Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases

References

• Mahapatra DK, Bharti SK, Asati V. Anti-cancer chalcones: structural and molecular target perspectives. Eur J Med Chem 2015;98:69–114
   PubMed Web of Science ®Google Scholar
• Dimmock JR, Kandepu NM, Hetherington M, et al. Cytotoxic activities of Mannich bases of chalcones and related compounds. J Med Chem 1998;41:1014–26
   PubMed Web of Science ®Google Scholar
• Gul HI, Ojanen T, Hanninen O. Antifungal evaluation of bis Mannich bases derived from acetophenones and their corresponding piperidinols and stability studies. Biol Pharm Bull 2002;25:1307–10.
   PubMed Web of Science ®Google Scholar
• Gul M, Gul HI, Das U, Hanninen O. Biological evaluation and structure-activity relationships of bis-(3-aryl-3-oxo-propyl)-methylamine hydrochlorides and 4-aryl-3-arylcarbonyl-1-methyl-4-piperidinol hydrochlorides as potential cytotoxic agents and their alkylating ability towards cellular glutathione in human leukemic T cells. Arzneimittelforschung 2005;55:332–7
   PubMed Web of Science ®Google Scholar
• Gul M, Atalay M, Gul HI, et al. The effects of some Mannich bases on heat shock proteins HSC70 and GRP75, and thioredoxin and glutaredoxin levels in Jurkat cells. Toxicol in Vitro 2005;19:573–80
   PubMed Web of Science ®Google Scholar
• Bandgar BP, Gawande SS, Bodade RG, et al. Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents. Bioorg Med Chem 2010;18:1364–70
   PubMed Web of Science ®Google Scholar
• Singh P, Anand A, Kumar V. Recent developments in biological activities of chalcones: a mini review. Eur J Med Chem 2014;85:758–77
   PubMed Web of Science ®Google Scholar
• Yamali C, Tugrak M, Gul HI, et al. The inhibitory effects of phenolic Mannich bases on carbonic anhydrase I and II isoenzymes. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. doi: 10.3109/14756366.2015.1126715
   Web of Science ®Google Scholar
• Gul HI, Yerdelen KO, Gul M, et al. Synthesis of 4′-hydroxy-3′-piperidinomethylchalcone derivatives and their cytotoxicity against PC-3 cell lines. Arch Pharm (Weinheim) 2007;340:195–201
   PubMed Web of Science ®Google Scholar
• Bilginer S, Unluer E, Gul HI, et al. Carbonic anhydrase inhibitors. Phenols incorporating 2- or 3-pyridyl-ethenylcarbonyl and tertiary amine moieties strongly inhibit Saccharomyces cerevisiae β-carbonic anhydrase. J Enzyme Inhib Med Chem 2014;29:495–9
   PubMed Web of Science ®Google Scholar
• Dimmock JR, Elias DW, Beazely MA, Kandepu NM. Bioactivities of chalcones. Curr Med Chem 1999;6:1125–49
   PubMed Web of Science ®Google Scholar
• Das U, Gul HI, Alcorn J, et al. Cytotoxic 5-aryl-1-(4-nitrophenyl)-3-oxo-1,4-pentadienes mounted on alicyclic scaffolds. Eur J Med Chem 2006;41:577–85
   PubMed Web of Science ®Google Scholar
• Ivanova Y, Momekov G, Petrov O, et al. Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones. Eur J Med Chem 2007;42:1382–7
   PubMed Web of Science ®Google Scholar
• Yerdelen KO, Gul HI, Sakagami H, Umemura N. Synthesis and biological evaluation of 1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one and its aminomethyl derivatives. J Enzyme Inhib Med Chem 2015;30:383–8
   PubMed Web of Science ®Google Scholar
• Gul HI, Cizmecioglu M, Zencir S, et al. Cytotoxic activity of 4′-hydroxychalcone derivatives against Jurkat cells and their effects on mammalian DNA topoisomerase I. J Enzyme Inhib Med Chem 2009;24:804–7
   PubMed Web of Science ®Google Scholar
• Bilginer S, Gul HI, Mete E, et al. 1-(3-aminomethyl-4-hydroxyphenyl)-3-pyridinyl-2-propen-1-ones: a novel group of tumor-selective cytotoxins. J Enzyme Inhib Med Chem 2013;28:974–80
   PubMed Web of Science ®Google Scholar
