(S)-3-((2'R)-allyl-1'-oxononanoyl)-4-phenyl ethyl-2-oxazolidinone | 202344-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-3-((2'R)-allyl-1'-oxononanoyl)-4-phenyl ethyl-2-oxazolidinone
• 英文别名: (4S)-4-Benzyl-3-((2R)-2-heptyl-pent-4-enoyl)oxazolidin-2-one；(4S)-4-benzyl-3-[(2R)-2-prop-2-enylnonanoyl]-1,3-oxazolidin-2-one
• CAS: 202344-79-4
• 化学式: C₂₂H₃₁NO₃
• 分子量: 357.493
• InChiKey: MMXMMCJLSSFVJI-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-((2'R)-allyl-1'-oxononanoyl)-4-phenyl ethyl-2-oxazolidinone 在 过氧化氢,锂盐(1:1) 、 碘 、 potassium hydrogencarbonate 、 potassium iodide 作用下， 生成 (R)-3-Heptyl-5-iodomethyl-dihydro-furan-2-one
  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：

  L-苯丙氨醇 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.17h， 生成 (S)-3-((2'R)-allyl-1'-oxononanoyl)-4-phenyl ethyl-2-oxazolidinone
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Minalemine A, a Guanidine Peptide from the Marine Tunicate Didemnum rodriguesi

  摘要：

  The total synthesis of the 3S,2S and 3R,2S diastereomers (1a and 1b) of minalemine A and the identification of the natural compound as the 3R,2S isomer is described. The key step in the synthesis is the preparation of the two enantiomers of the beta -amino diacid 3-(N-carboxymethyl)-aminodecanoic acid (Ncma), which were obtained by stereoselective alkylation with allyl bromide of two nonanoic acid imides bearing chiral oxazolidinones as chiral auxiliaries. Natural minalemine A shows identical (1)H NMR and very similar (13)C NMR spectra compared to the two synthetic diastereomers. Sufficient differences in their chromatographic behavior to allow conclusive identification were not found. However, the corresponding N-2-naphthoyl amides presented quite distinct circular dichroism spectra (CD), and these confirmed the 3R,2S configuration for the natural minalemines and the R configuration for the constituent beta -amino diacid, Ncma.

  DOI：

  10.1021/jo010076t

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
• US06124502
  申请人：——

  公开号：——

  公开（公告）日：——
• 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