n-(8-quinolyl)-L-alanine-carboxamide | 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: n-(8-quinolyl)-L-alanine-carboxamide
• 英文别名: (2R)-2-amino-N-quinolin-8-ylpropanamide
• CAS: 587832-37-9
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: ZSXAWWHQDYRCKP-MRVPVSSYSA-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：

  n-(8-quinolyl)-L-alanine-carboxamide 在 吡啶 、 4-羟基香豆素 、 palladium diacetate 、 溶剂黄146 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 64.0h， 生成
  参考文献：
  名称：

  Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization

  摘要：

  Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselective remote hydrocarbofunctionalization of several synthetically useful alkene-containing substrate classes, including 4-pentenoic acids, allylic alcohols, homoallyl amines, and bis-homoallylamiries, under Pd(II) catalysis. In conjunction with previous findings, we demonstrate regiodivergent hydro-functionalization of 34Dutenoic acid derivatives to afford either Markovnikov or anti-Markovnikov addition products depending on directing group choice. Preliminary mechanistic and computational data are presented to support the proposed catalytic cycle.

  DOI：

  10.1021/jacs.7b08383
• 作为产物：
  描述：

  8-氨基喹啉 在 氯甲酸乙酯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 n-(8-quinolyl)-L-alanine-carboxamide
  参考文献：
  名称：

  Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization

  摘要：

  Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselective remote hydrocarbofunctionalization of several synthetically useful alkene-containing substrate classes, including 4-pentenoic acids, allylic alcohols, homoallyl amines, and bis-homoallylamiries, under Pd(II) catalysis. In conjunction with previous findings, we demonstrate regiodivergent hydro-functionalization of 34Dutenoic acid derivatives to afford either Markovnikov or anti-Markovnikov addition products depending on directing group choice. Preliminary mechanistic and computational data are presented to support the proposed catalytic cycle.

  DOI：

  10.1021/jacs.7b08383

文献信息

• Novel Au(iii) complexes of aminoquinoline derivatives: crystal structure, DNA binding and cytotoxicity against melanoma and lung tumour cellsElectronic supplementary information (ESI) available: UV spectra of 3, 3 + NaCl, and 1 + calf thymus DNA; fluorescence spectra of the CT-DNA-EB system with increasing amounts of 1 or 3. See http://www.rsc.org/suppdata/dt/b3/b305109a/
  作者：Ting Yang、Chao Tu、Junyong Zhang、Liping Lin、Xianming Zhang、Qin Liu、Jian Ding、Qiang Xu、Zijian Guo

  DOI：10.1039/b305109a

  日期：——

  Three novel gold(III) complexes [Au(Quinpy)Cl]Cl (1), [Au(Quingly)Cl]Cl (2) and [Au(Quinala)Cl]Cl (3) [N-(8-quinolyl)pyridine-2-carboxamide = HQuinpy; N-(8-quinolyl)glycine-carboxamide = HQuingly; N-(8-quinolyl)-L-alanine-carboxamide = HQuinala] have been synthesized and characterized. The crystal structures of complexes 2 and 3 reveal that Au(III) is coordinated by three N atoms from the ligand and one Cl− anion. Complex 2 crystallized in the monoclinic system while complex 3 crystallized in the orthorhombic system. The complexes were tested against a series of tumour cell lines including B16-BL6, P388, HL-60, A-549 and BEL-7402. The data show that complex 1 is highly cytotoxic against the A-549 cells with an inhibition rate of 94.4% at a concentration of 10−6 mol L−1. Complex 3 is active against B16-BL6 with an inhibition rate of 67.52% at a concentration of 10−7 mol L−1. The interactions of complexes 1–3 with calf thymus (CT) DNA and 5′-GMP were investigated by UV-vis, fluorescence and ESMS spectroscopies. The data show that the interaction between Au(III) complexes and CT-DNA may be the intercalation effect, and complex 3 forms a 5′-GMP adduct as detected by ESMS.

  三种新型金 (III) 配合物 [Au(Quinpy)Cl]Cl (1)、[Au(Quingly)Cl]Cl (2) 和 [Au(Quinala)Cl]Cl (3) [N-(8-quinolyl)吡啶-2-甲酰胺 = HQuinpy; N-(8-喹啉基)甘氨酸甲酰胺 = HQuingly; N-(8-喹啉基)-L-丙氨酸-甲酰胺=HQuinala]已被合成并表征。配合物 2 和 3 的晶体结构表明，Au(III) 由配体中的三个 N 原子和一个 Cl− 阴离子配位。配合物2在单斜晶系中结晶，而配合物3在斜方晶系中结晶。该复合物针对一系列肿瘤细胞系进行了测试，包括 B16-BL6、P388、HL-60、A-549 和 BEL-7402。数据显示，复合物1对A-549细胞具有高度细胞毒性，在10−6 mol L−1浓度下抑制率为94.4%。复合物 3 对 B16-BL6 有活性，浓度为 10−7 mol L−1 时抑制率为 67.52%。通过 UV-vis、荧光和 ESMS 光谱研究了复合物 1-3 与小牛胸腺 (CT) DNA 和 5'-GMP 的相互作用。数据表明，Au(III)配合物与CT-DNA之间的相互作用可能是嵌入效应，ESMS检测到配合物3形成5'-GMP加合物。
• Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization
  作者：Miriam L. O’Duill、Rei Matsuura、Yanyan Wang、Joshua L. Turnbull、John A. Gurak、De-Wei Gao、Gang Lu、Peng Liu、Keary M. Engle

  DOI：10.1021/jacs.7b08383

  日期：2017.11.8

  Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselective remote hydrocarbofunctionalization of several synthetically useful alkene-containing substrate classes, including 4-pentenoic acids, allylic alcohols, homoallyl amines, and bis-homoallylamiries, under Pd(II) catalysis. In conjunction with previous findings, we demonstrate regiodivergent hydro-functionalization of 34Dutenoic acid derivatives to afford either Markovnikov or anti-Markovnikov addition products depending on directing group choice. Preliminary mechanistic and computational data are presented to support the proposed catalytic cycle.