3-bromo-1-hydroxyanthraquinone | 1116690-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-bromo-1-hydroxyanthraquinone
• 英文别名: 3-Bromo-1-hydroxyanthracene-9,10-dione
• CAS: 1116690-18-6
• 化学式: C₁₄H₇BrO₃
• 分子量: 303.112
• InChiKey: VJAQBWPFXHURDS-UHFFFAOYSA-N

物化性质

• 熔点：
  188-189 °C
• 沸点：
  473.6±45.0 °C(Predicted)
• 密度：
  1.745±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[3,4-bis(benzyloxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 、 3-bromo-1-hydroxyanthraquinone 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成
  参考文献：
  名称：

  [EN] NOVEL QUINIZARINE DERIVATIVE AND PREPARATION METHOD THEREFOR
  [FR] NOUVEAU DÉRIVÉ DE QUINIZARINE ET SON PROCÉDÉ DE PRÉPARATION
  [KO] 신규 퀴니자린 유도체 및 이의 제조 방법

  摘要：

  본원은 신규 퀴니자린 유도체에 관한 것으로서, 상기 퀴니자린 유도체는 BET(Bromodomain Extra-Terminal) 단백질 억제능을 가지며, 이로 인해 BET단백질 관련 질환인 암, 자가면역 또는 염증성 질환, 대사 질환, 및 바이러스성 질환 등의 예방 또는 치료용 약학적 조성물로서 이용될 수 있다. 특히, 본원에 따른 신규 퀴니자린 유도체는 지방생성억제능 및 지방합성인자 발현억제능을 가지므로 비알콜성 지방간의 치료용 약학적 조성물로서 이용될 수 있다.

  公开号：

  WO2023096111A1
• 作为产物：
  描述：

  苯酐 、 间溴苯酚 在 aluminum (III) chloride 、 sodium chloride 作用下， 生成 3-bromo-1-hydroxyanthraquinone
  参考文献：
  名称：

  3-Bromo-1-Hydroxy-9,10-Anthraquinone (BHAQ) Inhibits Growth and Migration of the Human Breast Cancer Cell Lines MCF-7 and MDA-MB231

  摘要：

  如今，乳腺癌在女性中变得越来越常见。截至目前，尚无治疗转移性乳腺癌的有效疗法。我们测试了 BHAQ（一种合成的蒽醌）对两种乳腺癌细胞系 MCF-7 和 MDA-MB231 的细胞毒性和抗迁移作用。蒽醌是一类有趣的分子，具有广泛的生物学应用，包括抗癌特性。通过MTT测定、吖啶橙/碘化丙啶双染色和FACS细胞周期分析来测试细胞抑制。通过伤口愈合方法和通过博伊登室的迁移来测试迁移的抑制。 BHAQ 对两种细胞系均具有剂量依赖性和可能细胞依赖性的细胞毒性。此外，BHAQ 还抑制高度转移的 MDA-MB231 细胞系的迁移。

  DOI：

  10.3390/molecules180910367

文献信息

• Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel - Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
  作者：Koushik Saha、Nordin H. Lajis、Faridah Abas、Nabil Ali Naji、A. Sazali Hamzah、Khozirah Shaari

  DOI：10.1071/ch08084

  日期：——

  Halogen rearrangement was observed during the Lewis acid-catalyzed Friedel–Crafts reaction of phthalic anhydride with bromophenols or bromoanisole. Further investigation revealed that 2-, 3-, and 4-bromophenols undergo rearrangement into other isomers under these reaction conditions. Product distribution from these reactions suggested that halogen rearrangement takes place during the s-complex intermediate

  在路易斯酸催化的邻苯二甲酸酐与溴酚或溴苯甲醚的傅克反应过程中观察到卤素重排。进一步研究表明，在这些反应条件下，2-、3-和 4-溴酚会重排成其他异构体。这些反应的产物分布表明卤素重排发生在缩合步骤的 s-配合物中间体期间。此外，碘苯酚会迅速加氢脱碘而不是重排，而氯苯酚根本不会重排。
• Verfahren zur Herstellung eines Gemisches von 1-Amino-2-chlor-4-hydroxyanthrachinon und 1-Amino-2-brom-4-hydroxyanthrachinon
  申请人：CIBA-GEIGY AG

  公开号：EP0250362A1

  公开（公告）日：1987-12-23

  Verfahren zur Herstellung eines Gemisches von 1-Amino-2-chlor-4-­hydroxyanthrachinon und 1-Amino-2-brom-4-hydroxyanthrachinon mit einem hohen Anteil an 1-Amino-2-chlor-4-hydroxyanthrachinon durch Chlorieren und Bromieren von 1-Aminoanthrachinon und anschliessende Umsetzung mit konzentrierter oder rauchender Schwefelsäure.

  通过对 1-氨基蒽醌进行氯化和溴化，然后与浓硫酸或发烟硫酸反应，制备 1-氨基-2-氯-4-羟基蒽醌和 1-氨基-2-溴-4-羟基蒽醌的混合物，其中 1-氨基-2-氯-4-羟基蒽醌的比例较高。
• Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines
  作者：Koushik Saha、Kok Wai Lam、Faridah Abas、A. Sazali Hamzah、Johnson Stanslas、Lim Siang Hui、Nordin H. Lajis

  DOI：10.1007/s00044-012-0197-5

  日期：2013.5

  Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell lines with IC50 range of 2-8 mu M. Structure-activity relationship (SAR) assessment was considered to rationalise the cytotoxic effect. Bromomethyl group at position C-2 of the anthraquinone was found to be important in exerting cytotoxic activity of this class of compounds. The presence of the flanking methoxyl or hydroxyl groups at C-1 and C-3 also contributes to this activity. Finally, the antioxidant effect of these compounds was evaluated. MTT assay was used to measure the cytotoxicity against different cancer cell lines. Antioxidant activity was measured by FTC and TBA methods. Only two anthraquinones, damnacanthal and nordamnacanthal, were found to be antioxidative.
• A NOVEL REAGENT, CATAL'S REAGENT, AND KIT FOR USING IRON SULPHATE DETERMINATION BY COLORIMETRIC METHOD
  申请人：T.C. Üsküdar Üniversitesi

  公开号：EP4062171A1

  公开（公告）日：2022-09-28
• [EN] A NOVEL REAGENT, CATAL'S REAGENT, AND KIT FOR USING IRON SULPHATE DETERMINATION BY COLORIMETRIC METHOD<br/>[FR] NOUVEAU RÉACTIF, RÉACTIF DE CATALYSE ET KIT POUR L'UTILISATION DE LA DÉTERMINATION DE SULFATE DE FER PAR UN PROCÉDÉ COLORIMÉTRIQUE
  申请人：T C UESKUEDAR UENIVERSITESI

  公开号：WO2021101470A1

  公开（公告）日：2021-05-27

  The invention relates to a novel reagent and kit for use in the determination of iron (II) sulphate in water systems, wastewater, biological materials, food products, soil samples and synthetic mixtures in the chemical, biochemistry, farming, agriculture and biotechnology industries.