5452-39-1Relevant academic research and scientific papers
Synthesis of Chromeno[4′,3′:4,5]pyrido[1,2- a ]pyrazines and -diazepines by the Reaction of Substituted 2-(3-Acetyl-2-oxo-2 H -chromen-4-yl)fumarates with 1, n -Diamines
Alizadeh, Abdolali,Jamal, Parinaz
, p. 1107 - 1111 (2018)
A two-step sequence was developed for the synthesis of chromeno[4′,3′:4,5]pyrido[1,2- a ]pyrazine-13-carboxylates and -diazepine-14-carboxylates by the reaction of substituted dimethyl 2-(3-acetyl-2-oxo-2 H -chromen-4-yl)fumarates with 1, n -diamines at room temperature. Advantages of this protocol include ease of handling and the absence of a metal catalyst.
Design, synthesis, antioxidant and anticancer activity of new coumarin derivatives linked with thiazole, isoxazole or pyrazole moiety
Abdellatif, Khaled R.A.,Abdelgawad, Mohamed A.,Elshemy, Heba A. H.,Kahk, Nesma M.,El Amir, Dalia M.
, p. 773 - 781 (2017)
Background: Three new series of coumarin derivatives 4a-e, 6a-d and 7a-d were synthesized and characterized by elemental analyses and spectral data including 2D NMR. All compounds 4a-e, 6a-d and 7a-d were evaluated for their in vitro antioxidant and antic
Crystal structure, photoluminescent and theoretical studies of 3-acetyl-8-methoxy-coumarin derivatives
Shu, Xin,Li, Jing,Li, Ming-Kai
, p. 8427 - 8430 (2014)
3-Acetyl-8-methoxy-coumarin and its derivative 3-(2,2′-dibromoacetyl)-8-methoxy-coumarin were synthesized and characterized. The structure of 3-(2,2′-dibromoacetyl)-8-methoxy-coumarin was verified by single-crystal X-ray crystallography. The UV-visible absorption and fluorescence of 3-acetyl-8-methoxy-coumarin and 3-(2,2′-dibromoacetyl)-8-methoxy-coumarin were also studied. Both compounds exhibit strong blue emission under ultraviolet light excitation. The molecular structure of 3-(2,2′-dibromoacetyl)-8-methoxy-coumarin was optimized using density functional theory at the B3LYP/6-31G(d) level, showing that the optimized geometer parameters are in good agreement with the experimental data. In addition, the HOMO and LUMO levels of 3-acetyl-8-methoxy-coumarin and 3-(2,2′-dibromoacetyl)-8-methoxy-coumarin were deduced.
3-Acetyl-8-methoxy-2[H]-chromen-2-one derived Schiff bases as potent antiproliferative agents: Insight into the influence of 4(N)-substituents on the in vitro biological activity
Kalaiarasi,Rex Jeya Rajkumar,Aswini,Dharani,Fronczek, Frank R.,Prabhakaran
, p. 246 - 262 (2018)
A series of 3-acetyl-8-methoxycoumarin appended thiosemicarbazones (1–4) was prepared from the reaction of 3-acetyl-8-methoxycoumarin with 4(N)-substituted thiosemicarbazides in a view of ascertaining their biological properties with the change of N-terminal substitution in the thiosemicarbazide moiety. Comprehensive characterization was brought about by various spectral and analytical methods. The molecular structures of all the compounds were determined by single crystal X-ray diffraction analysis. Binding studies with Calf thymus DNA (CT-DNA) and proteins such as Bovine Serum Albumin (BSA) and Human Serum Albumin (HSA) indicated an intercalative mode of binding with DNA and static quenching mechanism with proteins. The compounds cleaved plasmid DNA (pBR322) and acted well as free radical scavengers. A good spectrum of antimicrobial activity was observed against four bacterial and five fungal pathogens. The compounds exhibited profound antiproliferative activity on MCF-7 (human breast cancer) and A549 (human lung carcinoma) cell lines. Assay on human normal keratinocyte cell line HaCaT showed that the compounds were non-toxic to normal cells.
A facile one pot multi component synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetates and their antiviral activity
Kulkarni, Chandrashekhar V.,Vaarla, Krishnaiah,Vedula, Rajeswar Rao,Vermeire, Kurt,Vishwapathi, Vinod
, (2021/10/19)
An efficient one-pot synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetate derivatives has successfully been achieved via a three component cyclization reaction of various substituted 3-acetyl coumarins, thiosemicarbazide and dialkyl acetylenedicarboxylates, in presence of acetic acid. The isolated products were obtained in pure form with high yields through simple workup. The newly synthesised compounds structure was established on the basis of spectral (IR, 1H NMR, 13C NMR, ESI- mass) elemental analysis and single crystal X-ray data. All synthesised compounds were screened for their antiviral activity against a broad spectrum of human viruses in different cell cultures. Of the novel synthesised compounds, thirteen compounds exerted activity against Punta Toro virus, including compound IV-19, for which an antiviral potency was noted against a broad panel of DNA and RNA viruses as well.
