(R)-4-benzyl-3-(4-phenylbutanoyl)oxazolidin-2-one | 170450-83-6

• 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: (R)-4-benzyl-3-(4-phenylbutanoyl)oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-(4-phenylbutanoyl)-1,3-oxazolidin-2-one
• CAS: 170450-83-6
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: YBRNOEDQAAWPSA-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (R)-4-benzyl-3-(4-phenylbutanoyl)oxazolidin-2-one 在 双氧水 、 四氯化钛 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 9.67h， 生成 (S)-3-(2-phenylethyl)-oxetan-2-one
  参考文献：
  名称：

  酪蛋白水解蛋白酶（ClpP）抑制的机制

  摘要：

  如果可以，请联系我：ClpP蛋白酶介导蛋白质稳态，并且可以被β-内酯有效地抑制。分子对接，诱变，基于活性的蛋白质谱分析和动力学研究相结合，现在揭示了ClpP抑制的机制。活性位点旁边的疏水口袋允许长的脂肪族和芳香族残基结合。优选的立体异构体结合到氧阴离子孔中。

  DOI：

  10.1002/anie.201204690
• 作为产物：
  描述：

  4-苯基丁酸 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 (R)-4-benzyl-3-(4-phenylbutanoyl)oxazolidin-2-one
  参考文献：
  名称：

  (S)-β3-Homolysine- and (S)-β3-Homoserine-Containingβ-Peptides: CD Spectra in Aqueous Solution

  摘要：

  For further structural studies and for physiological investigations of beta-peptides, it is necessary to have H2O-soluble derivatives. Thus, we have prepared beta-hexa-, beta-hepta-, and beta-nonapeptides (1-6) with two, three, and seven side chains of lysine and serine. To detect possible pi-pi interactions, we also included the beta-amino acid beta(2)-HHop, resulting from homologation of so-called homophenylalanine (Hop) (5 and 6). The Fmoc-beta(2)- and beta(3)-amino-acid derivatives (11-14 and 19), and the corresponding beta-peptides were prepared by methods previously described (solid-phase peptide coupling; HPLC-pure samples, Fig. I). Circular-dichroism spectra (Fig.2) indicate the presence of less pronounced secondary structures (especially of the lysine analogues with multiple positive charge) in H2O as compared to MeOH. The beta(3)-heptapeptide (3) with two serine side chains is well soluble in H2O and exhibits the CD pattern typical of the 3(1)-helical structure.

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2141::aid-hlca2141>3.0.co;2-5

文献信息

• [EN] HYDROXY FORMAMIDE DERIVATIVES AND THEIR USE<br/>[FR] DÉRIVÉS D'HYDROXY FORMAMIDE ET LEUR UTILISATION
  申请人：GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO 2) LTD

  公开号：WO2017006295A1

  公开（公告）日：2017-01-12

  Disclosed are compounds having the formula: (I) wherein R1, R2 and R3 are as defined herein, and methods of making and using the same, including use as inhibitors of BMP1, TLL1 and/or TLL2 and in treatment of diseases associated with BMP1, TLL1 and/or TLL2 activity.

  揭示了具有以下化学式的化合物：(I)，其中R1、R2和R3如本文所定义，并且揭示了制备和使用这些化合物的方法，包括用作BMP1、TLL1和/或TLL2的抑制剂以及用于治疗与BMP1、TLL1和/或TLL2活性相关的疾病。
• HYDROXY FORMAMIDE DERIVATIVES AND THEIR USE
  申请人：GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED

  公开号：US20160340328A1

  公开（公告）日：2016-11-24

  Disclosed are compounds having the formula: wherein R1, R2 and R3 are as defined herein, and methods of making and using the same, including use as inhibitors of BMP1, TLL1 and/or TLL2 and in treatment of diseases associated with BMP1, TLL1 and/or TLL2 activity.

  揭示了具有以下公式的化合物：其中R1、R2和R3如本文所定义，并且制备和使用这些化合物的方法，包括用作BMP1、TLL1和/或TLL2的抑制剂以及用于治疗与BMP1、TLL1和/或TLL2活性相关的疾病。
• Design, synthesis and in vitro evaluation of a series of α-substituted phenylpropanoic acid PPARγ agonists to further investigate the stereochemistry–activity relationship
  作者：Masao Ohashi、Izumi Nakagome、Jun-ichi Kasuga、Hiromi Nobusada、Kenji Matsuno、Makoto Makishima、Shuichi Hirono、Yuichi Hashimoto、Hiroyuki Miyachi

  DOI：10.1016/j.bmc.2012.08.061

  日期：2012.11

  stereochemistry–activity relationship, that is, the (R)-enantiomer is a more potent PPARγ agonist than the (S)-enantiomer, compared with structurally similar α-ethylphenylpropanoic acid-type PPAR agonists. Here, we designed, synthesized and evaluated the optically active α-cyclohexylmethylphenylpropanoic acid derivatives 7 and α-phenethylphenylpropanoic acid derivatives 8, respectively. Interestingly, α-cyclohexylmethyl

  我们先前证明，α-苄基苯丙酸型PPARγ-选择性激动剂6表现出相反的立体化学-活性关系，即与结构上相比，（R）-对映体比（S）-对映体是更有效的PPARγ激动剂。类似的α-乙基苯基丙酸型PPAR激动剂。在此，我们分别设计，合成和评估了旋光性α-环己基甲基苯基丙酸衍生物7和α-苯乙基苯基丙酸衍生物8。有趣的是，α-环己基甲基衍生物显示出立体化学-活性关系的逆转[即（R）比（S）]，就像α-苄基衍生物一样，而α-苯乙基衍生物表现出“正常”关系[（S）比（R）更有效。这些结果表明，相对于羧基而言，β位上存在支链碳原子是逆转立体化学-活性关系的关键决定因素。
• Hydroxy formamide derivatives and their use
  申请人：GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED

  公开号：US10450288B2

  公开（公告）日：2019-10-22

  Disclosed are compounds having the formula: wherein R1, R2 and R3 are as defined herein, and methods of making and using the same, including use as inhibitors of BMP1, TLL1 and/or TLL2 and in treatment of diseases associated with BMP1, TLL1 and/or TLL2 activity.

  所公开的是具有以下式子的化合物 其中 R1、R2 和 R3 如本文所定义，以及制造和使用这些化合物的方法，包括用作 BMP1、TLL1 和/或 TLL2 的抑制剂以及治疗与 BMP1、TLL1 和/或 TLL2 活性有关的疾病。
• Asymmetric Synthesis of 2,3-Disubstituted Succinates via Chiral Oxazolidinone Controlled Displacement of .alpha.-Trifluoromethanesulfonate Substituted Esters
  作者：Carl P. Decicco、David J. Nelson、Ronald L. Corbett、Jason C. Dreabit

  DOI：10.1021/jo00120a022

  日期：1995.7

  The addition of chiral imides to alpha-trifluoromethanesulfonate esters gave chiral 2,3-disubstituted succinates with moderate to excellent diastereoselectivity and in good overall chemical yields. Both syn and anti chiral products are attainable via this methodology, with generally better diastereoselectivity and chemical yields observed in the production of the syn products. The reactions proceed through the predicted S(N)2 displacement of the triflate leaving group, as inferred from the absolute configuration of the products.