4-chloro-2-(2-methylphenoxy)benzoic acid | 69200-01-7

• 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: 4-chloro-2-(2-methylphenoxy)benzoic acid
• 英文别名: 4-Chloro-2-(2-methylphenoxy) benzoic acid
• CAS: 69200-01-7
• 化学式: C₁₄H₁₁ClO₃
• mdl: MFCD18062975
• 分子量: 262.693
• InChiKey: WBXNEKUDIIMTDN-UHFFFAOYSA-N

物化性质

• 熔点：
  158-159 °C(Solv: methanol (67-56-1))
• 沸点：
  376.7±37.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-2-(2-methylphenoxy)benzoic acid 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 4-bromomethyl-6-chloro-9-xanthenone
  参考文献：
  名称：

  一些带有哌嗪部分的新蒽酮衍生物的合成及药理性能评价

  摘要：

  一系列具有哌嗪部分[新呫吨酮衍生物的1 - 7 ]合成并评价它们的药理性质。他们受到结合测定为α 1和β 1肾上腺素能以及5-HT 1A，5-HT 6和5-HT 7B羟色胺受体。还评估了五种测试化合物的抗惊厥特性。化合物3a 3-甲氧基-5-{[4-（2-甲氧基苯基）哌嗪-1-基]甲基} -9 H-黄嘌呤-9-盐酸盐对5-羟色胺能5-HT 1A受体具有更高的亲和力（K i = 24 nM）。在抗惊厥活性而言，6-甲氧基-2 - {[4-（苄基）哌嗪-1-基]甲基} -9- ħ -呫吨-9-酮（5）被证明最好的性能。在最大电击（MES）癫痫发作测定中确定的ED 50为105 mg / kg bw（大鼠，口服）。an吨与哌嗪部分的组合导致口服给药后获得具有提高的生物利用度的化合物。

  DOI：

  10.1016/j.bmcl.2013.05.062
• 作为产物：
  描述：

  2,4-二氯苯甲酸 、 邻甲酚 在 Cu₂O#Cu 、 sodium ethanolate 作用下， 生成 4-chloro-2-(2-methylphenoxy)benzoic acid
  参考文献：
  名称：

  an吨酮的一些氨基异丙醇氧基衍生物的设计，合成和心血管评价。

  摘要：

  已经合成了一系列的蒽酮的氨基异丙醇氧基衍生物，并评估了它们与心血管系统有关的药理特性。在离体器官中进行放射性配体结合和功能研究表明，标题化合物对α1-（化合物2和8），β-（化合物1、3、4、7），α1/β-（化合物5和6）具有很高的亲和力和拮抗力）肾上腺素受体。此外，维拉帕米的结构类似物化合物7具有阻止钙进入的活性。标题化合物由于其肾上腺素受体阻断作用而显示出降压和抗心律不齐的特性。此外，它们没有影响QRS和QT间隔，并且在测试剂量下没有心律失常的可能。另外，它们发挥了抗聚集作用。

  DOI：

  10.1016/j.bmc.2018.04.038

文献信息

• Anti-Helicobacter pylori activity of some newly synthesized derivatives of xanthone
  作者：Karolina Klesiewicz、Elżbieta Karczewska、Alicja Budak、Henryk Marona、Natalia Szkaradek

  DOI：10.1038/ja.2016.36

  日期：2016.11

  and the compound 10 (against the clarithromycin-resistant strain). These preliminary results for screening of xanthone derivatives form a part of an ongoing study of the structure-activity relationships of a large group of compounds. Microbiological assays will be conducted afterwards to determine the mechanism of xanthones' action against H. pylori.The Journal of Antibiotics advance online publication

