(2-hydroxyphenyl)acetic acid disodium salt | 117571-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-hydroxyphenyl)acetic acid disodium salt
• 英文别名: 2-hydroxyphenylacetic acid disodium salt；disodium 2-oxidophenylacetate
• CAS: 117571-22-9
• 化学式: C₈H₆O₃*2Na
• 分子量: 196.113
• InChiKey: NTAHVQPVJZSMSA-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -3.94
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2-hydroxyphenyl)acetic acid disodium salt 在 硫酸 、 三(3,6-二氧杂庚基)胺 、 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 生成 (8-Methoxy-9-oxo-9H-xanthen-4-yl)-acetic acid
  参考文献：
  名称：

  Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo

  摘要：

  In a search for compounds related to flavoneacetic acid with activity against solid tumors, a series of methyl-, methoxy-, chloro-, nitro-, and hydroxy-substituted xanthenone-4-acetic acids have been synthesized and evaluated against subcutaneously implanted colon adenocarcinoma 38 in vivo, using a short-term histology assay as a primary screening system. A major goal of this work was to identify compounds with similar profiles of activity to that of flavoneacetic acid but of higher potency. The level of activity of the compounds appeared to depend more on the nature of the substituent than its positioning, in the order Cl greater than Me, OMe greater than NO2, OH. However, the potency of the compounds was related much more to the position rather than the nature of the substitution, with 5-substituted compounds being clearly the most dose potent. 5-Methylxanthenone-4-acetic acid has a similar level of activity to that of flavoneacetic acid in the test systems employed but is more than 7-fold as dose potent.

  DOI：

  10.1021/jm00124a012
• 作为产物：
  描述：

  苯并呋喃-2(3H)-酮 在 sodium hydroxide 作用下， 生成 (2-hydroxyphenyl)acetic acid disodium salt
  参考文献：
  名称：

  氧和硫对苯内酯系统中酮-烯醇化学的影响比较：苯并[b]-2,3-二氢呋喃-2-one和-2-硫酮和苯并[b]-2,3-二氢噻吩-2-one和-2-硫酮

  摘要：

  碳酸电离常数 Q(K)(a)（离子强度 = 0.10 M 时的浓度商）是通过分光光度法滴定水溶液中苯并[b]-2,3-二氢呋喃-2-one (3, pQ(K)(a) = 11.87), benzo[b]-2,3-dihydrothiophene-2-one (2, pQ(K)(a) = 8.85), and benzo[b]-2,3-dihydrofuran -2-硫酮 (1, pQ(K)(a) = 2.81)。还测量了后两种底物在高氯酸、氢氧化钠和缓冲溶液中接近酮 - 烯醇平衡的速率，根据这些数据构建的速率曲线给出了烯醇作为氧或硫酸电离的电离常数 pQ( E)(a) = 5.23 for 2 and pQ(E)(a) = 2.69 for 1. 根据关系 Q(K)(a)/Q(E) 将这些酸度常数与碳酸电离常数组合(a) = K(E) 然后给出酮-烯醇平衡常数 pK(E) = 3。62 for

  DOI：

  10.1021/ja020367z

文献信息

• Compounds having antitumor and antibacterial properties
  申请人：Cancer Research Campaign Technology Limited

  公开号：US05281620A1

  公开（公告）日：1994-01-25

  The novel class of xanthenone-4-acetic acids represented by the general formula (I) ##STR1## where R.sub.1 represents up to two of the groups lower alkyl, halogen, CF.sub.3, CN, NO.sub.2, NH.sub.2, CH.sub.2 COOH, OR.sub.2, OH, NHCOR.sub.2, NHSO.sub.2 R.sub.2, SR.sub.2, SO.sub.2 R.sub.2, CH.sub.2 CONHR.sub.2 or NHR.sub.2 (where R.sub.2 is lower alkyl optionally substituted with hydroxy, amino or methoxy functions), at any of the positions 1-8 which are available, R.sub.1 may also represent the substitution of an aza (--N.dbd.) group for one or two of the methine (--CH.dbd.) groups in the carbocyclic rings and two of R.sub.1 on any two available adjacent positions may also represent the grouping --CH.dbd.CH--CH.dbd.CH-- to form an additional fused benzene ring; and basic addition salts thereof, possess antitumour and antibacterial properties.

  新型黄色酮-4-乙酸类化合物的一般式(I)如下：其中R.sub.1代表最多两个以下的基团：低碳烷基、卤素、三氟甲基、氰基、硝基、氨基、甲基羧基、OR.sub.2、羟基、NHCOR.sub.2、NHSO.sub.2 R.sub.2、SR.sub.2、SO.sub.2 R.sub.2、CH.sub.2 CONHR.sub.2或NHR.sub.2（其中R.sub.2是低碳烷基，可选择地被羟基、氨基或甲氧基取代），在可用的1-8位置中的任何位置，R.sub.1也可以代表在碳环中的一个或两个亚甲基（--CH.dbd.）基团被一个氮杂基(--N.dbd.)取代，而且在任意两个相邻位置上的两个R.sub.1也可以代表--CH.dbd.CH--CH.dbd.CH--的基团，形成一个额外的融合苯环；以及其碱性加盐，具有抗肿瘤和抗菌特性。
• Design, synthesis and biological evaluation of acridone analogues as novel STING receptor agonists
  作者：Shi Hou、Xiu-juan Lan、Wei Li、Xin-lin Yan、Jia-jia Chang、Xiao-hong Yang、Wei Sun、Jun-hai Xiao、Song Li

