N-(3-(aminomethyl)phenyl)benzamide | 926203-34-1

• 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: N-(3-(aminomethyl)phenyl)benzamide
• 英文别名: N-[3-(aminomethyl)phenyl]benzamide
• CAS: 926203-34-1
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: XGIXEORXPRJHOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯并噻吩-2-羧酸 、 N-(3-(aminomethyl)phenyl)benzamide 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以41.5%的产率得到benzo[b]thiophene-2-carboxylic acid 3-benzoylaminobenzylamide
  参考文献：
  名称：

  Identification of SENP1 inhibitors through in silico screening and rational drug design

  摘要：

  The small ubiquitin-related modifier (SUMO)-specific proteases (SENPs) catalyze the deconjugation of SUMO from their substrate proteins. SENP1 which is the most studied isoform is closely related to many cancers such as prostate cancer and colon cancer, thus representing a potential therapeutic target for cancer treatment. In the present study, we identified eleven SENP1 inhibitors representing a variety of scaffolds through in silico screening. Based on these scaffolds, a series of new compounds were designed and synthesized in order to improve their SENP1 inhibitory potency. As a result, compounds with IC50 as low as 3.5 mu M (compound 13m) were obtained and a preliminary structure-activity relationship was discussed. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.06.018
• 作为产物：
  描述：

  3-氨基苄胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 N-(3-(aminomethyl)phenyl)benzamide
  参考文献：
  名称：

  Identification of SENP1 inhibitors through in silico screening and rational drug design

  摘要：

  The small ubiquitin-related modifier (SUMO)-specific proteases (SENPs) catalyze the deconjugation of SUMO from their substrate proteins. SENP1 which is the most studied isoform is closely related to many cancers such as prostate cancer and colon cancer, thus representing a potential therapeutic target for cancer treatment. In the present study, we identified eleven SENP1 inhibitors representing a variety of scaffolds through in silico screening. Based on these scaffolds, a series of new compounds were designed and synthesized in order to improve their SENP1 inhibitory potency. As a result, compounds with IC50 as low as 3.5 mu M (compound 13m) were obtained and a preliminary structure-activity relationship was discussed. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.06.018

文献信息

• Benzothiophene-2-carboxamide derivatives as SENPs inhibitors with selectivity within SENPs family
  作者：Zhongli Wang、Yunqi Liu、Jianchen Zhang、Shafi Ullah、Ning Kang、Yaxue Zhao、Huchen Zhou

  DOI：10.1016/j.ejmech.2020.112553

  日期：2020.10

  The SUMO (small ubiquitin-related modifier)-specific proteases (SENPs) are responsible for the cleavage of SUMO from its target proteins, thus play important roles in the dynamic SUMOylation and deSU-MOylation processes. SENPs are related to a variety of human diseases including cancer and represent a new class of potential therapeutic targets with mechanism of action that is likely to be different from that of current clinically used drugs. However, potent inhibitors that are selective within the SENPs family members still remain a challenge due to their high homology. In order to demonstrate the feasibility of developing selective inhibitors within the SENPs family, we chose SENP1/2/5 as representatives, aiming to identify inhibitors with selectivity among the members. Starting from a hit compound ZCL951 from virtual screening, a series of benzothiophene-2-carboxamide inhibitors were designed based on the protein structures of SENP1, 2, and 5. First, an unoccupied hydrophobic pocket was first identified which led to IC50 as low as 0.56 mu M. Furthermore, the ethylacetate 77 gave both submicromolar inhibitory activity and 33-fold selectivity for SENP2 versus SENP5. They are the most potent and selective nonpeptidic inhibitor reported so far for the SENPs family, as far as we are aware. Their structure-activity relationship was also discussed. (C) 2020 Elsevier Masson SAS. All rights reserved.
• Trisubstituted ureas as potent and selective mPGES-1 inhibitors
  作者：Jean-François Chiasson、Louise Boulet、Christine Brideau、Anh Chau、David Claveau、Bernard Côté、Diane Ethier、André Giroux、Jocelyne Guay、Sébastien Guiral、Joseph Mancini、Frédéric Massé、Nathalie Méthot、Denis Riendeau、Patrick Roy、Joel Rubin、Daigen Xu、Hongping Yu、Yves Ducharme、Richard W. Friesen

  DOI：10.1016/j.bmcl.2011.01.006

  日期：2011.3

  A novel series of trisubstituted ureas has been identified as potent and selective mPGES-1 inhibitors. These compounds are selective over other prostanoid enzymes such as PGF synthase and TX synthase. This series of inhibitors was developed by lead optimization of a hit from an internal HTS campaign. Lead compound 42 is potent in A549 cell assay (IC50 of 0.34 mu M) and in human whole blood assay (IC50 of 2.1 mu M). An efficient and versatile one-pot strategy for the formation of ureas, involving a reductive amination, was developed to generate these inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.
• ANILINE DERIVATIVES HAVING NITROGEN MONOXIDE SYNTHASE INHIBITORY ACTIVITY
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0798292B1

  公开（公告）日：2004-11-03
• US6534546B1
  申请人：——

  公开号：US6534546B1

  公开（公告）日：2003-03-18
• Identification of SENP1 inhibitors through in silico screening and rational drug design
  作者：Yaxue Zhao、Zhongli Wang、Jianchen Zhang、Huchen Zhou

  DOI：10.1016/j.ejmech.2016.06.018

  日期：2016.10

  The small ubiquitin-related modifier (SUMO)-specific proteases (SENPs) catalyze the deconjugation of SUMO from their substrate proteins. SENP1 which is the most studied isoform is closely related to many cancers such as prostate cancer and colon cancer, thus representing a potential therapeutic target for cancer treatment. In the present study, we identified eleven SENP1 inhibitors representing a variety of scaffolds through in silico screening. Based on these scaffolds, a series of new compounds were designed and synthesized in order to improve their SENP1 inhibitory potency. As a result, compounds with IC50 as low as 3.5 mu M (compound 13m) were obtained and a preliminary structure-activity relationship was discussed. (C) 2016 Elsevier Masson SAS. All rights reserved.