(R)-2-Amino-N-methoxy-N-methyl-3-phenyl-propionamide | 133657-45-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-Amino-N-methoxy-N-methyl-3-phenyl-propionamide
• 英文别名: (2R)-2-amino-N-methoxy-N-methyl-3-phenylpropanamide
• CAS: 133657-45-1
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: BLWFTPRCWDIXPK-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-Amino-N-methoxy-N-methyl-3-phenyl-propionamide 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 生成 Cbz-Leu-Leu-D-Phe-al
  参考文献：
  名称：

  Peptide inhibitors of IKB protease: Modification of the C-termini of Z-LLF-CHO

  摘要：

  A series of tripeptides (Z-LLF-R) with various modifications at their C-terminus were synthesized and evaluated for their ability to prevent the activation of NF-kappa B through inhibition of I kappa B protease. Of the compounds evaluated only the C-terminal aldehydes 5a,b were active in our Jurkat T-cell based assay. Compound 5a also decreased IL-2 and IL-8 levels in these cells indicating that inhibitors of I kappa B protease can have an effect on various signaling pathways. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00559-8
• 作为产物：
  描述：

  N-[(1R)-2-(甲氧基甲基氨基)-2-氧代-1-(苯基甲基)乙基]氨基甲酸1,1-二甲基乙基酯 在 三氟乙酸 作用下， 生成 (R)-2-Amino-N-methoxy-N-methyl-3-phenyl-propionamide
  参考文献：
  名称：

  Peptide inhibitors of IKB protease: Modification of the C-termini of Z-LLF-CHO

  摘要：

  A series of tripeptides (Z-LLF-R) with various modifications at their C-terminus were synthesized and evaluated for their ability to prevent the activation of NF-kappa B through inhibition of I kappa B protease. Of the compounds evaluated only the C-terminal aldehydes 5a,b were active in our Jurkat T-cell based assay. Compound 5a also decreased IL-2 and IL-8 levels in these cells indicating that inhibitors of I kappa B protease can have an effect on various signaling pathways. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00559-8

文献信息

• Gold(I)-Catalyzed Asymmetric Aldol Reaction of N-Methoxy-N-methyl-.alpha.-isocyanoacetamide (.alpha.-Isocyano Weinreb Amide). An Efficient Synthesis of Optically Active .beta.-Hydroxy .alpha.-Amino Aldehydes and Ketones
  作者：Masaya Sawamura、Yuki Nakayama、Tomoki Kato、Yoshihiko Ito

  DOI：10.1021/jo00111a034

  日期：1995.3

  Asymmetric aldol reaction of N-methoxy-N-methyl-alpha-isocyanoacetamide (alpha-isocyano Weinreb amide) with aldehydes [RCHO: R = Ph, Me, i-Pr, (E)-MeCH=CH, (E)-BnOCH(2)CH=CH] in the presence of a gold(I) catalyst prepared in situ from [Au(c-HexNC)(2)]BF4 and chiral ferrocenylphosphine ligand (R)-N-methyl-N-(2-morpholinoethyl)-1-[(S)-1',2-bis(diphenylphosphino)ferrocenyl]ethylamine gave high yields of optically active trans-5-alkyl-2-oxazoline-4-(N-methoxy-N-methylcarboxamides) with high diastereo- and enantioselectivities. The diastereoselectivities (trans:cis) and enantiomeric excesses of the trans-oxazolines for the reaction with 1 mol % of the catalyst are as follows: R = Ph, 97:3, 96% ee; R = Me, 95:5, 97% ee; R = i-Pr, 98:2, 97% ee; R = (E)-MeCH=CH, 97:3; 99% ee; (E)-BnOCH(2)CH=CH, 96:4, 95% ee. These optically active oxazolines were converted to N,O-protected beta-hydroxy-alpha-amino aldehydes and ketone in high yields. An N-protected alpha-amino aldehyde (R = Ph) lacking the beta-hydroxyl group was also obtained through the catalytic hydrogenolysis of the oxazoline.
• Peptide inhibitors of IKB protease: Modification of the C-termini of Z-LLF-CHO
  作者：Mark J. Suto、Robert W. Sullivan、Lynn J. Ransone

  DOI：10.1016/s0960-894x(96)00559-8

  日期：1996.12

  A series of tripeptides (Z-LLF-R) with various modifications at their C-terminus were synthesized and evaluated for their ability to prevent the activation of NF-kappa B through inhibition of I kappa B protease. Of the compounds evaluated only the C-terminal aldehydes 5a,b were active in our Jurkat T-cell based assay. Compound 5a also decreased IL-2 and IL-8 levels in these cells indicating that inhibitors of I kappa B protease can have an effect on various signaling pathways. Copyright (C) 1996 Elsevier Science Ltd
• Proteasome inhibition by peptide-semicarbazones
  作者：Johann Leban、Marcus Blisse、Babett Krauss、Sandra Rath、Roland Baumgartner、Markus H.J. Seifert

  DOI：10.1016/j.bmc.2008.02.042

  日期：2008.4

  Peptide-semicarbazones derived from Z-Trp-Trp-Phe-aldehyde inhibit the chymotryptic activity of the human proteasome at nanomolar concentrations, but are less active in a NF kappa B reporter gene assay. Cyclic semicarbazones, in contrast, combine a strong inhibitory effect on the enzyme with an inhibition of NF kappa B signaling in the nanomolar range. In addition, a practical synthesis for scale-up of such compounds was developed. (c) 2008 Elsevier Ltd. All rights reserved.