4-chloro-3-nitrophenylacetic acid methyl ester | 300355-23-1

• 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: 4-chloro-3-nitrophenylacetic acid methyl ester
• 英文别名: (4-chloro-3-nitrophenyl)acetic acid methyl ester；methyl 4-chloro-3-nitrobenzeneacetate；methyl (4-chloro-3-nitrophenyl)acetate；Methyl 2-(4-chloro-3-nitrophenyl)acetate
• CAS: 300355-23-1
• 化学式: C₉H₈ClNO₄
• 分子量: 229.62
• InChiKey: LOJNXJAUOTWCJE-UHFFFAOYSA-N

物化性质

• 沸点：
  336.0±27.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  4-chloro-3-nitrophenylacetic acid methyl ester 在 N,N-二甲基丙烯基脲 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 54.15h， 生成 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)propionic acid methyl ester
  参考文献：
  名称：

  Discovery of Piragliatin—First Glucokinase Activator Studied in Type 2 Diabetic Patients

  摘要：

  Glucokinase (GK) activation as a potential strategy to treat type 2 diabetes (T2D) is well recognized. Compound 1, a glucokinase activator (GKA) lead that we have previously disclosed, caused reversible hepatic lipidosis in repeat-dose toxicology studies. We hypothesized that the hepatic lipidosis was due to the structure-based toxicity and later established that it was due to the formation of a thiourea metabolite, 2. Subsequent SAR studies of 1 led to the identification of a pyrazine-based lead analogue 3, lacking the thiazole moiety. In vivo metabolite identification studies, followed by the independent synthesis and profiling of the cyclopentyl keto- and hydroxyl- metabolites of 3, led to the selection of piragliatin, 4, as the clinical lead. Piragliatin was found to lower pre- and postprandial glucose levels, improve the insulin secretory profile, increase beta-cell sensitivity to glucose, and decrease hepatic glucose output in patients with T2D.

  DOI：

  10.1021/jm3008689
• 作为产物：
  描述：

  4-chloro-3-nitrophenylacetamide 以 甲醇 为溶剂， 以89%的产率得到4-chloro-3-nitrophenylacetic acid methyl ester
  参考文献：
  名称：

  Heteroaromatic glucokinase activators

  摘要：

  2,3-二取代N-杂环丙酰胺，其中3位取代为取代苯基，2位取代为甲基环烷基环，这些丙酰胺是葡萄糖激酶激活剂，可增加胰岛素分泌，用于治疗2型糖尿病。

  公开号：

  US06610846B1

文献信息

• Tetrahydrocarbazol derivatives as ligands for G-protein-coupled receptors (GPCR)
  申请人：ZENTARIS AG

  公开号：US20030232873A1

  公开（公告）日：2003-12-18

  This invention provides new tetrahydrocarbazole derivatives that act as ligands for G-protein-coupled receptors (GPCR), especially as antagonists of the gonadotropin-releasing hormone (GnRH). A pharmaceutical composition that contains these new tetrahydrocarbazole derivatives as well as a process for the production of the new tetrahydrocarbazole derivatives are also provided. Moreover, this invention relates to the administration of tetrahydrocarbazole derivatives for treating pathologic conditions that are mediated by GPCR, especially for inhibiting GnRH, in mammals, especially humans, who require such an administration, as well as the use of tetrahydrocarbazole derivatives for the production of a pharmaceutical agent for treating GPCR-mediated pathologic conditions, especially for inhibiting GnRH.

  这项发明提供了作为G蛋白偶联受体（GPCR）配体的新四氢咔唑衍生物，特别是作为促性腺激素释放激素（GnRH）的拮抗剂。还提供了一种含有这些新四氢咔唑衍生物的药物组合物，以及一种生产这些新四氢咔唑衍生物的方法。此外，这项发明涉及给哺乳动物，特别是人类，需要这种给药的通过四氢咔唑衍生物治疗GPCR介导的病理状况，特别是抑制GnRH的治疗，以及利用四氢咔唑衍生物生产用于治疗GPCR介导的病理状况，特别是抑制GnRH的药物的用途。
• Fused heteroaromatic glucokinase activators
  申请人：——

  公开号：US20020103199A1

  公开（公告）日：2002-08-01

  Glucokinase activating amides are useful for increasing insulin secretion in the treatment of type II diabetes.

  葡萄糖激酶活化酰胺在治疗II型糖尿病中增加胰岛素分泌方面非常有用。
• [EN] NOVEL BENZIMIDAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THESE COMPOUNDS<br/>[FR] NOUVEAU DERIVES DE BENZIMIDAZOLE ET COMPOSITIONS PHARMACEUTIQUES COMPRENANT CES COMPOSES
  申请人：NEUROSEARCH AS

  公开号：WO2004089912A1

  公开（公告）日：2004-10-21

  The present invention relates to novel benzimidazole derivatives of the formula (I) as defined in the description and in the claims, pharmaceutical compositions containing these compounds, and methods of treatment therewith. The compounds of the invention are useful in the treatment of central nervous system diseases and disorders, which are responsive to modulation of the GABAA receptor complex, and in particular for inducing and maintaining anaesthesia, sedation and muscle relaxation, as well as for combating febrile convulsions in children. The compounds of the invention may also be used by veterinarians.

  本发明涉及新型苯并咪唑衍生物的公式（I），如描述和索赔中定义的，包含这些化合物的药物组合物，以及使用这些药物进行治疗的方法。本发明的化合物在治疗对GABAA受体复合物调节敏感的中枢神经系统疾病和障碍方面是有用的，特别是用于诱导和维持麻醉、镇静和肌肉松弛，以及对抗儿童的发热性惊厥。本发明的化合物也可被兽医使用。
• [EN] A PROCESS FOR THE PREPARATION OF ARYLCYCLOPROPANE CARBOXYLIC CARBONITRILES, AND COMPOUNDS DERIVED THEREFROM<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ARYLCYCLOPROPANECARBONITRILES CARBOXYLIQUES ET COMPOSÉS DÉRIVÉS DE CEUX-CI
  申请人：RELIANCE LIFE SCIENCES PVT LTD

  公开号：WO2009150660A1

  公开（公告）日：2009-12-17

  The present invention relates to an efficient process for preparing an arylcyclopropanecarbonitrile, which involves the use of sulfolane as a solvent.

  本发明涉及一种高效制备芳基环丙烷碳腈的方法，其中使用亚砜作为溶剂。
• PROCESS FOR THE PREPARATION OF ARYLCYCLOPROPOANE CARBOXYLIC CARBONITRILES, AND COMPOUNDS DERIVED THEREFROM
  申请人：Bhujbal Sandeep Pandurang

  公开号：US20090312558A1

  公开（公告）日：2009-12-17

  The present invention relates to an efficient process for preparing an arylcyclopropanecarbonitrile, which involves the use of sulfolane as a solvent.

  本发明涉及一种高效制备芳基环丙烷腈的方法，其中使用硫醇烷作为溶剂。