874
Views
17
CrossRef citations to date
0
Altmetric
Reserach Article

Synthesis and in vitro pharmacological evaluation of N-[(1-benzyl-1,2,3-triazol-4-yl)methyl]-carboxamides on d-secoestrone scaffolds

, , , , , , , , & show all
Pages 574-579 | Received 23 Dec 2014, Accepted 28 Apr 2015, Published online: 11 Sep 2015

References

  • Newman DJ, Cragg GM. Natural products, derivatives and mimics as antitumor agents. R Soc Chem 2011;320:3–36
  • Saha SK, Khuda-Bukhsh AR. Molecular approaches towards development of purified natural products and their structurally known derivatives as efficient anti-cancer drugs: current trends. Eur J Pharm 2013;714:239–48
  • Gupta A, Kumar SB, Negi AS. Current status on development of steroids as anticancer agents. J Steroid Biochem Mol Biol 2013;137:242–70
  • Numazawa M, Ando M, Watari Y, et al. Structure–activity relationships of 2-, 4-, or 6-substituted estrogens as aromatase inhibitors. J Steroid Biochem Mol Biol 2005;96:51–8
  • Poirier D. Contribution to the development of inhibitors of 17β-hydroxysteroid dehydrogenase types 1 and 7: key tools for studying and treating estrogen-dependent diseases. J Steroid Biochem Mol Biol 2011;125:83–94
  • Lordan S, Mackrill JJ, O’Brien NM. Oxysterols and mechanisms of apoptopic signalling: implications in the pathology of degenerative diseases. J Nutr Biochem 2009;20:321–36
  • Minorics R, Bozsity N, Wölfling J, et al. Antiproliferative effect of normal and 13-epi-D-homoestrone and their 3-methyl ethers on human reproductive cancer cell lines. J Steroid Biochem Mol Biol 2012;132:168–75
  • Jovanovic-Santa S, Petrovic J, Andric S, et al. Synthesis, structure, and screening of estrogenic and antiestrogenic activity of new 3,17-substituted-16,17-seco-estratriene derivatives. Bioorg Chem 2003;31:475–84
  • Ayan D, Roy J, Maltais R, Poirier D. Impact of estradiol structural modifications (18-methyl and/or 17-hydroxy inversion of configuration) on the in vitro and in vivo estrogenic activity. J Steroid Biochem 2011;127:324–30
  • Mernyak E, Szabo J, Huber J, et al. Synthesis and antiproliferative effects of D-homo- and D-secoestrones. Steroids 2014;87:128–36
  • Mernyak E, Fiser G, Szabo J, et al. Synthesis and in vitro antiproliferative evaluation of D-secooxime derivatives of 13β- and 13α-estrone. Steroids 2014;89:47–55
  • Berenyi A, Minorics R, Ivanyi Z, et al. Synthesis and investigation of the anticancer effects of estrone-16-oxime ethers in vitro. Steroids 2013;78:69–78
  • Schneider G, Hackler L, Sohar P. Steroids, XXXVIII. Neighboring group participation. IX. Preparation of 16a-(hydroxymethyl)-3-methoxyestra-1,3,5(10)-trien-17a-ol and solvolysis investigations. Liebigs Ann Chem 1988:679–83
  • Wölfling J, Mernyák E, Forgó P, Schneider G. Stereoselective halogenation of the 16-hydroxymethyl-3-methoxy-13α-estra-1,3,5(10)-trien-17-ols and their solvolytic investigation. Steroids 2003;68:451–8
  • Frank É, Mernyák E, Wölfling J, Schneider Gy. Stereoselective approach to some novel 16-methylated and 16-halomethylated tetrahydropyran and δ-lactone derivatives in both the normal and the 13α-estrone series. Syn Lett 2002;11:1803–6
  • Pedersen DS, Abell A. 1,2,3-Triazoles in peptidomimetic chemistry. Eur J Org Chem 2011;2011:2399–411
  • Kadar Z, Molnar J, Schneider G, et al. A facile “click” approach to novel 15β-triazolyl-5α-androstane derivatives, and an evaluation of their antiproliferative activities in vitro. Bioorg Med Chem 2012;20:1396–402
  • Frank E, Molnar J, Zupko I, Wölfling J. Synthesis of novel steroidal 17α-triazolyl derivatives via Cu(I)-catalyzed azide-alkyne cycloaddition, and an evaluation of their cytotoxic activity in vitro. Steroids 2011;76:1141–8
  • Kadar Z, Baji A, Zupko I, et al. Efficient approach to novel 1α-triazolyl-5α-androstane derivatives as potent antiproliferative agents. Org Biomol Chem 2011;9:8051–7
