- Novel coumarin-pyrazoline hybrids: synthesis, cytotoxicity evaluation and molecular dynamics study
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A novel series of coumarin-pyrazoline hybrids3a-f,4a-cand5a-chave been synthesized and tested for their antiproliferative activity against the breast cancer cell line MCF-7. The most active compounds3d,3e,3f,5aand5cwere also evaluated for their ability to
- Eissa, Amal A. M.,Fahim, Samar H.,Gamal, Mona A.,Nissan, Yassin M.,Ragab, Fatma A.,Salem, Mohammad Alaraby
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p. 19043 - 19055
(2021/10/26)
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- Synthesis and biological evaluation of new coumarin derivatives as cytotoxic agents
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New coumarin derivatives 9a–f, 10a–e, and 11a–f were synthesized and evaluated for their cytotoxic activity against a human breast cancer cell line (MCF-7). All compounds exhibited good activity in the nanomolar range, using doxorubicin and erlotinib as positive controls. The most active compound 9d with IC50 of 21 nM was tested against the HCT-116, HepG-2, A549, and SGC-7901 cell lines, with IC50 values of 0.021, 0.170, 0.028, and 0.11 μM, respectively. Compound 9d was further investigated for its ability to suppress the expression of epidermal growth factor receptor (EGFR). Compound 9d decreased the concentration of EGFR by 87%, using erlotinib as a positive control. A docking study revealed similar or higher scores than for erlotinib and similar binding poses providing interactions with the hinge region of the tyrosine kinase (TK). Besides the effect on expression, this in silico investigation predicts the possibility of direct binding between the new coumarin derivatives and the EGFR TK. Moreover, computational calculation for ADME properties for the most active compounds 9d, 9e, 10c, and 11c revealed the expected high gastrointestinal tract absorption, moderate water solubility with no central nervous system toxicity, and druglikeness.
- Ragab, Fatma A.,Eissa, Amal A. M.,Fahim, Samar H.,Salem, Mohammad A.,Gamal, Mona A.,Nissan, Yassin M.
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- ZnS nanoparticles immobilized on graphitic carbon nitride as a recyclable and environmentally friendly catalyst for synthesis of 3-cinnamoyl coumarins
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Abstract: Zinc oxide nanoparticles immobilized on a graphitic carbon nitride (ZnS NPs/g-C3N4) nanocomposite were applied as an organometallic recyclable catalyst in the synthesis of coumarin–chalcone hybrids through the Claisen–Schmi
- Safaei-Ghomi, Javad,Akbarzadeh, Zeinab,Teymuri, Raheleh
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p. 3425 - 3439
(2019/09/06)
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- Thiazolyl-pyrazole-biscoumarin synthesis and evaluation of their antibacterial and antioxidant activities
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Abstract: A series of novel 3-(2-oxo-2H-chromen-3-yl)-1-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-5-aryl-1H-pyrazol-1-ium bromides have been prepared through a one-pot three-component cyclocondensation of various coumarin chalcones, thiosemicarbazide and 2-
- Mahmoodi, Nosrat O.,Ghodsi, Shahryar
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p. 661 - 678
(2017/02/10)
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- Synthesis and optical properties research of some novel trichromophore compounds containing coumarin, pyrazoline and naphthalimide groups
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A series of novel trichromophore compounds containing coumarin, pyrazoline and naphthalimide groups were synthesized and their properties were elucidated using absorption and fluorescence. In chloroform solution, their maximal absorption bands and the max
- Wu, Gongying,Zhao, Fang,Hu, Yang,Hu, Shengli
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- An Efficient One-Pot Synthesis of New Coumarin Derivatives as Potent Anticancer Agents under Microwave Irradiation
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An efficient and rapid synthesis of coumarin derivatives was accomplished via reactions of 3-(3-(4-methoxyphenyl)acryloyl)-2H-chromen-2-one (3) with different carbon nucleophiles such as ethyl acetoacetate, ethyl cyanoacetate, malononitrile, and ethyl benzoylacetate via conventional heating and microwave irradiation conditions and were used as source of pyran and pyridine derivatives bearing coumarin moiety 4–11. Compound 9a was condensed with different carbon electrophiles triethylorthoformate, phenylisothiocyanate, carbon disulfide, benzoylchloride, and acetylchloride that afforded the corresponding chromen derivatives 12–16. All the newly synthesized compounds were characterized by elemental and spectroscopic evidences. All of synthesized compounds were tested for in vitro cytotoxicity. The preliminary screening results showed that most of the compounds had moderate cytotoxic activity against HCT-116 and MCF-7 cell lines. Nevertheless, compound 10 exhibited potent activity against the two cell lines, which was comparable with the standard drug 5-fluorouracil.
- El-Naggar, Abeer M.,Hemdan, Magdy M.,Atta-Allah, Saad R.
