N-Fmoc-norleucinal | 301544-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-Fmoc-norleucinal
• 英文别名: (S)-N-(9-fluorenylmethoxycarbonyl)-2-aminohexanal；Fmoc-L-Nle-Wang Resin (200-400 mesh, 1% DVB)；9H-fluoren-9-ylmethyl N-[(2S)-1-oxohexan-2-yl]carbamate
• CAS: 301544-33-2
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: POPRQQFFYDYQEB-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Fmoc-norleucinal 在 四(三苯基膦)钯 、 三正丁基氢锡 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 N-Fmoc-acrylicnorleucine
  参考文献：
  名称：

  Synthesis of a PNA-encoded cysteine protease inhibitor library

  摘要：

  Peptide nucleic acids (PNAs) have been used to encode a combinatorial library whereby each compound is labeled with a PNA tag which reflects its synthetic history and localizes the compound upon hybridization to an oligonucleotide array. We report herein the full synthetic details for a 4000 member PNA-encoded library targeted towards cysteine protease. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.107
• 作为产物：
  描述：

  芴甲氧羰酰基正亮氨酸 在 三乙基硅烷 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.0h， 生成 N-Fmoc-norleucinal
  参考文献：
  名称：

  具有不同亲脂性的三氨基酸构件的合成。

  摘要：

  为了获得具有不同亲脂性且最多可携带三个正电荷的不同氨基酸，我们开发了许多新的三氨基酸构件。一组结构单元是通过鸟氨酸，二氨基丙酸和二氨基丁酸的侧链通过氨基还原进行氨乙基延伸而实现的。由二氨基丁酸合成具有氨基乙基延伸的具有烃侧链的第二组三氨基酸。通过相应的Fmoc-L-2-氨基脂肪酸分两步合成了还原胺化反应所需的醛。将这些化合物用Boc-L-Dab-OH还原胺化，得到C4-C8烷基支链的三氨基酸。

  DOI：

  10.1371/journal.pone.0124046

文献信息

• Small molecule compositions for sexual dysfunction
  申请人：Palatin Technologies, Inc.

  公开号：US07550602B1

  公开（公告）日：2009-06-23

  Compounds of the general formula: or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, and X are as defined. Further provided are methods for treatment of sexual dysfunction, including erectile dysfunction and female sexual dysfunction, and combination drugs and method of use thereof, including a compound of the invention and one or more second sexual dysfunction pharmaceutical agents.

  通用公式的化合物： 或其药用可接受的盐，其中R1、R2、R3和X如定义。还提供了治疗性功能障碍的方法，包括勃起功能障碍和女性性功能障碍，以及联合药物和使用方法，包括本发明的化合物和一个或多个第二性功能障碍药物。
• 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。
• Ligands for prevention of neurotoxicity of the alzheimer's disease related amyloid-beta peptide
  申请人：AlphaBeta AB

  公开号：US10023610B2

  公开（公告）日：2018-07-17

  The present invention relates to the field of molecular biochemistry and medicine, and in particular to ligands comprising modified amino acid residues, targeting the amyloid-β peptide associated with Alzheimer's disease for prevention of aggregation, neurotoxicity and use thereof as drugs for treatment of Alzheimer's disease.

  本发明涉及分子生物化学和医学领域，特别是涉及由修饰氨基酸残基组成的配体，其靶标是与阿尔茨海默氏症相关的淀粉样蛋白-β肽，用于预防聚集、神经毒性以及将其用作治疗阿尔茨海默氏症的药物。
• Discovery of a Novel Class of Potent HCV NS4B Inhibitors: SAR Studies on Piperazinone Derivatives
  作者：Ramesh Kakarla、Jian Liu、Devan Naduthambi、Wonsuk Chang、Ralph T. Mosley、Donghui Bao、Holly M. Micolochick Steuer、Meg Keilman、Shalini Bansal、Angela M. Lam、William Seibel、Sandra Neilson、Phillip A. Furman、Michael J. Sofia

  DOI：10.1021/jm4012643

  日期：2014.3.13

  HTS screening identified compound 2a (piper-azinone derivative) as a low micromolar HCV genotype 1 (GT-1) inhibitor. Resistance mapping studies suggested that this piperazinone chemotype targets the HCV nonstructural protein NS4B. Extensive SAR studies were performed around 2a and the amide function and the C-3/C-6 cis stereochemistry of the piperazinone core were essential for HCV activity. A 10-fold increase in GT-1 potency was observed when the chiral phenylcyclopropyl amide side chain of 2a was replaced with p-fluorophenylisoxazole-carbonyl moiety (67). Replacing the C-6 nonpolar hydrophobic moiety of 67 with a phenyl moiety (95) did not diminish the GT-1 potency. A heterocyclic thiophene moiety (103) and an isoxazole moiety (108) were incorporated as isosteric replacements for the C-6 phenyl moiety (95), resulting in significant improvement in GT-1b and la potency. However, the piperazonone class of compounds lacks GT-2 activity and, consequently, were not pursued further into development.
• NOVEL LIGANDS FOR PREVENTION OF NEUROTOXICITY OF THE ALZHEIMER'S DISEASE RELATED AMYLOID-BETA PEPTIDE
  申请人：Alphabeta AB

  公开号：EP3094641A1

  公开（公告）日：2016-11-23