2-乙酰氧基甲基-3,5-二甲基-4-硝基吡啶 | 142885-95-8

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 2-乙酰氧基甲基-3,5-二甲基-4-硝基吡啶
• 中文别名: 2-乙酰氧甲基-3,5-二甲基-4-硝基吡啶氮氧化物
• 英文名称: 2-acetyloxymethyl-3,5-dimethyl-4-nitropyridine
• 英文别名: 2-acetoxymethyl-3,5-dimethyl-4-nitropyridine；4-nitro-3,5-dimethyl-2-acetoxymethylpyridine；(3,5-dimethyl-4-nitropyridin-2-yl)methyl acetate
• CAS: 142885-95-8
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: NQXDXTJWDZWWAX-UHFFFAOYSA-N

物化性质

• 沸点：
  340.4±37.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-乙酰氧基甲基-3,5-二甲基-4-硝基吡啶 在 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2-bromomethyl-3,5-dimethyl-4-nitropyridine
  参考文献：
  名称：

  Rationally Designed High-Affinity 2-Amino-6-halopurine Heat Shock Protein 90 Inhibitors That Exhibit Potent Antitumor Activity

  摘要：

  Heat shock protein 90 (Hsp90) is a molecular chaperone protein implicated in stabilizing the conformation and maintaining the function of many cell-signaling proteins. Many oncogenic proteins are more dependent on Hsp90 in maintaining their conformation, stability, and maturation than their normal counterparts. Furthermore, recent data show that Hsp90 exists in an activated form in malignant cells but in a latent inactive form in normal tissues, suggesting that inhibitors selective for the activated form could provide a high therapeutic index. Hence, Hsp90 is emerging as an exciting new target for the treatment of cancer. We now report on a novel series of 2-amino-6-halopurine Hsp90 inhibitors exemplified by 2-amino-6-chloro-9-(4-iodo-3,5-dimethylpyridin-2-ylmethyl)purine (30). These highly potent inhibitors (IC50 of 30 = 0.009 mu M in a HER-2 degradation assay) also display excellent antiproliferative activity against various tumor cell lines (IC50 of 30 = 0.03 mu M in MCF7 cells). Moreover, this class of inhibitors shows higher affinity for the activated form of Hsp90 compared to our earlier 8-sulfanylpurine Hsp90 inhibitor series. When administered orally to mice, these compounds exhibited potent tumor growth inhibition (> 80%) in an N87 xenograft model, similar to that observed with 17-allylamino-17-desmethoxygeldanamycin (17-AAG), which is a compound currently in phase I/II clinical trials.

  DOI：

  10.1021/jm050752+
• 作为产物：
  描述：

  2,3,5-三甲基吡啶 在 硫酸 、 硝酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-乙酰氧基甲基-3,5-二甲基-4-硝基吡啶
  参考文献：
  名称：

  Rationally Designed High-Affinity 2-Amino-6-halopurine Heat Shock Protein 90 Inhibitors That Exhibit Potent Antitumor Activity

  摘要：

  Heat shock protein 90 (Hsp90) is a molecular chaperone protein implicated in stabilizing the conformation and maintaining the function of many cell-signaling proteins. Many oncogenic proteins are more dependent on Hsp90 in maintaining their conformation, stability, and maturation than their normal counterparts. Furthermore, recent data show that Hsp90 exists in an activated form in malignant cells but in a latent inactive form in normal tissues, suggesting that inhibitors selective for the activated form could provide a high therapeutic index. Hence, Hsp90 is emerging as an exciting new target for the treatment of cancer. We now report on a novel series of 2-amino-6-halopurine Hsp90 inhibitors exemplified by 2-amino-6-chloro-9-(4-iodo-3,5-dimethylpyridin-2-ylmethyl)purine (30). These highly potent inhibitors (IC50 of 30 = 0.009 mu M in a HER-2 degradation assay) also display excellent antiproliferative activity against various tumor cell lines (IC50 of 30 = 0.03 mu M in MCF7 cells). Moreover, this class of inhibitors shows higher affinity for the activated form of Hsp90 compared to our earlier 8-sulfanylpurine Hsp90 inhibitor series. When administered orally to mice, these compounds exhibited potent tumor growth inhibition (> 80%) in an N87 xenograft model, similar to that observed with 17-allylamino-17-desmethoxygeldanamycin (17-AAG), which is a compound currently in phase I/II clinical trials.

