L-alanine-N'-8-quinolylamide | 587832-37-9

• 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-alanine-N'-8-quinolylamide
• 英文别名: Propanamide, 2-amino-N-8-quinolinyl-, (2S)-；(2S)-2-amino-N-quinolin-8-ylpropanamide
• CAS: 587832-37-9
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: ZSXAWWHQDYRCKP-QMMMGPOBSA-N

物化性质

• 沸点：
  465.2±25.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-alanine-N'-8-quinolylamide 在 1-羟基苯并三唑 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  通过配体启用的 β-C(sp3)-H 丙氨酸在 C 端芳基化对肽的组装后修饰：克服肽键的抑制作用

  摘要：

  通过脂肪族侧链上的C(sp 3 )–H 功能化对肽进行组装后修饰提供了一种直接的方法来获取功能化肽作为治疗剂。然而，由于主链中仲酰胺的抑制作用，C 末端残基的C(sp 3 )–H 功能化仍然不发达。在此，我们报告了一种配体启用的双齿辅助辅助 β-C(sp 3 )-H 芳基化方法，该方法对仲酰胺具有良好的耐受性。多种肽（三到十二肽）在 C 端进行了丙氨酸的位置特异性修饰。

  DOI：

  10.1021/acs.orglett.1c01481
• 作为产物：
  描述：

  8-氨基喹啉 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 L-alanine-N'-8-quinolylamide
  参考文献：
  名称：

  仿生钯催化分子内 C(sp3)-H 活化用于脯氨酸天然产物的集体合成

  摘要：

  仿生钯 (II) 催化的通过 C-H 活化对含有碘乙烯部分的氨基酸衍生物进行分子内环化，可以快速获得具有环外双键的各种功能化脯氨酸衍生物。这种功能化的脯氨酸被用作几种天然产物全合成的中间体：光亮霉素 A、巴木霉素、氧代梅霉素和氧代原霉素。

  DOI：

  10.1002/anie.202207088

文献信息

• Monofunctional Platinum Complexes Showing Potent Cytotoxicity against Human Liver Carcinoma Cell Line BEL-7402
  作者：Junyong Zhang、Xiaoyong Wang、Chao Tu、Jun Lin、Jian Ding、Liping Lin、Zheming Wang、Cheng He、Chunhua Yan、Xiaozeng You、Zijian Guo

  DOI：10.1021/jm020593j

  日期：2003.7.1

  Complex II crystallized in the monoclinic system with space group P2(1), a = 9.502(2) A, b = 4.724(1) A, c = 14.800(3) A, while complex III crystallized in the orthorhombic system with space group P2(1)2(1)2(1), a = 5.441(1) A, b = 12.978(3) A, c = 29.438(6) A. These complexes have been tested against a wide range of tumor cell lines including BEL-7402, HCT-116, SPC-A4, MOLT-4, P388, HL-60, A-549, SGC-7901

  三个新型Pt（II）配合物[PtL（1）'Cl] I（L（1）'=甘氨酸-N'-8-喹啉酰胺），[PtL（2）'Cl] II（L（2）'= l -丙氨酸-N'-8-喹啉酰胺）和[PtL（3）Cl] III [L（3）= N-（叔丁氧基羰基）-1-蛋氨酸-N'-8-喹啉酰胺]的合成和表征。配合物II和III的晶体结构表明，配体是三配位的，只有一个Cl（-）作为离去基团。配合物II在具有空间群P2（1）的单斜晶系系统中结晶，a = 9.502（2）A，b = 4.724（1）A，c = 14.800（3）A，而配合物III在具有空间群的正交晶系中结晶。 P2（1）2（1）2（1），a = 5.441（1）A，b = 12.978（3）A，c = 29.438（6）A。这些复合物已针对多种肿瘤细胞系进行了测试包括BEL-7402，HCT-116，SPC-A4，MOLT-4，P388，HL-60，
• Total synthesis and biological evaluation of histone deacetylase inhibitor WF-3161
  作者：Michael Kohr、Niklas Papenkordt、Manfred Jung、Uli Kazmaier