  • Kadar Z, Frank E, Schneider G, et al. Efficient synthesis of novel A-ring-substituted 1,2,3-triazolylcholestane derivatives via catalytic azide-alkyne cycloaddition. Arkivoc 2012;3:279–96
  • Jurasek M, Dzubak P, Sedlak D, et al. Preparation, preliminary screening of new types of steroid conjugates and their activities on steroid receptors. Steroids 2013;78:356–61
  • Yu F, Peng Y, Wang Q, et al. Development of bivalent oleanane-type triterpenes as potent HCV entry inhibitors. Eur J Med Chem 2014;77:258–68
  • Miller MJ, Moraski GC, Stefely J. Triazole derivatives as anticancer agents and preparation thereof. 2009; WO 2009111502
  • Haiying S, Zaneta N-C, Jianfeng L, et al. Design, synthesis and characterization of a potent, non-peptide, cell-permeable, bivalent smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP. J Am Chem Soc 2007;129:15279–94
  • Allan GM, Lawrence HR, Cornet J, et al. Modification of estrone at the 6, 16, and 17 positions: novel potent inhibitors of 17β-hydroxysteroid dehydrogenase type 1. J Med Chem 2006;49:1325–45
  • Messinger J, Husen B, Koskimies P, et al. Estrone C15 derivatives–A new class of 17b-hydroxysteroid dehydrogenase type 1 inhibitors. Mol Cell Endocrinol 2009;301:216–24
  • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63
  • Tóth I, Szécsi M, Julesz J, Faredin I. Activity and inhibition of 3-beta-hydroxysteroid dehydrogenase/delta-5-4-isomerase in human skin. Skin Pharmacol 1997;10:160–8
  • Darvas B, Székács A, Fónagy A, et al. Progesterone in Periplaneta americana and Neobellieria bullata adults from the procuticle phase until first progeny production. Gen Comp Endocrinol 1997;107:450–60
  • Djurendic EA, Klisurić O, Szécsi M, et al. X-ray structural analysis and antitumor activity of new salicylic acid derivatives. Struct Chem 2014;25:1747–58
  • Tremblay MR, Auger S, Poirier D. Synthesis of 16-(bromoalkyl)-estradiols having inhibitory effect on human placental estradiol 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD type 1). Bioorg Med Chem 1995;3:505–23
  • Poirier D, Dionne P, Auger S. A 6beta-(thiaheptanamide) derivative of estradiol as inhibitor of 17beta-hydroxysteroid dehydrogenase type 1. J Steroid Biochem Mol Biol 1998;64:83–90
  • Wetzel M, Gargano EM, Hinsberger S, et al. Discovery of a new class of bicyclic substituted hydroxyphenylmethanones as 17β-hydroxysteroid dehydrogenase type 2 (17β-HSD2) inhibitors for the treatment of osteoporosis. Eur J Med Chem 2012;47:1–17
  • Pardin C, Roy I, Lubell WD, Keillor JW. Reversible and competitive cinnamoyl triazole inhibitors of tissue transglutaminase. Chem Biol Drug Des 2008;72:189–96 (9a, 9b)
  • Maycock CD, Santos JP, Duarte MF, et al. Study of selected benzyl azides by UV photoelectron spectroscopy and mass spectrometry. J Mol Struct 2010;980:163–71 (9a, 9c)
  • Pötzsch R, Voit B. Thermal and photochemical crosslinking of hyperbranched polyphenylene with organic azides. Macromol Rapid Commun 2012;33:635–9 (9d)
  • Barr L, Lincoln SF, Easton CJ. A cyclodextrin molecular reactor for the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles. Supramol Chem 2005;17:547–55 (9e)
  • Chura JC, Ryu HS, Simard M, et al. Steroid-converting enzymes in human ovarian carcinomas. Mol Cell Endocrinol 2009;301:51–8
  • Day JM, Tutill HJ, Newman SP, et al. 17β-hydroxysteroid dehydrogenase type 1 and type 2: association between mRNA expression and activity in cell lines. Mol Cell Endocrinol 2006;248:246–9
  • Kruchten P, Werth R, Bey E, et al. Selective inhibition of 17β-hydroxysteroid dehydrogenase type 1 (17βHSD1) reduces estrogen responsive cell growth of T47-D breast cancer cells. J Steroid Biochem Mol Biol 2009;114:200–6

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.