(R)-2-Isobutyl-pent-4-enoic acid dimethylamide | 202344-84-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-2-Isobutyl-pent-4-enoic acid dimethylamide
• 英文别名: (2R)-N,N-dimethyl-2-(2-methylpropyl)pent-4-enamide
• CAS: 202344-84-1
• 化学式: C₁₁H₂₁NO
• 分子量: 183.294
• InChiKey: PTHUHFSVMBMKTH-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-Isobutyl-pent-4-enoic acid dimethylamide 在 咪唑 、 sodium hydroxide 、 sodium tetrahydroborate 、 碘 、 sodium hydride 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成
  参考文献：
  名称：

  The asymmetric synthesis and in vitro characterization of succinyl mercaptoalcohol and mercaptoketone inhibitors of matrix metalloproteinases

  摘要：

  A series of succinyl based mercaptoketones and diastereomeric mercaptoalcohols were prepared and evaluated in vitro as inhibitors of the matrix metalloproteinases collagenase-1 (MMP-1), stromelysin (MMP-3), and gelatinase-B (MMP-9). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00186-3
• 作为产物：
  描述：

  (S)-4-benzyl-3-[(R)-2-isobutylpent-4-enoyl]oxazolidin-2-one 在 过氧化氢,锂盐(1:1) 、 氰基磷酸二乙酯 作用下， 生成 (R)-2-Isobutyl-pent-4-enoic acid dimethylamide
  参考文献：
  名称：

  The asymmetric synthesis and in vitro characterization of succinyl mercaptoalcohol and mercaptoketone inhibitors of matrix metalloproteinases

  摘要：

  A series of succinyl based mercaptoketones and diastereomeric mercaptoalcohols were prepared and evaluated in vitro as inhibitors of the matrix metalloproteinases collagenase-1 (MMP-1), stromelysin (MMP-3), and gelatinase-B (MMP-9). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00186-3

文献信息

• Mercaptoketones and mercaptoalcohols and a process for their preparation
  申请人：American Cyanamid Company

  公开号：US05852213A1

  公开（公告）日：1998-12-22

  This invention relates to matrix metalloproteinase (MMP) inhibiting compounds of the formula: ##STR1## where R.sup.1 is C.sub.1 -C.sub.12 alkyl, straight or branched and optionally substituted by halogen, hydroxy, C.sub.1 -C.sub.6 alkoxy, amino, carboxyl, C.sub.1 -C.sub.6 alkoxycarbonyl, carboxamido, nitrile, mono- or di-(C.sub.1 -C.sub.6)alkylamino, thio, C.sub.1 -C.sub.6 alkylthio, aryl, --Oaryl or --OCH.sub.2 aryl where aryl is optionally substituted with C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, carboxy, halogen, cyano, nitro, carboxamido, or hydroxy; and C.sub.1 -C.sub.6 alkanesulfonyloxy. R.sup.2 is .alpha.-OH or .beta.-OH and R.sup.6 is H or R.sup.2 and R.sup.6 together are carbonyl; the chemical intermediates; and processes for the preparation of these compounds and the intermediates thereto. Matrix metalloproteinases (MMP) are a family of zinc-containing calcium dependent proteinases, including stromelysins, collagenases, and gelatinases. These MMP enzymes are capable of degrading the proteinaceous components of connective tissue and appear to be involved in tissue remodeling, i.e., wound healing and connective tissue turnover. Unexpectedly, the mercaptoalcohols with the S-configuration at the hydroxyl-bearing carbon have been found to be at least 4 times more potent than the analogous (R)-alcohols both in vitro and in vivo in inhibiting the MMP enzyme.

  这项发明涉及以下结构的基质金属蛋白酶（MMP）抑制化合物：其中R.sup.1是C.sub.1 -C.sub.12烷基，直链或支链，可选择地被卤素、羟基、C.sub.1 -C.sub.6烷氧基、氨基、羧基、C.sub.1 -C.sub.6烷氧羰基、羧胺基、腈基、单或双（C.sub.1 -C.sub.6）烷基氨基、硫基、C.sub.1 -C.sub.6烷硫基、芳基、--O芳基或--OCH.sub.2芳基取代，其中芳基可选择地被C.sub.1 -C.sub.6烷基、C.sub.1 -C.sub.6烷氧基、羧基、卤素、氰基、硝基、羧胺基或羟基取代；以及C.sub.1 -C.sub.6烷磺酰氧基。R.sup.2是α-OH或β-OH，R.sup.6是H或R.sup.2，且R.sup.6与R.sup.2一起是羰基；这些化合物及其中间体的化学中间体；以及制备这些化合物和中间体的方法。基质金属蛋白酶（MMP）是一类含锌的依赖钙的蛋白酶家族，包括基质金属蛋白酶、胶原酶和明胶酶。这些MMP酶能够降解结缔组织的蛋白质成分，并似乎参与组织重塑，即伤口愈合和结缔组织更新。令人意外的是，在羟基位碳上具有S构型的巯基醇发现至少比类似的（R）-醇在体内外抑制MMP酶时更有效4倍。
• Mercaptoketones and mercaptoalcohols, a process for their preparation and their use as inhibitors of matrix metalloproteinases
  申请人：American Cyanamid Company

  公开号：EP0818443B1

  公开（公告）日：2001-12-05
• US5852213A
  申请人：——

  公开号：US5852213A

  公开（公告）日：1998-12-22
• US6124502A
  申请人：——

  公开号：US6124502A

  公开（公告）日：2000-09-26
• US6160132A
  申请人：——

  公开号：US6160132A

  公开（公告）日：2000-12-12