  DOI：10.1016/j.bioorg.2019.103556

  日期：2020.1

  STING (Stimulator of Interferon Genes) has become a focal point in immunology research and a target in drug discovery. The discovery of a potent human-STING agonist is expected to revolutionize current anti-virus or cancer immunotherapy. Inspired by the structure and function of murine STING-specific agonists (DMXAA and CMA), we rationally designed and synthesized four series of novel compounds for

  STING（干扰素基因的刺激物）已成为免疫学研究的重点和药物发现的目标。有望发现有效的人类STING激动剂，将彻底改变当前的抗病毒或癌症免疫疗法。受鼠STING特异性激动剂（DMXAA和CMA）的结构和功能的启发，我们合理设计和合成了四组新化合物以增强人类敏感性。在基于细胞的分析中，我们从所有合成的小分子中鉴定出六种化合物：2g，9g和12b是STING激动剂，在整个物种中均有效，并且都具有a啶酮的骨架。1b，1c和12c仅在鼠STING途径中起作用。值得注意的是，12b在六种激动剂中表现出最好的活性，其对人和鼠STING依赖性信号转导的诱导作用均与众所周知的STING诱导剂2'3'-cGAMP相似。蛋白质分析表明2 g，9 g和12b可通过直接结合人STING激活该途径，而12b也显示出最强的结合亲和力。此外，我们的研究表明，与2'3'-cGAMP相比，在天然系统中12b可以诱导更快，更
• Potential antitumor agents. 61. Structure-activity relationships for in vivo colon 38 activity among disubstituted 9-oxo-9H-xanthene-4-acetic acids
  作者：Gordon W. Rewcastle、Graham J. Atwell、Li Zhuang、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00105a034

  日期：1991.1

  Analogues of 9-oxo-9H-xanthene-4-acetic acid (XAA) bearing small, lipophilic 5-substituents are among the most dose-potent compounds yet reported with the capability of causing hemorrhagic necrosis of implanted colon 38 tumors in mice. To further extend structure-activity relationships among this class of compound, a series of XAA derivatives bearing two small lipophilic groups at various positions

  带有小的，亲脂性的5个取代基的9-氧代9H-氧杂蒽-4-乙酸（XAA）的类似物是迄今已报道的最强剂量化合物，具有引起小鼠植入的结肠38肿瘤出血性坏死的能力。为了进一步扩展这类化合物之间的构效关系，已经制备并评估了一系列在不同位置带有两个小的亲脂基团的XAA衍生物。特别是5，6-二取代的化合物始终显示出高水平的剂量效力和活性，这表明这是取代的9-氧代-9H-氧杂蒽-4-乙酸中的最佳构型。5,6-二甲基和5-甲基-6-甲氧基是最有效的类似物，
• [EN] CRYSTALLINE FORMS OF DMXAA SODIUM SALT<br/>[FR] FORMES CRISTALLINES D'UN SEL DE SODIUM DMXAA
  申请人：ANTISOMA RES LTD

  公开号：WO2009053681A1

  公开（公告）日：2009-04-30

  The present invention relates to pharmaceutically stable crystalline forms of (5, 6-Dimethyl-9- oxo-9H-xanthene-4-yl) acetic acid (DMXAA) sodium salt,- processes for preparing those stable crystalline forms; pharmaceutical compositions comprising at least one of those crystalline forms in solid form or in dissolved form and a pharmaceutically acceptable carrier. Disclosed are methods of using those pharmaceutical compositions to treat tumours, optionally in combination with other active pharmaceutical agents.

  本发明涉及药用稳定的晶体形式的（5,6-二甲基-9-氧基-9H-黄芪-4-基）乙酸（DMXAA）钠盐，制备这些稳定晶体形式的方法；包含至少一种这些晶体形式的固体形式或溶解形式以及药用可接受载体的药物组合物。公开了使用这些药物组合物治疗肿瘤的方法，可选择性地与其他活性药物剂联合使用。
• Synthesis and Biological Activity of Azido Analogues of 5,6-Dimethylxanthenone-4-acetic Acid for Use in Photoaffinity Labeling
  作者：Brian D. Palmer、Kimiora Henare、See-Tarn Woon、Rachel Sutherland、Charu Reddy、Liang-Chuan S. Wang、Claudine Kieda、Lai-Ming Ching

  DOI：10.1021/jm0702175

  日期：2007.8.1

  (1) is scheduled for phase III clinical trials as a vascular disrupting agent. However, its biochemical receptor(s) have yet to be identified. In this report, the synthesis of azido analogues of 1 that could be used for photoaffinity labeling of proteins as an approach toward identifying its molecular targets is described. While 5-azidoxanthenone-4-acetic acid (2) and 5-azido-6-methylxantheone-4-acetic

  5,6-二甲基黄嘌呤酮-4-乙酸（1）计划作为血管分裂剂进入III期临床试验。但是，尚未确定其生化受体。在此报告中，描述了1叠氮基类似物的合成，该合成可用于蛋白质的光亲和标记，作为鉴定其分子靶标的方法。虽然发现5-叠氮杂蒽酮-4-乙酸（2）和5-叠氮杂6-甲基methyl吨酮-4-乙酸（3）的生物活性与1，6-叠氮杂-5-甲基x吨酮-4-的生物活性相似。乙酸（4）不稳定，无法评估。叠氮基化合物2和3均激活了NF-κB，在培养的小鼠脾细胞中诱导了肿瘤坏死因子的产生，并在小鼠中诱导了结肠38肿瘤的出血性坏死。