2',6-dimethoxy-4'-[(tetrahydro-2H-pyran-2-yloxy)methyl]biphenyl-2-carbaldehyde | 1186304-32-4

• 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',6-dimethoxy-4'-[(tetrahydro-2H-pyran-2-yloxy)methyl]biphenyl-2-carbaldehyde
• 英文别名: 3-Methoxy-2-[2-methoxy-4-(oxan-2-yloxymethyl)phenyl]benzaldehyde
• CAS: 1186304-32-4
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: FXYMDBLMNVJBSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2',6-dimethoxy-4'-[(tetrahydro-2H-pyran-2-yloxy)methyl]biphenyl-2-carbaldehyde 在 盐酸 、 18-冠醚-6 、 四溴化碳 、 5%-palladium/activated carbon 、 水 、 氢气 、 sodium methylate 、 三溴化硼 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， -40.0~20.0 ℃ 、300.01 kPa 条件下， 反应 132.0h， 生成 4-[(Dimethylamino)methyl]-14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-3,16,24-triol
  参考文献：
  名称：

  Synthesis of macrocyclic bisbibenzyl derivatives and their anticancer effects as anti-tubulin agents

  摘要：

  Based on the core skeleton of the total synthesized bisbibenzyl marchantin C, riccardin D and plagiochin E, a series of brominated and aminomethylated derivatives of above three bisbibenzyls have been synthesized and their cytotoxic activity against KB, MCF-7 and PC3 cell lines has been preliminary evaluated. The bio-test results revealed that the brominated derivatives 21, 22, 24, 25 and 28 exhibited excellent antiproliferative activity, with IC50 value lower than their parent compounds. As a most potent microtubule depolymerization agent, compound 28 was found to arrest cells at the G(2)/M phase of the cell cycle as determined by the flow cytometry assay in PC3 cell line. The remarkable biological profile and novel structure of these bisbibenzyl derivatives make them possible as promising candidates for clinical development as chemotherapeutic agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.004
• 作为产物：
  描述：

  4-溴-3-甲氧基苯甲酸甲酯 在 potassium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 生成 2',6-dimethoxy-4'-[(tetrahydro-2H-pyran-2-yloxy)methyl]biphenyl-2-carbaldehyde
  参考文献：
  名称：

  作为有效抗菌剂的蓖麻毒素D衍生物的合成

  摘要：

  我们描述了蓖麻素D衍生物，一类新型的抗菌分子的合成和生物学评估。这些衍生物的结构多样化是通过将羟基，甲氧基和溴引入蓖麻毒素D的芳环中实现的。这些化合物的抗微生物性评估是针对临床分离出的细菌和真菌的体外测定方法。将溴原子引入蓖麻毒素D的芳烃B中导致了几种强活性抗菌化合物，对于金黄色葡萄球菌（对甲氧西林敏感和耐药的菌株）的MIC值为0.5至4μg/ mL 。抗真菌测试发现化合物34是最有效的分子，对白色念珠菌的MIC值为2μg/ mL。最初的生物学评估表明，这些新型分子作为潜在的抗菌剂值得进一步研究。

  DOI：

  10.1016/j.bmcl.2016.06.006

文献信息

• Design, synthesis and biological evaluation of nitrogen-containing macrocyclic bisbibenzyl derivatives as potent anticancer agents by targeting the lysosome
  作者：Bin Sun、Jun Liu、Yun Gao、Hong-bo Zheng、Lin Li、Qing-wen Hu、Hui-qing Yuan、Hong-xiang Lou

  DOI：10.1016/j.ejmech.2017.05.050

  日期：2017.8

  A series of novel nitrogen-containing macrocyclic bisbibenzyl derivatives was designed, synthesized, and evaluated for antiproliferative activity against three anthropic cancer cell lines. Among these novel molecules, the tri-O-alkylated compound 18a displayed the most potent anticancer activity against the A549, MCF-7, and k562 cancer cell lines, with IC50 values of 0.51, 0.23, and 0.19 μM, respectively

  设计，合成了一系列新颖的含氮大环双联苄基衍生物，并评估了其对三种人类癌细胞系的抗增殖活性。在这些新分子中，三-O-烷基化的化合物18a对A549，MCF-7和k562癌细胞系表现出最强的抗癌活性，IC 50值分别为0.51、0.23和0.19μM 。明显优于母体化合物蓖麻毒素D，并且比临床使用的药物ADR好3-10倍。bis-Mannich衍生物11b的亚微摩尔IC 50也显示出显着增强的抗增殖能力价值观。还对这些新合成的化合物进行了构效关系分析。机理研究表明，这些化合物可靶向溶酶体以诱导溶酶体膜通透化，并且还可以诱导显示细胞凋亡和坏死特征的细胞死亡。
• A Synthesis-Driven Structure Revision of ‘Plagiochin E’, a Highly Bioactive Bisbibenzyl
  作者：Andreas Speicher、Matthias Groh、Josef Zapp、Anu Schaumlöffel、Michael Knauer、Gerhard Bringmann

