title: Chrysin-piperazine conjugates as antioxidant and anticancer agents.
abstract: Synthesis of 7-(4-bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one intermediate treating chrysin with 1,4-dibromobutane facilitated combination of chrysin with a wide range of piperazine moieties which were equipped via reacting the corresponding amines with bis(2-chloroethyl)amine hydrochloride in diethylene glycol monomethyl ether solvent. Free radical scavenging potential of prepared products was analyzed in vitro adopting DPPH and ABTS bioassay in addition to the evaluation of in vitro anticancer efficacies against cervical cancer cell lines (HeLa and CaSki) and an ovarian cancer cell line SK-OV-3 using SRB assay. Bearable toxicity of 7a-w was examined employing Madin-Darby canine kidney (MDCK) cell line. In addition, cytotoxic nature of the presented compounds was inspected utilizing Human bone marrow derived mesenchymal stem cells (hBM-MSCs). Overall, 7a-w indicated remarkable antioxidant power in scavenging DPPH(·) and ABTS(·+), particularly analogs 7f, 7j, 7k, 7l, 7n, 7q, 7v, 7w have shown promising free radical scavenging activity. Analogs 7j and 7o are identified to be highly active candidates against HeLa and CaSki cell lines, whereas 7h and 7l along with 7j proved to be very sensitive towards ovarian cancer cell line SKOV-3. None of the newly prepared scaffolds showed cytotoxic nature toward hBM-MSCs cells. From the structure-activity point of view, nature and position of the electron withdrawing and electron donating functional groups on the piperazine core may contribute to the anticipated antioxidant and anticancer action. Different spectroscopic techniques (FT-IR, (1)H NMR, (13)C NMR, Mass) and elemental analysis (CHN) were utilized to confirm the desired structure of final compounds.
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany ASCR & Palacky´ University, Šlechtitelu° 27, 783 71 Olomouc, Czech Republic; Department of Food Science and Biotechnology, Dongguk University, Biomedical Campus, 32 Dongguk-ro, Ilsandong-gu, Goyang-si, Gyenggi-do, Republic of Korea. Electronic address: rahul.svnit11@gmail.com.
authors.forename: Rahul V
authors.initials: RV
authors.lastname: Patel
authors.affiliation: Organic Research Laboratory, Department of Bioresources and Food Sciences, College of Life and Environmental Sciences, Konkuk University, Seoul, Republic of Korea.
authors.forename: Bhupendra
authors.initials: B
authors.lastname: Mistry
authors.affiliation: Department of Chemistry, J.N.T. University, Kukatpally, Hyderabad 500 085, India.
authors.forename: Riyaz
authors.initials: R
authors.lastname: Syed
authors.affiliation: Regional Centre of Advanced Technologies and Materials, Department of Physical Chemistry, Faculty of Science, Palacky University, Šlechtitelů 11, Olomouc, Czech Republic.
authors.forename: Anuj K
authors.initials: AK
authors.lastname: Rathi
authors.affiliation: Department of Life Science, Dongguk University, Goyang, Gyeonggi-do 10326, Republic of Korea.
authors.forename: Yoo-Jung
authors.initials: YJ
authors.lastname: Lee
authors.affiliation: Department of Life Science, Dongguk University, Goyang, Gyeonggi-do 10326, Republic of Korea.
authors.forename: Jung-Suk
authors.initials: JS
authors.lastname: Sung
authors.affiliation: Department of Food Science and Biotechnology, Dongguk University, Biomedical Campus, 32 Dongguk-ro, Ilsandong-gu, Goyang-si, Gyenggi-do, Republic of Korea.
authors.forename: Han-Seung
authors.initials: HS
authors.lastname: Shinf
authors.affiliation: Organic Research Laboratory, Department of Bioresources and Food Sciences, College of Life and Environmental Sciences, Konkuk University, Seoul, Republic of Korea. Electronic address: rational@konkuk.ac.kr.
authors.forename: Young-Soo
authors.initials: YS
authors.lastname: Keum
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D002626:Chemistry, Pharmaceutical; D004285:Dogs; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D000077489:Piperazine; D010879:Piperazines / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D000975:Antioxidants; D005419:Flavonoids; D010879:Piperazines; D000077489:Piperazine; C043561:chrysin
keywords: Anticancer; Antioxidant; Chrysin; Flavones; Piperazines