methyl 2'-chlorocarbonyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate | 502621-95-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: methyl 2'-chlorocarbonyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate
• 英文别名: Methyl 4-(5-carbonochloridoyl-7-methoxy-1,3-benzodioxol-4-yl)-7-methoxy-1,3-benzodioxole-5-carboxylate
• CAS: 502621-95-6
• 化学式: C₁₉H₁₅ClO₉
• 分子量: 422.776
• InChiKey: DOKVAIQDBJTDSM-UHFFFAOYSA-N

物化性质

• 沸点：
  616.3±55.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2'-chlorocarbonyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate 在 溶剂黄146 、 三乙胺 、 β-丙氨酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (Z)-5-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)-2-methoxyphenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel dimethyl[1,1′-biphenyl]-2,2′-dicarboxylate derivatives containing thiazolidine-2,4-dione for the treatment of concanavalin A-induced acute liver injury of BALB/c mice

  摘要：

  In this paper, we reported the synthesis of bifendate derivatives and evaluation of anti-inflammatory activity by detecting the production of the Nitric Oxide (NO) in the lipopolysaccharide(LPS)-stimulated RAW 264.7 cell lines. Among the newly derivatives, compound 7k was the most potent one and two other compounds (7e and 7f) also exhibited greater anti-inflammatory activity than bifendate. Further in vivo studies confirmed that 7k significantly and dose-dependently inhibited carrageenan-induced paw edema and decreased the serum levels of alanine aminotransaminase, and aspartate aminotransaminase in concanavalin A-induced hepatitis model. Histopathological evaluation demonstrated that 7k has better hepatoprotective effect on acute liver injury induced by concanavalin A than bifendate, suggesting that 7k is a potential drug candidate for the treatment of hepatic injuries. (C) 2011 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.10.005
• 作为产物：
  描述：

  联苯双酯 在 氯化亚砜 、 乙酸酐 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 29.0h， 生成 methyl 2'-chlorocarbonyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel dimethyl[1,1′-biphenyl]-2,2′-dicarboxylate derivatives containing thiazolidine-2,4-dione for the treatment of concanavalin A-induced acute liver injury of BALB/c mice

  摘要：

  In this paper, we reported the synthesis of bifendate derivatives and evaluation of anti-inflammatory activity by detecting the production of the Nitric Oxide (NO) in the lipopolysaccharide(LPS)-stimulated RAW 264.7 cell lines. Among the newly derivatives, compound 7k was the most potent one and two other compounds (7e and 7f) also exhibited greater anti-inflammatory activity than bifendate. Further in vivo studies confirmed that 7k significantly and dose-dependently inhibited carrageenan-induced paw edema and decreased the serum levels of alanine aminotransaminase, and aspartate aminotransaminase in concanavalin A-induced hepatitis model. Histopathological evaluation demonstrated that 7k has better hepatoprotective effect on acute liver injury induced by concanavalin A than bifendate, suggesting that 7k is a potential drug candidate for the treatment of hepatic injuries. (C) 2011 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.10.005

文献信息

• 双环醇的制备方法及其中间体化合物
  申请人：浙江奥翔药业股份有限公司

  公开号：CN106243079B

  公开（公告）日：2019-02-15

  本发明涉及双环醇的制备方法及其中间体化合物。具体而言，本发明涉及式(1)的双环醇，即4,4'‑二甲氧基‑5,6,5',6'‑双(亚甲二氧基)‑2‑羟甲基‑2'‑甲氧羰基联苯的制备方法及其中间体化合物。
• 联苯双酯衍生物、制备方法及其在治疗自身免 疫性疾病中的应用
  申请人：四川大学

  公开号：CN103059015B

  公开（公告）日：2016-01-13

  本发明属于化学医药技术领域，特别涉及联苯双酯衍生物、制备方法及其在治疗自身免疫性疾病中的应用。联苯双酯衍生物，结构如式I所示，具有较优的抑制急性肝炎、慢性肝纤维化或肺纤维化等自身免疫性疾病的作用，为治疗该类疾病的药物开发提供了一种新的选择。
• Absolute configurations and CD spectra of axially chiral biphenyls prepared in a facile manner by crystallization-induced configuration transformation
  作者：Limin Wang、Senxiang Cheng、Rongfeng Chen、Junbiao Chang

