(-)-(S)-N²-(tert-butoxycarbonyl)-N¹-(4-chlorophenyl)alaninamide | 179683-44-4

• 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: (-)-(S)-N²-(tert-butoxycarbonyl)-N¹-(4-chlorophenyl)alaninamide
• 英文别名: N-(N-(tert-butoxycarbonyl)-L-alanyl)-4-chloroaniline；tert-butyl (1-((4-chlorophenyl)amino)-1-oxopropan-2-yl)carbamate；tert-butyl N-[(2S)-1-(4-chloroanilino)-1-oxopropan-2-yl]carbamate
• CAS: 179683-44-4
• 化学式: C₁₄H₁₉ClN₂O₃
• 分子量: 298.769
• InChiKey: OAWPZUNZBQKPRN-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(S)-N²-(tert-butoxycarbonyl)-N¹-(4-chlorophenyl)alaninamide 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以42%的产率得到(S)-2-amino-N-p-chlorophenylpropionamide
  参考文献：
  名称：

  一种化合物及其用途

  摘要：

  本发明提供了一种新化合物，该化合物对氧化还原酶吲哚胺2，3‑双加氧酶(IDO)有一定的抑制活性，或可用于治疗与之相关的疾病，包括癌症及免疫相关疾病的用途。

  公开号：

  CN109575022B
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 18.08h， 生成 (-)-(S)-N²-(tert-butoxycarbonyl)-N¹-(4-chlorophenyl)alaninamide
  参考文献：
  名称：

  Synthesis of analogues of the benzodiazepine Ro 5-3335, antagonist of Tat HIV-1. Biological evaluation by Luciferase transactivation and anti-viral assay

  摘要：

  Ro 5-3335 is a benzodiazepine which is an antagonist of the Tat protein of HIV-1. A series of Ro 5-3335-derived compounds have been synthesized in order to evaluate whether opened analogues of the benzodiazepine tricyclic structure possess biological activity. The analogues are constituted by two aromatic rings variously substituted, linked by an amino acid. The activity of these compounds has been determined by the quantification of both inhibition of Tat activity using a cell-based transfection assay and inhibition of HIV replication in acutely infected cells. No analogue provided a notable inhibition of Tat-dependent transactivation or any anti-HIV activity.

  DOI：

  10.1016/0223-5234(96)85171-3

文献信息

• Synthesis of Highly Substituted Imidazolidine-2,4-dione (Hydantoin) through Tf₂O-Mediated Dual Activation of Boc-Protected Dipeptidyl Compounds
  作者：Hui Liu、Zhimin Yang、Zhengying Pan

  DOI：10.1021/ol502900j

  日期：2014.11.21

  Highly substituted chiral hydantoins were readily synthesized from simple dipeptides in a single step under mild conditions. This reaction proceeded through the dual activation of an amide and a tert-butyloxycarbonyl (Boc) protecting group by Tf2O-pyridine. This method was successfully applied in the preparation of a variety of biologically active compounds, including drug analogs and natural products

  高取代度的手性乙内酰脲很容易在温和的条件下一步一步由简单的二肽合成。该反应通过Tf 2 O-吡啶双重活化酰胺和叔丁氧羰基（Boc）保护基而进行。该方法已成功地用于制备多种生物活性化合物，包括药物类似物和天然产物。
• One-pot mechanosynthesis of aromatic amides and dipeptides from carboxylic acids and amines
  作者：Vjekoslav Štrukil、Boris Bartolec、Tomislav Portada、Ivica Đilović、Ivan Halasz、Davor Margetić

  DOI：10.1039/c2cc36613d

  日期：——

  Environmentally friendly one-pot synthesis of amides, bis-amides and dipeptides by mechanochemical carbodiimide-mediated coupling of carboxylic acids and amines is described; high reaction yields and simple aqueous work-up allow for the clean, practical and fast preparation of a variety of compounds containing the amide bond from readily accessible reagents.

  通过机械化学碳二亚胺介导的羧酸和胺的偶联，描述了环境友好的一锅合成酰胺，双酰胺和二肽。高反应产率和简单的水后处理使得可以从容易获得的试剂中清洁，实用，快速地制备各种含有酰胺键的化合物。
• Synthesis and Biological Evaluation of Chiral α-Aminoanilides with Central Antinociceptive Activity
  作者：Filomena Corbo、Carlo Franchini、Giovanni Lentini、Marilena Muraglia、Carla Ghelardini、Rosanna Matucci、Nicoletta Galeotti、Elisa Vivoli、Vincenzo Tortorella

  DOI：10.1021/jm061078e

  日期：2007.4.1

  Tocainide and related optically active chiral alpha-aminoanilides were synthesized and tested in vivo via the hot plate test to evaluate their central analgesic action. The aims of the study were to verify if a) the increase in lipophilicity, obtained by the introduction of an alkyl group on the steric center (3f-i), and the replacement of the C=O group with the C=S (10) group as well as the introduction of a methyl or ethyl group on the amidic nitrogen atom (8a-c) would produce an increase in central analgesic efficacy with respect to Tocainide; b) the 2,6-xylidide moiety is crucial for high analgesic activity (3b-e); c) the hydrogen atom bonded to the amidic nitrogen moiety is an essential pharmacophoric element for analgesic activity. Among all the synthesized compounds, 3f showed antinociceptive properties with a good enantioselective index.
• Discovery of potent and selective phenylalanine derived CCR3 receptor antagonists. Part 2
  作者：Dashyant Dhanak、Lisa T Christmann、Michael G Darcy、Richard M Keenan、Steven D Knight、Judithann Lee、Lance H Ridgers、Henry M Sarau、Dinubhai H Shah、John R White、Lily Zhang

  DOI：10.1016/s0960-894x(01)00249-9

  日期：2001.6

  Highly potent CCR3 antagonists have been developed from a previously reported series of phenylalanine ester-based leads. Solution-phase, parallel synthesis optimization was utilized to identify highly potent, functional CCR3 antagonists. (C) 2001 Elsevier Science Ltd. All rights reserved.