N-hydroxy-3-[2-oxo-1-[4-(toluene-4-sulfonylamino)-benzyl]-1,2,5,6-tetrahydro-pyridin-3-yl]-propionamide

• 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-hydroxy-3-[2-oxo-1-[4-(toluene-4-sulfonylamino)-benzyl]-1,2,5,6-tetrahydro-pyridin-3-yl]-propionamide
• 英文别名: N-hydroxy-3-[1-[[4-[(4-methylphenyl)sulfonylamino]phenyl]methyl]-6-oxo-2,3-dihydropyridin-5-yl]propanamide
• 化学式: C₂₂H₂₅N₃O₅S
• 分子量: 443.524
• InChiKey: YKAMAXPMUZNLTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-硝基苄胺 在 Grubbs catalyst first generation 4-二甲氨基吡啶 、 TEA 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 锌 作用下， 以 甲醇 为溶剂， 生成 N-hydroxy-3-[2-oxo-1-[4-(toluene-4-sulfonylamino)-benzyl]-1,2,5,6-tetrahydro-pyridin-3-yl]-propionamide
  参考文献：
  名称：

  Modification of cap group in δ-lactam-based histone deacetylase (HDAC) inhibitors

  摘要：

  Novel delta-lactam-based HDAC inhibitors which have various substituted benzyl, bi-aromatic cap groups were prepared using ring closure metathesis reaction, and evaluated their HDAC inhibitory activities and anti-proliferative effects. Among prepared analogues, 11m and 11o have very strong HDAC enzymatic inhibition and showed the most potent growth inhibitory activity to five human tumor cell lines including PC-3, ACHN, NUGC-3, HCT-15, and MBA-MB-231 tumor cell lines. Compounds 11m and 11o also showed good tumor growth inhibition of MDA-MB-231 cells in in vivo xenograft model. Structure-activity relationship study using docking model explained the significance of hydrophobic aromatic cap groups for their in vitro activities. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.034

文献信息

• Novel 2-Oxo-Heterocyclic Compounds And The Pharmaceutical Compositions Comprising The Same
  申请人：KHO Yung Hee

  公开号：US20100286207A1

  公开（公告）日：2010-11-11

  The present invention is related to new 2-oxo-cyclic compound, the process for preparing them and a pharmaceutical composition comprising the same. The present invention provides a pharmaceutical composition for preventing and treating the inflammatory disease comprising the pain or inflammation caused by rheumatic disease, for example, rheumatoid arthritis, spondyloarthopathies, gout, osteoarthritis, systemic lupus erythematosus and juvenile arthritis, and inflammatory syndrome for example, from myositis, gingivitis, synovitis, ankylosing spondylitis, burstitis, burns and scar, inflammatory Crohn's disease, Types I diabetes. therefore, it can be used as the therapeutics for treating and preventing inflammatory diseases.

  本发明涉及一种新的2-氧代环状化合物、其制备方法以及包含其的药物组合物。本发明提供了一种预防和治疗炎症性疾病的药物组合物，包括由风湿性疾病引起的疼痛或炎症，例如风湿性关节炎、脊柱关节病、痛风、骨关节炎、系统性红斑狼疮和少年关节炎，以及由肌炎、牙龈炎、滑膜炎、强直性脊柱炎、滑囊炎、烧伤和瘢痕、炎症性克罗恩病、1型糖尿病等引起的炎症综合征。因此，它可以用作治疗和预防炎症性疾病的治疗药物。
• US7723376B2
  申请人：——

  公开号：US7723376B2

  公开（公告）日：2010-05-25
• Modification of cap group in δ-lactam-based histone deacetylase (HDAC) inhibitors
  作者：Hwan Mook Kim、Sung Hee Hong、Myung Sook Kim、Chang Woo Lee、Jong Soon Kang、Kiho Lee、Song-Kyu Park、Jeung Whan Han、Hee Yoon Lee、Yongseok Choi、Ho Jeung Kwon、Gyoonhee Han

  DOI：10.1016/j.bmcl.2007.09.034

  日期：2007.11

  Novel delta-lactam-based HDAC inhibitors which have various substituted benzyl, bi-aromatic cap groups were prepared using ring closure metathesis reaction, and evaluated their HDAC inhibitory activities and anti-proliferative effects. Among prepared analogues, 11m and 11o have very strong HDAC enzymatic inhibition and showed the most potent growth inhibitory activity to five human tumor cell lines including PC-3, ACHN, NUGC-3, HCT-15, and MBA-MB-231 tumor cell lines. Compounds 11m and 11o also showed good tumor growth inhibition of MDA-MB-231 cells in in vivo xenograft model. Structure-activity relationship study using docking model explained the significance of hydrophobic aromatic cap groups for their in vitro activities. (C) 2007 Elsevier Ltd. All rights reserved.