  DOI：

  10.1021/jm050752+

文献信息

• A process for the preparation of omeprazol
  申请人：CENTRO GENESIS PARA LA INVESTIGACION, S.L.

  公开号：EP0484265A1

  公开（公告）日：1992-05-06

  The process starts by reacting 2,3,5 trimethylpyridine with hydrogen peroxide in the presence of catalysts, giving new reactive ionic species allowing the number of required steps to be substantially reduced. In the final important step, oxidation to omeprazol, there are used new salts of 5-methoxy-2-((3,5-dimethyl-4-methoxy-2-pyridine)methylthio)-1H-benzimidazole which, as the oxidation evolves, precipitate the omeprazol. The new oxidation method avoids superoxidations, provide for faster oxidation, high purity and yields of over 90%.

  该过程首先是通过在催化剂存在下，将2,3,5-三甲基吡啶与过氧化氢反应，产生新的具有反应性的离子物种，从而大大减少所需步骤的数量。在最后一个重要步骤中，氧化成奥美拉唑时，使用了5-甲氧基-2-((3,5-二甲基-4-甲氧基-2-吡啶基)甲硫基)-1H-苯并咪唑的新盐，随着氧化的进行，沉淀出奥美拉唑。这种新的氧化方法避免了超氧化反应，实现了更快的氧化速度，高纯度和超过90%的产率。
• Omeprazole synthesis
  申请人：Cipla Limited

  公开号：EP1085019B1

  公开（公告）日：2003-01-29
• US6303787B1
  申请人：——

  公开号：US6303787B1

  公开（公告）日：2001-10-16
• [EN] PYRIDINE BUILDING BLOCKS AS INTERMEDIATES IN THE SYNTHESIS OF PHARMACEUTICALLY ACTIVE COMPOUNDS<br/>[FR] BLOCS CONSTITUTIFS DE PYRIMIDINE UTILISES COMME INTERMEDIAIRES DANS LA SYNTHESE DE COMPOSES PHARMACEUTIQUEMENT ACTIFS
  申请人：RUSSINSKY LTD

  公开号：WO2000000474A1

  公开（公告）日：2000-01-06

  Complexes of formulae (II or III) are useful intermediates for preparing compounds of formula (IV) which in turn may be converted into a pyridine benzimidazole.
• [EN] PROCESS FOR THE PRODUCTION OF 2-(2-PYRIDINYLMETHYLSULPHINYL)-1H-BENZIMIDAZOLES<br/>[FR] PROCEDE DE PRODUCTION DE 2-(2-PYRIDINYLMETHYLSULPHINYLE)-1H-BENZIMIDAZOLES
  申请人：SINT QUIMICA SA

  公开号：WO2001004109A1

  公开（公告）日：2001-01-18

  Procedure for obtaining derivatives of 2-(2-pyridinilmethylsulphinyl) - 1H-benyimidazole of general formula (I), where R = H or analkyl radical; R'= Alkyl chain, which may or may not be interrupted by an atom of oxygen; R'= alkyl or alkoxy radical such as methyl and methoxy; R'''= H or alkoxy remnant which may or may not be substituted, characterised in that it is carried out by the replacement of an halogen in position '4' of the pyridine ring of the compounds of general formula (VIII) by an alkoxide in the presence of a base and within an aprotic polar solvent; or by replacement of a 'nitro' group in position '4' of the pyridine ring of the compounds of the compounds of formula (XVII) by an alkoxide radical R'O- in the presence of a base and within a mixture of solvents made up of the corresponding to alcohol R'OH and another aprotic polar solvent. It is useful for the treatment or prevention of gastric ulcers.