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p. 3519 - 3526
(2017/11/21)
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- Synthesis and antimicrobial evaluation of some new asymmetrically substituted 4-aryl- 2,6-di(coumarinyl) pyridines
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In the present work the synthesis of various 4-aryl-2-(coumarin-3-yl)-6-(4-methyl-3-phenyl coumarin-6-yl)pyridines (6a-i) and 4-aryl-2-(coumarin-3-yl)-6-(4-methyl-7-methoxy coumarin-8-yl)pyridines (7a-i) have been carried out by reacting 1-[2(H)-1-benzopy
- Chovatiya, Yogita L.,Kundaliya, Kaushik N.,Giri, Rakesh R.,Brahmbhatt, Dinker I.
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p. 2788 - 2791
(2016/07/12)
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- Synthesis and florescent properties of 5-aryl-3-(3-coumarinyl)-1-benzothiazolyl-2-pyrazolines
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A series of novel 5-Aryl-3-(3-coumarinyl)-1-benzothiazolyl-2-pyrazolines have been synthesized by the reaction of 3-coumarinyl chalcones with 2-hydrazinobenzothiazole in hot ethanol. And the structures of these new compounds have been characterized by 1HNMR, MS and elemental analysis. The fluorescence spectra of these compounds were also measured. All the compounds showed up strong green light emissions (λem: 557-570nm). The results showed that the absorption maxima of the compound vary from 415 to 420nm depending on the group bonded to pyrazolines rings.
- Liu, Manman,Liu, Qian,Zhang, Jian
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p. 301 - 306
(2016/08/20)
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- Bismuth triflate: A highly efficient catalyst for the synthesis of bio-active coumarin compounds via one-pot multi-component reaction
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A series of coumarin-chalcone hybrid compounds and coumarins linked to pyrazoline was synthesized in good yield and short time using a simple and efficient method. This method involved the one-pot reaction of salicylaldehyde, an α-ketoester and an aromatic aldehyde (in the case of the coumarin-chalcone derivatives) in addition to hydrazine hydrate (in the case of the pyrazolyl coumarins) in the presence of a catalytic amount of bismuth triflate [Bi(OTf)3, 5 mol%]. The synthesized compounds showed scavenging activity towards the free radical 2,2-diphenyl-1-picrylhydrazyl. All compounds were characterized using IR, 1H NMR and 13C NMR spectroscopy.
- El-Remaily, Mahmoud. Abd El Aleem. Ali. Ali.
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p. 1124 - 1130
(2015/07/07)
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- Antidiabetic effect of novel benzenesulfonylureas as PPAR-γ agonists and their anticancer effect
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Twenty one pyrazoline containing benzenesulfonylureas were synthesized and docked against PPAR-γ target. All the compounds were first screened for their antidiabetic potential by oral glucose tolerance test and then six active compounds were assessed on S
- Kharbanda, Chetna,Alam, Mohammad Sarwar,Hamid, Hinna,Javed, Kalim,Dhulap, Abhijeet,Bano, Sameena,Ali, Yakub
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p. 4601 - 4605
(2015/10/12)
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- Novel 2H-chromen derivatives: Design, synthesis and anticancer activity
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A series of novel dihydropyrazole derivatives linked with 2H-chromen were designed and synthesized. All of the compounds have been screened for their antiproliferative activity against MGC-803, Bcap-37, SGC-7901 and HepG 2 cell lines in vitro. The results revealed that compounds 4a and 10a exhibited strong inhibitory activity against HepG2 cell and manifested obvious un-toxic effect on GES-1 and L-02 cell lines. Some title compounds were tested against telomerase, compound 10a showed the most potent inhibitory activity with IC50 value at 0.98 ± 0.11 μM, it could fit well into the active site of TERT. The further molecular mechanism of antiproliferation was explored, the data suggested that compound 10a could inhibit hTERT expression and Wnt/β-catenin signaling.
- Qiang, Dong Zhi,Shi, Jing Bo,Song, Bao An,Liu, Xin Hua
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p. 5607 - 5617
(2014/01/23)
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- Discovery of a novel fluorescent HSP90 inhibitor and its anti-lung cancer effect
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A series of novel fluorescent pyrazoline coumarin derivatives were synthesized. From them, we screened a compound possessing strong growth inhibitory effects on lung cancer cells. By taking advantage of fluorescence combined with LC-MS/MS and chemoinforma
- Bai, Su-Yun,Dai, Xi,Zhao, Bao-Xiang,Miao, Jun-Ying
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p. 19887 - 19890
(2014/05/20)
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- Chalcone-based derivatives as new scaffolds for hA3 adenosine receptor antagonists
