N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-nitrophenyl)methyl]-2-phenoxyacetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-nitrophenyl)methyl]-2-phenoxyacetamide
• 英文别名: N-((5-chloro-8-hydroxyquinolin-7-yl)(4-nitrophenyl)methyl)-2-phenoxyacetamide；N-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-nitrophenyl)methyl]-2-phenoxyacetamide
• 化学式: C₂₄H₁₈ClN₃O₅
• 分子量: 463.877
• InChiKey: QIYPSJBTWQBWJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯氧乙酰胺 、 对硝基苯甲醛 、 5-氯-8-羟基喹啉 生成 N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-nitrophenyl)methyl]-2-phenoxyacetamide
  参考文献：
  名称：

  N-((8-Hydroxy-5-substituted-quinolin-7-yl)(phenyl)methyl)-2-phenyloxy/amino-acetamide inhibitors of ADAMTS-5 (Aggrecanase-2)

  摘要：

  N-((8-Hydroxy-5-substituted-quinolin-7-yl)(phenyl)methyl)-2-phenyloxy/amino-acetamide inhibitors of ADAMTS-5 (Aggrecanase-2) have been prepared. Selected compounds 10, 14, 25, and 53 show sub-mu M ADAMTS-5 potency and good selectivity over the related metalloproteases ADAMTS-4 (Aggrecanase-1), MMP-13, and MMP-12. Compound 53 shows a good balance of potent ADAMTS-5 inhibition, moderate CYP3A4 inhibition and good rat liver microsome stability. This series of compounds represents progress towards selective ADAMTS-5 inhibitors as disease modifying osteoarthritis agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.065

文献信息

• 8-Hydroxyquinoline compounds and methods thereof
  申请人：Bursavich Matthew G.

  公开号：US20080269213A1

  公开（公告）日：2008-10-30

  The present invention relates to 8-Hydroxyquinoline Compounds; compositions comprising an 8-Hydroxyquinoline Compound; and methods for treating or preventing a metalloproteinase-related disorder, such as, an arthritic disorder, osteoarthritis, malignant neoplasm, rheumatoid arthritis, asthma, chronic obstructive pulmonary disease, atherosclerosis, age-related macular degeneration, myocardial infarction, a corneal ulceration, an ocular surface disease, hepatitis, an aortic aneurysm, tendonitis, a central nervous system disorder, abnormal wound healing, angiogenesis, restenosis, cirrhosis, multiple sclerosis, glomerulonephritis, graft versus host disease, diabetes, an inflammatory bowel disease, shock, invertebral disc degeneration, stroke, osteopenia or a periodontal disease or comprising administering an effective dose of an 8-Hydroxyquinoline Compound to a mammal in need thereof.

  本发明涉及8-羟基喹啉化合物；包含一种8-羟基喹啉化合物的组合物；以及治疗或预防金属蛋白酶相关疾病的方法，例如关节炎、骨关节炎、恶性肿瘤、类风湿性关节炎、哮喘、慢性阻塞性肺病、动脉粥样硬化、年龄相关性黄斑变性、心肌梗死、角膜溃疡、眼表疾病、肝炎、主动脉瘤、肌腱炎、中枢神经系统疾病、异常伤口愈合、血管生成、再狭窄、肝硬化、多发性硬化症、肾小球肾炎、移植物抗宿主病、糖尿病、炎性肠病、休克、椎间盘退化、中风、骨质疏松或牙周疾病；或者包括向需要的哺乳动物施用有效剂量的8-羟基喹啉化合物。
• 8-HYDROXYQUINOLINE COMPOUNDS AND METHODS THEREOF
  申请人：Wyeth

  公开号：EP2056823A2

  公开（公告）日：2009-05-13
• GLYCOSAMINOGLYCAN INHIBITORS
  申请人：Crawford Brett E.

  公开号：US20120295890A1

  公开（公告）日：2012-11-22

  Provided herein are chondroitin sulfate inhibitors, including modulators of glycosylation, and/or sulfation of galactose or N-acetyl galactosamine glycosaminoglycans.
• US7947712B2
  申请人：——

  公开号：US7947712B2

  公开（公告）日：2011-05-24
• [EN] 8-HYDROXYQUINOLINE COMPOUNDS AND METHODS THEREOF<br/>[FR] COMPOSÉS DE 8-HYDROXYQUINOLÉINE ET PROCÉDÉS ASSOCIÉS À CEUX-CI
  申请人：WYETH CORP

  公开号：WO2008024922A2

  公开（公告）日：2008-02-28

  [EN] The present invention relates to 8-Hydroxyquinoline Compounds; compositions comprising an 8-Hydroxyquinoline Compound; and methods for treating or preventing a metalloproteinase-related disorder, such as, an arthritic disorder, osteoarthritis, malignant neoplasm, rheumatoid arthritis, asthma, chronic obstructive pulmonary disease, atherosclerosis, age-related macular degeneration, myocardial infarction, a corneal ulceration, an ocular surface disease, hepatitis, an aortic aneurysm, tendonitis, a central nervous system disorder, abnormal wound healing, angiogenesis, restenosis, cirrhosis, multiple sclerosis, glomerulonephritis, graft versus host disease, diabetes, an inflammatory bowel disease, shock, invertebral disc degeneration, stroke, osteopenia or a periodontal disease or comprising administering an effective dose of an 8-Hydroxyquinoline Compound to a mammal in need thereof.
  [FR] La présente invention concerne des composés de 8-hydroxyquinoléine ; des compositions comprenant un composé de 8-hydroxyquinoléine ; et des procédés servant à traiter ou à prévenir un trouble lié aux métalloprotéinases, tel qu'une maladie arthritique, l'arthrose, un néoplasme malin, la polyarthrite rhumatoïde, l'asthme, une bronchopneumopathie chronique obstructive, l'athérosclérose, la dégénérescence maculaire liée à l'âge, l'infarctus du myocarde, un ulcère cornéen, une maladie de la surface de l'oel, l'hépatite, un anévrisme de l'aorte, une tendinite, une maladie du système nerveux central, une cicatrisation de plaie anormale, l'angiogenèse, la resténose, la cirrhose, la sclérose en plaques, la glomérulonéphrite, la réaction de greffe contre hôte, le diabète, une maladie abdominale inflammatoire, un choc, une dégénérescence de disques intervertébraux, une attaque, l'ostéopénie ou une parodontopathie, ou consistant à administrer une dose efficace d'un composé de 8-hydroxyquinoléine à un mammifère qui en a besoin.