dihydro-(4S-amino-[N-Boc-L-tert-butylalanyl])-5S-methyl-3(2H)-furanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dihydro-(4S-amino-[N-Boc-L-tert-butylalanyl])-5S-methyl-3(2H)-furanone
• 英文别名: tert-butyl N-[(2S)-2-amino-1-[(2S,3S)-2-methyl-4-oxooxolan-3-yl]-1-oxopropan-2-yl]-N-tert-butylcarbamate
• 化学式: C₁₇H₃₀N₂O₅
• 分子量: 342.436
• InChiKey: HVRBMAKQKSBUOD-BFCNOCSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  98.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(4-氨基吡啶-3-基)-1,1-二甲基脲 、 Boc-L-tert-butylalanine pentafluorophenyl ester 、 1-羟基苯并三唑一水物 在 N-甲基吗啉 、 盐酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 dihydro-(4S-amino-[N-Boc-L-tert-butylalanyl])-5S-methyl-3(2H)-furanone
  参考文献：
  名称：

  Cysteine protease inhibitors

  摘要：

  公式（IV）的翻译如下： 其中： R1=R′C(O)，R′SO2， R′=含有0-4个来自S、O和N的杂原子的8-12元环系统，可以选择饱和或不饱和的双环，可选地取代最多四个从下面的a)、b)和c)组中独立选择的取代基；或 R′=含有0-3个来自S、O和N的杂原子的5-7元环，该单环至少带有从a)组和/或c)组中选择的一个取代基，并且可选地带有从b)组中选择的一个或两个进一步的取代基； R4=H，C1-7-烷基，Ar-C1-7-烷基，Ar，C3-7-环烷基；C2-7-烯基； R3=C1-7-烷基，C2-C7烯基，C2-C7烯基，C3-7-环烷基，Ar-C1-7-烷基，Ar； R5=C1-7-烷基，卤素，Ar-C1-7-烷基，C1-3-烷基-CONR3R4或体积庞大的胺 R6为H，C1-7-烷基，Ar-C1-7-烷基，C1-3-烷基-SO2-R ix ，C1-3-烷基-C(O)—NHR ix 或CH 2 XAr q为0或1 具有作为半胱氨酸蛋白酶抑制剂的实用性，例如卡特普辛K和疟原虫蛋白酶。

  公开号：

  US20030186962A1

文献信息

• Furanone derivatives as inhibitors of Cathepsin S
  申请人：Medivir UK Ltd

  公开号：EP1413580A1

  公开（公告）日：2004-04-28

  Cathepsin S is a highly active cysteine protease belonging to the papain superfamily. It is found mainly in lymph nodes, spleen, and macrophages and this limited occurrence suggests the potential involvement of this enzyme in the pathogenesis of degenerative disease. The invention relates to novel protease inhibitors, particularly inhibitors of the cysteine proteases of the papain superfamily and more particularly to Cathepsin S. The inhibitors are Furanone derivatives of Formula (II) which have a characteristic non-hydrogen substituent R5. They are selective over other members of the family and in particular show selectivity over other members of the Cathepsin family such as L and K.

  Cathepsin S 是一种属于木瓜蛋白酶超家族的高活性半胱氨酸蛋白酶。它主要存在于淋巴结、脾脏和巨噬细胞中，这种有限的存在表明这种酶可能参与了变性疾病的发病机制。本发明涉及新型蛋白酶抑制剂，特别是木瓜蛋白酶超家族半胱氨酸蛋白酶的抑制剂，尤其是 Cathepsin S。它们对该家族的其他成员具有选择性，特别是对酪蛋白酶家族的其他成员如 L 和 K 具有选择性。
• FURANONE DERIVATIVES AS INHIBITORS OF CATHEPSIN S
  申请人：Medivir UK Ltd

  公开号：EP1178986A2

  公开（公告）日：2002-02-13
• CYSTEINE PROTEASE INHIBITORS
  申请人：MEDIVIR AB

  公开号：EP1358183A2

  公开（公告）日：2003-11-05
• [EN] FURANONE DERIVATIVES AS INHIBITORS OF CATHEPSIN S<br/>[FR] DERIVES FURANONES INHIBITEURS DE CATHEPSINE S
  申请人：MEDIVIR UK LTD

  公开号：WO2000069855A2

  公开（公告）日：2000-11-23

  Cathepsin S is a highly active cysteine protease belonging to the papain superfamily. It is found mainly in lymph nodes, spleen, and macrophages and this limited occurrence suggests the potential involvement of this enzyme in the pathogenesis of degenerative disease. The invention relates to novel protease inhibitors, particularly inhibitors of the cysteine proteases of the papain superfamily and more particularly to Cathepsin S. The inhibitors are Furanone derivatives of Formula (II) which have a characteristic non-hydrogen substituent R5. They are selective over other members of the family and in particular show selectivity over other members of the Cathepsin family such as L and K.
• [EN] CYSTEINE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE LA CYSTEINE PROTEASE
  申请人：MEDIVIR AB

  公开号：WO2002088106A2

  公开（公告）日：2002-11-07

  In formula (IV) R1 = R'C(O), R'SO2, R' = a bicyclic, saturated or unsaturated, 8-12 membered ring system containing 0-4 hetero atoms selected from S, O and N, which is optionally substituted with up to four substituents independently selected from groups a), b), and c) below; or R'= a monocyclic, saturated or unsaturated, 5-7 membered ring containing 0-3 hetero atoms selected from S, O and N, which monocyclic ring bears at least one substituent selected from group a) and/or c) and which may optionally bear one or two further substituents selected from group b); R4 = H, C1-7-alkyl, Ar-C1-7-alkyl, Ar, C3-7-cycloalkyl; C2-7-alkenyl; R3 = C1-7-alkyl, C2-C7 alkenyl, C2-C7 alkenyl, C3-7-cycloalkyl, Ar-C1-7-alkyl, Ar; R5 = C1-7-alkyl, halogen, Ar-C1-7-alkyl, C0-3-alkyl-CONR3R4 or a bulky amine, R6 is H, C1-7-alkyl, Ar-C1-7-alkyl, C1-3-alkyl-SO2-Rix, C1-3-alkyl-C(O)-NHRix or CH¿2?XAr, q is 0 or 1, have utility as inhibitors of cysteine proteases such as cathepsin K and falcipain.