1,5-二氯-10H-蒽-9-酮 | 50259-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1,5-二氯-10H-蒽-9-酮
• 英文名称: 1,5-dichloroanthrone
• 英文别名: 1,5-dichloro-9(10H)-anthracenone；1,5 dichloro-9(10H)-anthracenone；1,5-dichloro-10H-anthracen-9-one
• CAS: 50259-92-2
• 化学式: C₁₄H₈Cl₂O
• 分子量: 263.123
• InChiKey: HNDVRSZCIGFZGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,5-二氯-10H-蒽-9-酮 在 sodium tetrahydroborate 作用下， 生成 1,5-二氯蒽
  参考文献：
  名称：

  Conversion of 9,10-anthraquinones to anthracenes

  摘要：

  DOI：

  10.1021/jo00920a007
• 作为产物：
  描述：

  1,5-Dichlor-9,10-dihydro-anthracen-9,10-diol, trans 在 盐酸 作用下， 生成 1,5-二氯-10H-蒽-9-酮
  参考文献：
  名称：

  Conversion of 9,10-anthraquinones to anthracenes

  摘要：

  DOI：

  10.1021/jo00920a007

文献信息

• Synthesis and Cytotoxicity of 9-Alkoxy-1, 5-dichloroanthracene Derivatives in Murine and Human Cultured Tumor Cells
  作者：Hsu-Shan Huang、Jeng-Fong Chiou、Hui-Fen Chiu、Rong-Fu Chen、Yu-Liang Lai

  DOI：10.1002/1521-4184(200201)335:1<33::aid-ardp33>3.0.co;2-g

  日期：2002.1

  this structural class of anthracenes. Contrary to mitoxantrone, cytotoxic properties were observed as documented by the reactivity of the novel compounds and potent in vitro activity against C6 cells and hep G2 cells over a wide range of structural variants. Among these compounds, 5c, 5h, 5land 5n are potent cytotoxins. They inhibit C6 cell growth in culture, indicated by using 2, 3‐bis(2‐methoxy‐4‐n

  9-Alkoxy-1, 5-二氯蒽制备成功。它们的细胞毒性分别在大鼠神经胶质瘤 C6 细胞系和人肝癌 G2 细胞系上进行了体外评估。在硫酸或氢化钠存在下，1, 5-二氯-9(10H)-蒽酮分别与适当的醇或烷基氯化物烷基化，提供了这种结构类型的蒽。与米托蒽醌相反，通过新化合物的反应性和针对 C6 细胞和 hep G2 细胞的有效体外活性在广泛的结构变体上观察到了细胞毒性特性。在这些化合物中，5c、5h、5和 5n 是有效的细胞毒素。通过使用 2, 3-双(2-甲氧基-4-硝基-5-磺苯基)-2H-四唑鎓-5-甲酰苯胺钠盐 (XTT) 比色测定，它们抑制培养中的 C6 细胞生长。通过使用该测定，还表明 5c、5d 和 5l 对 hep G2 细胞具有有效的细胞毒性。与米托蒽醌的 IC50 值为 0.07 μM 相比，表现出体外细胞毒性的最活性化合物是 9-丁氧基衍生物，其对 C6 细胞的 IC50
• Studies on Anthracenes. 1. Human Telomerase Inhibition and Lipid Peroxidation of 9-Acyloxy 1,5-Dichloroanthracene Derivatives.
  作者：Hsu-Shan HUANG、Jing-Min HWANG、Yee-Min JEN、Jing-Jer LIN、Kung-Yuan LEE、Chang-Hsin SHI、Hsien-Chin HSU

  DOI：10.1248/cpb.49.969

  日期：——

  The synthetically useful approaches to 9-acyloxy 1, 5-dichloroanthracene derivatives are reported. The system selectively reduces the carbonyl group flanked by the peri substituents of the anthracenediones to give the corresponding 1, 5-dichloro-9(10H)-anthracenone. Simple regioselective acylation of anthracenone is applied with appropriate acyl chlorides in CH2Cl2 with catalytic amount of pyridine to give the novel 9-acyloxy 1, 5-dichloroanthracene derivatives. Considerable interest has developed in the mechanism of how anthracenone achieves this desirable selectivity. In an attempt to understand the mechanism of this reaction, solid-state structures of anthracene derivatives have been obtained. In addition, the inhibition of lipid peroxidation in model membranes was determined as was their ability to inhibit the telomere-addition function of the human telomerase enzyme together with their inhibition of the Taq polymerase enzyme. In contrast to (+)-α-tocopherol, 3b, 3c, 3d, 3g, and 3i do not enhance lipid peroxidation in model membranes. Implications for 9-acyloxy 1, 5-dichloroanthracene analogues as potential anticancer agents are discussed.

