Design and synthesis of new coumarin-chalcone/NO hybrids of potential biological activity

被引:25
作者
El-Sherief, Hany A. [1 ,2 ]
Abuo-Rahma, Gamal El-Din A. [3 ]
Shoman, Mai E. [3 ]
Beshr, Eman A. [3 ,4 ]
Abdel-baky, Rehab M. [5 ]
机构
[1] Nahda Univ, Dept Pharmaceut Chem, Fac Pharm, Benisuef, Egypt
[2] Al Jouf Univ, Dept Med Chem, Fac Pharm, Al Jouf, Saudi Arabia
[3] Menia Univ, Dept Med Chem, Fac Pharm, Al Minya 61519, Egypt
[4] Umm Al Qura Univ, Dept Pharmaceut Chem, Coll Pharm, Mekka 21955, Saudi Arabia
[5] Menia Univ, Dept Microbiol & Immunol, Fac Pharm, Al Minya 61519, Egypt
关键词
Coumarins; Chalcones; Anti-proliferative; Antibacterial; Nitric oxide donors; Oximes; NITRIC-OXIDE; INHIBITORY-ACTIVITY; DERIVATIVES; CANCER; AGENTS; ANTICANCER; FLAVONOIDS; CELLS; DOCKING; PATHWAY;
D O I
10.1007/s00044-017-2004-9
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
This study aims at investigating a synthesis approach based on molecular hybridization strategy through grafting an nitric oxide-releasing moiety, oxime, to coumarin-chalcone hybrids. In vitro anti-proliferative activity of some of the prepared compounds showed moderate activity (growth inhibition values = 45.85, 40.86, 39.25 for compound 8a against leukemia, Central Nervous system and breast cancer cells, respectively). Also, IC50 = 9.62 and 14.40 for compounds 8h and 8f, respectively against breast Michigan Cancer Foundation-7 cell lines. The antibacterial screening results suggest a possible role for nitric oxide in enhancement of the antibacterial activity where nitric oxide is not the only factor but other factors like physicochemical properties should be investigated for their potential role on the activity. [GRAPHICS] .
引用
收藏
页码:3077 / 3090
页数:14
相关论文
共 52 条
[1]   Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: Synthesis, physicochemical properties, anticancer and topoisomerase I and II inhibitory activity [J].
Abdel-Aziz, Mohamed ;
Park, So-Eun ;
Abuo-Rahma, Gamal El-Din A. A. ;
Sayed, Mohamed A. ;
Kwon, Youngjoo .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 69 :427-438
[2]   Plant extracts with anti-inflammatory properties-A new approach for characterization of their bioactive compounds and establishment of structure-antioxidant activity relationships [J].
Amaral, Sonia ;
Mira, Lurdes ;
Nogueira, J. M. F. ;
da Silva, Alda Pereira ;
Florencio, M. Helena .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (05) :1876-1883
[3]   The role of gasotransmitters NO, H2S and CO in myocardial ischaemia/reperfusion injury and cardioprotection by preconditioning, postconditioning and remote conditioning [J].
Andreadou, Ioanna ;
Iliodromitis, Efstathios K. ;
Rassaf, Tienush ;
Schulz, Rainer ;
Papapetropoulos, Andreas ;
Ferdinandy, Peter .
BRITISH JOURNAL OF PHARMACOLOGY, 2015, 172 (06) :1587-1606
[4]   Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents [J].
Bandgar, Babasaheb P. ;
Gawande, Shrikant S. ;
Bodade, Ragini G. ;
Gawande, Nalini M. ;
Khobragade, Chandrahasya N. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (24) :8168-8173
[5]   Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity [J].
Borges, F ;
Roleira, F ;
Milhazes, N ;
Santana, L ;
Uriarte, E .
CURRENT MEDICINAL CHEMISTRY, 2005, 12 (08) :887-916
[6]   Hybrid Molecules Incorporating Natural Products: Applications in Cancer Therapy, Neurodegenerative Disorders and Beyond [J].
Decker, M. .
CURRENT MEDICINAL CHEMISTRY, 2011, 18 (10) :1464-1475
[7]   Flavonoids: Old and new aspects of a class of natural therapeutic drugs [J].
Di Carlo, G ;
Mascolo, N ;
Izzo, AA ;
Capasso, F .
LIFE SCIENCES, 1999, 65 (04) :337-353
[8]   Antimitotic Chalcones and Related Compounds as Inhibitors of Tubulin Assembly [J].
Ducki, Sylvie .
ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2009, 9 (03) :336-347
[9]   Inhibitors and promoters of tubulin polymerization: Synthesis and biological evaluation of chalcones and related dienones as potential anticancer agents [J].
Dyrager, Christine ;
Wickstrom, Malin ;
Friden-Saxin, Maria ;
Friberg, Annika ;
Dahlen, Kristian ;
Wallen, Erik A. A. ;
Gullbo, Joachim ;
Grotli, Morten ;
Luthman, Kristina .
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (08) :2659-2665
[10]  
ELKOUSSI NA, 2006, BULL PHARM SCI 1, V29, P127