Ahn

  DOI：10.1002/(sici)1521-4184(199812)331:12<380::aid-ardp380>3.0.co;2-v

  日期：1998.12

  A series of 2-alleviated anthracene-1,4,9,10-tetraone (ATO) derivatives were synthesized, and their antitumor action in ICR mice bearing S-180 cells and antiproliferative activity against L1210 cells were evaluated. Overall, the introduction of an alkyl group (CI-Cs) at C-2 enhanced the antiproliferative activity. Among 2-(1-hydroxyalkyl)- or 2-(1-acetoxyalkyl)-ATO derivatives, four compounds possessing alkyl chain of an intermediate size (G-Cs) gave T/C values of >300%. Acetylation at 1'-OH failed to cause an enhancement in the antitumor action. in contrast to a remarkable increase in antiproliferative activity. Although there was no direct relationship between antiproliferative activity and antitumor action, the compounds with lower antiproliferative activity tended to show higher antitumor activity. Further study shows that the antiproliferative activity of ATO derivatives may be explained properly neither by redox cycling nor arylating capacity.
• Esters of chlorambucil with 2-substituted 1,4-dihydroxy-9,10-anthraquinones as multifunctional anticancer agents
  作者：G Jin

  DOI：10.1016/s0223-5234(01)01229-6

  日期：2001.4

  Novel twelve esters of chlorambucil with 2-(1-hydroxyalkyl)-1,4-dihydroxy-9,10-anthraquinone were synthesized and tested for their antitumor activity in mice bearing S-180 ascitic cells as well as cytotoxic activity against L1210 cells. Eight of them were highly cytotoxic on L1210 cells (ED50, <6 g mL(-1)) and derivatives 1 and 12 (T/C, 200 and 205%) appeared more active in vivo than chlorambucil (T/C, 168%). (C) 2001 Editions scientifiques et medicales Elsevier SAS.
• KROHN K.; HEMME C., LIEBIGS ANN. CHEM., 1979, NO 1, 19-34
  作者：KROHN K.、 HEMME C.

  DOI：——

  日期：——
• Facile Installation of a Hydroxyalkyl Group into Hydroxyanthraquinones and Aminoanthraquinones through the Modified Marschalk Reaction
  作者：Li-Ming Zhao、Feng-Yan Ma、Hai-Shan Jin、Jiao Ma、Huan Wang、Chuan-Zhao Fu

  DOI：10.1002/ejoc.201300891

  日期：2013.11

  skeleton through a simple yet efficient transformation, which could be potentially useful for the drug discovery process. We describe herein a simple and efficient method to derivatize 1,4-dihydroxyanthraquinone by using a modified Marschalk reaction. This method provides a clear advantage over traditional approaches, which often require the protection and deprotection of the OH groups. We also demonstrate

  1,4-二羟基蒽醌广泛存在于众多天然产品和药物中。能够通过简单而有效的转化使 1,4-二羟基蒽醌骨架功能化非常重要，这可能对药物发现过程有用。我们在此描述了一种通过使用改进的 Marschalk 反应衍生 1,4-二羟基蒽醌的简单有效的方法。与通常需要保护和脱除 OH 基团的传统方法相比，该方法具有明显的优势。我们还证明了该反应对其他羟基蒽醌和氨基蒽醌的适用性。