  DOI：10.1039/d3ob00641g

  日期：——

  A novel synthesis of the naturally occurring HDAC inhibitor WF-3161 is described. Key steps include the Matteson homologation to generate the stereogenic centres in the side chain, and Pd-catalysed C–H functionalisation to connect the side chain to the peptide backbone. WF-3161 was found to be highly selective for HDAC1, whereas no activity was observed towards HDAC6. High activity was also found against

  描述了天然存在的 HDAC 抑制剂 WF-3161 的新合成。关键步骤包括 Matteson 同源化以在侧链中生成立体中心，以及 Pd 催化的 C-H 功能化以将侧链连接到肽主链。WF-3161 被发现对 HDAC1 具有高度选择性，而对 HDAC6 没有观察到活性。还发现了针对癌细胞系 HL-60 的高活性。
• Palladium-Catalyzed Stereoretentive Olefination of Unactivated C(sp³)–H Bonds with Vinyl Iodides at Room Temperature: Synthesis of β-Vinyl α-Amino Acids
  作者：Bo Wang、Chengxi Lu、Shu-Yu Zhang、Gang He、William A. Nack、Gong Chen

  DOI：10.1021/ol503248f

  日期：2014.12.5

  A method is reported for palladium-catalyzed N-quinolyl carboxamide-directed olefination of the unactivated C(sp(3))H bonds of phthaloyl alanine with a broad range of vinyl iodides at room temperature. This reaction represents the first example of the stereoretentive installation of multisubstituted terminal and internal olefins onto unactivated C(sp(3))H bonds. These methods enable access to a wide range of challenging beta-vinyl a-amino acid products in a streamlined and controllable fashion, beginning from simple precursors.
• Synthesis of Cyclophane-Braced Peptide Macrocycles via Palladium-Catalyzed Intramolecular C(sp³)–H Arylation of <i>N</i>-Methyl Alanine at C-Termini
  作者：Xinghua Li、Liping Qi、Bo Li、Zhenxiang Zhao、Gang He、Gong Chen

  DOI：10.1021/acs.orglett.0c02342

  日期：2020.8.7

  A method for the construction of cyclophane-braced peptide macrocycles via Pd-catalyzed aminoquinoline-directed intramolecular C(sp(3))-H arylation with aryl iodides is developed. Unlike our previous AQ-directed exo-type intramolecular C-H arylation of long alkyl tails, this endo-type C-H cyclization reaction takes places on the beta-methyl group of N-methyl alanine at the C-termini of peptides. Unusual C-N cleavage side products of Ala were observed and attributed to intramolecular deprotonation-assisted alpha,beta-elimination of the palladacycle intermediate.
• Steric effect on the nuclease activity of Cu(II) complexes with aminoquinoline derivatives
  作者：Ying Shao、Junyong Zhang、Chao Tu、Chunhui Dai、Qiang Xu、Zijian Guo

  DOI：10.1016/j.jinorgbio.2005.04.007

  日期：2005.7

  Three copper(II) complexes of aminoquinoline derivatives, L-glycine-N'-8-quinolylamide (L1), L-alanine-N-8-quinolylamide (L2), and N-(8-quinolyl) pyridine-2-carboxamide (L3) have been shown to cleave plasmid DNA pBR322 and pUC18 with or without the presence of H2O2/ascorbate. Crystallographic data reveal that the Cu(II) coordination plane in [Cu(L1)(Ac)(H2O)] (1) and [Cu(L2)(Ac)] (2) is nearly co-planar with the quinoline ring. The cleavage activity follows the order of complex 1 > complex 2 > complex 3, which is in agreement with the reverse order of the steric hindrance of the amino-substituent of the ligands. The presence of the standard radical scavengers does not have a clear effect on the cleavage efficiency of the Cu(II) complexes, suggesting the reactive species leading to DNA damage could be DNA-bound copper-centered radicals rather than the free diffusible ones. (c) 2005 Elsevier Inc. All rights reserved.