35773-42-3Relevant academic research and scientific papers
Synthesis, photo-and electro-luminescence of 3-benzoxazol-2-yl-coumarin derivatives
Zhao, Yuling,Yu, Tianzhi,Wu, Youzhi,Zhang, Hui,Fan, Duowang,Gan, Zunwei,Yang, Liangliang,Han, Xiaoqian,Zhang, Yumei
, p. 631 - 638 (2012)
Two coumarin derivatives containing electrontransporting benzoxazolyl moiety, 7-(diethylamino)-3- (benzoxazol-2-yl)coumarin (DABOC) and 3-(benzoxazol- 2-yl)benzo[5,6]coumarin (BOBC), were synthesized and characterized. The photoluminescence and electroluminescence of the compounds were investigated detailedly. The compounds exhibited strong blue-green emissions in both solution and solid states, but the devices with DABOC as the emitting layer exhibited orange emission and maximum luminous efficiency of 2.8 cd/A and maximum luminance of 8,800 cd/m2, and the devices with BOBC displayed orange-white emission and maximum luminous efficiency of 0.13 cd/A and maximum luminance of 540 cd/m2. Springer Science+Business Media, LLC 2011.
Discovery of fluorescent 3-heteroarylcoumarin derivatives as novel inhibitors of anaplastic lymphoma kinase
Mah, Shinmee,Song, Daesun,Shin, Yongje,Jung, Yongwon,Hong, Sungwoo,Jang, Jaebong,Latif, Muhammad
, p. 186 - 194 (2019/01/11)
Altered expression or hyperactivation of anaplastic lymphoma kinase (ALK), as a consequence of translocations or point mutations, is one of the main oncogenic drivers in non-small cell lung cancer. Using structure-based design and in vitro enzyme assays, we identified 3-heteroarylcoumarin as a new template for the development of novel fluorescent ALK inhibitors. Molecular simulation provided structural insights for the design of 3-heteroarylcoumarin derivatives, which were easily prepared through efficient synthetic approaches including direct C-H cross coupling. Importantly, these coumarin-based ALK inhibitors can be tracked using microscopy techniques: we illustrated the use of the most potent compound in this series, 5a, (ALK/IC50 = 0.51 μM, λemi = 500 nm, φF = 0.29) to monitor its subcellular distribution pattern by confocal fluorescence microscopy.
Organic–inorganic hybrid material, dichloro N,N'-(1,2-phenylene)bis(2-aminobenzamide) cobalt(II)@Al-SBA-15: an environment friendly catalyst for the synthesis of 3-benzoxazol-2-yl-chromen-2-ones
Safaei Ghomi, Javad,Akbarzadeh, Zeinab,Bakhtiari, Atefeh
, p. 826 - 840 (2019/05/17)
A new organic-inorganic hybrid material, CoCl2N,N'-(1,2-phenylene)bis(2-aminobenzamide)@Al-SBA-15, was synthesized by modification of Al-SBA-15 with (3-chloropropyl) trimethoxysilane (CPTMS), then the ligand was covalently attached to CPTMS@Al-SBA-15 and finally addition of CoCl2 to form the complex. The mesoporous CoCl2NN'PhBIA@Al-SBA-15 was an efficient catalyst in the preparation of 3-benzoxazol-2-yl-chromen-2-one derivatives through reaction of different coumarin-3-carboxylates and 2-aminophenol derivatives. The nanocatalyst increased rate and facility of the aforementioned reaction and had influence in the green synthesis of different 3-benzoxazol-2-yl-2H-chromen-2-one derivatives. The nanocatalyst was characterized by N2 adsorption–desorption, Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), powder X-ray diffraction (XRD), and energy dispersive spectroscopy (EDS). Some advantages of this procedure are mild reaction condition, high yields of 3-benzoxazol-2-yl-2H-chromen-2-one, short reaction times, environmentally benign, recoverability of the catalyst and reusability without significant loss of its catalytic performance.
