5614-82-4Relevant academic research and scientific papers
Synthesis and properties of fluorescent coumarin/perylene-3,4,9,10-tetracarboxylic diimide hybrid as cold dye
Ferasat, Erisa,Golshan, Marzieh,Roghani-Mamaqani, Hossein,Salami-Kalajahi, Mehdi
, (2021)
Perylene-3,4,9,10-tetracarboxylic dianhydride (PTCDA) was modified by ethylenediamine to obtain perylene-3,4,9,10-tetracarboxylic diimide (PTCDI). PTCDI as an initial core was used to bond coumarin derivatives. Successful conjugating of coumarin derivatives onto PTCDI was confirmed by Fourier-transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1H NMR), X-ray diffraction (XRD), and field emission scanning electron microscope (FE-SEM). XRD peaks of various samples showed that the crystalline structure of PTCDA retained during the modification processes. The morphology of the nanoparticles by FE-SEM showed that the dyes were fibrillar. Fluorescence microscopy was used to evaluate the fluorescence properties of the dyes. In order to determine the amount of absorption and reflection in the near-infrared region, NIR test was used in both white and black fields. High absorption on a white background and high reflection on a black background indicated the transparency of the dye in the near-infrared region. The synthesized dye was identified and reported as a cold dye.
Fluorescence chemosensor containing 4-methyl-7-coumarinyloxy, acetylhydrazono and N-phenylaza-15-crown-5 moieties for K+ and Ba2+ ions
Zhang, Qiang,Duan, Kaifei
, p. 141 - 145 (2018)
A new aza-15-crown-5 derivative 1 bearing coumarin and hydrazone moieties was synthesized and characterized. The fluorescent sensing behavior and selectivity of 1 toward different metal ions in ethanol were investigated. There are 4-fold and 2-fold fluore
Reversible light-driven polymerization of polyoxometalate tethered with coumarin molecules
Tong, Unsong,Chen, Wei,Ritchie, Chris,Wang, Xiaoting,Song, Yu-Fei
, p. 1500 - 1504 (2014)
A new photosensitive polyoxometalate (POM) organic-inorganic hybrid compound has been prepared by covalently tethering coumarin moieties onto a Mn-Anderson cluster. This compound has been fully characterized by 1H NMR, 13C NMR, FTIR, and UV/Vis spectroscopy, and ESI-MS. This organic-inorganic hybrid compound can undergo reversible light-driven polymerization and this process has been characterized in detail. Polymerizing POMs: A new photosensitive polyoxometalate (POM) organic-inorganic hybrid compound has been prepared by covalently tethering coumarin moieties onto a Mn-Anderson cluster. This compound has been fully characterized by 1H NMR, 13C NMR, FTIR, and UV/Vis spectroscopy, and ESI-MS. This compound can undergo reversible light-driven polymerization (see scheme) and this process has been characterized in detail. Copyright
Synthesis of N1-Substituted Coumarino[4,3-c] pyrazoles
Cacic, Milan,Trkovnik, Mladen,Has-Schoen, Elizabeta
, p. 833 - 836 (2003)
3-Acyl-4-hydroxy-2-oxo-2H-chromen derivatives 1a-d were condensed with (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid hydrazide 2, (4-methyl-2-oxo-2H-chromen-7-yloxy)-acetic acid hydrazide 3, and (7-hydrazinocarbonylmethoxy-2-oxo-2H-chromen-4-yl)-acetic acid hydrazide 4, to give corresponding 3-alkyl-1-[2-(7-hydroxy-2-oxo-2H-chromeno-4-yl)-acetyl]-1H-chromeno[4,3-c] pyrazole-4-one 5a-d, 3-alkyl-1-[2-(4-methyl-2-oxo-2H-chromeno-7-yloxy)-acetyl]-1H-chromeno[4,3-c] pyrazole-4-one 6a-d, and 1-{4-[(3-alkyl-1H-chromeno[4,3-c]pyrazole-4-one-1-yl)-carbonylmethyl] -2-oxo-2H-chromen-7-yloxy-acetyl}-3-alkyl-1H-chromeno[4,3-c]pyrazole-4-one 7a-d.
