N-benzyloxycarbonyl-1(S)-(5-methoxybenzimidazol-2-yl)-3-methylbutylamine | 184685-12-9

• 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-benzyloxycarbonyl-1(S)-(5-methoxybenzimidazol-2-yl)-3-methylbutylamine
• 英文别名: benzyl N-[(1S)-1-(6-methoxy-1H-benzimidazol-2-yl)-3-methylbutyl]carbamate
• CAS: 184685-12-9
• 化学式: C₂₁H₂₅N₃O₃
• 分子量: 367.448
• InChiKey: DGEWGXDZKTVJIT-IBGZPJMESA-N

物化性质

• 沸点：
  590.3±40.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-1(S)-(5-methoxybenzimidazol-2-yl)-3-methylbutylamine 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成
  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 、 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 0.33h， 生成 N-benzyloxycarbonyl-1(S)-(5-methoxybenzimidazol-2-yl)-3-methylbutylamine
  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

• Hydroxamic acid compounds as metalloprotease and TNF inhibitors
  申请人：The DuPont Merck Pharmaceutical Company

  公开号：US05703092A1

  公开（公告）日：1997-12-30

  The present invention provides novel hydroxamic acids and carbocyclic acids and derivatives thereof and to pharmaceutical compositions and methods of use of these novel compounds for the inhibition of matrixmetalloproteinases, such as stromelysin and other matrix metalloproteinases, and also inhibit the production of tumor necrosis factor (TNF), and are therefore useful for the treatment of arthritis and other related inflammatory diseases. These novel compounds are represented by Formula I below: ##STR1##

  本发明提供了新型的羟胺酸和环烷酸及其衍生物，以及这些新化合物的药物组合物和使用方法，用于抑制基质金属蛋白酶，如STromelysin和其他基质金属蛋白酶的作用，并且抑制肿瘤坏死因子（TNF）的产生，因此对治疗关节炎和其他相关炎症性疾病有用。这些新化合物由下式I表示：##STR1##
• NOVEL HYDROXAMIC ACID AND AMINO-CARBOXYLATE COMPOUNDS AS METALLOPROTEASE AND TNF INHIBITORS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0821675A1

  公开（公告）日：1998-02-04
• US5703092A
  申请人：——

  公开号：US5703092A

  公开（公告）日：1997-12-30
• [EN] NOVEL HYDROXAMIC ACID AND AMINO-CARBOXYLATE COMPOUNDS AS METALLOPROTEASE AND TNF INHIBITORS<br/>[FR] NOUVEAUX COMPOSES D'ACIDES HYDROXAMIQUES ET D'AMINOCARBOXYLATES SERVANT D'INHIBITEURS DES METALLOPROTEASES ET DU TNF
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1996033176A1

  公开（公告）日：1996-10-24

  (EN) The present invention provides novel hydroxamic acids and carbocyclic acids and derivatives thereof and to pharmaceutical compositions and methods of use of these novel compounds for the inhibition of matrixmetalloproteinases, such as stromelysin and other matrix metalloproteinases, and also inhibit the production of tumor necrosis factor (TNF), and are therefore useful for the treatment of arthritis and other related inflammatory diseases. These novel compounds are represented by Formula (I).(FR) L'invention porte sur de nouveaux acides hydroxamiques et carboxyliques et leurs dérivés et sur des compositions pharmaceutiques et des méthodes d'utilisation de ces nouveaux composés pour l'inhibition des métalloprotéases matricielles telles que la stromélysine et autres métalloprotéases matricielles, et de la production du facteur de nécrose tumorale (TNF), lesdits composés s'avérant ainsi utiles pour le traitement de l'arthrite et autres maladies inflammatoires associées. Ces nouveaux composés sont représentés par la formule (I).