N-[(4-bromophenyl)methyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide | 1024276-54-7

• 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-bromophenyl)methyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide
• CAS: 1024276-54-7
• 化学式: C₁₂H₁₃BrN₂O₃S
• mdl: MFCD16386319
• 分子量: 345.217
• InChiKey: WMVYWUHLVUCJJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(4-bromophenyl)methyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide 、 5-氟-2-甲氧基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[[4-(5-fluoro-2-methoxyphenyl)phenyl]methyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide
  参考文献：
  名称：

  Discovery and optimisation of a selective non-steroidal glucocorticoid receptor antagonist

  摘要：

  High-throughput screening of 3.87 million compounds delivered a novel series of non-steroidal GR antagonists. Subsequent rounds of optimisation allowed progression from a non-selective ligand with a poor ADMET profile to an orally bioavailable, selective, stable, glucocorticoid receptor antagonist. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.11.054
• 作为产物：
  描述：

  3,5-二甲基异唑-4-磺酰氯 、 对溴苄胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到N-[(4-bromophenyl)methyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide
  参考文献：
  名称：

  Discovery and optimisation of a selective non-steroidal glucocorticoid receptor antagonist

  摘要：

  High-throughput screening of 3.87 million compounds delivered a novel series of non-steroidal GR antagonists. Subsequent rounds of optimisation allowed progression from a non-selective ligand with a poor ADMET profile to an orally bioavailable, selective, stable, glucocorticoid receptor antagonist. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.11.054

文献信息

• Design and synthesis of aryl sulfonamide-based nonsteroidal mineralocorticoid receptor antagonists
  作者：Kentaro Futatsugi、David W. Piotrowski、Agustin Casimiro-Garcia、Shaughn Robinson、Matthew Sammons、Paula M. Loria、Mary E. Banker、Donna N. Petersen、Natalia J. Schmidt

  DOI：10.1016/j.bmcl.2013.09.099

  日期：2013.12

  Hit-to-lead medicinal chemistry efforts are described starting from a screening hit 1, leading to a new class of aryl sulfonamide-based MR antagonist, exemplified by 17, that possesses favourable MR binding affinity, selectivity profile against closely related NHRs, physicochemical properties and metabolic stability. (C) 2013 Elsevier Ltd. All rights reserved.
• Discovery and optimisation of a selective non-steroidal glucocorticoid receptor antagonist
  作者：Angus R. Brown、Michael Bosies、Helen Cameron、John Clark、Angela Cowley、Mark Craighead、Moira A. Elmore、Alistair Firth、Richard Goodwin、Susan Goutcher、Emma Grant、Morag Grassie、Simon J.A. Grove、Niall M. Hamilton、Hannah Hampson、Alison Hillier、Koc-Kan Ho、Michael Kiczun、Celia Kingsbury、Steven G. Kultgen、Peter T.A. Littlewood、Scott J. Lusher、Susan MacDonald、Lorraine McIntosh、Theresa McIntyre、Ashvin Mistry、J. Richard Morphy、Olaf Nimz、Michael Ohlmeyer、Jack Pick、Zoran Rankovic、Brad Sherborne、Alasdair Smith、Michael Speake、Gayle Spinks、Fiona Thomson、Lynn Watson、Mark Weston

  DOI：10.1016/j.bmcl.2010.11.054

  日期：2011.1

  High-throughput screening of 3.87 million compounds delivered a novel series of non-steroidal GR antagonists. Subsequent rounds of optimisation allowed progression from a non-selective ligand with a poor ADMET profile to an orally bioavailable, selective, stable, glucocorticoid receptor antagonist. (C) 2010 Published by Elsevier Ltd.