4-(4-methyl-2-oxo-2H-chromen-7-ylamino)-4-oxobutanoic acid | 120783-21-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-(4-methyl-2-oxo-2H-chromen-7-ylamino)-4-oxobutanoic acid
• 英文别名: 3-(4-methyl-2-oxo-2H-chromen-7-ylcarbamoyl)propanoic acid；4-[(4-methyl-2-oxo-2H-chromen-7-yl)amino]-4-oxobutanoic acid；4-[(4-methyl-2-oxochromen-7-yl)amino]-4-oxobutanoic acid
• CAS: 120783-21-3
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: HBIXHZONDRHFBR-UHFFFAOYSA-N

物化性质

• 熔点：
  170 °C
• 沸点：
  589.8±50.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-methyl-2-oxo-2H-chromen-7-ylamino)-4-oxobutanoic acid 、 在 焦磷酸硫胺素 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以81%的产率得到
  参考文献：
  名称：

  Synthesis of Water-Soluble Highly Charged and Methylene-Bridged ­Resorcin[4]arenes

  摘要：

  具有电活性亲水性紫罗碱单元、化学结合于其“边缘”区域以及多种悬挂基团（“足部”）的亚甲基桥联间苯二酚[4]芳烃已合成。这些化合物被设计为发挥电活性腔体作用，并尤其作为分枝杆菌通道蛋白的客体（通道阻断剂）。

  DOI：

  10.1055/s-2008-1032192
• 作为产物：
  描述：

  丁二酸酐 、 7-氨基-4-甲基香豆素 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到4-(4-methyl-2-oxo-2H-chromen-7-ylamino)-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis of Water-Soluble Highly Charged and Methylene-Bridged ­Resorcin[4]arenes

  摘要：

  具有电活性亲水性紫罗碱单元、化学结合于其“边缘”区域以及多种悬挂基团（“足部”）的亚甲基桥联间苯二酚[4]芳烃已合成。这些化合物被设计为发挥电活性腔体作用，并尤其作为分枝杆菌通道蛋白的客体（通道阻断剂）。

  DOI：

  10.1055/s-2008-1032192

文献信息

• FLUORESCENT ANTICANCER PLATINUM DRUGS
  申请人：INVICTUS ONCOLOGY PVT. LTD.

  公开号：US20180312534A1

  公开（公告）日：2018-11-01

  The present disclosure is in relation to the field of nanotechnology and cancer therapeutics. In particular, the present disclosure relates to fluorescent platinum based compounds. The disclosure further relates to synthesis of said fluorescent platinum based compounds, nanoparticles and compositions comprising said fluorescent platinum based compounds/nanoparticles. The disclosure also relates to methods of managing cancer by the fluorescence changes between aforesaid platinum based compounds and corresponding free ligands, nanoparticles and compositions.

  本公开涉及纳米技术和癌症治疗领域。具体而言，本公开涉及荧光铂基化合物。该公开进一步涉及合成所述荧光铂基化合物、纳米颗粒和包含所述荧光铂基化合物/纳米颗粒的组合物。该公开还涉及通过上述铂基化合物与相应的游离配体、纳米颗粒和组合物之间的荧光变化来管理癌症的方法。
• 具有线粒体靶向的光敏感载体材料及其制备方法和应用
  申请人：温州大学

  公开号：CN115708876A

  公开（公告）日：2023-02-24

  本发明属于纳米载药技术领域，具体涉及一种具有线粒体靶向的光敏感载体材料及其制备方法和应用。该载体材料通过引入具有良好生物相容性的聚合物来提高其在水中的溶解度；引入线粒体靶向分子三苯基膦(TPP+)衍生物，将不同的生物活性分子直接递送到线粒体基质中；同时利用上转换纳米粒子将对组织透过率高、损伤小的近红外光/红外光转化为能量更高的紫外光，促使光敏感分子7‑氨基‑4‑甲基香豆素衍生物上的酰胺键发生光解断裂控制释放药物，达到靶向治疗病症的效果。
• Pt(IV) Prodrugs Designed to Bind Non-Covalently to Human Serum Albumin for Drug Delivery
  作者：Yao-Rong Zheng、Kogularamanan Suntharalingam、Timothy C. Johnstone、Hyunsuk Yoo、Wei Lin、Jamar G. Brooks、Stephen J. Lippard

  DOI：10.1021/ja5038269

  日期：2014.6.18

  Albumin is the most abundant protein in human serum and drugs that are administered intravenously inevitably interact with it. We present here a series of platinum(IV) prodrugs designed specifically to enhance interaction with human serum albumin (HSA) for drug delivery. This goal is achieved by asymmetrically functionalizing the axial ligands of the prodrug so as to mimic the overall features of a fatty acid. Systematic variation of the length of the aliphatic tail tunes the cellular uptake and, consequently, the cytotoxicity of cis,cis,trans-[Pt(NH3)2Cl2(O2CCH2CH2COOH)(OCONHR)], 4, where R is a linear alkyl group. Investigation of an analogue bearing a fluorophore conjugated to the succinate ligand confirmed that these compounds are reduced by biological reductants with loss of the axial ligands. Intracellular release of cisplatin from 4 was further confirmed by observing the characteristic effects of cisplatin on the cell cycle and morphology following treatment with the prodrug. The most potent member of series 4, for which R is a hexadecyl chain, interacts with HSA in a 1:1 stoichiometry to form the platinum-protein complex 7. The interaction is non-covalent and extraction with octanol completely removes the prodrug from an aqueous solution of HSA. Construct 7 is robust and can be isolated following fast protein liquid chromatography. The nature of the tight interaction was investigated computationally, and these studies suggest that the prodrug is buried below the surface of the protein. Consequently, complexation to HSA is able to reduce the rate of reduction of the prodrug by ascorbate. The lead compound from series 4 also exhibited significant stability in whole human blood, attributed to its interaction with HSA. This favorable redox profile, in conjunction with the established nonimmunogenicity, biocompatibility, and enhanced tumor accumulation of HSA, produces a system that holds significant therapeutic potential.
• KESSLER, H.;HAUPT, A.;SCHUDOK, M.;ZIEGLER, K.;FRIMMER, M., INT. J. PEPTIDE AND PROTEIN RES., 32,(1988) N 3, C. 183-193
  作者：KESSLER, H.、HAUPT, A.、SCHUDOK, M.、ZIEGLER, K.、FRIMMER, M.

  DOI：——

  日期：——
• [EN] FLUORESCENT ANTICANCER PLATINUM DRUGS<br/>[FR] MÉDICAMENTS ANTICANCÉREUX FLUORESCENTS AU PLATINE
  申请人：INVICTUS ONCOLOGY PVT LTD

  公开号：WO2017064657A1

  公开（公告）日：2017-04-20

  The present disclosure is in relation to the field of nanotechnology and cancer therapeutics. In particular, the present disclosure relates to fluorescent platinum based compounds. The disclosure further relates to synthesis of said fluorescent platinum based compounds, nanoparticles and compositions comprising said fluorescent platinum based compounds/nanoparticles. The disclosure also relates to methods of managing cancer by the fluorescence changes between aforesaid platinum based compounds and corresponding free ligands, nanoparticles and compositions.