Ultrasound-promoted Greener Synthesis of Novel Trifurcate 3-substituted-chroman-2,4-dione Derivatives and Their Drug-likeness Evaluation

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2012 Nov 30

PMID 23192190

Citations 2

Authors

Chengyuan Liang

Hailong Jiang

Zhiguang Zhou

Dong Lei

Yu Xue

Qizheng Yao

Affiliations

Soon will be listed here.

Abstract

An efficient and convenient approach for one-pot synthesis of 3-substituted chroman-2,4-diones via a three-component reaction of aromatic aldehydes, 4-hydroxy-coumarins and diverse pyrazolone derivatives was described. The combinatorial synthesis for this methodology was achieved by applying ultrasound irradiation in the absence of activator while making use of water as green solvent. Additionally, novel chroman-2,4-dione derivatives attached to an edaravone moiety represent an exploitable source of brand new anticancer agents. In comparison with conventional methods, experimental simplicity, good functional group tolerance, excellent yields, short routine, and atom efficiency are prominent features of this sonocatalyzed procedure.

Citing Articles

Coumarins as Potential Antioxidant Agents Complemented with Suggested Mechanisms and Approved by Molecular Modeling Studies.

Al-Majedy Y, Al-Duhaidahawi D, Al-Azawi K, A Al-Amiery A, H Kadhum A, Mohamad A Molecules. 2016; 21(2):135.

PMID: 26805811 PMC: 6273302. DOI: 10.3390/molecules21020135.

Synthesis and characterization of some new 4-hydroxy-coumarin derivatives.

Al-Majedy Y, H Kadhum A, A Al-Amiery A, Mohamad A Molecules. 2014; 19(8):11791-9.

PMID: 25105917 PMC: 6271054. DOI: 10.3390/molecules190811791.

References

Kelly R, Gelfand J, Pincus S . Cutaneous necrosis caused by systemically administered heparin. JAMA. 1981; 246(14):1582-3. View

Blaskovicova M, Gaplovsky A, Blasko J . Synthesis and photochemistry of 1-iodocyclohexene: influence of ultrasound on ionic vs. radical behaviour. Molecules. 2007; 12(2):188-93. PMC: 6149510. DOI: 10.3390/12020188. View

Huang L, Yuan X, Yu D, Lee K, Chen C . Mechanism of action and resistant profile of anti-HIV-1 coumarin derivatives. Virology. 2005; 332(2):623-8. DOI: 10.1016/j.virol.2004.11.033. View

Murakami A, Kuki W, Takahashi Y, Yonei H, Nakamura Y, Ohto Y . Auraptene, a citrus coumarin, inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in ICR mouse skin, possibly through suppression of superoxide generation in leukocytes. Jpn J Cancer Res. 1997; 88(5):443-52. PMC: 5921462. DOI: 10.1111/j.1349-7006.1997.tb00402.x. View

Gao D, Ma W, Li T, Huang L, Du Z . An improved synthesis of 1,2-diarylethanols under conventional heating and ultrasound irradiation. Molecules. 2012; 17(9):10708-15. PMC: 6268955. DOI: 10.3390/molecules170910708. View

Laporte J, Carne X, Vidal X, Moreno V, Juan J . Upper gastrointestinal bleeding in relation to previous use of analgesics and non-steroidal anti-inflammatory drugs. Catalan Countries Study on Upper Gastrointestinal Bleeding. Lancet. 1991; 337(8733):85-9. DOI: 10.1016/0140-6736(91)90744-a. View

Xiao L, Liu C, Li Y . Ultrasound promoted synthesis of bis(substituted pyrazol-4-ylcarbonyl)-substituted thioureas. Molecules. 2009; 14(4):1423-8. PMC: 6254392. DOI: 10.3390/molecules14041423. View

Gomha S, Khalil K . A convenient ultrasound-promoted synthesis of some new thiazole derivatives bearing a coumarin nucleus and their cytotoxic activity. Molecules. 2012; 17(8):9335-47. PMC: 6268604. DOI: 10.3390/molecules17089335. View

Thaisrivongs S, Watenpaugh K, Howe W, Tomich P, Dolak L, Chong K . Structure-based design of novel HIV protease inhibitors: carboxamide-containing 4-hydroxycoumarins and 4-hydroxy-2-pyrones as potent nonpeptidic inhibitors. J Med Chem. 1995; 38(18):3624-37. DOI: 10.1021/jm00018a023. View

10.

Kokura S, Yoshida N, Sakamoto N, Ishikawa T, Takagi T, Higashihara H . The radical scavenger edaravone enhances the anti-tumor effects of CPT-11 in murine colon cancer by increasing apoptosis via inhibition of NF-kappaB. Cancer Lett. 2005; 229(2):223-33. DOI: 10.1016/j.canlet.2005.06.039. View

11.

Liu C, Wang J . Ultrasound-assisted synthesis of novel 4-(2-phenyl-1,2,3-triazol-4-yl)-3,4-dihydropyrimidin-(1H)-(thio)ones catalyzed by Sm(ClO(4))(3). Molecules. 2010; 15(4):2087-95. PMC: 6257392. DOI: 10.3390/molecules15042087. View

12.

Iguchi T, Nishikawa M, Chang B, Muroya O, Sato E, Nakatani T . Edaravone inhibits acute renal injury and cyst formation in cisplatin-treated rat kidney. Free Radic Res. 2004; 38(4):333-41. DOI: 10.1080/10715760310001646886. View

13.

AGGELER P, OReilly R, Leong L, Kowitz P . Potentiation of anticoagulant effect of warfarin by phenylbutazone. N Engl J Med. 1967; 276(9):496-501. DOI: 10.1056/NEJM196703022760904. View

14.

Dias L, Salvador R . Pyrazole carbohydrazide derivatives of pharmaceutical interest. Pharmaceuticals (Basel). 2013; 5(3):317-24. PMC: 3763639. DOI: 10.3390/ph5030317. View

15.

Stanchev S, Momekov G, Jensen F, Manolov I . Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives. Eur J Med Chem. 2007; 43(4):694-706. DOI: 10.1016/j.ejmech.2007.05.005. View

16.

Baba M, Jin Y, Mizuno A, Suzuki H, Okada Y, Takasuka N . Studies on cancer chemoprevention by traditional folk medicines XXIV. Inhibitory effect of a coumarin derivative, 7-isopentenyloxycoumarin, against tumor-promotion. Biol Pharm Bull. 2002; 25(2):244-6. DOI: 10.1248/bpb.25.244. View

17.

Kostova I . Synthetic and natural coumarins as cytotoxic agents. Curr Med Chem Anticancer Agents. 2005; 5(1):29-46. DOI: 10.2174/1568011053352550. View

18.

Chandrasekharan N, Dai H, Roos K, Evanson N, Tomsik J, Elton T . COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc Natl Acad Sci U S A. 2002; 99(21):13926-31. PMC: 129799. DOI: 10.1073/pnas.162468699. View

19.

Wang X, Wang X, Liang Y, Shi Z, Zhang J, Chen L . A cell-based screen for anticancer activity of 13 pyrazolone derivatives. Chin J Cancer. 2010; 29(12):980-7. DOI: 10.5732/cjc.010.10309. View

20.

Chohan Z, Shaikh A, Rauf A, Supuran C . Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin. J Enzyme Inhib Med Chem. 2007; 21(6):741-8. DOI: 10.1080/14756360600810340. View