One-pot synthesis of novel (E)-3-(3,8a-dihydro-2H-oxazolo[3,2-a]pyridin-2-ylidene)chroman-2-one derivatives
Olyaei, Abolfazl,Feizy, Elaheh,Aghajanzadeh, Atiye
, p. 757 - 765 (2021/01/12)
An efficient synthetic procedure for the preparation of novel (E)-3-(3,8a-dihydro-2H-oxazolo[3,2-a]pyridin-2-ylidene)chroman-2-one derivatives was developed. A sequential one-pot, two-step tandem reaction starting from 3-(2-bromoacetyl)-2H-chromen-2-one derivatives synthesized, pyridine, and naphthols in the presence of triethylamine proceeded smoothly in acetonitrile under reflux conditions. In this process, 2-oxo-2H-chromen-3-yl)ethyl)pyridinium bromide derivatives as intermediate produced in situ, followed by Michael addition of naphthoxide anion and intramolecular cylization, resulted the corresponding products in good to high yields. All of the compounds were obtained in high purity without any use of more purification.
Design, synthesis, and structure–activity relationship study of O-prenylated 3-acetylcoumarins as potent inhibitors of soybean 15-lipoxygenase
Zerangnasrabad, Sara,Jabbari, Atena,Khavari Moghadam, Elahe,Sadeghian, Hamid,Seyedi, Seyed Mohammad
, p. 826 - 834 (2021/01/18)
In this work, the design, synthesis, and structure–activity relationships of a novel array of geranyloxy and farnesyloxy 3-acetylcoumarins were reported as potent soybean 15-lipoxygenase inhibitors. Among the prepared coumarins, 7-farnesyloxy-3-acetylcoumarin (12b) was found to be the most potent inhibitor by IC50?= 0.68 μM while O-geranyl substituents at positions 5 and 6 of 3-acetylcoumarin (10a and 11a) were not inhibitors. Using docking studies, the binding affinity and the preferred pose of synthetic compounds were considered. It was found that lipoxygenase inhibitory activity and prenyl length chain were directly related. The hydrophobic cavity of the enzyme was more effectively occupied by the farnesyl moiety of the potent inhibitor 12b rather than other derivatives. Also, with this pose of farnesyl chain in 7-farnesyloxy-3-acetylcoumarins, the acetyl group could be directed to the hydrophilic pocket in the active site.
Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives
Cao, Lian-Gong,Cao, Zhi-Ling,Jiang, Kai-Jun,Liu, Shu-Hao,Liu, Wei-Wei,Lu, Xing,Shao, Zhong-Bai,Shi, Da-Hua,Wang, Lei,Wang, You-Xian
, p. 359 - 364 (2020/12/28)
Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.
Synthesis and antiproliferative activity of hybrid thiosemicarbazone derivatives bearing coumarin and d-galactose moieties with EGFR inhibitory activity and molecular docking study
Toan, Vu Ngoc,Thanh, Nguyen Dinh
, p. 1868 - 1885 (2021/08/23)
A series of substituted N-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)thiosemicarbazones 5a–5j of substituted 3-acetylcoumarins were synthesized with yields of 45–68%. All synthesized thiosemicarbazones were evaluated for cytotoxic activity against several cancer cell lines, such as human breast adenocarcinoma cells MCF7, human liver cancer cells HepG2, human cervical cancer cells HeLa, human melanoma cancer cells SK-Mel-2, and human lung cancer cells LU-1 by using the standard MTT assay. The IC50 values for these cancer cell lines were 1.28–11.81 μM (for MCF-7), 1.53–22.12 μM (for HepG2), 1.43–48.16 μM (for HeLa), 1.82–14.62 μM (for SK-Mel-2), and 1.74–14.62 μM (for LU-1). Most of the compounds were noncytotoxic against human WI-38 normal cell line (IC50 > 16.9 μM). The antiproliferative mechanisms were studied via EGFR inhibition and molecular docking. Docking studies revealed that there are strong interactions between a typical compound with the receptor of the EGFR tyrosine kinase domain with Erlotinib. [Figure not available: see fulltext.]
Design, synthesis of coumarin tethered 1,2,3-triazoles analogues, evaluation of their antimicrobial and α-amylase inhibition activities
Channabasappa, Vagish,Kariyappa, Ajay Kumar,Kumara, Karthik
, (2021/12/01)
A vital transition metal Cu(II) ion catalyzed reaction was encrypted in the synthesis of new coumarin tethered triazoles 6(a-i) using the substituted azidobenzenes and substituted 3-acetyl-2H-chromen-2-ones in the presence of oxidative potassium persulfate, and DMF as a solvent and C5-H source. The structure proofs of the new compounds were provided by the spectral analysis. The in vitro antimicrobial activities of the target compounds indicate that compounds 6c and 6g of the series have potent inhibition against the tested bacteria and fungi species. Among the synthesized series compound 6g was found potent for α-amylase inhibition activity. Graphical abstract: Synopsis. Dimethylformamide was used as a solvent and C5-H source reagent in the synthesis of triazole rings. The reaction of substituted azides, 2(a-e) and substituted 3-acetyl-2-oxo-2H-chromenes, 5(a-b) in the presence of a catalytic amount of Cu(NO3)2 and an oxidant K2S2O8 was carried out under reflux conditions using an oil bath for 36-48 h. From the reaction mixture, the target compounds 6(a-i) were extracted with ethyl acetate. The synthesized coumarin-triazole hybrids, 6(a-i) were spectroscopically characterized and evaluated for antimicrobial and α-amylase inhibitory activities.[Figure not available: see fulltext.]
