4-(4,4-二甲基哌啶-1-基)苯酸乙酯 | 406233-25-8

• 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: 4-(4,4-二甲基哌啶-1-基)苯酸乙酯
• 中文别名: 4-(4,4-二甲基哌啶-1-基)苯甲酸乙酯
• 英文名称: ethyl 4-(4,4-dimethylpiperidin-1-yl)benzoate
• CAS: 406233-25-8
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: NXQBRXZLDJYLMH-UHFFFAOYSA-N

物化性质

• 熔点：
  88-90°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-(4,4-二甲基哌啶-1-基)苯酸乙酯 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 4-(4,4-二甲基哌啶-1-基)苯甲酸
  参考文献：
  名称：

  N-Acylsulfonamide apoptosis promoters

  摘要：

  N-苯甲酰芳基磺胺酰胺具有以下化学式，是BCL-X1抑制剂，有助于促进细胞凋亡。还公开了BCL-X1抑制组合物和在哺乳动物中促进细胞凋亡的方法。

  公开号：

  US20020086887A1
• 作为产物：
  描述：

  4-(4,4-二甲基-2,6-哌啶二酮-1-基)苯酸乙酯 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 various solvent(s) 为溶剂， 反应 4.25h， 以76%的产率得到4-(4,4-二甲基哌啶-1-基)苯酸乙酯
  参考文献：
  名称：

  Discovery and Structure−Activity Relationship of Antagonists of B-Cell Lymphoma 2 Family Proteins with Chemopotentiation Activity in Vitro and in Vivo

  摘要：

  Development of a rationally designed potentiator of cancer chemotherapy, via inhibition of Bcl-X-L function, is described. Lead compounds generated by NMR screening and directed parallel synthesis displayed sub mu M binding but were strongly deactivated in the presence of serum. The dominant component of serum deactivation was identified as domain III of human serum albumin (HSA); NMR solution structures of inhibitors bound to both Bcl-X-L and HSA domain III indicated two potential optimization sites for separation of affinities. Modifications at both sites resulted in compounds with improved Bcl-X-L binding and greatly increased activity in the presence of human serum, culminating in 73R, which bound to Bcl-X-L with a K-i of 0.8 nM. In a cellular assay 73R reversed the protection afforded by Bcl-X-L overexpression against cytokine deprivation in FL5.12 cells with an EC50 of 0.47 mu M. 73R showed little effect on the viability of the human non small cell lung cancer cell line A549. However, consistent with the proposed mechanism, 73R potentiated the activity of paclitaxel and UV irradiation in vitro and potentiated the antitumor efficacy of paclitaxel in a mouse xenograft model.

  DOI：

  10.1021/jm050754u

文献信息

• N-acylsulfonamide apoptosis promoters
  申请人：——

  公开号：US20020055631A1

  公开（公告）日：2002-05-09

  N-Benzoyl arylsulfonamides having the formula 1 are BCL-Xl inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-Xl inhibiting compositions and methods of promoting apoptosis in a mammal.

  N-苯甲酰芳基磺胺酰胺具有以下化学式，是BCL-Xl抑制剂，有助于促进细胞凋亡。还公开了BCL-Xl抑制组合物和在哺乳动物中促进细胞凋亡的方法。
• N-ACYLSULFONAMIDE APOPTOSIS PROMOTERS
  申请人：Augeri David J.

  公开号：US20090137585A1

  公开（公告）日：2009-05-28

  N-Benzoyl arylsulfonamides having the formula are BCL-Xl inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-Xl inhibiting compositions and methods of promoting apoptosis in a mammal.

  具有以下式子的N-苯甲酰基芳基磺酰胺是BCL-Xl抑制剂，有助于促进细胞凋亡。本文还披露了BCL-Xl抑制剂组合物和在哺乳动物中促进细胞凋亡的方法。
• Bcl-X_L-Templated Assembly of Its Own Protein−Protein Interaction Modulator from Fragments Decorated with Thio Acids and Sulfonyl Azides
  作者：Xiangdong Hu、Jiazhi Sun、Hong-Gang Wang、Roman Manetsch

  DOI：10.1021/ja802683u

  日期：2008.10.22

  Protein-protein interactions have key importance in various biological processes and modulation of particular protein-protein interactions has been shown to have therapeutic effects. However, disrupting or modulating protein-protein interactions with low-molecular-weight compounds is extremely difficult due to the lack of deep binding pockets on protein surfaces. Herein we describe the development of an unprecedented lead synthesis and discovery method that generated only biologically active compounds from a library of reactive fragments. Using the protein Bcl-X-L, a central regulator of programmed cell death, we demonstrated that an amidation reaction between thio acids and sulfonyl azides is applicable for Bcl-X-L-templated assembly of inhibitory compounds. We have demonstrated for the first time that kinetic target guided synthesis can be applied not only on enzymatic targets but also for the discovery of small molecules modulating protein-protein interactions.
• [EN] ACYLSULFONAMIDES AND PROCESSES FOR PRODUCING THE SAME<br/>[FR] ACYLSULFONAMIDES ET PROCÉDÉS POUR PRODUIRE CEUX-CI
  申请人：UNIV SOUTH FLORIDA

  公开号：WO2012021486A3

  公开（公告）日：2012-05-31
• Acylsulfonamides and Processes for Producing the Same
  申请人：Manetsch Roman

  公开号：US20110130568A1

  公开（公告）日：2011-06-02

  The present disclosure relates to acylsulfonamides and processes for their preparation. The processes involve a target-guided synthesis approach, whereby a thioacid and a sulfonyl azide are reacted in the presence of a biological target protein, a Bcl-2 family protein, to form the acylsulfonamide.