N-hydroxy-3-(1-(3-(naphthalen-2-yl)propyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanamide | 798543-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-hydroxy-3-(1-(3-(naphthalen-2-yl)propyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanamide
• 英文别名: A452；N-hydroxy-3-[1-(3-naphthalen-2-yl-propyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-propionamide；N-hydroxy-3-[1-(3-naphthalene-2-yl-propyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-propionamide；N-hydroxy-3-[1-(3-naphthalen-2-ylpropyl)-5-oxo-2H-pyrrol-4-yl]propanamide
• CAS: 798543-42-7
• 化学式: C₂₀H₂₂N₂O₃
• 分子量: 338.406
• InChiKey: ZIQAJFVTKUTVEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-methoxy-2-methylene-5-oxopentanoic acid 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 羟胺钾盐 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-hydroxy-3-(1-(3-(naphthalen-2-yl)propyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanamide
  参考文献：
  名称：

  基于结构和性能的γ-内酰胺基HDAC抑制剂的设计，合成和生物学评估

  摘要：

  组蛋白脱乙酰基酶（HDAC）参与翻译后修饰和基因表达。癌细胞通过Epi募集了一定数量的HDAC来维持生存-肿瘤抑制基因的基因下调。HDAC已经成为治疗癌症的有希望的靶标，并且如今已经研究了许多HDAC抑制剂。在先前的研究中，我们合成了δ-内酰胺核心HDAC抑制剂，该抑制剂具有强大的HDAC抑制活性以及癌细胞生长抑制活性。通过对δ-内酰胺类抑制剂的QSAR研究，表明较小的核比较大的核更有活性，因为它更适合HDAC酶活性口袋的狭窄疏水通道。设计和合成了较小的γ-内酰胺核心HDAC抑制剂，以优化生物学和性能。引入苯基，萘基和硫代苯基作为帽基。疏水性和大体积的帽基团由于HDAC与抑制剂之间的疏水性相互作用而提高了HDAC抑制能力。

  DOI：

  10.1016/j.bmcl.2010.12.079

文献信息

• [EN] NOVEL 2-OXO-HETEROCYCLIC COMPOUNDS AND THE PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME<br/>[FR] NOUVEAUX COMPOSES 2-OXO-HETEROCYCLIQUES ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CES COMPOSES
  申请人：KOREA RES INST OF BIOSCIENCE

  公开号：WO2004101523A1

  公开（公告）日：2004-11-25

  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.

  本发明涉及新的2-氧代环化合物及其制备方法和包含其的药物组合物。本发明提供了一种用于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，例如类风湿性关节炎、脊柱关节病、痛风、骨关节炎、全身性红斑狼疮和儿童关节炎，以及炎症综合征，例如肌炎、牙龈炎、滑囊炎、强直性脊柱炎、滑囊炎、烧伤和疤痕、炎症性克罗恩病、I型糖尿病等。因此，它可以用作治疗和预防炎症性疾病的治疗药物。
• Structure and property based design, synthesis and biological evaluation of γ-lactam based HDAC inhibitors
  作者：Eunhyun Choi、Chulho Lee、Jung Eun Park、Jeong Jea Seo、Misun Cho、Jong Soon Kang、Hwan Mook Kim、Song-Kyu Park、Kiho Lee、Gyoonhee Han

  DOI：10.1016/j.bmcl.2010.12.079

  日期：2011.2

  enzyme. The smaller γ-lactam core HDAC inhibitors were designed and synthesized for biological and property optimization. Phenyl, naphthyl and thiophenyl groups were introduced as the cap groups. Hydrophobic and bulky cap groups increase potency of HDAC inhibition because of hydrophobic interaction between HDAC and inhibitors. In overall, γ-lactam based HDAC inhibitors showed more potent than δ-lactam analogues

  组蛋白脱乙酰基酶（HDAC）参与翻译后修饰和基因表达。癌细胞通过Epi募集了一定数量的HDAC来维持生存-肿瘤抑制基因的基因下调。HDAC已经成为治疗癌症的有希望的靶标，并且如今已经研究了许多HDAC抑制剂。在先前的研究中，我们合成了δ-内酰胺核心HDAC抑制剂，该抑制剂具有强大的HDAC抑制活性以及癌细胞生长抑制活性。通过对δ-内酰胺类抑制剂的QSAR研究，表明较小的核比较大的核更有活性，因为它更适合HDAC酶活性口袋的狭窄疏水通道。设计和合成了较小的γ-内酰胺核心HDAC抑制剂，以优化生物学和性能。引入苯基，萘基和硫代苯基作为帽基。疏水性和大体积的帽基团由于HDAC与抑制剂之间的疏水性相互作用而提高了HDAC抑制能力。
• Use of novel 2-oxo-heterocyclic compounds and the pharmaceutical compositions comprising the same
  申请人：Han Hee Gyoon

  公开号：US20060173043A1

  公开（公告）日：2006-08-03

  The present invention is related to novel use of 2-oxo-heterocyclic compounds having anticancer activity and the process for preparing them and a pharmaceutical composition comprising the same. The present invention provides a pharmaceutical composition for preventing and treating the cancer disease comprising lung cancer, bone cancer, pancreatic cancer, skin cancer, cancer of the head and neck, cutaneous or intraocular melanoma, uterine cancer, ovarian cancer, rectal cancer or cancer of the anal region, stomach cancer, colon cancer, breast cancer, gynecologic tumors, Hodgkin's disease, cancer of the esophagus, cancer of the small intestine, cancer of the endocrine system, sarcomas of soft tissues, cancer of the urethra, cancer of the penis, prostate cancer, chronic or acute leukemia, solid tumors of childhood, lymphocytic lymphonas, cancer of the bladder, cancer of the kidney or ureter, or neoplasms of the central nervous system, therefore, it can be used as the therapeutics for treating and preventing cancer diseases.

  本发明涉及具有抗癌活性的2-氧代杂环化合物的新用途及其制备过程，以及包含它们的药物组合物。本发明提供了一种用于预防和治疗肺癌、骨癌、胰腺癌、皮肤癌、头颈部癌症、皮肤或眼内黑色素瘤、子宫癌、卵巢癌、直肠癌或肛门区癌症、胃癌、结肠癌、乳腺癌、妇科肿瘤、霍奇金病、食管癌、小肠癌、内分泌系统癌症、软组织肉瘤、尿道癌、阴茎癌、前列腺癌、慢性或急性白血病、儿童实体瘤、淋巴细胞性淋巴瘤、膀胱癌、肾或输尿管癌或中枢神经系统肿瘤的药物组合物，因此，它可以用作治疗和预防癌症疾病的治疗药物。
• Novel 2-oxo-heterocyclic compounds and the pharmaceutical compositions comprising the same
  申请人：Kho Hee Yung

  公开号：US20070167486A1

  公开（公告）日：2007-07-19

  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.

  本发明涉及新的2-氧代环状化合物及其制备方法和包含它们的药物组合物。本发明提供了一种用于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、全身性红斑狼疮和儿童关节炎，以及炎症综合征，例如肌炎、牙龈炎、滑膜炎、强直性脊柱炎、滑囊炎、烧伤和疤痕、炎性克罗恩病、1型糖尿病等。因此，它可以用作治疗和预防炎症性疾病的治疗剂。
• 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。