  DOI：10.1002/chir.20828

  日期：——

  the biphenyls was thus achieved. It was found that amide formation of an (S)‐valinol or (S)‐phenylalaninol at the 2′‐position of the biphenyl usually induced the deposition of crystals with the (M)‐configuration from ethanol in yields higher than 50%. The absolute configurations (ACs) of two crystalline biphenyls have been determined by X‐ray crystallographic analysis. The ACs of nine biphenyls have been

  轴向手性联苯如（M，S）‐ 3k可通过将其非对映异构体混合物结晶而方便地获得，它们是由外消旋4,4'-二甲氧基-5,6,5'，6'-双（亚甲基二氧基）-合成的2-羧酸酯基-2'-羧基联苯4个手性氨基醇（[R）-alaninol，（小号）-alaninol，（小号） -缬氨醇，和（小号） -苯丙氨醇。由此实现了联苯的结晶诱导构型转变。发现（S）-缬氨醇或（S的酰胺形成）联苯2'-位处的苯丙氨醇通常会诱导乙醇中具有（M）构型的晶体沉积，产率高于50％。X射线晶体学分析确定了两个结晶联苯的绝对构型（AC）。九个联苯的AC已根据其CD光谱进行分配。此外，对这些轴向手性联苯的稳定性研究表明，AC可以在重新溶解后还原。能量势垒，以（差向异构化之间P，- [R ）-图3b和（中号，- [R ）- 3b中被测量为Δ G ^ ＃= 21.45 kcal / mol，在301 K下的乙醇半衰期为17.1 h。手性，2010年。©2010
• 他克林-联苯双酯杂合物、其制备方法及应用
  申请人：河南大学

  公开号：CN105111195B

  公开（公告）日：2018-06-19

  他克林‑联苯双酯杂合物、其制备方法及应用，属于医药与化工领域，所述杂合物具有下述式（I）或式（II）的通式结构：其中，R1=H或Cl，R2=H或Cl；Y=CH2，NCH3，NH，羰基，乙二酰基，1,3‑丙二酰基，对环己烷基，或OCH2CH2O；m=0~4，n=0~4；且m、n均为整数，式（II）的‑CH2‑NH‑的碳端在苯环的3‑位或4‑位。由上述结构式（I）和（II）表示的化合物显示优越的乙酰胆碱酯酶抑制作用。因此本发明另一方面涉及它们以及以它们为活性成分的药物组合物，在治疗、改善或预防乙酰胆碱酯酶介导的相关疾病的药物的用途。
• Potent Inhibition of Nitric Oxide-Releasing Bifendate Derivatives against Drug-Resistant K562/A02 Cells in Vitro and in Vivo
  作者：Xiaoke Gu、Zhangjian Huang、Zhiguang Ren、Xiaobo Tang、Rongfang Xue、Xiaojun Luo、Sixun Peng、Hui Peng、Bin Lu、Jide Tian、Yihua Zhang

  DOI：10.1021/acs.jmedchem.6b01075

  日期：2017.2.9

  Multidrug resistance is a major obstacle to successful chemotherapy for leukemia. In this study; a series of nitric oxide (NO)-releasing bifendate derivatives (7a-n) were synthesized. Biological evaluation indicated that the most active compound (7a) produced relatively high levels of NO and significantly inhibited the proliferation of drug-resistant K562/A02 cells in vitro and in-vivo. In addition, 7a induced the mitochondrial tyrosine nitration and the intracellular accumulation of rhodamine 123 by inhibiting P-gp activity in K562/A02 cells. Furthermore, 7a remarkably down-regulated AKT, NF-kappa B, and ERK activation and HIF-1 alpha expression in K562/A02 cells, which are associated with the tumor cell proliferation and drug resistance. Notably, the antitumor effects were dramatically attenuated by an NO scavenger or elimination of the NO-releasing capability of 7a, indicating that NO produced by 7a contributed to, at least partly, its cytotoxicity against drug-resistant K562/A02 cells. Overall, 7a may be a potential agent against drug-resistant myelogenous leukemia.