1,3-dihydroxy-7-methyl-9H-xanthen-9-one | 1042437-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1,3-dihydroxy-7-methyl-9H-xanthen-9-one
• 英文别名: 1,3-dihydroxy-7-methyl-9H-xanthone；1,3-dihydroxy-7-methylxanthone；1,3-Dihydroxy-7-methylxanthen-9-one
• CAS: 1042437-76-2
• 化学式: C₁₄H₁₀O₄
• 分子量: 242.231
• InChiKey: VYPRWINZZQUWKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dihydroxy-7-methyl-9H-xanthen-9-one 在 吡啶 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 7.0h， 生成 6-methoxy-3,3,9-trimethylpyrano[2,3-c]xanthen-7(3H)-one
  参考文献：
  名称：

  Anti-AIDS agents 85. Design, synthesis, and evaluation of 1R,2R-dicamphanoyl-3,3-dimethyldihydropyrano-[2,3-c]xanthen-7(1H)-one (DCX) derivatives as novel anti-HIV agents

  摘要：

  In this study, 1R,2R-dicamphanoyl-3,3-dimethydihydropyrano[2,3-c]xanthen-7(1H)-one (DCX) derivatives were designed and synthesized as novel anti-HIV agents against both wild-type and non-nucleoside reverse transcriptase (RT) inhibitor-resistant HIV-1 (RTMDR-1) strains. Twenty-four DCX analogs (6-29) were synthesized and evaluated against the non-drug-resistant HIV-1 NL4-3 strain, and selected analogs were also screened for their ability to inhibit the RTMDR-1 strain. Compared with the control 2-ethyl-3',4'-di-O-(-)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (2-EDCP, 2), one of the best anti-HIV coumarin derivatives in our prior study, three DCX compounds (7, 12, and 22) showed better activity against both HIV strains with an EC50 range of 0.062-0.081 mu M, and five additional compounds (8, 11, 16, 18, and 21) exhibited comparable anti-HIV potency. Six DCX analogs (7, 11-12, 18, and 21-22) also showed enhanced selectivity index (SI) values in comparison to the control. Structure-activity relationship (SAR) information suggested that the extended conjugated system of the pyranoxanthone skeleton facilitates the interaction of the small DCX molecule within the viral binding pocket, consequently leading to enhanced anti-HIV activity and selectivity. Compared to DCP compounds, DCX analogs are a more promising new class of anti-HIV agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.025
• 作为产物：
  描述：

  间苯三酚 、 5-甲基水杨酸 在 Eaton′s Reagent 作用下， 反应 2.0h， 生成 1,3-dihydroxy-7-methyl-9H-xanthen-9-one
  参考文献：
  名称：

  The Design and Synthesis of N-Xanthone Benzenesulfonamides as Novel Phosphoglycerate Mutase 1 (PGAM1) Inhibitors

  摘要：

  磷酸甘油酸变位酶1（PGAM1）的上调已被发现是多种癌症中的一个常见现象。抑制PGAM1为癌症治疗提供了一种新的有希望的策略。基于我们之前的工作，我们发现了一系列新的N-呫吨酮苯磺酰胺化合物作为新型PGAM1抑制剂。代表性分子15h，其IC50值为2.1 μM，与PGMI-004A相比，表现出增强的PGAM1抑制活性和更高的酶抑制特异性，同时其抗增殖活性略有提高。

  DOI：

  10.3390/molecules23061396

文献信息

• 1,3-二羟基呫吨酮衍生物及其在医药中的用 途
  申请人：成都格瑞赛斯科技有限公司

  公开号：CN105418597B

  公开（公告）日：2018-10-16

  本发明涉及医药领域，公开了一类新型1,3‑二羟基呫吨酮衍生物及其在医药中的用途。本发明的新型1,3‑二羟基呫吨酮衍生物的通式如图（I）所示。通过测定新型1,3‑二羟基呫吨酮衍生物对恶性肿瘤细胞的抑制活性，证明此类1,3‑二羟基呫吨酮衍生物具有良好的抗肿瘤活性，为制备抗肿瘤药物提供了一种新的选择。
• (2-Arylhydrazonomethyl)-substituted xanthones as antimycotics: synthesis and fungistatic activity against Candida species
  作者：Stéphane Moreau、Martine Varache-Lembège、Stéphane Larrouture、Djibril Fall、Arlette Neveu、Gérard Deffieux、Joseph Vercauteren、Alain Nuhrich

