2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester) | 170450-78-9

• 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: 2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester)
• 英文别名: tert-butyl (2S,3R)-3-[(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]-2,5-dimethylhexanoate
• CAS: 170450-78-9
• 化学式: C₂₃H₃₃NO₅
• 分子量: 403.519
• InChiKey: ZBKQMHWGIFHDBD-YTQUADARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester) 在 lithium hydroxide 、 甲酸 、 双氧水 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 (2R,3S)-N4-Benzyloxy-2-isobutyl-3-methyl-N1-((S)-methylcarbamoyl-phenyl-methyl)-succinamide
  参考文献：
  名称：

  Synthesis and biological evaluation of orally active matrix metalloproteinase inhibitors

  摘要：

  The synthesis and biological evaluation of orally active inhibitors of matrix metalloproteinase are reported. Modifications of the P2' position and the a-substituent of hydroxamic acid derivatives were carried out, and revealed that the P2' substituent influenced the MMP inhibitory activities in vitro and in plasma after oral administration. The hydroxamates with phenylglycine at the P2' position were absorbed well orally. Compound 15e, which exhibited the longest duration of inhibitory activity in plasma after oral administration among the phenylglycine derivatives (5a-5d, 15a, 15c, 15e), was evaluated in a rat adjuvant arthritis model. A reduction in hind foot pad swelling and improvements of some inflammatory parameters were demonstrated when the compound was administered orally. These results indicate the potential of MMP inhibitors for rheumatoid arthritis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00028-x
• 作为产物：
  描述：

  L-乳酸叔丁酯 在 吡啶 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 生成 2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester)
  参考文献：
  名称：

  Asymmetric Synthesis of 2,3-Disubstituted Succinates via Chiral Oxazolidinone Controlled Displacement of .alpha.-Trifluoromethanesulfonate Substituted Esters

  摘要：

  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.

  DOI：

  10.1021/jo00120a022

文献信息

• Synthesis and biological evaluation of orally active matrix metalloproteinase inhibitors
  作者：Ryoichi Hirayama、Minoru Yamamoto、Takahiro Tsukida、Konomi Matsuo、Yuji Obata、Fumio Sakamoto、Shoji Ikeda

  DOI：10.1016/s0968-0896(97)00028-x

  日期：1997.4

  The synthesis and biological evaluation of orally active inhibitors of matrix metalloproteinase are reported. Modifications of the P2' position and the a-substituent of hydroxamic acid derivatives were carried out, and revealed that the P2' substituent influenced the MMP inhibitory activities in vitro and in plasma after oral administration. The hydroxamates with phenylglycine at the P2' position were absorbed well orally. Compound 15e, which exhibited the longest duration of inhibitory activity in plasma after oral administration among the phenylglycine derivatives (5a-5d, 15a, 15c, 15e), was evaluated in a rat adjuvant arthritis model. A reduction in hind foot pad swelling and improvements of some inflammatory parameters were demonstrated when the compound was administered orally. These results indicate the potential of MMP inhibitors for rheumatoid arthritis. (C) 1997 Elsevier Science Ltd.
• 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.