4-([4-(2-butynyloxy)phenyl]sulfonyl}-morpholine-3-carboxylic acid,methyl ester | 287408-02-0

• 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: 4-([4-(2-butynyloxy)phenyl]sulfonyl}-morpholine-3-carboxylic acid,methyl ester
• 英文别名: 4-([4-(2-Butynyloxy)phenyl]sulfonyl}-morpholine-3-carboxylic acid, methyl ester；methyl 4-(4-but-2-ynoxyphenyl)sulfonylmorpholine-3-carboxylate
• CAS: 287408-02-0
• 化学式: C₁₆H₁₉NO₆S
• 分子量: 353.396
• InChiKey: JXVXHIZWHLNNKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  90.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-([4-(2-butynyloxy)phenyl]sulfonyl}-morpholine-3-carboxylic acid,methyl ester 在 lithium hydroxide 、 草酰氯 、 羟胺 、 N,N-二甲基甲酰胺 作用下， 生成 4-([4-(2-Butynyloxy)phenyl]sulfonyl}-N-hydroxy-3-morpholinecarboxamide
  参考文献：
  名称：

  Acetylenic TACE inhibitors. Part 2: SAR of six-membered cyclic sulfonamide hydroxamates

  摘要：

  The SAR of a series of potent sulfonamide hydroxamate TACE inhibitors bearing a butynyloxy P1' group was explored. In particular, compound 5k has excellent in vitro potency against TACE enzyme and in cells, and oral activity in an in vivo model of TNF-alpha production and a collagen-induced arthritis model.

  DOI：

  10.1016/j.bmcl.2005.06.072
• 作为产物：
  描述：

  methyl 2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-3-hydroxypropanoate 在 三氟化硼乙醚 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-([4-(2-butynyloxy)phenyl]sulfonyl}-morpholine-3-carboxylic acid,methyl ester
  参考文献：
  名称：

  Acetylenic TACE inhibitors. Part 2: SAR of six-membered cyclic sulfonamide hydroxamates

  摘要：

  The SAR of a series of potent sulfonamide hydroxamate TACE inhibitors bearing a butynyloxy P1' group was explored. In particular, compound 5k has excellent in vitro potency against TACE enzyme and in cells, and oral activity in an in vivo model of TNF-alpha production and a collagen-induced arthritis model.

  DOI：

  10.1016/j.bmcl.2005.06.072

文献信息

• Acetylenic alpha -amino acid-based sulfonamide hydroxamic acid tace inhibitors
  申请人：——

  公开号：US20030008849A1

  公开（公告）日：2003-01-09

  Compounds of the formula: 1 are useful in treating disease conditions mediated by TNF-&agr;, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.

  公式为1的化合物可用于治疗由TNF-&agr;介导的疾病条件，例如类风湿性关节炎、骨关节炎、败血症、艾滋病、溃疡性结肠炎、多发性硬化症、克罗恩病和退行性软骨丢失。
• Acetylenic alpha-amino acid-based sulfonamide hydroxamic acid tace inhibitors
  申请人：Levin I. Jeremy

  公开号：US20050113346A1

  公开（公告）日：2005-05-26

  Compounds of the formula: are useful in treating disease conditions mediated by TNF-α, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.

  式为的化合物在治疗由TNF-α介导的疾病条件方面非常有用，例如类风湿性关节炎、骨关节炎、败血症、艾滋病、溃疡性结肠炎、多发性硬化症、克罗恩病和退行性软骨损失。
• Acetylenic &agr;-amino acid-based sulfonamide hydroxamic acid tace inhibitors
  申请人：American Cyanamid Company

  公开号：US06225311B1

  公开（公告）日：2001-05-01

  Compounds of the formula: are useful in treating disease conditions mediated by TNF-&agr;, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.

  分子式为的化合物在治疗由TNF-α介导的疾病条件方面非常有用，例如类风湿性关节炎，骨关节炎，败血症，艾滋病，溃疡性结肠炎，多发性硬化症，克罗恩病和退行性软骨丢失。
• ACETYLENIC ALPHA-AMINO ACID-BASED SULFONAMIDE HYDROXAMIC ACID TACE INHIBITORS
  申请人：Wyeth Holdings Corporation

  公开号：EP1144368B1

  公开（公告）日：2004-07-14
• Acetylenic TACE inhibitors. Part 2: SAR of six-membered cyclic sulfonamide hydroxamates
  作者：J.I. Levin、J.M. Chen、L.M. Laakso、M. Du、X. Du、A.M. Venkatesan、V. Sandanayaka、A. Zask、J. Xu、W. Xu、Y. Zhang、J.S. Skotnicki

  DOI：10.1016/j.bmcl.2005.06.072

  日期：2005.10

  The SAR of a series of potent sulfonamide hydroxamate TACE inhibitors bearing a butynyloxy P1' group was explored. In particular, compound 5k has excellent in vitro potency against TACE enzyme and in cells, and oral activity in an in vivo model of TNF-alpha production and a collagen-induced arthritis model.