  DOI：10.1016/s0223-5234(01)01332-0

  日期：2002.3

  A series of arylhydrazones derived from various 6,8-diacetoxy- or 6,8-dihydroxy-9-oxo-9H-xanthene carboxaldehydes were synthesized and evaluated for their in vitro antifungal properties against two human pathogenic yeasts (Candida albicans and C. krusei) according to a diffusion method. The activity was strongly dependent from the position of the (1-arylhydrazinyl-2-ylidene)methyl chain in the xanthone molecular skeleton. Compounds having the nitrogen side chain in the 4-position, with a further halogen substitution on the terminal phenyl ring showed fungistatic effects. Within this series, the 4-fluorophenylhydrazinyl derivative 13g exhibited the highest activity, particularly against C. krusei, with a greater efficacy than that of econazole, used as reference. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.
• Synthesis and antiproliferative activity of aryl- and heteroaryl-hydrazones derived from xanthone carbaldehydes
  作者：Martine Varache-Lembège、Stéphane Moreau、Stéphane Larrouture、Danièle Montaudon、Jacques Robert、Alain Nuhrich

  DOI：10.1016/j.ejmech.2007.09.003

  日期：2008.6

  In order to explore the antiproliferative effect associated with the xanthone framework, several arylhydrazonomethyl derivatives were synthesized from various isomeric 1,3-dihydroxyxanthone carbaldehydes. Variation in the position of the aldehydic function led to three sets of compounds, bearing the hydrazonomethyl chain at positions 5, 6 or 7 on the xanthone nucleus, respectively.The antiproliferative effect of the compounds was evaluated in vitro using the MTT colorimetric method against two human cancer cell lines (MCF-7, breast adenocarcinoma, and KB 3.1, squamous, cell oral carcinoma) for two time periods (24 h and 72 h).Among the series, four compounds exhibited interesting growth inhibitory effects against both the cell lines, with IC(50) values in the micromolar concentration range. When compared with doxorubicin, the xanthone derivatives showed moderate cytotoxic effects. Surprisingly, unlike doxorubicin, these compounds displayed no significant time-dependent change in the concentration causing 50% inhibitory effect in proliferation.This unusual cytotoxicity profile led to the hypothesis that these molecules could be endowed with a mechanism of action distinct to that of doxorubicin. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Anti-AIDS agents 83. Efficient microwave-assisted one-pot preparation of angular 2,2-dimethyl-2H-chromone containing compounds
  作者：Ting Zhou、Qian Shi、Kuo Hsing Lee

  DOI：10.1016/j.tetlet.2010.06.058

  日期：2010.8

  A novel and efficient microwave-assisted one-pot reaction was developed to synthesize angular 2,2-dimethyl-2H-chromone-containing compounds, which is the first and key step in the synthesis of potent DCK and DCP anti-HIV agents The newly developed microwave synthesis conditions dramatically shortened the reaction time from 2 clays to 4 h with improved yields (c) 2010 Elsevier Ltd All rights reserved
• Toward potent α-glucosidase inhibitors based on xanthones: A closer look into the structure–activity correlations
  作者：Gai-Li Li、Jia-Yun He、Aiqin Zhang、Yiqian Wan、Bo Wang、Wen-Hua Chen

  DOI：10.1016/j.ejmech.2011.06.003

  日期：2011.9

  A series of novel xanthone derivatives 6-16 having non-coplanar and flexible structures were synthesized as potent alpha-glucosidase inhibitors. Biological evaluation indicated that compounds 6-12 bearing one or two naphthol moieties exhibited up to 30-fold enhanced activities compared with their corresponding parent compounds 2-5, whereas compounds 13-16 bearing one dihydroxylnaphthalenyl group showed decreased activities compared with their corresponding analogs 6-9 having one naphthol group. Among them, compounds 7-8, 10-12 and 15 were more active than 1-deoxynojirimycin, a well-known inhibitor for alpha-glucosidase. The structure-activity correlations suggested that inhibiting of alpha-glucosidase was a result of multiple interactions with the enzyme, including pi-stacking, hydrophobic effect and conformational flexibility due to the structural non-coplanarity. In addition, compounds 4, 8 and 15 showed non-competitive inhibition. (C) 2011 Elsevier Masson SAS. All rights reserved.