chelidamic acid | 184870-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: chelidamic acid
• 英文别名: 4-Oxo-1,4-dihydropyridine-2,6-dicarbonyl dichloride；4-oxo-1H-pyridine-2,6-dicarbonyl chloride
• CAS: 184870-12-0
• 化学式: C₇H₃Cl₂NO₃
• 分子量: 220.012
• InChiKey: SDVCBQMQTVFCDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  chelidamic acid 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 二甲基4-氨基-2,6-吡啶二羧酸酯
  参考文献：
  名称：

  Selective cytotoxicity and luminescence imaging of cancer cells with a dipicolinato-based Eu^III complex

  摘要：

  四种新的镧系金属络合物与配体dipicNH2 2- (dipic = dipicolinato) 显示出选择性的癌细胞毒性，并用于细胞发光成像。

  DOI：

  10.1039/c7cc06753d
• 作为产物：
  描述：

  4-氧代-1,4-二氢-2,6-吡啶二甲酸 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 chelidamic acid
  参考文献：
  名称：

  Synthesis of chromophores combining second harmonic generation and two photon induced fluorescence properties

  摘要：

  报告了同时具有SHG和TPEF性质的新发色团的设计。

  DOI：

  10.1039/b610557b

文献信息

• LUMINESCENT COMPOUNDS
  申请人：Terpetschnig Ewald A.

  公开号：US20100266507A1

  公开（公告）日：2010-10-21

  Luminescent reporter compounds that are rotaxanes having the structure where B—Z—C is a reporter molecule based on a cyanine, squaric acid, or other reporter, and K is a macrocycle that encircles and interlocks with the reporter molecule. Applications of the reporter compounds are provided, as well as reactive intermediates used to synthesize the reporter compounds, and methods of synthesizing the reporter compounds.

  具有以下结构的轮烷的发光报告化合物，其中B—Z—C是基于青菁、方酸或其他报告物质的报告分子，K是环绕并与报告分子相互锁定的大环。提供了报告化合物的应用，以及用于合成报告化合物的反应中间体和合成报告化合物的方法。
• Sol–gel emulsion synthesis of biphotonic core–shell nanoparticles based on lanthanide doped organic–inorganic hybrid materials
  作者：Xianmin Guo、Jean-Louis Canet、Damien Boyer、Arnaud Gautier、Rachid Mahiou

  DOI：10.1039/c2jm15470f

  日期：——

  Eu3+ and Tb3+ complexes based on an organo-alkoxysilane derived from 4-azido dipicolinic acid by “click chemistry” were coated onto silica nanoparticles previously prepared by the water in oil emulsion method. Structural and optical properties of the resulting luminescent core–shell monodisperse (30 nm) nanohybrids were fully characterized by infrared and Raman spectroscopies as well as by electron microscopy. Fluorescence spectroscopy evidenced that an efficient ligand-to-Ln3+ energy transfer—both in the mono- and biphotonic modes—occurs. Furthermore, surface modification by amino groups was realized, paving the way for nanotags of biological interest.

  基于4-叠氮基二吡啶酸的有机烷氧基硅烷衍生物的Eu3+和Tb3+络合物通过“点击化学”方法涂覆在之前通过水包油乳液法制备的二氧化硅纳米颗粒上。所得到的发光核壳单分散（30纳米）纳米混合物的结构和光学特性通过红外光谱和拉曼光谱以及电子显微镜进行了全面表征。荧光光谱显示，发生了高效的配体向Ln3+的能量转移——无论是在单光子模式还是双光子模式下。此外，进行了氨基表面修饰，为生物相关的纳米标签铺平了道路。
• Synthetic Approaches to the Bifunctional Chelators for Radio­nuclides Based On Pyridine-Containing Azacrown Compounds
  作者：Anastasia D. Zubenko、Anna A. Shchukina、Olga A. Fedorova

  DOI：10.1055/s-0039-1691540

  日期：——

  Synthetic ways to introduce functional groups (CO2Me, CO2H, OCH2CO2H, OCH2C≡CH, CH2OH, CH2Cl, CH2N3) into the pyridine ring of pyridine-containing azacrown compounds are described. These groups were introduced at position-4 of the pyridine ring, while keeping the macrocyclic carboxylate groups available for metal chelation. The derivatives were obtained by macrocyclization reaction of 4-substituted

  合成的方式引进的官能团（CO 2 Me中，CO 2 H，OCH 2 CO 2 H，OCH 2 C≡CH，CH 2 OH，CH 2氯，CH 2 Ñ 3）描述了将含吡啶的氮杂冠化合物引入吡啶环中的方法。这些基团被引入吡啶环的4位，同时保持大环羧酸盐基团可用于金属螯合。所述衍生物通过4-取代的三甲基吡啶-2,4,6-三羧酸酯的大环化反应或通过修饰大环吡啶片段中的甲酯基而获得。通过与不同的载体生物分子缀合，可以将获得的衍生物用于制备放射治疗剂，以将药物靶向性递送至癌细胞而不会损害健康组织。
• Polydiacetylenes Functionalized with Chelidamic Acid and 2,2'‐Dipicolylamine for Colorimetric Responses to Cadmium Ions
  作者：Thanh Chung Pham、Hyun Sung Kim、Songyi Lee

  DOI：10.1002/bkcs.12177

  日期：2021.1

  A novel polydiacetylene‐linked ligand derived from the reaction between chelidamic acid and bis(pyridin‐2‐ylmethyl)amine (PDA‐CB) showed excellent selectivity and sensitivity for Cd2+ ions compared with other metal ions, including Zn2+. An obvious color change between PDA‐CB and PDA‐CB + Cd2+ is clearly visible to the naked eye. The Cd2+‐responsive color change of PDA‐CB is attributed to the coordination

  一种新的聚二乙炔连接的配体，其与氯胺酸和双（吡啶-2-基甲基）胺（PDA-CB）反应生成，与其他金属离子（包括Zn 2+）相比，对Cd 2+离子具有极好的选择性和灵敏度。肉眼可以清楚地看到PDA-CB和PDA-CB + Cd 2+之间的明显颜色变化。PDA-CB的Cd 2+反应性颜色变化归因于Cd 2+和CB配体单元之间的配位，并已通过1 H NMR滴定进行了表征。
• Tuning selectivity in macrotricyclic carbohydrate receptors; CH ? N mutations in aromatic spacersElectronic supplementary information (ESI) available: experimental details for the synthesis of receptors 3 and 4, binding studies of receptors 3 and 4 with monosaccharide 2, and extraction experiments. See http://www.rsc.org/suppdata/ob/b3/b315447e/
  作者：Trinidad Velasco、Gregory Lecollinet、Theo Ryan、Anthony P. Davis

  DOI：10.1039/b315447e

  日期：——

  Dipicolinoyl spacer groups are used to control the conformational and H-bonding properties of tricyclic carbohydrate receptors 3 and 4. Binding selectivities are changed in relation to all-isophthaloyl system 1b.

  二吡啶甲酰基间隔基团用于控制三环碳水化合物受体3和4的构象和氢键特性。相对于全间苯二甲酰基系统1b，结合选择性发生变化。