(1S,2R)-2-[4-(2-methylquinolin-4-ylmethoxyl)benzenesulfonylamino]cyclopentane carboxylic acid | 910331-90-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2R)-2-[4-(2-methylquinolin-4-ylmethoxyl)benzenesulfonylamino]cyclopentane carboxylic acid
• 英文别名: (1S,2R)-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid；(1S,2R)-2-[[4-[(2-methylquinolin-4-yl)methoxy]phenyl]sulfonylamino]cyclopentane-1-carboxylic acid
• CAS: 910331-90-7
• 化学式: C₂₃H₂₄N₂O₅S
• 分子量: 440.52
• InChiKey: YXTGNUTYAKNZOM-RBBKRZOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-[4-(2-methylquinolin-4-ylmethoxyl)benzenesulfonylamino]cyclopentane carboxylic acid 在 1-羟基苯并三唑 、 1,2-二氯乙烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以76.8%的产率得到(1S, 2R)-2-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]cyclopentane carboxylic acid hydroxyamide
  参考文献：
  名称：

  Development of a Suitable Process for the Preparation of a TNF-α Converting Enzyme Inhibitor, WAY-281418

  摘要：

  A suitable process for the preparation of kilogram quantities of a TNF-alpha converting enzyme (TACE) inhibitor (WAY-281418) was developed using isatin 13 as starting material and an efficient coupling step for the formation of sulfonamide 8 in a 15% overall yield. Process preparation of (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid (7, (+)-cispentacin), a chiral component for WAY-281418, was successfully scaled up via an asymmetric hydrogenation reaction. Crystallization allowed the isolation of all intermediates and the final product 9.

  DOI：

  10.1021/op800090s
• 作为产物：
  描述：

  2-甲基喹啉-4-甲酸 在 N-甲基吗啉 、 氯化亚砜 、 三氟化硼乙醚 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 49.92h， 生成 (1S,2R)-2-[4-(2-methylquinolin-4-ylmethoxyl)benzenesulfonylamino]cyclopentane carboxylic acid
  参考文献：
  名称：

  Development of a Suitable Process for the Preparation of a TNF-α Converting Enzyme Inhibitor, WAY-281418

  摘要：

  A suitable process for the preparation of kilogram quantities of a TNF-alpha converting enzyme (TACE) inhibitor (WAY-281418) was developed using isatin 13 as starting material and an efficient coupling step for the formation of sulfonamide 8 in a 15% overall yield. Process preparation of (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid (7, (+)-cispentacin), a chiral component for WAY-281418, was successfully scaled up via an asymmetric hydrogenation reaction. Crystallization allowed the isolation of all intermediates and the final product 9.

  DOI：

  10.1021/op800090s

文献信息

• Beta-sulfonamide hydroxamic acid inhibitors of tace/matrix metalloproteinase
  申请人：Levin I. Jeremy

  公开号：US20060211730A1

  公开（公告）日：2006-09-21

  This invention provides compounds of Formula I, having the structure: that are useful in treating diseases or disorders mediated by TNF-α, such as arthritis (rheumatoid arthritis (RA), juvenile RA, psoriatic arthritis, osteoarthritis etc), tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection, ankylosing spondylitis, psoriasis, sepsis, multiple sclerosis, Crohn's disease, degenerative cartilage loss, asthma, idiopathic pulmonary fibrosis, vasculitis, systemic lupus erythematosus, irritable bowel syndrome, acute coronary syndrome, hepatitis C, cachexia, COPD, stroke or type 2 diabetes, and for alleviation of symptoms thereof. The invention further provides methods for use of the compounds.

  这项发明提供了具有结构的Formula I的化合物，这些化合物在治疗由TNF-α介导的疾病或紊乱方面非常有用，如关节炎（类风湿关节炎（RA），幼年RA，银屑病性关节炎，骨关节炎等），肿瘤转移，组织溃疡，异常伤口愈合，牙周病，骨病，糖尿病（胰岛素抵抗）和HIV感染，强直性脊柱炎，银屑病，败血症，多发性硬化，克罗恩病，退行性软骨丢失，哮喘，特发性肺纤维化，血管炎，系统性红斑狼疮，肠易激综合征，急性冠状动脉综合征，丙型肝炎，虚弱，慢性阻塞性肺病，中风或2型糖尿病的缓解症状。该发明还提供了使用这些化合物的方法。
• US7595327B2
  申请人：——

  公开号：US7595327B2

  公开（公告）日：2009-09-29