  DOI：10.1055/s-0029-1217510

  日期：2009.7

  from Marchantia polymorpha, a liverwort. The total synthesis of the proposed structure for plagiochin E and of two structurally and biosynthetically related bisbibenzyls and comparison of the NMR data of the synthetic compounds with those of the isolated bisbibenzyls necessitates a structure revision for plagiochin E. Exemplarily for this metabolite, the stereostructure was investigated, by racemate

  最近，一种名为 plagiochin E 的双苄基显示出显着的抗真菌和抗肿瘤活性，从地钱地衣中分离出来。plagiochin E 和两种结构和生物合成相关的双苄基的拟议结构的全合成以及合成化合物的 NMR 数据与分离的双苄基的 NMR 数据的比较需要对 plagiochin E 进行结构修正。 例如，对于这种代谢物，立体结构是通过对手性 Lux Cellulose-1 相的外消旋体拆分进行研究，使用 HPLC-CD 偶联和量子化学 CD 计算，清楚地将 P 构型分配给较快的对映体，将 M 构型分配给较慢的对映体。
• Syntheses of Macrocyclic Bis(bibenzyl) Compounds Derived from Perrottetin E
  作者：Andreas Speicher、Matthias Groh、Markus Hennrich、Anh-Minh Huynh

  DOI：10.1002/ejoc.201001023

  日期：2010.12

  Macrocyclic bis(bibenzyl) compounds are natural products from liverworts and are of growing interest due to recent reports on new isolated compounds and on their remarkable biological activities. We report here on a flexible and general approach to the total set of nine bis(bibenzyl) compounds of the riccardin and plagiochin type derived from perrottetin E. The structures were confirmed through their

  大环双（联苄）化合物是来自苔类植物的天然产物，由于最近关于新的分离化合物及其显着生物活性的报道，人们越来越感兴趣。我们在此报告了对源自 perrottetin E 的 riccardin 和 plagiochin 类型的九种双（联苄基）化合物的总集合的灵活和通用方法。 通过光谱数据确认了结构，并与分离产品的数据进行了仔细比较排除芳烃连接和替代模式中的任何错误。
• Synthesis of macrocyclic bisbibenzyl derivatives and their anticancer effects as anti-tubulin agents
  作者：Juan Jiang、Bin Sun、Yan-yan Wang、Min Cui、Li Zhang、Chang-zhi Cui、Yan-feng Wang、Xi-gong Liu、Hong-xiang Lou

  DOI：10.1016/j.bmc.2012.02.004

  日期：2012.4

  Based on the core skeleton of the total synthesized bisbibenzyl marchantin C, riccardin D and plagiochin E, a series of brominated and aminomethylated derivatives of above three bisbibenzyls have been synthesized and their cytotoxic activity against KB, MCF-7 and PC3 cell lines has been preliminary evaluated. The bio-test results revealed that the brominated derivatives 21, 22, 24, 25 and 28 exhibited excellent antiproliferative activity, with IC50 value lower than their parent compounds. As a most potent microtubule depolymerization agent, compound 28 was found to arrest cells at the G(2)/M phase of the cell cycle as determined by the flow cytometry assay in PC3 cell line. The remarkable biological profile and novel structure of these bisbibenzyl derivatives make them possible as promising candidates for clinical development as chemotherapeutic agents. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of riccardin D derivatives as potent antimicrobial agents
  作者：Bin Sun、Ming Zhang、Ying Li、Qing-wen Hu、Hong-bo Zheng、Wen-qiang Chang、Hong-xiang Lou

  DOI：10.1016/j.bmcl.2016.06.006

  日期：2016.8

  We describe the synthesis and biological evaluation of riccardin D derivatives, a novel class of antimicrobial molecules. Structural diversification of these derivatives was achieved by introducing hydroxy, methoxy, and bromine into the aromatic rings of riccardin D. The antimicrobial evaluation of these compounds was performed as in vitro assays against clinically isolated bacteria and fungi. The

  我们描述了蓖麻素D衍生物，一类新型的抗菌分子的合成和生物学评估。这些衍生物的结构多样化是通过将羟基，甲氧基和溴引入蓖麻毒素D的芳环中实现的。这些化合物的抗微生物性评估是针对临床分离出的细菌和真菌的体外测定方法。将溴原子引入蓖麻毒素D的芳烃B中导致了几种强活性抗菌化合物，对于金黄色葡萄球菌（对甲氧西林敏感和耐药的菌株）的MIC值为0.5至4μg/ mL 。抗真菌测试发现化合物34是最有效的分子，对白色念珠菌的MIC值为2μg/ mL。最初的生物学评估表明，这些新型分子作为潜在的抗菌剂值得进一步研究。