4-pyridylcarbonylamino acetic acid methyl ester | 90557-95-2

• 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: 4-pyridylcarbonylamino acetic acid methyl ester
• 英文别名: methyl isonicotinoylglycinate；isonicotinoyl-Gly-O-Me；methyl 2-(pyridine-4-carbonylamino)acetate
• CAS: 90557-95-2
• 化学式: C₉H₁₀N₂O₃
• mdl: MFCD09778470
• 分子量: 194.19
• InChiKey: JKAJOIWGPIUOEX-UHFFFAOYSA-N

物化性质

• 沸点：
  415.6±25.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-pyridylcarbonylamino acetic acid methyl ester 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 26.0h， 以98%的产率得到2-(isonicotinamid-4-yl)acetohydrazide
  参考文献：
  名称：

  El-Naggar; Hussein; El-Nemma, Farmaco, Edizione Scientifica, 1985, vol. 40, # 9, p. 662 - 670

  摘要：

  DOI：
• 作为产物：
  描述：

  异烟酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 4-pyridylcarbonylamino acetic acid methyl ester
  参考文献：
  名称：

  Synthesis, biological activity screening and molecular modeling study of acylaminoacetamide derivatives

  摘要：

  In this study, non-rigid analogs of thalidomide have been designed in order to develop potentially active, more effective and safer lead molecules for disorders caused or contributed by inflammation. Five different series of acylaminoacetamide compounds were synthesized, and the biological inhibitory potency of the title compounds has been determined by evaluating their effects on COX-2 isoenzyme expression and PGE(2) production in A549 (human lung adenocarcinoma) cell lines. Among the studied series, N-[2-(isopropylamino)-2-oxoethyl]isonicotinamide is the most active inhibitory compound on COX-2 isoenzyme expression, and N-[2-oxo-2-(pyrolydine-1-yl)etyl]isonicotinamide is the most active inhibitory compound on the biosynthesis of PGE(2). Molecular docking studies and molecular dynamics simulations were also applied to investigate non-covalent interactions of the most active compounds inside the active side of the crystal structure of murine cyclooxygenase 2 (mCOX-2) isoenzyme.

  DOI：

  10.1007/s00044-015-1419-4

文献信息

• A new series of fluorescent 5-methoxy-2-pyridylthiazoles with a pH-sensitive dual-emission
  作者：Ming-Hua Zheng、Jing-Yi Jin、Wei Sun、Chun-Hua Yan

  DOI：10.1039/b604910a

  日期：——

  A new series of fluorophores, 5-methoxy-2-(2-, 3- or 4-pyridyl)thiazoles (2-, 3- or 4-MPT, respectively), were synthesized and their photophysical properties investigated. 2- and 4-MPT are highly fluorescent in polar solvents. Combined with theoretical calculations, studies of the excited state lifetimes in different solvents reveal that their fluorescence mainly results from the internal charge transfer excited state. Acidobasic properties of their ground states and excited states were studied with steady and transient fluorescence spectroscopy. 2- and 4-MPT displayed a pH sensitive fluorescent behavior with a dual-emission in the range 2 to 6 in an aqueous system.

  合成了一系列新的荧光团，5-美氧基-2-(2、3或4-吡啶基)噻唑（分别为2-MPT、3-MPT和4-MPT），并研究了它们的光物理性质。2-MPT和4-MPT在极性溶剂中具有高度荧光特性。结合理论计算，对不同溶剂中激发态寿命的研究表明，它们的荧光主要源自内部电荷转移激发态。通过静态和瞬态荧光光谱研究了它们基态和激发态的酸碱性质。2-MPT和4-MPT在水相系统中表现出pH敏感的荧光行为，在pH值2至6的范围内具有双重发射。
• 氟喹诺酮类氨基衍生物及其防治柑橘病害的 用途
  申请人：西南大学