Synthesis, X-ray characterization and biological evaluation of some new 2-(4-methy-2-oxo-2H-chromen-7yloxy) acetamide derivatives
Diwakar, Bhagavathula S.,Govindh,Nagendra Sastry,Kaladhar,Murthy
, p. 1546 - 1557 (2015)
Newly designed coumarinyloxy acetamide derivatives (7a-7n) were synthesized in good yields and characterised by advanced spectroscopic studies and the XRD studies indicated that no polymorphism is observed in the molecules. Synthesized coumarinyloxy aceta
Design synthesis and anti-proliferative activity of some new coumarin substituted hydrazide–hydrazone derivatives
Duangdee, Nongnaphat,Mahavorasirikul, Wiratchanee,Prateeptongkum, Saisuree
, (2020/04/29)
Abstract: A series of 21 coumarin hydrazide–hydrazone derivatives were designed, synthesized and evaluated potential cytotoxicity effects at 25 μg/mL for 48 h against liver cancer (HepG2) cell line in vitro. Then, seven out of 21 compounds with % cell via
Identification of a Novel Oxadiazole Inhibitor of Mammalian Target of Rapamycin
Lim, Sunwoo,Lee, Hyomin,Kim, Euijung,Hur, Wooyoung
, p. 296 - 303 (2020/02/04)
We performed a biochemical screen against mTOR using in-house small molecule library. Two novel, structurally distinct hits were identified. Among them, a novel oxadiazole scaffold compound (2) suppressed the phosphorylation of both S6K1 and Akt1 in HeLa cells. Docking study suggested that 2 is ATP-competitive and shows a pi-pi interaction with Trp2239 and hydrogen bonds with Trp2239 and Thr2245. Through derivatization, a slightly more potent analogue (2a) was identified with IC50 of 9.6 μM. Our study provides a starting point for discovery of novel potent mTOR inhibitors.
Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides
Jin, Can,Sun, Bin,Xu, Tengwei,Yan, Zhiyang,Zhang, Xun
supporting information, p. 1585 - 1591 (2019/08/07)
A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.
Synthesis and evaluation of bi-functional 7-hydroxycoumarin platinum(IV) complexes as antitumor agents
Wang, Qingpeng,Chen, Yan,Li, Guoshuai,Liu, Zhifang,Ma, Jing,Liu, Min,Li, Dacheng,Han, Jun,Wang, Bingquan
, p. 2112 - 2121 (2019/04/10)
A series of bi-functional 7-hydroxycoumarin platinum(IV) complexes were synthesized, characterized, and evaluated for antitumor activities. The 7-hydroxycoumarin platinum(IV) complexes display moderate to effective antitumor activities toward the tested cell lines and show much potential in overcoming drug resistance of platinum(II) drugs. In reducing microenvironment, the title compounds could be reduced to platinum(II) complex accompanied with two equivalents of coumarin units. By a unique mechanism, the 7-hydroxycoumarin platinum(IV) complex attacks DNA via the released platinum(II) compound, meanwhile it also inhibits the activities of cyclooxygenase by coumarin fragment. This action mechanism might be of much benefit for reducing tumor-related inflammation in the progress of inhibiting tumor proliferation and overcoming cisplatin resistance. The incorporation of 7-hydroxycoumarin leads to significantly enhanced platinum accumulation in both whole tumor cells and DNA. The HSA interaction investigation reveals that the tested coumarin platinum(IV) compound could effectively combine with HSA via van der Waals force and hydrogen bond.
Synthesis and biological evaluation of coumarin-1,3,4-oxadiazole hybrids as selective carbonic anhydrase IX and XII inhibitors
Narella, Sridhar Goud,Shaik, Mohammed Ghouse,Mohammed, Arifuddin,Alvala, Mallika,Angeli, Andrea,Supuran, Claudiu T.
, p. 765 - 772 (2019/04/13)
With an aim to develop novel heterocyclic hybrids as potent anticancer agents, we synthesized a series of coumarin-1,3,4-oxadiazole hybrids (7a-t) and evaluated for their inhibitory activity against the four physiologically relevant human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms CA I, CA II, CA IX and CA XII. The CA inhibition results clearly indicated that the coumarin-1,3,4-oxadiazole derivatives (7a-t) exhibited selective inhibition of the tumor associated isoforms, CA IX and CA XII over CA I and II isoforms. Among all, compound 7b, exhibited significant inhibition in lower micromolar potency against hCA XII, with a Ki of 0.16 μM and compound 7n, exhibited significant inhibition in lower micromolar potency against hCA IX, with a Ki of 2.34 μM respectively. Therefore, compound 7b and 7n could be the potential leads for development of selective anticancer agents by exhibiting a novel mechanism of action through hCA IX and XII inhibition.
