methyl 4-(5-hydroxymethyl-2-methoxyphenoxy)benzoate | 113275-15-3

• 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: methyl 4-(5-hydroxymethyl-2-methoxyphenoxy)benzoate
• 英文别名: Methyl 4-<5-(hydroxymethyl)-2-methoxyphenoxy>benzoate；Methyl 4-[5-(hydroxymethyl)-2-methoxyphenoxy]benzoate
• CAS: 113275-15-3
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: SGVCORSJTUKEGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-(5-hydroxymethyl-2-methoxyphenoxy)benzoate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢溴酸 、 氢气 、 sodium methylate 、 sodium 、 三溴化磷 、 1,1,2,2-四苯乙烯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 、 苯 为溶剂， 反应 8.0h， 生成 1,2,13,14-tetrahydro-9,17,22-trimethoxy-3,6:5,18-dietheno-8,12-metheno-12H-7-benzooxacycloeicosine
  参考文献：
  名称：

  Gottsegen, Agnes; Nogradi, Mihaly; Vermes, Borbala, Journal of the Chemical Society. Perkin transactions I, 1990, # 2, p. 315 - 320

  摘要：

  DOI：
• 作为产物：
  描述：

  isovanilline dimethyl acetal 在 sodium tetrahydroborate 、 copper(II) oxide 作用下， 以 吡啶 为溶剂， 生成 methyl 4-(5-hydroxymethyl-2-methoxyphenoxy)benzoate
  参考文献：
  名称：

  The constitution of riccardin B

  摘要：

  DOI：

  10.1016/s0040-4039(00)96239-7

文献信息

• Design, synthesis and biological evaluation of novel macrocyclic bisbibenzyl analogues as tubulin polymerization inhibitors
  作者：Bin Sun、Lin Li、Qing-wen Hu、Fei Xie、Hong-bo Zheng、Huan-min Niu、Hui-qing Yuan、Hong-xiang Lou

  DOI：10.1016/j.ejmech.2016.06.007

  日期：2016.10

  analysis and a tubulin polymerization assay in HCC1482 cells. The binding mode of compound 88 to tubulin was also investigated utilizing a molecular docking study. In conclusion, the present study improves our understanding of the action of bisbibenzyl-based tubulin polymerization inhibitors and provides a new molecular scaffold for the further development of antitumor agents that target tubulin.

  设计，合成了一系列新颖的大环双联二苄基类似物，并对其体外抗增殖活性进行了评估。所有化合物均在包括多药耐药表型在内的五种人类癌细胞系中进行了测试。在这些新的分子，化合物88，92和94表现出优异的抗癌活性针对Hela细胞，K562，HCC1428，HT29，和PC-3 /文件的细胞系，具有平均IC 50值范围为2.23μM到3.86μM，和更有效的比亲本化合物马可汀C的效力要强于阳性对照阿霉素。此外，化合物88的作用机理通过在HCC1482细胞中的细胞周期分析和微管蛋白聚合测定法研究了TGF-β。还利用分子对接研究来研究化合物88与微管蛋白的结合模式。总之，本研究提高了我们对基于双联苄基微管蛋白聚合抑制剂作用的理解，并为靶向微管蛋白的抗肿瘤药物的进一步开发提供了新的分子支架。
• Bisbibenzyl derivatives sensitize vincristine-resistant KB/VCR cells to chemotherapeutic agents by retarding P-gp activity
  作者：Guang-min Xi、Bin Sun、Hui-hui Jiang、Feng Kong、Hui-qing Yuan、Hong-xiang Lou

  DOI：10.1016/j.bmc.2010.07.055

  日期：2010.9

  transport chemotherapeutic agents out of carcinoma cells. Inhibition of P-gp function may represent one of the strategies to reverse MDR. We have previously reported that marchantin C (MC), a macrocyclic bisbibenzyl compound from liverworts, exerts anti-tumor activity as an antimitotic agent. This study was designed to evaluate the possible modulatory effect of MC and its three synthetic derivatives (MC1