  公开号：CN107827815B

  公开（公告）日：2021-08-03

  柑橘溃疡病和褐斑病是柑橘常见病害，目前能够防治这两种病害的药物不多，并且都具有一定的缺陷。本发明将氟喹诺酮类药物7位氨基与活性片段通过连接结构连接得到如式I或式II所示化合物，实验表明，本发明的化合物具有防治柑橘溃疡病和和褐斑病的效果，具有非常好的应用前景。
• Solvent-sensitive charge-transfer absorption behaviours and dual-emissive fluorescent properties of a thiazole-conjugated pyridinium complex
  作者：Zhan-Xian Li、Chun-Hu Xu、Wei Sun、Yan-Chun Bai、Chao Zhang、Chen-Jie Fang、Chun-Hua Yan

  DOI：10.1039/b819016j

  日期：——

  neutral electron donor Et3N, only I− shows a similar influence on the absorption spectrum of 4-Me++ to that of bromide anion, confirming the bromide-dependent spectral properties of 4-MeB. With the help of theoretical calculations, the absorption in visible region is attributed to the charge-transfer from bromide anion to thiazolyl-pyridinium cation, which is tuned by the distance between the bromide

  合成了一种新型的荧光团，即1-（乙氧基-羰基-甲基）-4- [2-（5-甲氧基）噻唑基]溴化吡啶鎓（4-MeB），并对其光物理性质进行了研究。在具有较大介电常数（ε）的溶剂中，4-MeB被离子化为自由离子，在UV区显示出以噻唑基-吡啶鎓阳离子为中心的π→π*电子跃迁吸收带。在具有较小ε值的溶剂中，例如四氢呋喃 （THF）， 1,4-二恶烷 （二恶烷） 和 乙酸乙酯（EtOAc），4-MeB以紧密离子对的形式存在，并在可见光区和UV区同时显示特征性的溴离子依赖性吸收。在其他一些阴离子，如PF 6 - ，我-和Cl - ，和中性电子供体的Et 3 N，只有我-节目上的吸收光谱相似的影响4-ME + +至溴化物阴离子的，证实了4-MeB的溴化物依赖性光谱特性。借助理论计算，可见光区域的吸收归因于从溴化物阴离子到噻唑基-吡啶鎓阳离子的电荷转移，该电荷转移通过溴化物阴离子与噻唑基-吡啶基部分之间的距
• Concise Total Synthesis of (−)‐Quinocarcin Enabled by Catalytic Enantioselective Reductive 1,3‐Dipolar Cycloaddition of Secondary Amides
  作者：Kan‐Lei Ji、Shu‐Fan He、Dong‐Dong Xu、Wen‐Xin He、Jian‐Feng Zheng、Pei‐Qiang Huang

  DOI：10.1002/anie.202302832

  日期：2023.6.19

  A concise asymmetric total synthesis of (−)-quinocarcin has been accomplished with high step economy. A catalytic enantioselective reductive 1,3-dipolar cycloaddition reaction of secondary amides using iridium/copper relay catalysis was developed to prepare the key chiral pyrrolidine intermediate with three stereocenters. This protocol features excellent enantioselectivity, broad substrate scope, and

  (−)-quinocarcin 的简明不对称全合成已经以高步骤经济性完成。开发了使用铱/铜中继催化的仲酰胺催化对映选择性还原 1,3-偶极环加成反应，以制备具有三个立体中心的关键手性吡咯烷中间体。该协议具有出色的对映选择性、广泛的底物范围和良好的官能团耐受性。
• CERIC(IV) AMMONIUM NITRATE MEDIATED TRANSESTERIFICATION AND ESTERIFICATION
  作者：Bogdan Štefane、Marijan Kočevar、Slovenko Polanc

  DOI：10.1081/scc-120004264

  日期：2002.1

  The transesterification of carboxylic esters and the esterification of carboxylic acids are effected under mild conditions in the presence of ceric(IV) ammonium nitrate (CAN).