2-羟基-4-甲基苯-1,3-二甲酸二甲酯 | 75716-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-4-甲基苯-1,3-二甲酸二甲酯
• 英文名称: dimethyl 2-hydroxyl-4-methylbenzene-1,3-dicarboxylate
• 英文别名: dimethyl 2-hydroxy-4-methylbenzene-1,3-dicarboxylate；dimethyl 2-hydroxy-4-methylisophthalate
• CAS: 75716-69-7
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: CSTDQHZKPMTJNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-羟基-4-甲基苯-1,3-二甲酸二甲酯 在 甲醇 、 氯化亚砜 、 lithium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.83h， 生成 5-Chloro-8-hydroxy-1-oxo-3,4-dihydroisochromene-7-carboxylic acid
  参考文献：
  名称：

  Dechlorination and demethylation of ochratoxin A enhance blocking activity of PXR activation, suppress PXR expression and reduce cytotoxicity

  摘要：

  The pregnane X receptor (PXR) has been established to induce chemoresistance and metabolic diseases. Ochratoxin A (OTA), a mycotoxin, decreases the expression of PXR protein in human primary hepatocytes. OTA is chlorinated and has a methylated lactone ring. Both structures are associated with OTA toxicity. The study was to test the hypothesis that structural modifications differentially impact PXR blocking activity over cytotoxicity. To test this hypothesis, OTA-M and OTA-Cl/M were synthesized. OTA-M lacked the methyl group of the lactonering, whereas OTA-Cl/M had neither the methyl group nor the chlorine atom. The blocking activity of PXR activation was determined in a stable cell line, harboring both PXR (coding sequence) and its luciferase element reporter. OTA-Cl/M showed the highest blocking activity, followed by OTA-M and OTA. OTA-Cl/M was 60 times as potent as the common PXR blocker ketoconazole based on calculated IC50 values. OTA-Cl/M decreased by 90 % the expression of PXR protein and was the least cytotoxic among the tested compounds. Molecular docking identified that OTA and its derivatives interacted with different sets of residues in PXR, providing a molecular basis for selectivity. Excessive activation of PXR has been implicated in chemoresistance and metabolic diseases. Downregulation of PXR protein expression likely delivers an effective mechanism against structurally diverse PXR agonists.

  DOI：

  10.1016/j.toxlet.2020.07.012
• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 在 氮气 、 盐酸 、 乙酸乙酯 、 Brine 、 magnesium sulfate 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、1.33 kPa 条件下， 反应 16.0h， 以to afford 21.76 g (24%) of dimethyl 2-hydroxy-4-methylbenzene-1,3-dicarboxylate (17) as a pale yellow oil which的产率得到2-羟基-4-甲基苯-1,3-二甲酸二甲酯
  参考文献：
  名称：

  COMPOUNDS AND COMPOSITIONS USEFUL IN THE TREATMENT OF NEOPLASIA

  摘要：

  本文描述了用于治疗的化合物，该化合物由公式（1）定义：还描述了一种抗增殖组合物，其中包括一个或多个符合公式（1）的化合物，以及一种治疗肿瘤的方法，包括给予这样的化合物或组合物。

  公开号：

  US20090047221A1

文献信息

• A New and Expedient Total Synthesis of Ochratoxin A and d5-Ochratoxin A
  作者：Bartolo Gabriele、Mohamed Attya、Alessia Fazio、Leonardo Di Donna、Pierluigi Plastina、Giovanni Sindona

  DOI：10.1055/s-0028-1088076

  日期：2009.6

  5-phenylalanine, leading to the first total synthesis of d 5-OTA, a molecular tracer for the detection and analytical quantification of the natural mycotoxin in food samples by means of stable isotope dilution assay (SIDA). heterocycles - natural products - ochratoxin A - stable isotope dilution assay - total synthesis

  提出了一种新的真菌毒素曲霉毒素A（OTA）的全合成方法，该方法以市售底物的总收率为9％制备。关键步骤包括受保护的1-苯丙氨酸与5-氯-8-羟基-3-甲基-1-甲基-1-氧代异色烷-7-羧酸（och曲霉毒素α，OTα）之间的缩合反应。相同的策略可以成功地应用于l - d 5-苯丙氨酸，导致首次完全合成d 5 -OTA，这是一种分子示踪剂，用于通过稳定同位素稀释测定法检测和分析定量食品中的天然霉菌毒素（SIDA）。 杂环-天然产物-曲霉毒素A-稳定同位素稀释法-全合成
• One Pot Synthesis of Phenolic Compounds from Aliphatic Ones.
  作者：Adrián Covarrubias-Zúñiga

  DOI：10.1080/00397919808006855

  日期：1998.5

  Abstract Synthesis of tetra and pentasubstituted phenols from dimethyl 1,3-acetonedicarboxilate anion 1 and alkinones 2 is described. The salient feature of this procedure is to provide phenols with regiocontrol at the 3/5 positions. This research was supported by a Grant-in-Aid for Scientific Research No. 40361-53352E from CONACYT, Mexico. Contribution No. 0000 of Instituto de Quimica, UNAM.

  摘要 描述了由 1,3-丙酮二羧酸二甲酯阴离子 1 和烷酮 2 合成四取代和五取代苯酚。该程序的显着特点是在 3/5 位置提供具有区域控制的酚类。这项研究得到了墨西哥 CONACYT 的科学研究资助编号 40361-53352E 的支持。墨西哥国立自治大学 Quimica 研究所的第 0000 号文稿。
• WO2006/46071
  申请人：——

  公开号：——

  公开（公告）日：——
• Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers
  作者：Benedikt Cramer、Henning Harrer、Kazuhiko Nakamura、Daisuke Uemura、Hans-Ulrich Humpf

  DOI：10.1016/j.bmc.2009.10.050

  日期：2010.1

  The mycotoxin ochratoxin A is a potent inhibitor of the protein biosynthesis and known to be cytotoxic in nanomolar concentrations. In order to investigate the relationship between stereochemistry and cytotoxicity of this compound, all four ochratoxin A stereoisomers have been synthesized. Using the liver cell line Hep G2, the compounds were tested for cytotoxic and apoptotic potential. It could be shown, that the L-configuration of the phenylalanine moiety of the molecule is mostly responsible for the high cytotoxicity of ochratoxin A while the stereocenter at the dihydroisocoumarine structure is of less importance. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of (+)- and (-)-Mellein Utilkizing an Annelation Reaction of Isoxazoles with Dimethyl 3-Oxoglutarate
  作者：Naoki Takeuchi、Kaori Goto、Yuki Sasaki、Takashi Fujita、Kohsuke Okazaki、Kohji Kamata、Seisho Tobinaga

  DOI：10.3987/com-91-s47

  日期：——

  Naturally occurring dihydroisocoumarins, (+)- and (-)-mellein (2 and 3), metabolites of fungals, Cercospora sp. and Aspergillus sp., etc., were synthesized from the isoxazoles (32) and (33) by the annelation reactions with dimethyl 3-oxoglutarate.