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Objectives With the aim of finding new adenosine receptor (AR) ligands based on the chalcone scaffold, we report the synthesis of a new series of coumarin-chalcone hybrids and the pharmacological characterization of their actions at four subtypes of AR. Methods The synthesized compounds 5-10 were characterized in radioligand binding (A1, A2A and A 3) and adenylyl cyclase activity assays (A2B) to determine the affinity of the compounds for the four human AR (hAR) subtypes. Key findings Coumarin-chalcone hybrids were found to be ligands with a novel structure, not reported thus far, that showed varying affinity and selectivity for AR subtypes. Conclusions The coumarin-chalcone hybrids in which ring B of the chalcone scaffold was a thiophene (compounds 5 and 9) were found to be the most potent compounds of the series. Compound 9, in which ring A of the chalcone moiety was the phenyl ring of the coumarin, showed similar activity against hA1, hA2A and hA3 ARs, while compound 5, in which ring A of the chalcone was substituted by the benzopyrone ring of the coumarin moiety, showed similar activity only at the hA3 AR and, therefore, was deemed to be selective (Ki (dissociation constant) = 5160 nm). A new series of chalcone-based derivatives, including a coumarin moiety in their structures, have been synthesized and binding assays for the hA1, hA2A, and hA3 adenosine receptors were employed to assess the affinity for receptor subtypes. Isosterical substitutions of one or both phenyl rings of the chalcone moiety reveal that thiophene-containing compounds 5 and 9 have good binding affinity for ARs. Compound 5, in which both phenyl rings of the original chalcone scaffold (rings A and B) were substituted for a thiophene and pyrone rings, resulted selective for the hA3 adenosine receptor (Ki = 5,160 nM). Based on the obtained results, a preliminary structure-activity relationship (SAR) study showed a high selectivity and good potency of these thiophene-containing compounds. 2013 The Authors. JPP
- Vazquez-Rodriguez, Saleta,Matos, Maria Joao,Santana, Lourdes,Uriarte, Eugenio,Borges, Fernanda,Kachler, Sonja,Klotz, Karl-Norbert
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p. 697 - 703
(2013/06/05)
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- Antioxidant effectiveness generated by one or two phenolic hydroxyl groups in coumarin-substituted dihydropyrazoles
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A cascade operation was designed to synthesize nine coumarin-substituted dihydropyrazoles with only one or two phenolic hydroxyl groups contained. Antioxidant abilities of the obtained compounds were evaluated by inhibiting 2,2′-azobis(2-amidinopropanehydrochloride) (AAPH)-, Cu2+/ glutathione (GSH)-, and .OH-induced oxidation of DNA. It was found that less phenolic hydroxyl groups can enhance the abilities of coumarin-substituted dihydropyrazoles to protect DNA against the oxidation. Moreover, these coumarin-substituted dihydropyrazoles were employed to scavenge 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+.), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that double phenolic hydroxyl groups were more beneficial for enhancing the abilities of coumarin-substituted dihydropyrazoles to quench the aforementioned radicals. Therefore, dihydropyrazole linked with coumarin exhibited powerful antioxidant effectiveness even in the case of less phenolic hydroxyl groups involved.
- Xi, Gao-Lei,Liu, Zai-Qun
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p. 385 - 393
(2013/10/01)
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- Synthesis and biological evaluation of a novel series of 1,3-dicoumarinyl-5-aryl-2-pyrazolines
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In the present paper novel 1,3,5-trisubstituted 2-pyrazolines (4a-q) were synthesized via condensation of different substituted 3-cinnamoyl-2-oxo-2H- chromenes (2a-q) with 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetohydrazide (3). Chalcones were prepared vi
- Cacic, Milan,Molnar, Maja,Strelec, Ivica
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experimental part
p. 1553 - 1566
(2011/08/06)
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- Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents
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A novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines (3a-l) were synthesized by reacting various substituted 3-aryl-1-(3-coumarinyl)propan-1-ones (2a-l) with phenylhydrazine in the presence of hot pyridine. Structures of all new s
- Khode, Suresh,Maddi, Veeresh,Aragade, Prashant,Palkar, Mahesh,Ronad, Pradeep Kumar,Mamledesai, Shivalingarao,Thippeswamy,Satyanarayana
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experimental part
p. 1682 - 1688
(2009/06/20)
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- Synthesis of some new 3-cummamoyl counarin oximes and related cyclisation products derived from 3-acetyl coumarin
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3-Acetylcoumarin 1 reacts with aldehydes to form corresponding 3-cummamoyl counarin 2a-g. Oximation of 2a-g with hydroxylamine hydrochloride in ethanol and (or) isopropanol aqueous solution give new 3-[1-oxo-3-(substituted-phenyl)]-2- propenyl-2H-1-benzop
- Ji,Hu,Hua,Hu
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p. 1223 - 1225
(2007/10/03)
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- CONDENSATION OF 3-ACETYL- AND 3-ACETYL-4-METHYL-2H-1-BENZOPYRAN-2-ONE WITH AROMATIC ALDEHYDES
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The reactivities of 3-acetyl-2H-1-benzopyran-2-one (2) and 3-acetyl-4-methyl-2H-1-benzopyran-2-one (4) are compared in the condensation with aromatic aldehydes.It is established that the benzopyrones 2 and 4 condense with various aromatic aldehydes in chl
- Dimitrova, E.,Anghelova, Y.
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p. 1195 - 1205
(2007/10/02)
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- Some Reactions of 3-Cinnamoylcoumarins
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3-Acetylcoumarin (I) reacts with aromatic aldehydes to give substituted 3-cinnamoylcoumarins (IIa,b). 3-Cinnamoylcoumarin (IIa) on condensation with phenylhydrazine or p-toluidine furnishes the corresponding phenylhydrazone (IIIa) or imine (IIIb).Alkylati
- Essawy, A. I.,Elkady, M.,Mohamed, A. Y.
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p. 567 - 570
(2007/10/02)
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