2-(1-哌啶甲基)-苯甲酸甲酯 | 914347-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 2-(1-哌啶甲基)-苯甲酸甲酯
• 英文名称: Methyl 2-(piperidin-1-ylmethyl)benzoate
• CAS: 914347-17-4
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: JWLYKHGRBOJVGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  335.4±25.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-(1-哌啶甲基)-苯甲酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 2-(N-piperidinyl)methyl benzoic acid
  参考文献：
  名称：

  Discovery of a Benzamide Derivative That Protects Pancreatic β-Cells against Endoplasmic Reticulum Stress

  摘要：

  Endoplasmic reticulum (ER) stress-mediated pancreatic insulin-producing beta-cell dysfunction and death are critical elements in the onset and progression of both type 1 and type 2 diabetes. Here, through cell-based high throughput screening we identified benzamide derivatives as a novel class of beta-cell protective agents against ER stress-induced dysfunction and death. Through structure activity relationship optimization, a 3-(N-piperidinyl)methylbenzamide derivative 13d markedly protects beta-cells against ER stress-induced dysfunction and death with near 100% maximum rescue activity and an EC50 of 0.032 mu M. Compound 13d alleviates ER stress in beta-cells by suppressing ER stress-mediated activation of all three branches of unfolded protein response (UPR) and apoptotic genes. Finally, we show that 13d significantly lowers blood glucose levels and increases concomitant beta-cell survival and number in a streptozotocin-induced diabetic mouse model. Identification of beta-cell-protective small molecules against ER stress provides a new promising modality for the treatment of diabetes.

  DOI：

  10.1021/acs.jmedchem.7b00435
• 作为产物：
  描述：

  哌啶 、 2-溴甲基苯甲酸甲酯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 2-(1-哌啶甲基)-苯甲酸甲酯
  参考文献：
  名称：

  Discovery of a Benzamide Derivative That Protects Pancreatic β-Cells against Endoplasmic Reticulum Stress

  摘要：

  Endoplasmic reticulum (ER) stress-mediated pancreatic insulin-producing beta-cell dysfunction and death are critical elements in the onset and progression of both type 1 and type 2 diabetes. Here, through cell-based high throughput screening we identified benzamide derivatives as a novel class of beta-cell protective agents against ER stress-induced dysfunction and death. Through structure activity relationship optimization, a 3-(N-piperidinyl)methylbenzamide derivative 13d markedly protects beta-cells against ER stress-induced dysfunction and death with near 100% maximum rescue activity and an EC50 of 0.032 mu M. Compound 13d alleviates ER stress in beta-cells by suppressing ER stress-mediated activation of all three branches of unfolded protein response (UPR) and apoptotic genes. Finally, we show that 13d significantly lowers blood glucose levels and increases concomitant beta-cell survival and number in a streptozotocin-induced diabetic mouse model. Identification of beta-cell-protective small molecules against ER stress provides a new promising modality for the treatment of diabetes.

  DOI：

  10.1021/acs.jmedchem.7b00435

文献信息

• [EN] FUSED PYRAZOLE DERIVATIVES AS NOVEL ERK INHIBITORS<br/>[FR] DÉRIVÉS CONDENSÉS DE PYRAZOLE UTILISÉS COMME NOUVEAUX INHIBITEURS ERK
  申请人：SCHERING CORP

  公开号：WO2012036997A1

  公开（公告）日：2012-03-22

  Disclosed are the ERK inhibitors of Formula (I): (Formula (I)) and the pharmaceutically acceptable salts thereof. All substitutents are as defined herein. Also disclosed are methods of treating cancer using the compounds of Formula (I).

  公开了化学式（I）的ERK抑制剂：（化学式（I））及其药学上可接受的盐。所有取代基如本文所定义。还公开了使用化合物（I）治疗癌症的方法。
• Benzamide derivatives for inhibiting endoplasmic reticulum (ER) stress
  申请人：The Board of Regents of the University of Oklahoma

  公开号：US11203582B2

  公开（公告）日：2021-12-21

  Novel 3-(N-piperidinyl)methyl benzamide derivatives are disclosed. The compounds can be used in treating diseases and conditions which are associated with abnormal cell function related to endoplasmic reticulum (ER) stress. For example, the compounds can be used as suppressors of ER stress-induced pancreatic β-cell dysfunction and death, for example in the treatment of diabetes.

  新型3-(N-哌啶基)甲基苯甲酰胺衍生物被披露。这些化合物可用于治疗与内质网(ER)应激相关的异常细胞功能相关的疾病和病症。例如，这些化合物可作为ER应激诱导的胰腺β细胞功能障碍和死亡的抑制剂，例如在治疗糖尿病中使用。
• FUSED PYRAZOLE DERIVATIVES AS NOVEL ERK INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2615916B1

  公开（公告）日：2017-01-04
• BENZAMIDE DERIVATIVES FOR INHIBITING ENDOPLASMIC RETICULUM (ER) STRESS
  申请人：The Board of Regents of the University of Oklahoma

  公开号：US20200199094A1

  公开（公告）日：2020-06-25

  Novel 3-(N-piperidinyl)methyl benzamide derivatives are disclosed. The compounds can be used in treating diseases and conditions which are associated with abnormal cell function related to endoplasmic reticulum (ER) stress. For example, the compounds can be used as suppressors of ER stress-induced pancreatic β-cell dysfunction and death, for example in the treatment of diabetes.
• [EN] IMIDAZOPYRIDINE COMPOUND<br/>[FR] COMPOSÉ IMIDAZOPYRIDINE
  申请人：ASTELLAS PHARMA INC

  公开号：WO2012165399A1

  公开（公告）日：2012-12-06

  【課題】可溶性グアニル酸シクラーゼ活性化作用によるcGMP 産生増強作用に基づく、心血管疾患の優れた治療又は予防薬の提供。 【解決手段】イミダゾ[1,2-a]ピリジン骨格の３位にカルバモイル基及び８位に酸素原子を介して結合する置換基を有するイミダゾピリジン化合物が、強力な可溶性グアニル酸シクラーゼ活性化作用によるcGMP 産生増強作用を示し、可溶性グアニル酸シクラーゼが関与する種々の心血管疾患の優れた治療又は予防薬となりうることを見い出し、本発明を完成した。