ε-[[2-Hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-N-methylbenzeneheptanamide

• 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: ε-[[2-Hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-N-methylbenzeneheptanamide
• 英文别名: 6-[2-Hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-7-phenyl-heptanoic acid methylamide；6-[[2-hydroxy-2-[4-hydroxy-3-(methanesulfonamido)phenyl]ethyl]amino]-N-methyl-7-phenylheptanamide
• 化学式: C₂₃H₃₃N₃O₅S
• 分子量: 463.598
• InChiKey: AEQVWHWUJWAWAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  136
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-(5-乙酰基-2-(苄氧基)苯基)甲磺酰胺 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 copper(ll) bromide 作用下， 以 甲醇 、 乙醇 、 氯仿 、 乙酸乙酯 、 乙腈 为溶剂， 反应 0.5h， 生成 ε-[[2-Hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-N-methylbenzeneheptanamide
  参考文献：
  名称：

  Beta 3 agonists. Part 1: evolution from inception to BMS-194449

  摘要：

  Screening of the BMS collection identified 4-hydroxy-3-methylsulfonanilidoethanolamines as full beta 3 agonists. Substitution of the ethanolamine nitrogen with a benzyl group bearing a para hydrogen bond acceptor promoted beta (3) selectivity. SAR elucidation established that highly selective beta (3) agonists were generated upon substitution of C-alpha with either benzyl to form (R)-1,2-diarylethylamines or with aryl to generate 1,1-diarylmethylamines. This latter subset yielded a clinical candidate, BMS-194449 (35).(1) (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00628-x

文献信息

• Catecholamine surrogates useful as beta 3 agonists
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0659737B1

  公开（公告）日：2003-03-26
• Beta 3 agonists. Part 1: evolution from inception to BMS-194449
  作者：W.N. Washburn、P.M. Sher、K.M. Poss、R.N. Girotra、P.J. McCann、A.V. Gavai、A.B. Mikkilineni、A. Mathur、P. Cheng、T.C. Dejneka、C.Q. Sun、T.C. Wang、T.W. Harper、A.D. Russell、D.A. Slusarchyk、S. Skwish、G.T. Allen、D.E. Hillyer、B.H. Frohlich、B.E. Abboa-Offei、M. Cap、T.L. Waldron、R.J. George、B. Tesfamariam、C.P. Ciosek、D. Ryono、D.A. Young、K.E. Dickinson、A.A. Seymour、C.M. Arbeeny、R.E. Gregg

  DOI：10.1016/s0960-894x(01)00628-x

  日期：2001.12

  Screening of the BMS collection identified 4-hydroxy-3-methylsulfonanilidoethanolamines as full beta 3 agonists. Substitution of the ethanolamine nitrogen with a benzyl group bearing a para hydrogen bond acceptor promoted beta (3) selectivity. SAR elucidation established that highly selective beta (3) agonists were generated upon substitution of C-alpha with either benzyl to form (R)-1,2-diarylethylamines or with aryl to generate 1,1-diarylmethylamines. This latter subset yielded a clinical candidate, BMS-194449 (35).(1) (C) 2001 Elsevier Science Ltd. All rights reserved.