Discovery and Optimization of Small Molecule Splicing Modifiers of Survival Motor Neuron 2 as a Treatment for Spinal Muscular Atrophy
Woll, Matthew G.,Qi, Hongyan,Turpoff, Anthony,Zhang, Nanjing,Zhang, Xiaoyan,Chen, Guangming,Li, Chunshi,Huang, Song,Yang, Tianle,Moon, Young-Choon,Lee, Chang-Sun,Choi, Soongyu,Almstead, Neil G.,Naryshkin, Nikolai A.,Dakka, Amal,Narasimhan, Jana,Gabbeta, Vijayalakshmi,Welch, Ellen,Zhao, Xin,Risher, Nicole,Sheedy, Josephine,Weetall, Marla,Karp, Gary M.
, p. 6070 - 6085 (2016/07/26)
The underlying cause of spinal muscular atrophy (SMA) is a deficiency of the survival motor neuron (SMN) protein. Starting from hits identified in a high-throughput screening campaign and through structure-activity relationship investigations, we have developed small molecules that potently shift the alternative splicing of the SMN2 exon 7, resulting in increased production of the full-length SMN mRNA and protein. Three novel chemical series, represented by compounds 9, 14, and 20, have been optimized to increase the level of SMN protein by >50% in SMA patient-derived fibroblasts at concentrations of 160 nM. Daily administration of these compounds to severe SMA Δ7 mice results in an increased production of SMN protein in disease-relevant tissues and a significant increase in median survival time in a dose-dependent manner. Our work supports the development of an orally administered small molecule for the treatment of patients with SMA.
One-pot catalyst-free synthesis of 3-heterocyclic coumarins
Jiang, Shaoliang,Gao, Jianrong,Han, Liang
, p. 1017 - 1028 (2016/04/26)
3-Heterocyclic coumarins were prepared in one-pot three-component reaction without catalyst. The mixture of salicylaldehydes, ethyl cyanoacetate, and o-aminophenols or o-phenylenediamines in refluxing n-butanol gave title compounds with good yields and hi
Direct C-H cross-coupling approach to heteroaryl coumarins
Min, Minsik,Kim, Bomi,Hong, Sungwoo
experimental part, p. 2692 - 2698 (2012/04/23)
A Pd-catalyzed direct cross-coupling of 3-bromocoumarins with heteroarenes provided an efficient route to synthesizing 3-heteroarylcoumarins. The reaction scope for the transformation was fairly broad, affording modest to good yields of various 3-heteroarylcoumarin scaffolds, which are privileged structures and prevalent motifs in many biologically active compounds and fluorophores. The Royal Society of Chemistry 2012.
Microwave-promoted one-pot syntheses of coumarin dyes
Nourmohammadian, Farahnaz,Gholami, Mahnaz Davoodzadeh
experimental part, p. 901 - 909 (2010/05/18)
To one pot synthesis of coumarins with benzimidazol or benzoxazol moieties, three different microwave irradiations based procedures are reported here which take place within a few minutes. In spite of fairly well yield of the products using solvent free procedures, 25-30% further yields were achieved within 3 minutes at 110C using 2mL n-pentanol as solvent.
Synthesis and anti-angiogenesis activity of coumarin derivatives
Lee, Seokjoon,Sivakumar, Krishnamoorthy,Shin, Woon-Seob,Xie, Fang,Wang, Qian
, p. 4596 - 4599 (2007/10/03)
A series of 7-diethylaminocoumarin compounds were synthesized and the cytotoxicities were tested against human umbilical vein endothelial cell (HUVEC) and some cancer cells. We found that the introduction of cyano groups at the 4-position will promote the bioactivity. In particular, compounds 9 and 10 strongly inhibited the proliferation of various cancer cell lines, and 12 and 15 showed a high selectivity for HUVEC. Therefore, these coumarin molecules can be utilized as lead compounds to develop potential nontoxic angiogenesis inhibitors and small molecular ligands to target HUVEC.
