5,7-dichloroemodin | 19697-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5,7-dichloroemodin
• 英文别名: 1,3-dichloro-2,4,5-trihydroxy-7-methylanthracene-9,10-dione；1,3,8-Trihydroxy-2,4-dichlor-6-methyl-anthrachinon
• CAS: 19697-87-1
• 化学式: C₁₅H₈Cl₂O₅
• 分子量: 339.132
• InChiKey: ANEHFIKAXIZHIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  556.2±50.0 °C(Predicted)
• 密度：
  1.743±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 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：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  大黄素 在 N-氯代丁二酰亚胺 、 氯化锆(IV) 作用下， 以 1,4-二氧六环 为溶剂， 以77%的产率得到5,7-dichloroemodin
  参考文献：
  名称：

  大黄素及其衍生物对耐甲氧西林的金黄色葡萄球菌的合成及抑菌活性

  摘要：

  使用Friedel-Crafts酰化反应作为关键步骤可提高抗菌素大黄素的合成，从而使总收率达到37％。此外，通过对大黄素的羟基和甲基以及芳香环进行结构修饰，合成了21种类似物。耐甲氧西林金黄色葡萄球菌的抗菌活性（MRSA）和针对非癌性Vero细胞的细胞毒性进行了评估。结构-活性关系（SAR）研究表明，大黄素骨架中的羟基和甲基对于抗MRSA活性至关重要。此外，芳环上碘原子或乙基氨基的存在以更高的选择性指数增强了抗MRSA的活性，而含溴，氯原子或季铵盐的衍生物则与大黄素一样具有活性。芳香环上的季铵基团还导致了对Vero细胞的非细胞毒性。

  DOI：

  10.1016/j.tetlet.2019.151004

文献信息

• Antiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL63
  作者：Monika Horvat、Martina Avbelj、María Beatriz Durán-Alonso、Mihailo Banjanac、Hrvoje Petković、Jernej Iskra

  DOI：10.3390/molecules26226825

  日期：——

  improve its antiviral activity. The most active compound in this study was the iodinated emodin analogue E_3I, whose anti-HCoV-NL63 activity was comparable to that of remdesivir. Evaluation of the emodin analogues also revealed some unwanted toxicity to Vero cells. Since new synthetic routes are now available that allow modification of the emodin structure, it is reasonable to expect that analogues with

  当前的 COVID-19 疫情凸显了开发新疫苗和药物来对抗严重急性呼吸系统综合症冠状病毒 2 (SARS-CoV-2) 的必要性。最近，多种药物被认为可能对 COVID-19 有效，例如瑞德西韦、英夫利昔单抗和伊马替尼。数千年来，天然植物一直被用作药物的替代来源，其中一些对治疗各种病毒性疾病有效。大黄素（1,3,8-三羟基-6-甲基蒽-9,10-二酮）是一种具有生物活性的蒽醌，具有抗病毒活性，存在于多种植物中。我们研究了大黄素核心上亲电芳香族取代反应（卤化、硝化和磺化）的选择性，从而产生了大黄素衍生物库。这项工作的主要目的是对提高大黄素对抗人类冠状病毒 NL63 (HCoV-NL63) 活性的潜力进行初步评估，并制定一套初步的 SAR 指南。我们制备了具有显着抗HCoV-NL63活性的大黄素衍生物。我们观察到大黄素的卤化可以提高其抗病毒活性。本研究中活性最强的化合物是碘化大黄素类似物E_3I
• The anthraquinones of Heterodermia obscurata
  作者：Peter A. Cohen、G.H. Neil Towers

  DOI：10.1016/0031-9422(95)00407-x

  日期：1995.10

  (Physciaceae). The structures were inferred from their spectra (UV, mass, 1 H and 13 C NMR): emodin, 7-chloroemodin, 5,7-dichloroemodin, flavoobscurin A, flavoobscurin B and 7,7′-dichlorohypericin, with the latter being recently discovered as a lichen anthraquinone. 7-Chloroemodin and 5,7-dichloroemodin were synthesized by a new method, and characterized spectroscopically. The synthetic and natural products were

  摘要 从地衣 Heterodermia obscurata (Nyl.) Trevis 中分离得到 3 种蒽醌、2 种双酮和 1 种苯亚萘醌。（植物科）。从它们的光谱（UV、质量、1 H 和 13 C NMR）推断结构：大黄素、7-氯大黄素、5,7-二氯大黄素、flavoobscurin A、flavoobscurin B 和 7,7'-dichlorohypericin，后者是最近的被发现为地衣蒽醌。采用新方法合成了7-氯大黄素和5,7-二氯大黄素，并对其进行了光谱表征。发现合成产品和天然产品在所有方面都相同。
• Chlorination of anthraquinones by lichen and fungal enzymes
  作者：Peter A. Cohen、G.H.Neil Towers

  DOI：10.1016/s0031-9422(96)00384-6

  日期：1997.1

  Chlorination of the anthraquinones, emodin and 7-chloroemodin, was studied with an enzyme preparation from the lichen Nephroma laevigatum, and a commerically available fungal chloroperoxidase (EC 1.11.1.10). The fungal enzyme converted emodin to a mixture of 5-chloro, 7-chloro and 5,7-dichloroemodin, while converting the 7-chloro isomer to 5,7-dichloroemodin in nearly quantitative yield. The lichen enzyme, however, chlorinated emodin only at C-7 and failed to chlorinate 7-chloroemodin further. In non-enzymic controls, emodin gave the same set of products as the fungal enzyme but 7-chloroemodin did not undergo further chlorination. The chemical structures of the products were confirmed from UV, EI-mass and H-1 NMR spectral data. Copyright (C) 1996 Elsevier Science Ltd
• Haloemodins, a new class of endothelin-1 type B (ETB) receptor binding inhibitors.
  作者：YUE-ZHONG SHU、MAREDITH ARCURI、MICHAEL R. KOZLOWSKI、RICHARD R. WANG、KIN SING LAM、LI-PING CHANG、DOLORES M. PIRNIK、PATRICIA M. ROSE

  DOI：10.7164/antibiotics.47.1328

  日期：——
• [EN] EMODIN DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS D'ÉMODINE ET UTILISATIONS ASSOCIÉES
  申请人：[en]UNIVERZA V LJUBLJANI

  公开号：WO2022254047A1

  公开（公告）日：2022-12-08

  The invention generally relates to emodin derivatives of general structure (I), to pharmaceutical compositions comprising same and to their uses in medicine, especially in the treatment of bacterial or viral infections. The invention further relates to textiles, such as fabrics, comprising at least one emodin derivative of general structure (I). R1- R2- R3and R4are independently selected from the group consisting of hydrogen, halogen, NO2, SO3H and COOR; R is H, C1-6-alkyl, C2-6alkenyl or C2-6alkynyl; with the proviso that at least one of R1, R2, R3and R4is not hydrogen.