  合成了一系列20种黄嘌呤衍生物，并评估了其抗幽门螺杆菌（H. pylori）的活性。使用Kirby-Bauer方法（琼脂圆盘扩散法）进行了定性和定量体外测试。筛选针对幽门螺杆菌的克拉霉素和/或甲硝唑抗性菌株的测试化合物。作为参考，检查了革兰氏阳性菌（金黄色葡萄球菌）和革兰氏阴性菌（大肠杆菌）。根据微生物学测定，氧杂蒽酮可被认为是潜在的抗H抗体。幽门螺杆菌制剂。它们对所检验的菌株显示出显着的活性，对甲硝唑的抗细菌性比克拉霉素高。对于以下化合物，观察到的最低MIC值高达20 mg l-1：3、4、8、9、12 19（针对甲硝唑抗性菌株）和化合物10（针对克拉霉素抗性菌株）。这些用于筛选an吨酮衍生物的初步结果，是对大量化合物的构效关系进行研究的一部分。随后将进行微生物学测定，以确定氧杂蒽酮对幽门螺杆菌的作用机理。《抗生素杂志》在线提前出版，2016年3月30日；doi：10.1038 / ja
• Synthesis ofN-(9H-Xanthen-9-yl)aminoalkanamide andN-(9H-Thioxanthen-9-yl)aminoalkanamide Derivatives and theirin vitro Evaluation as Potential Intercalators and Antitumor Drugs
  作者：Evangelos Filippatos、Aspasia Papadaki-Valiraki、Ourania Todoulou、Alain Jacquemin-Sablon

  DOI：10.1002/ardp.19943270202

  日期：——

  A series of new N‐(9H‐xanthen‐9‐yl)aminoalkanamide and N‐(9H‐thio‐xanthen‐9‐yl)aminoalkanamide derivatives was synthesized and evaluated as potential intercalators by measuring their DNA binding affinity. They were also tested for cytotoxic activity against L1210. The results suggest that the cytotoxicity of these molecules was not due to an intercalating mechanism.

  合成了一系列新的 N-(9H-xanthen-9-yl) 氨基链烷酰胺和 N-(9H-thio-xanthen-9-yl) 氨基链烷酰胺衍生物，并通过测量它们的 DNA 结合亲和力来评估它们作为潜在的嵌入剂。还测试了它们对 L1210 的细胞毒活性。结果表明这些分子的细胞毒性不是由于嵌入机制。
• 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.

  通式（I）所代表的新型黄色素-4-乙酸类化合物，其中R.sub.1代表以下任意一个或两个基团：低碳链烷基，卤素，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或NHR.sub.2（其中R.sub.2为低碳链烷基，可选地带有羟基，氨基或甲氧基功能），在可用的1-8位置中的任意位置。R.sub.1还可以代表将一个或两个亚胺（-N.dbd.）基团取代为碳环中的一个或两个甲烷（-CH.dbd.）基团，而在任意两个可用的相邻位置上的两个R.sub.1也可以代表群-CH.dbd.CH-CH.dbd.CH-以形成额外的融合苯环;以及其基本加成盐，具有抗肿瘤和抗菌性能。
• Anticonvulsant evaluation of aminoalkanol derivatives of 2- and 4-methylxanthone
  作者：Natalia Szkaradek、Agnieszka Gunia、Anna M. Waszkielewicz、Lucyna Antkiewicz-Michaluk、Marek Cegła、Edward Szneler、Henryk Marona

  DOI：10.1016/j.bmc.2012.12.051

  日期：2013.3

  A series of 17 new aminoalkanol derivatives of 6-methoxy- or 7-chloro-2-methylxanthone as well as 6-methoxy-4-methylxanthone was synthesized and evaluated for anticonvulsant activity. All compounds were verified in mice after intraperitoneal (ip) administration in maximal electroshock (MES) and subcutaneous pentetrazole (scMet) induced seizures as well as neurotoxicity assessment. Eleven of the tested substances showed protection against electrically evoked seizures in the majority of the tested mice at the dose of 100 mg/kg. Additionally, one was effective at the dose of 30 mg/kg. Five substances were active at the dose of 300 mg/kg or at the dose of 100 mg/kg in the minority of the tested mice. The most promising compound revealed ED50 value of 47.57 mg/kg in MES (mice, ip, 1 h after administration) and at the same time its TD50 was evaluated as above 400 mg/kg. Those values gave PI (calculated as TD50/ED50) of more than 8.41. Three other synthesized xanthone derivatives also proved to act as anticonvulsants and showed ED50 values in MES test (mice, ip) ranged 80-110 mg/kg. Results were quite encouraging and suggested that in the group of xanthone derivatives new potential anticonvulsants might be found. (C) 2013 Elsevier Ltd. All rights reserved.
• Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo
  作者：Gordon W. Rewcastle、Graham J. Atwell、Bruce C. Baguley、Stephen B. Calveley、William A. Denny

  DOI：10.1021/jm00124a012

  日期：1989.4

  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.