(4-甲氧基-3-甲基-2-吡啶基)甲基乙酸酯 | 102625-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (4-甲氧基-3-甲基-2-吡啶基)甲基乙酸酯
• 英文名称: 2-acetoxymethyl-4-methoxy-3-methylpyridine
• 英文别名: 2-acetoxymethyl-3-methyl-4-methoxy-pyridine；(4-methoxy-3-methylpyridin-2-yl)methyl acetate
• CAS: 102625-98-9
• 化学式: C₁₀H₁₃NO₃
• mdl: MFCD09817657
• 分子量: 195.218
• InChiKey: RKTJYHWFUSJKOW-UHFFFAOYSA-N

物化性质

• 沸点：
  278.2±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-甲氧基-3-甲基-2-吡啶基)甲基乙酸酯 在 sodium hydroxide 、 氯化亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 6-tert-butyl-2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-1H-benzimidazole
  参考文献：
  名称：

  Structure-Activity Relationship of Omeprazole and Analogs as Helicobacter pylori Urease Inhibitors

  摘要：

  Helicobacter pylori urease belongs to a family of highly conserved urea-hydrolyzing enzymes. A common feature of these enzymes is the presence of two Lewis acid nickel ions and a reactive cysteine residue in the active site. The H+/K(+)-ATPase inhibitor omeprazole is a prodrug of a sulfenamide which covalently modifies cysteine residues on the luminal side of the H+/K(+)-ATPase of gastric parietal cells. Omeprazole and eight analogues were selected based on their chemical, electronic, and kinetic properties, and each was incubated with viable H. pylori in phosphate-buffered saline at pH 7.4 for 30 min, after which 100 mM urea was added and the amount of ammonia formed analyzed after a further 10 min. Inhibition between 0% and 100% at a 0.1 mM concentration was observed for the different analogues and could be expressed as a function of the pKa-value of the pyridine, the pKa-value of the benzimidazole, the overall lipophilicity, and, most importantly, the rate of sulfenamide formation, in a quantitative structure-activity relationship. The inhibition was potentiated by a lower pH (favoring the formation of the sulfenamide) but abolished in the presence of beta-mercaptoethanol (a scavenger of the sulfenamide). Structural analogues incapable of yielding the sulfenamide did not inhibit ammonia production. Treatment of Helicobacter felis-infected mice with 230 mumol/kg flurofamide b.i.d. for 4 weeks, known to potently inhibit urease activity in vivo, as a means of eradicating the infection, was tested and compared with the effect of 125 mumol/kg omeprazole b.i.d. for 4 weeks. Neither treatment proved efficacious.

  DOI：

  10.1021/jm00025a008
• 作为产物：
  描述：

  2,3-二甲基-4-氯吡啶-N-氧化物 在 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (4-甲氧基-3-甲基-2-吡啶基)甲基乙酸酯
  参考文献：
  名称：

  Diversified Synthesis of Novel Quinoline and Dibenzo Thiazepine Derivatives Using Known Active Intermediates

  摘要：

  新型药物的开发以控制常规药物治疗中抗药性感染是当今的需求。通过趋同合成法开发了少量与抗溃疡相关的衍生物。成功合成的衍生物包括二苯并噻嗪啶-吡啶（SLN11-SLN15）和苯并咪唑-氢奎宁基衍生物（SLN16-SLN20）。在最终步骤中采用了微波、超声和常规技术进行耦合。有效的技术被识别为超声技术，主要体现在时间和产率上。报告的化合物通过元素分析和谱学研究（如1H、13C NMR和质谱）进行了结构表征。

  DOI：

  10.14233/ajchem.2013.14818

文献信息

• 2-[(2-Pyridylmethyl)sulfinyl]-1H-thieno[3,4-d]imidazoles. A novel class of gastric H+/K+-ATPase inhibitors
  作者：Klaus Weidmann、Andreas W. Herling、Hans Jochen Lang、Karl Heinz Scheunemann、Robert Rippel、Hildegard Nimmesgern、Thomas Scholl、Martin Bickel、Heinz Metzger

  DOI：10.1021/jm00081a004

  日期：1992.2

  2-[(2-Pyridylmethyl)sulfinyl]thienoimidazoles were synthesized and investigated as potential inhibitors of gastric H+/K(+)-ATPase. The [3,4-d] isomers of the two possible thienoimidazole series were found to be potent inhibitors of gastric acid secretion in vitro and in vivo. Structure-activity relationships indicate that especially lipophilic alkoxy, benzyloxy, and phenoxy substituents with additional