  据报道，存在合成9-酰氧基-1,5-二氯蒽衍生物的有效途径。该体系能够选择性地还原蒽醌中毗连周边取代基的羰基，得到相应的1,5-二氯-9(10H)-蒽酮。通过在CH2Cl2中使用适量酰氯和催化量的吡啶，对蒽酮进行简单的区域选择性酰化反应，得到了新型的9-酰氧基-1,5-二氯蒽衍生物。关于蒽酮如何实现这种理想选择性的机理，引起了相当大的兴趣。为了理解这一反应机理，我们获得了蒽衍生物的固态结构。此外，还测定了它们抑制模型膜中脂质过氧化的能力，以及它们抑制人端粒酶的端粒添加功能和Taq聚合酶酶活性的能力。与(+)-α-生育酚不同，3b、3c、3d、3g和3i在模型膜中并不增强脂质过氧化。本文还讨论了9-酰氧基-1,5-二氯蒽类似物作为潜在抗癌药物的意义。
• Chiral Bicyclic Guanidine-Catalyzed Enantioselective Reactions of Anthrones
  作者：Juan Shen、Thanh Truc Nguyen、Yong-Peng Goh、Weiping Ye、Xiao Fu、Junye Xu、Choon-Hong Tan

  DOI：10.1021/ja064636n

  日期：2006.10.1

  catalyst for reactions between anthrones and various dienophiles. The catalyst can tolerate a range of substituents and substitution patterns, making several anthrone derivatives suitable for this reaction. Both Diels-Alder and Michael adducts were obtained in excellent yields, high regioselectivities, and high enantioselectivities. This is the first case of a highly enantioselective base-catalyzed anthrone

  手性双环胍 1 被发现是蒽酮和各种亲二烯体之间反应的极好催化剂。该催化剂可以耐受一系列取代基和取代模式，使几种蒽酮衍生物适用于该反应。Diels-Alder 和 Michael 加合物均以优异的产率、高区域选择性和高对映选择性获得。这是高度对映选择性碱催化蒽酮 Diels-Alder 反应的第一个案例。
• Synthesis, antiproliferative activity and inhibition of tubulin polymerization by anthracenone-based oxime derivatives
  作者：Georg Surkau、Konrad J. Böhm、Klaus Müller、Helge Prinz

  DOI：10.1016/j.ejmech.2010.04.019

  日期：2010.8

  order to evaluate their antiproliferative activity. Several investigated compounds displayed strong antiproliferative activity against K562 leukemia cells and proved to be strong inhibitors of tubulin polymerization. In this context, anthracenone-based oxime ethers and -esters are considered to contribute to the development of novel antiproliferative drugs, based on tubulin interaction.

  为了评估它们的抗增殖活性，合成了一系列基于蒽醌的肟醚和酯。几种研究过的化合物显示出对K562白血病细胞的强抗增殖活性，并被证明是微管蛋白聚合的强抑制剂。在这种情况下，基于微管蛋白的相互作用，基于蒽醌的肟醚和-酯被认为有助于新型抗增殖药的开发。
• Copper-catalyzed asymmetric propargylic substitution of anthrones and propargylic esters
  作者：Zhiheng Li、Danran Li、Huaming Xiang、Jian Huang、Yinuo Zheng、Cuiju Zhu、Xiuling Cui、Chao Pi、Hao Xu

  DOI：10.1016/j.cclet.2021.08.009

  日期：2022.2

  motifs in many natural products, bioactive compounds and pharmaceutical chemicals. Earth-abundant-metal-catalyzed asymmetric functionalization of anthrones has not proved to be viable. Herein, we disclosed a highly enantioselective propargylic substitution of anthrones with propargylic esters using copper salts with chiral N, N, P-ligand. This strategy is amenable to a broad range of substrates, uses

  蒽酮是许多天然产物、生物活性化合物和药物化学品中的关键结构基序。地球丰富的金属催化的蒽酮不对称功能化尚未被证明是可行的。在此，我们公开了使用具有手性N、N、P-配体的铜盐，用炔丙基酯对蒽酮进行高度对映选择性的炔丙基取代。该策略适用于广泛的底物，使用现成的起始材料，在温和条件下提供优异的产率和显着的对映选择性，并实现有吸引力的产品多样化路线。