3-<amino>pyridine | 88932-69-8

• 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: 3-<amino>pyridine
• 英文别名: tert-butyl N-[(2S)-1-oxo-3-phenyl-1-(pyridin-3-ylamino)propan-2-yl]carbamate
• CAS: 88932-69-8
• 化学式: C₁₉H₂₃N₃O₃
• 分子量: 341.41
• InChiKey: HXSLKYUGINIHLC-INIZCTEOSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  569.5±50.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  80.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-<amino>pyridine 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 3-(L-phenylalanylamino)pyridine dihydrochloride
  参考文献：
  名称：

  L-苯丙氨酸双酰胺的超分子凝胶：合成、结构和材料应用

  摘要：

  基于L-苯丙氨酸的双酰胺的水杨酸甲酯和水凝胶能够表现出流变可逆性、材料应用和抗菌性能。

  DOI：

  10.1002/asia.202200660
• 作为产物：
  描述：

  3-氨基吡啶 、 BOC-L-苯丙氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 3-<amino>pyridine
  参考文献：
  名称：

  L-苯基丙氨酸的双吡啶基双酰胺衍生的超分子凝胶显示出显着的形状维持，承重和自我修复特性

  摘要：

  合成了一系列由衍生自具有纯正侧链的L-氨基酸（L-丙氨酸和L-苯基丙氨酸）的吡啶基和苯基部分修饰的双酰胺，作为潜在的低分子量胶凝剂（LMWG）。发现大多数双酰胺都会使质子和非质子溶剂胶凝，且胶凝效率中等至极佳（最低胶凝剂浓度= 0.32–4.0 wt。％，凝胶-溶胶解离温度T gel = 52–110°C）。凝胶通过流变学，DSC，SEM，TEM和温度可变1进行表征1 H NMR测量。pH依赖性凝胶化研究表明，吡啶基部分参与了凝胶化。尝试使用单晶X射线和粉末X射线衍射数据进行结构与属性的关联。值得注意的是，一种双吡啶基双酰胺胶凝剂，即3,3-Phe（L-苯丙氨酸的3-吡啶基双酰胺）表现出出色的形状保持，承重和自愈特性。

  DOI：

  10.1002/asia.201402053

文献信息

• Metal-driven folding and assembly of a minimal β-sheet into a 3D-porous honeycomb framework
  作者：Nikhil Bajpayee、Salil Pophali、Thangavel Vijayakanth、Shyamapada Nandi、Aamod V. Desai、Vinod Kumar、Rahul Jain、Santu Bera、Linda J. W. Shimon、Rajkumar Misra

  DOI：10.1039/d3cc05185d

  日期：——

  Metal-mediated supramolecular assembly of a minimal β-sheet peptide revealed a hetero terminal peptide assembled into a 3D porous honeycomb framework.

  金属介导的最小 β 片肽超分子组装揭示了异端肽组装成三维多孔蜂巢框架的过程。
• Synthesis of pyridine derivatives of L-phenylalanine as antisickling reagents
  作者：Janina Altman、Marian Gorecki、Meir Wilchek、Joseph R. Votano、Alexander Rich

  DOI：10.1021/jm00371a007

  日期：1984.5

  Several bicyclic agents composed of L-phenylalanine coupled to various pyridines were synthesized: 2-, 3-, and 4-(L- phenylalanylamino )pyridine. All three compounds at 3 mM gave positive morphological antisickling effects on homozygous SS cells under reduced O2 tension. Studies on two of these compounds, 2- and 3-(L- phenylalanylamino )pyridine, showed that these agents increase the deoxy-HbS solubility ratio, Cs/ Cs0 , by 14% at 20 mM. Observed changes in the mean corpuscular hemoglobin concentration (MCHC) values of treated cells ranged from 4% at 1.3 mM to 15% at 5.6 mM in compound concentration. Very minor lytic activity was found for treated cells, indicating water uptake is responsible for changes in the MCHC. Further, exposure of sickle cells to a 3 mM concentration of these agents also increased by 6- to 7-fold cellular deformability of a treated erythrocyte population as compared to an untreated one at the same total O2 saturation of 47%. These agents demonstrate the potential of bicyclic compounds composed of a common constituent, L-Phe, in the development toward a viable therapeutic agent.
• Development of Potent Bifunctional Endomorphin-2 Analogues with Mixed μ-/δ-Opioid Agonist and δ-Opioid Antagonist Properties
  作者：Yoshio Fujita、Yuko Tsuda、Tingyou Li、Takashi Motoyama、Motohiro Takahashi、Yoshiro Shimizu、Toshio Yokoi、Yusuke Sasaki、Akihiro Ambo、Atsuko Kita、Yunden Jinsmaa、Sharon D. Bryant、Lawrence H. Lazarus、Yoshio Okada