  合成2-[（（2-吡啶基甲基）亚磺酰基]噻吩并咪唑类化合物，并研究其作为胃H + / K（+）-ATPase的潜在抑制剂。已发现两种可能的噻吩并咪唑系列的[3,4-d]异构体在体外和体内都是有效的胃酸分泌抑制剂。结构活性关系表明，特别是在吡啶部分的4位具有额外的电子要求特性的亲脂性烷氧基，苄氧基和苯氧基取代基与未取代的噻吩并[3,4-d]咪唑结合会导致具有高活性的化合物。良好的化学稳定性。噻吩并[3,4-d]咪唑部分的各种取代方式导致较低的生物活性。选择了七氟丁氧基衍生物萨维拉唑（HOE 731，5d）进行进一步开发，目前正在临床评估中。
• Structure−Activity Relationship of 2-[[(2-Pyridyl)methyl]thio]-1<i>H</i>- benzimidazoles as Anti <i>Helicobacter pylori </i>Agents in Vitro and Evaluation of their in Vivo Efficacy
  作者：Thomas C. Kühler、Marianne Swanson、Vladimir Shcherbuchin、Håkan Larsson、Björn Mellgård、Jan-Eric Sjöström

  DOI：10.1021/jm970165r

  日期：1998.5.1

  A relationship between the structure of 21 2-[[(2-pyridyl)methyl]thio]-1H-benzimidazoles (6) and their anti Helicobacter pylori activity expressed as minimum bactericidal concentration (MBC) values is described. Observed MBCs ranged from 256 to 1 microg/mL. The structure-activity relationship (SAR) showed that larger and more lipophilic compounds, especially compounds with such substituents in the

  描述了21个2-[[[（2-吡啶基）甲基]硫基] -1H-苯并咪唑类化合物（6）的结构与其以最小杀菌浓度（MBC）值表示的抗幽门螺杆菌活性之间的关系。观察到的MBC范围为256至1微克/毫升。结构-活性关系（SAR）表明，更大和更多的亲脂性化合物，特别是在吡啶基部分的4-位具有这种取代基的化合物，通常具有较低的MBC值。合成并测试了通过建立的SAR模型预测可能有效的四种新化合物。测试了一种这样的化合物，即2-[[（（[4-[（环丙基甲基）氧基] -3-甲基-2-吡啶基）甲基]硫代] -1H-苯并咪唑（18）在小鼠体内的功效。幽门螺杆菌模型（125 micromol / kg口服，持续4天，n = 4）。很遗憾，该模型不能清楚地证明其抗菌活性。相反，观察到有效的酸分泌抑制作用。该发现归因于甲硫基化合物在体内被氧化成相应的甲基亚磺酰基衍生物，即质子泵抑制剂。尽管该抗菌活性具有体内降低粪便链球菌
• Helicobacter pylori eradicating agent having inhibitory activity on gastric acid secretion
  申请人：Ito Masaharu

  公开号：US08778975B2

  公开（公告）日：2014-07-15

  Disclosed are: a compound which is stable in an acid, has an antibacterial effect against a bacterium Helicobacter pylori, can exert a satisfactory level of an antibacterial effect when used singly, does not affect an enteric bacterium, has an antibacterial effect against a bacterium resistant to an antibacterial agent, and has an inhibitory effect on gastric acid secretion; and a pharmaceutical composition comprising the compound. Specifically disclosed are: a compound represented by the general formula (I) or a salt thereof; and a pharmaceutical composition comprising the compound or the salt thereof: wherein R represents a linear alkyl group having 4 to 8 carbon atoms, preferably 5 to 7 carbon atoms.

  本发明涉及一种在酸性条件下稳定，对幽门螺杆菌具有抗菌作用，单独使用时能够发挥满意的抗菌作用，不影响肠道细菌，对抗抗菌剂抗性菌株具有抗菌作用，并且对胃酸分泌具有抑制作用的化合物；以及包含该化合物的制药组合物。具体揭示了一种由通式（I）表示的化合物或其盐；以及包含该化合物或其盐的制药组合物：其中R表示具有4至8个碳原子的线性烷基，优选5至7个碳原子。
• 雷贝拉唑类似物的合成方法及应用
  申请人：湖北省医药工业研究院有限公司

  公开号：CN117534657A

  公开（公告）日：2024-02-09

  本发明涉及雷贝拉唑类似物的合成方法及应用，尤其涉及(R)‑2‑((4‑甲氧基‑3‑甲基吡啶‑2‑基)甲基亚硫酰基)‑1H‑苯并咪唑的合成方法。该合成方法包括以2,3‑二甲基‑4‑甲氧基‑吡啶氮氧化物为原料一步合成2‑氯甲基‑3‑甲基‑4‑甲氧基吡啶，并进一步合成(R)‑2‑((4‑甲氧基‑3‑甲基吡啶‑2‑基)甲基亚硫酰基)‑1H‑苯并咪唑。本发明大大减少合成工艺步骤，节约了合成成本，提高了合成效率，并且相对于现有的合成路线，合成过程温和，有毒危险试剂使用较少。
• HELICOBACTER PYLORI ERADICATING AGENT HAVING INHIBITORY ACTIVITY ON GASTRIC ACID SECRETION
  申请人：Arigen Pharmaceuticals, Inc.

  公开号：EP2103608B1

  公开（公告）日：2012-08-29