N-α-Boc-argininal | 186261-75-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-α-Boc-argininal
• 英文别名: tert-butyl N-[(3S)-2-hydroxy-1-(N-nitrocarbamimidoyl)piperidin-3-yl]carbamate
• CAS: 186261-75-6
• 化学式: C₁₁H₂₁N₅O₅
• 分子量: 303.318
• InChiKey: ZQTRZLWIKVJESW-JAMMHHFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-α-Boc-argininal 在 palladium on activated charcoal 盐酸 、 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 生成
  参考文献：
  名称：

  新型，选择性和口服可生物利用的凝血酶抑制剂的设计，合成和进化：掺有P3-P4内酰胺磺酰胺基团的P1-精氨酸衍生物。

  摘要：

  DOI：

  10.1021/jm960572n
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-α-Boc-argininal
  参考文献：
  名称：

  Atom-Economical Synthesis of the N(10)−C(17) Fragment of Cyclotheonamides via a Novel Passerini Reaction−Deprotection−Acyl Migration Strategy¹

  摘要：

  [GRAPHICS]A novel variant of the atom-economical Passerini reaction between suitably protected argininal, dipeptide isonitrile, and proline components afforded adduct 13. Orthogonal N-deprotection of 13 led, via a smooth O- to N-acyl migration, to 14, which constitutes the N(10)-C(17) fragment of the cyclotheonamide family of serine protease inhibitors. Each reaction in this three-step protocol proceeds in good yield and under very mild conditions.

  DOI：

  10.1021/ol0165239

文献信息

• New Synthetic Technology for Efficient Construction of α-Hydroxy-β-amino Amides via the Passerini Reaction¹
  作者：J. Edward Semple、Timothy D. Owens、Khanh Nguyen、Odile E. Levy

  DOI：10.1021/ol0061485

  日期：2000.9.1

  [reaction: see text] The Passerini reaction of N-protected amino aldehydes, isonitriles, and TFA using pyridine-type bases proceeds under mild conditions and directly affords alpha-hydroxy-beta-amino amide derivatives in moderate to high yields. These adducts are readily hydrolyzed to alpha-hydroxy-beta-amino carboxylic acids. Application of these key intermediates to concise syntheses of P(1)-alpha-ketoamide

  [反应：见正文]使用吡啶型碱的N-保护的氨基醛，异腈和TFA的Passerini反应在温和的条件下进行，并以中等至高收率直接提供α-羟基-β-氨基酰胺衍生物。这些加合物容易水解成α-羟基-β-氨基羧酸。说明了这些关键中间体在简明P（1）-α-酮酰胺蛋白酶抑制剂合成中的应用。
• Novel protocol for the solid-phase synthesis of peptidyl and peptidomimetic P1-argininal derivatives
  作者：Daniel V. Siev、John A. Gaudette、J.Edward Semple

  DOI：10.1016/s0040-4039(99)00870-9

  日期：1999.7

  The design, synthesis and application of novel argininal aminals 1 tethered onto AM resin is described. Efficient solid-phase synthesis routes to a wide array of the title derivatives 2 have been implemented using this convenient technology. The resulting P-1-argininal targets serve as useful exploratory scaffolds for serine and cysteine protease inhibitor discovery. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Inhibition studies of some serine and thiol proteinases by new leupeptin analogs
  作者：Rose M. McConnell、J. Lyndal York、Donna Frizzell、Carole Ezell

  DOI：10.1021/jm00060a016

  日期：1993.4

  Fifteen tripeptide analogues of leupeptin containing either a C-terminal argininal or lysinal were synthesized. The synthetic analogues were tested, using spectrophotometric assay techniques, as inhibitors of trypsin, kallikrein, thrombin, plasmin, and cathepsin B. The lysinal analogues were fairly selective as inhibitors of cathepsin B activity, Acetyl-L-leucyl-L-valyl-L-lysinal (21) showed a stronger inhibition of cathepsin B (IC50 = 4 nanomolar) than leupeptin. Acetyl-L-phenylalanyl-L-valyl-L-argininal (2i) was found to be a good inhibitor of cathepsin B (IC50 = 0.039 muM), thrombin (IC50 = 1.8 muM), and plasmin (IC50 = 2.2 muM).
• Synthesis and biological activity of P2–P4 azapeptidomimetic P1-argininal and P1-ketoargininamide derivatives: a novel class of serine protease inhibitors
  作者：J.Edward Semple、David C. Rowley、Terence K. Brunck、William C. Ripka

  DOI：10.1016/s0960-894x(97)00005-x

  日期：1997.2

  Molecular modeling and topographic considerations of the thrombin-specific sequences Boc-Asp-Pro-Arg-TS or Ac-d-Phe-Pro-Arg-TS (TS = transition state analog electrophilic center) and related scaffolds led to the design of novel P-2-P-4-azapeptidomimetic P-1-argininal and P-1-ketoargininamide derivatives (3a-j). The synthesis and biological activity of these potential serine protease inhibitors are presented. (C) 1997, Elsevier Science Ltd.
• RATIONAL DESIGN, SYNTHESIS, AND SERINE PROTEASE INHIBITORY ACTIVITY OF NOVEL P1-ARGININOYL HETEROCYCLES
  作者：Susan Y Tamura、Brian M Shamblin、Terence K Brunck、William C Ripka

  DOI：10.1016/s0960-894x(97)00227-8

  日期：1997.5

  Peptidomimetic derivatives featuring a P-1-argininoyl heterocycle were designed. The preparation of two key building blocks containing benzoxazole or benzimidazole rings and their incorporation into thrombin and factor Xa specific sequences is described. The serine protease inhibitory activity of these targets was evaluated. Molecular modeling of two representative structures is presented. (C) 1997 Elsevier Science Ltd.