L-phenylalanine isopropylamide hydrochloride

• 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: L-phenylalanine isopropylamide hydrochloride
• 英文别名: H-Phe-NH-isopropyl hydrochloride；(2S)-2-amino-3-phenyl-N-propan-2-ylpropanamide;hydrochloride
• 化学式: C₁₂H₁₈N₂O*ClH
• 分子量: 242.749
• InChiKey: CBUPJSGYVNGTDY-MERQFXBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  L-phenylalanine isopropylamide hydrochloride 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 生成
  参考文献：
  名称：

  Structure-activity relationships for macrocyclic peptidomimetic inhibitors of HIV-1 protease

  摘要：

  A rational approach to developing inhibitors of proteolytic enzymes is the systematic modification of their peptide substrates to proteolytically stable, low molecular weight, nonpeptidic inhibitors. Replacing the scissile amide bond with a noncleavable transition state isostere usually gives potent protease inhibitors, but the remaining hydrolysable amide bonds render the inhibitors unstable to peptidases generally. Attempts to replace them with retention of inhibitor potency has proved difficult(1,2) due to the unpredictable cooperative influences of such variations on the conformations of both neighbouring inhibitor groups and enzyme residues. We recently described a method(3) for regioselectively fixing the conformation of inhibitor components and now show effects on activity of varying both the 'free' and 'fixed' components.

  DOI：

  10.1016/0960-894x(96)00468-4

文献信息

• Acid catalyzed monodehydro-2,5-diketopiperazine formation from N-α-ketoacyl amino acid amides
  作者：Yuri Yamazaki、Yuki Mori、Akiko Oda、Yuka Okuno、Yoshiaki Kiso、Yoshio Hayashi

  DOI：10.1016/j.tet.2009.02.058

  日期：2009.5

  developed a new synthetic method for monodehydro-2,5-diketopiperazines (monodehydroDKPs), which is based on an acid catalyzed cyclization of N-α-ketoacyl amino acid amides. Using this cyclization reaction, monodehydroDKP was formed with no or slight racemization in case that N-α-ketoacyl amino acid amides with β-aliphatic-α-ketoacyl groups and sterically unhindered N-substituting groups at the C-terminal amide

  我们已经开发出一种新的合成方法，用于基于2，5-二酮哌嗪单脱氢（monodehydroDKPs）的合成方法，该方法基于N -α-酮酰基氨基酸酰胺的酸催化环化反应。利用这种环化反应，monodehydroDKP用无或轻微消旋形成在情况下Ñ -α酮脂酰氨基与β -脂肪族-α酮脂基团空间位阻羧酸酰胺和Ñ -substituting基团在C末端酰胺氮是在使用催化量的对-TsOH（3-5％（mol））或10％TFA的存在。对于β-芳基-α-酮酰基氨基酸衍生物，其中主要通过与芳环的结合存在烯醇形式，可以通过优化反应条件来最大程度地减少外消旋化作用（5 mol％p-TsOH，回流6 h），尽管化学收率不能得到显着提高。但是，该反应条件成功地应用于微管蛋白解聚剂（-）-叔丁基-氧杂-苯基组蛋白的合成，没有消旋作用。
• Synthesis of enantiopure 7-azanorbornane proline–α-amino acid chimeras by highly efficient HPLC resolution of a phenylalanine analogue
  作者：Ana M. Gil、Elena Buñuel、Pilar López、Carlos Cativiela

  DOI：10.1016/j.tetasy.2003.12.008

  日期：2004.3

  4S)-2-phenyl-7-azabicyclo [2.2.1]heptane-1-carboxylic acid hydrochlorides, which are proline–phenylalanine chimeras, have been separately obtained by resolution of a key intermediate using chiral high performance liquid chromatography. The efficiency of the chromatographic resolution provides a general methodology for the preparation of both enantiomers of a broad variety of proline–α-amino acid chimeras with a

  对映体纯的构象受限的脯氨酸（1 S，2 S，4 R）-和（1 R，2 R，4 S）-2-苯基-7-氮杂双环[2.2.1]庚烷-1-羧酸盐酸盐，它们是脯氨酸-苯丙氨酸嵌合体，是通过使用手性高效液相色谱拆分关键中间体而单独获得的。色谱分离的效率为制备具有7-氮杂降硼烷骨架的多种脯氨酸-α-氨基酸嵌合体的两种对映异构体提供了一种对映体纯形式的通用方法。
• EPOXYSUCCINAMIDE DERIVATIVES OR SALTS THEREOF, AND DRUGS CONTAINING THE SAME
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：EP0808839A1

  公开（公告）日：1997-11-26

  The invention relates an epoxysuccinamide derivative represented by the general formula (1) wherein R1 and R2 are the same or different from each other and independently represent H or an aromatic hydrocarbon group or aralkyl group which may be substituted, or R1 and R2 may form a nitrogen-containing heterocyclic ring together with the adjacent nitrogen atoms, R3 is H or an acyl group, R4 is H or an aralkyl group, and R5 is an aromatic hydrocarbon group or aralkyl group which may be substituted, or R5 may form an amino acid residue, which may be protected, together with the adjacent nitrogen atom, or a salt thereof, and a medicine comprising the derivative as an active ingredient. This compound has an inhibiting activity against cathepsin, and particularly, specifically inhibits cathepsin L and is hence useful for prevention and treatment of osteopathy such as osteoporosis.

  本发明涉及一种由通式（1）表示的环氧琥珀酰胺衍生物 其中 R1 和 R2 彼此相同或不同，并独立地代表 H 或可被取代的芳香烃基或芳基，或 R1 和 R2 可与相邻的氮原子一起形成含氮杂环，R3 为 H 或酰基，R4 为 H 或芳基，R5 为可被取代的芳香烃基或芳基，或 R5 可与相邻的氮原子一起形成可被保护的氨基酸残基，或其盐，以及包含该衍生物作为活性成分的药物。 该化合物具有抑制酪蛋白酶的活性，特别是对酪蛋白酶 L 有特异性抑制作用，因此可用于预防和治疗骨质疏松症等骨病。
• US5883121A
  申请人：——

  公开号：US5883121A

  公开（公告）日：1999-03-16
• Structure-activity relationships for macrocyclic peptidomimetic inhibitors of HIV-1 protease
  作者：G. Abbenante、D.A. Bergman、R.I. Brinkworth、D.R. March、R.C. Reid、P.A. Hunt、I.W. James、R.J. Dancer、B. Garnham、M.L. Stoermer、D.P. Fairlie

  DOI：10.1016/0960-894x(96)00468-4

  日期：1996.11

  A rational approach to developing inhibitors of proteolytic enzymes is the systematic modification of their peptide substrates to proteolytically stable, low molecular weight, nonpeptidic inhibitors. Replacing the scissile amide bond with a noncleavable transition state isostere usually gives potent protease inhibitors, but the remaining hydrolysable amide bonds render the inhibitors unstable to peptidases generally. Attempts to replace them with retention of inhibitor potency has proved difficult(1,2) due to the unpredictable cooperative influences of such variations on the conformations of both neighbouring inhibitor groups and enzyme residues. We recently described a method(3) for regioselectively fixing the conformation of inhibitor components and now show effects on activity of varying both the 'free' and 'fixed' components.