N-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-methyl-beta-alanine | 287096-74-6

• 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-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-methyl-beta-alanine
• 英文别名: 3-[(4-But-2-ynoxyphenyl)sulfonyl-methylamino]propanoic acid
• CAS: 287096-74-6
• 化学式: C₁₄H₁₇NO₅S
• 分子量: 311.359
• InChiKey: UENULLRIXRZBLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  522.0±60.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-methyl-beta-alanine 在 草酰氯 、 羟胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-({[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino)-N-hydroxypropanamide
  参考文献：
  名称：

  Acetylenic TACE inhibitors. Part 1. SAR of the acyclic sulfonamide hydroxamates

  摘要：

  The SAR of a series of potent sulfonamide hydroxamate TACE inhibitors, all bearing a butynyloxy P1' group, was explored. In particular, compound 5j has excellent in vitro potency against isolated TACE enzyme and in cells, good selectivity over MMP-1 and MMP-9, and oral activity in an in vivo model of TNF-alpha production and a collagen-induced arthritis model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00514-6
• 作为产物：
  描述：

  sodium p-hydroxybenzenesulfonate 在 sodium hydroxide 、 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-methyl-beta-alanine
  参考文献：
  名称：

  Acetylenic TACE inhibitors. Part 1. SAR of the acyclic sulfonamide hydroxamates

  摘要：

  The SAR of a series of potent sulfonamide hydroxamate TACE inhibitors, all bearing a butynyloxy P1' group, was explored. In particular, compound 5j has excellent in vitro potency against isolated TACE enzyme and in cells, good selectivity over MMP-1 and MMP-9, and oral activity in an in vivo model of TNF-alpha production and a collagen-induced arthritis model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00514-6

文献信息

• ACETYLENIC (BETA)-SULFONAMIDO AND PHOSPHINIC ACID AMIDE HYDROXAMIC ACID TACE INHIBITORS
  申请人：American Cyanamid Company

  公开号：EP1147078A1

  公开（公告）日：2001-10-24
• US6326516B1
  申请人：——

  公开号：US6326516B1

  公开（公告）日：2001-12-04
• [EN] ACETYLENIC DOLLAR G(b)-SULFONAMIDO AND PHOSPHINIC ACID AMIDE HYDROXAMIC ACID TACE INHIBITORS<br/>[FR] INHIBITEURS DES TACE A BASE D'ACIDES HYDROXAMIQUES DES ACIDES PHOSPHINIQUE ET DOLLAR G(b)-SULFONAMIDO ACETYLENIQUE
  申请人：AMERICAN CYANAMID CO

  公开号：WO2000044711A1

  公开（公告）日：2000-08-03

  The invention discloses hydroxamide acids of formula (B) which 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. In the above formula, the dotted line represents an optional double bond, and R5, R6, R7, R8, R11, R12, X, Y and Z have the meanings given in the specification.
• Acetylenic TACE inhibitors. Part 1. SAR of the acyclic sulfonamide hydroxamates
  作者：J.I. Levin、J.M. Chen、K. Cheung、D. Cole、C. Crago、E.Delos Santos、X. Du、G. Khafizova、G. MacEwan、C. Niu、E.J. Salaski、A. Zask、T. Cummons、A. Sung、J. Xu、Y. Zhang、W. Xu、S. Ayral-Kaloustian、G. Jin、R. Cowling、D. Barone、K.M. Mohler、R.A. Black、J.S. Skotnicki

  DOI：10.1016/s0960-894x(03)00514-6

  日期：2003.8

  The SAR of a series of potent sulfonamide hydroxamate TACE inhibitors, all bearing a butynyloxy P1' group, was explored. In particular, compound 5j has excellent in vitro potency against isolated TACE enzyme and in cells, good selectivity over MMP-1 and MMP-9, and oral activity in an in vivo model of TNF-alpha production and a collagen-induced arthritis model. (C) 2003 Elsevier Ltd. All rights reserved.