(S)-2-[1-(N-Benzyloxycarbonylamino)-3-methyl]butylimidazole | 149357-58-4

• 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: (S)-2-[1-(N-Benzyloxycarbonylamino)-3-methyl]butylimidazole
• 英文别名: benzyl N-[(1S)-1-(1H-imidazol-2-yl)-3-methylbutyl]carbamate
• CAS: 149357-58-4
• 化学式: C₁₆H₂₁N₃O₂
• 分子量: 287.362
• InChiKey: ZIDGYXDWSCCEHE-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-[1-(N-Benzyloxycarbonylamino)-3-methyl]butylimidazole 在 palladium on activated charcoal 氢气 作用下， 生成 (S)-2-(1-Amino-3-methyl)butylimidazole
  参考文献：
  名称：

  Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P2′-P3′ amide bond isostere

  摘要：

  A novel series of hydroxamate-based inhibitors of matrix metalloproteinases containing benzimidazole and imidazole heterocycles as amide bond isosteres have been prepared. Potent inhibition (in the low nanomolar range) and selectivity (> 100-fold) can be attained with inhibitors containing only one amide bond. X-ray crystal structures of matrilysin (MMP-7) with two different inhibitors bound confirm that imidazole is an excellent amide bond isostere. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00283-1
• 作为产物：
  描述：

  N-苄氧羰基-L-亮氨酸 在 N-甲基吗啉 、 ammonium acetate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 溶剂黄146 为溶剂， 反应 11.0h， 生成 (S)-2-[1-(N-Benzyloxycarbonylamino)-3-methyl]butylimidazole
  参考文献：
  名称：

  Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P2′-P3′ amide bond isostere

  摘要：

  A novel series of hydroxamate-based inhibitors of matrix metalloproteinases containing benzimidazole and imidazole heterocycles as amide bond isosteres have been prepared. Potent inhibition (in the low nanomolar range) and selectivity (> 100-fold) can be attained with inhibitors containing only one amide bond. X-ray crystal structures of matrilysin (MMP-7) with two different inhibitors bound confirm that imidazole is an excellent amide bond isostere. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00283-1

文献信息

• MERCAPTOALKYLPEPTIDYL COMPOUNDS HAVING AN IMIDAZOLE SUBSTITUENT AND THEIR USE AS INHIBITORS OF MATRIX METALLOPROTEINASES (MMP) AND/OR TUMOUR NECROSIS FACTOR (TNF)
  申请人：Darwin Discovery Limited

  公开号：EP0874842B1

  公开（公告）日：2002-04-10
• US6048841A
  申请人：——

  公开号：US6048841A

  公开（公告）日：2000-04-11
• Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P2′-P3′ amide bond isostere
  作者：Jian Jeffrey Chen、Yiping Zhang、Scott Hammond、Nolan Dewdney、Teresa Ho、Xiaohong Lin、Michelle F. Browner、Arlindo L. Castelhano

  DOI：10.1016/s0960-894x(96)00283-1

  日期：1996.7

  A novel series of hydroxamate-based inhibitors of matrix metalloproteinases containing benzimidazole and imidazole heterocycles as amide bond isosteres have been prepared. Potent inhibition (in the low nanomolar range) and selectivity (> 100-fold) can be attained with inhibitors containing only one amide bond. X-ray crystal structures of matrilysin (MMP-7) with two different inhibitors bound confirm that imidazole is an excellent amide bond isostere. Copyright (C) 1996 Elsevier Science Ltd