  已知P-糖蛋白（P -gp）通过充当外排泵主动将化疗药物转运出癌细胞来介导多药耐药性（MDR）。P -gp功能的抑制可能代表逆转MDR的策略之一。我们以前曾报道过，番石榴素C（MC）是一种来自地蒿的大环双联二苄基化合物，可作为抗有丝分裂剂发挥抗肿瘤活性。本研究旨在评估MC及其三种合成衍生物（MC1，MC2和MC3）对P的可能调节作用。-gp在抗VCR的KB / VCR单元中。细胞毒性试验的结果表明，在这四种化合物中，MC是KB和KB / VCR细胞中最有效的细胞增殖抑制剂，而三种MC衍生的化学物质在相同条件下几乎没有抗增殖活性。然而，在表达P -gp的MDR细胞中，对这些化合物增强VCR细胞毒性的效力的分析导致鉴定出MC2是逆转耐药性更有效的化学物质。进一步的研究表明，MC2能够降低罗丹明123的流出，进而增加KB / VCR细胞中罗丹明123和阿霉素的积累，表明MC2通过抑制P重新使细胞
• Design, synthesis, biological evaluation and molecular modeling study of novel macrocyclic bisbibenzyl analogues as antitubulin agents
  作者：Bin Sun、Lin Li、Qing-wen Hu、Hong-bo Zheng、Hui Tang、Huan-min Niu、Hui-qing Yuan、Hong-xiang Lou

  DOI：10.1016/j.ejmech.2017.02.021

  日期：2017.3

  A series of macrocyclic bisbibenzyls with novel skeletons was designed, synthesized, and evaluated for antiproliferative activity against five anthropic cancer cell lines. Among these novel molecules, compound 47 displayed excellent anticancer activity against HeLa, k562, HCC1428, HT29 and PC-3/Doc cell lines, with IC50 values ranging from of 1.51 μM-5.51 μM, which were more potent than the parent

  设计，合成了一系列具有新颖骨架的大环双联二苄基，并评估了它们对五种人类癌细胞系的抗增殖活性。在这些新分子中，化合物47对HeLa，k562，HCC1428，HT29和PC-3 / Doc细胞系表现出优异的抗癌活性，IC50值范围为1.51μM-5.51μM，比母体化合物马氏菌素更有效。具有新的双联苄基骨架的化合物44和55也显示出显着改善的抗增殖能力。还对这些合成的化合物进行了结构活性关系（SAR）分析。此外，化合物47有效抑制HCC1482细胞中的微管蛋白聚合，并以浓度依赖的方式诱导HCC1482细胞在G2 / M期的周期停滞。还利用分子对接研究来研究化合物47与微管蛋白的结合模式。总之，本研究发现了几种具有新型双联苄基骨架的有效抗微管蛋白化合物，我们的系统研究揭示了靶向微管蛋白和有丝分裂的新型支架，并为发现新型抗肿瘤药物提供了进展。
• Synthesis and multidrug resistance reversal activity of dihydroptychantol A and its novel derivatives
  作者：Bin Sun、Hui-qing Yuan、Guang-min Xi、Yu-dao Ma、Hong-xiang Lou

  DOI：10.1016/j.bmc.2009.05.077

  日期：2009.7

  The macrocyclic bisbibenzyl dihydroptychantol A (DHA), previously isolated from Asterella angusta, was synthesized and showed significant multidrug resistance (MDR) reverting activity in chemoresistant cancer cells. In an attempt to discover more potent MDR reversal agents for efficient cancer chemotherapy, DHA derivatives with thiazole rings (19-22) were synthesized, and their cytotoxicities and MDR reversal activities were evaluated in adriamycin-resistant K562/A02, vincristine-resistant KB/VCR and in their parental cells by MTT assays. In response to treatment with each compound, the K562 cell line was the most sensitive, and the vincristine-resistant KB/VCR cell line was the most resistant. Marked decreases in K562 and K562/A02 cell viability were detectable after treatment with the synthesized derivatives of DHA, while less inhibitory effects on cell growth were observed in chemical- resistant KB/VCR and KB cells. Moreover, among the tested compounds, the intermediate 17 and the analogues 19, 20, and 21 showed potent MDR reversal activities and increased vincristine cytotoxicity in KB/VCR cells, with the reversal fold ranges from 10.54 to 13.81 (10 mu M), which is 3.2-4.3-fold stronger than the natural product DHA. (C) 2009 Elsevier Ltd. All rights reserved.
• Bezencon, Olivier; Seebach, Dieter, Liebigs Annalen, 1996, # 8, p. 1259 - 1276
  作者：Bezencon, Olivier、Seebach, Dieter

  DOI：——

  日期：——