  DOI：10.1021/jm030649p

  日期：2004.7.1

  The C terminus of endomorphin-2 (EM-2) analogues (Tyr-Pro-Phe-NH-X) was modified with aromatic, heteroaromatic, or aliphatic groups (X = phenethyl,benzyl, phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, tert-butyl, cyclohexyl, or adamantyl; 3-18) to study their effect on opioid activity. Only 9 (1-naphthyl), 11 (5-quinolyl), 16 (cyclohexyl), and 18 (2-adamantyl) exhibited mu-opioid receptor affinity in the nanomolar range (K-i = 2.41-6.59 nM), which, however, was 3- to 10-fold less than the parent peptide. Replacement of Tyr(1) by Dmt (2',6'-dimethyl-L-tyrosine) (19-32) exerted profound effects: (i) acquisition of high mu-opioid receptor affinity (K-i = 0.11-0.52 nM) except 23 (Ph); (ii) presence of potent functional mu-opioid receptor agonism (IC50 < 1 nM) for 19 ([Dmt(1)]EM-2), 27 (1-naphthyl), 29 (5-quinolyl), and 32 (5-isolquinolyl); (iii) association of weak delta-opioid antagonist activity (pA(2) = 5.41-7.18) except 19 ([Dmt(1)]EM-2), 20 (H), 27 (1-naphthyl), and in particular 29 (5-quinolyl) with its potent delta-agonism (IC50 = 0.62 nM, pA(2) = 5.88); (iv) production of antinociception after ic administration of 32 (5-isoquinolyl) in mice, a bioactivity absent in the corresponding Tyr(1) analogue (14); and (v) preferential cis orientation (cis/trans = 3:2 to 7:3) at the Dmt-Pro amide bond, in contrast to the Tyr-Pro amide trans orientation (cis/trans = 1:2 to 1:3). Thus, [Dmt(1)]EM-2 analogues with hydrophobic C-terminal extensions provide model compounds with potent mu-opioid receptor bioactivity and dual functional agonism.
• Hydrogelation Through Self-Assembly of Fmoc-Peptide Functionalized Cationic Amphiphiles: Potent Antibacterial Agent
  作者：Sisir Debnath、Anshupriya Shome、Dibyendu Das、Prasanta Kumar Das

  DOI：10.1021/jp909520w

  日期：2010.4.8

  The present work reports a new class of antibacterial hydrogelators based on anti-inflammatory N-fluorenyl-9-methoxycarbonyl (Fmoc) amino acid/peptides functionalized cationic amphiphiles. These positively charged hydrogelators were rationally designed and developed by the incorporation of a pyridinium moiety at the C-terminal of Fmoc amino acid/peptides, because the pyridinium-based amphiphiles are a known antibacterial agent due to their cell membrane penetration properties. The Fmoc amino acid/peptide-based cationic amphiphiles efficiently gelate (minimum gelation concentration similar to 0.6-2.2%, w/v) water at room temperature. Judicious variation of amino acid and their sequences revealed the architectural dependence of the molecules on their gelation ability. Several microscopic techniques like field-emission scanning electron microscopy (FESEM) and atomic force microscopy (AFM) were used to obtain the visual insight of the morphology of the gel network. A number of spectroscopic techniques like circular dichroism, FTIR, photoluminescence, and XRD were utilized to know the involvement of several noncovalent interactions and participation of the different segments of the molecules during gelation. Spectroscopic results showed that the pi-pi interaction and intermolecular hydrogen bonding are the major responsible factors for the self-assembled gelation process that are oriented through an antiparallel beta-sheet arrangement of the peptide backbone. These Fmoc-based cationic molecules exhibited efficient antibacterial activity against both Gram-positive and Gram-negative bacteria.
• Zn(II)-Coordination Complex(s) from Chiral Bisamides of <i>L</i>-Phenylalanine: Nanoscale-Based Biological Applications and Metallogelation
  作者：Utsab Manna、Abhishek Dutta、Manoj Kumar Baskey

  DOI：10.1021/acs.inorgchem.3c02731

  日期：2023.9.25