• Roman G. Mannich bases in medicinal chemistry and drug design. Eur J Med Chem 2015;89:743–816
   PubMed Web of Science ®Google Scholar
• Gul HI, Calis U, Vepsalainen J. Synthesis and evaluation of anticonvulsant activities of some bis Mannich bases and corresponding piperidinols. Arzneimittelforschung 2002;52:863–9
   PubMed Web of Science ®Google Scholar
• Gul HI, Gul M, Erciyas E. Toxicity of some bis Mannich bases and corresponding piperidinols in the brine shrimp (Artemia salina) bioassay. J Appl Toxicol 2003;23:53–7
   PubMed Web of Science ®Google Scholar
• Gul HI, Das U, Pandit B, Li PK. Evaluation of the cytotoxicity of some mono-mannich bases and their corresponding azine derivatives against androgen-independent prostate cancer cells. Arzneimittelforschung 2006;56:850–4
   PubMed Web of Science ®Google Scholar
• Tugrak M, Yamali C, Sakagami H, Gul HI. Synthesis of mono Mannich bases of 2-(4-hydroxybenzylidene)-2,3-dihydroinden-1-one and evaluation of their cytotoxicities. J Enzyme Inhib Med Chem 2016;31:818--23
   PubMed Web of Science ®Google Scholar
• Gul HI, Yamali C, Yasa AT, et al. Carbonic anhydrase inhibition and cytotoxicity studies of Mannich base derivatives of thymol. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. doi: 10.3109/14756366.2016.1140755
   Web of Science ®Google Scholar
• Subramaniapillai SG. Mannich reaction: A versatile and convenient approach to bioactive skeletons. J Chem Sci 2013;125:467–82
   Web of Science ®Google Scholar
• Xiaowu Dong TL, Jing C, Huazhou Y, Yongzhou H. Microwave-assisted Mannich reaction of 2-hydroxy-chalcones. Synt Comm 2009;39:733–42
   Web of Science ®Google Scholar
• Dimmock JR, Kandepu NM, Nazarali AJ, et al. Sequential cytotoxicity: a theory evaluated using novel 2-[4-(3-aryl-2-propenoyloxy)phenylmethylene]cyclohexanones and related compounds. J Med Chem 2000;43:3933–40
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81
   PubMed Web of Science ®Google Scholar
• Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146–89
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases as drug targets – an overview. Curr Top Med Chem 2007;7:825–33
   PubMed Web of Science ®Google Scholar
• Supuran CT. Structure and function of carbonic anhydrases. Biochem J 2016;473:2023–32
   PubMed Web of Science ®Google Scholar
• Bayram E, Senturk M, Kufrevioglu OI, Supuran CT. In vitro inhibition of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II. Bioorg Med Chem 2008;16:9101–5
   PubMed Web of Science ®Google Scholar
• Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem 2010;18:2159–64
   PubMed Web of Science ®Google Scholar
• Gorlach A, Kietzmann T. Superoxide and derived reactive oxygen species in the regulation of hypoxia-inducible factors. Meth Enzymol 2007;435:421–46
   PubMed Web of Science ®Google Scholar
• Sakagami H, Shimada C, Kanda Y, et al. Effects of 3-styrylchromones on metabolic profiles and cell death in oral squamous cell carcinoma cells. Toxicol Rep 2015;2:1281–90
   PubMed Web of Science ®Google Scholar
• Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971;246:2561–73
   PubMed Web of Science ®Google Scholar
• Maresca A, Temperini C, Pochet L, et al. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem 2010;53:335–44
   PubMed Web of Science ®Google Scholar
• D’Ambrosio K, Smaine FZ, Carta F, et al. Development of potent carbonic anhydrase inhibitors incorporating both sulfonamide and sulfamide groups. J Med Chem 2012;55:6776–83
   PubMed Web of Science ®Google Scholar
• Robles-Escajeda E, Das U, Ortega NM, et al. A novel curcumin-like dienone induces apoptosis in triple-negative breast cancer cells. Cell Oncol (Dordr) 2016;39:265–77
   PubMed Web of Science ®Google Scholar