Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol

Čižmáriková, R.; Habala, L.; Valentová, J.; Némethy, A.; Bruchatá, K; Hroboňová, K.

doi:10.2478/afpuc-2023-0015

Abstract

The present work describes the synthesis, physico-chemical characteristics, antioxidative properties, and high-performance liquid chromatography (HPLC) enantioseparation of novel, potentially bioactive aryloxyaminopropanols – derivatives of naphthalen-2-ol modified in the basic part of their molecules. Reaction of naphthalene-2-ol with chloromethyloxirane leads to 2-[(naphthalen-2-yloxy)methyl]oxirane, which reacts in the next step with branched aliphatic amines (isopropylamine, tert-butylamine, and dimethylamine), aromatic amines (aniline, 3,4-dimethoxyphenylethylamine), and heterocyclic amines (pyrrolidine, imidazole, 2-methylimidazole, piperidine, morpholine, 4-methylpiperidine, or 2-methoxyphenylpiperidine). The target compounds were isolated in the form of free bases, as well as their salts with fumaric or hydrochloric acid. Their purity was established by thin-layer chromatography and their IR, UV, ¹H-NMR, and ¹³C-NMR spectra were recorded. The antioxidant activities of prepared compounds were measured by the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method and they were compared with the values for the corresponding salts. Enantioseparation was accomplished by means of enantioselective HPLC using amylose tris(3,5-dimethylphenyl)carbamate (Chiralpak AD), as well as Chirobiotic T (native teicoplanin) in some cases.

References

Baker JG, Hill SJ, Summera RJ. Evolution of β-blocker from anti-anginal drugs to ligand-directed signalling. Trends Pharmacol Sci. 2011;32(4):227–234.
Search in Google Scholar Back to article
Tobe SW. β-adrenergic receptor blockers in hypertension. Can J Cardiol. 2014;30(5):S1–S2.
Search in Google Scholar Back to article
Akbar S, Alorainy MS. The current status of beta blockers’ use in the management of hypertension. Saudi Med J. 2014;35(11):1307–1317.
Search in Google Scholar Back to article
Zicha S, Tsuji Y, Shiroshita-Takeshita A, Nattel S. Beta-blockers as antiarrhythmic agents. In: Kass RS, Clancy CE, eds. Handbook of Experimental Pharmacology Vol. 171. Heidelberg: Springer-Verlag; 2006.
Search in Google Scholar Back to article
Cruickshank JM. Beta-blockers and heart failure. Indian Heart J. 2010;62(2):101–110.
Search in Google Scholar Back to article
Tsujimoto T, Kajio H. Beta-blocker use and cardiovascular event risk in patients with heart failure with preserved ejection fiction. Sci Rep. 2018;8:9556.
Search in Google Scholar Back to article
Fumagalli C, Maurizi N, Marchionni N, Fornasari D. β-Blockers: Their new life from hypertension to cancer and migraine. Pharmacol Res. 2020;151:1045287.
Search in Google Scholar Back to article
Brogden RN, Heel RC, Speight TM, Avery GS. Metoprolol: a review of its pharmacological properties and therapeutic efficacy in hypertension and angina pectoris. Drugs. 1977;14(5):321–48.
Search in Google Scholar Back to article
Kukin ML, Mannino MM, Freudenberger RS, Kalman J, Buchholz-Varley C, Ocampo O. Hemodynamic comparison of twice daily metoprolol tartrate with once daily metoprolol succinate in congestive heart failure. J Am Coll Cardiol. 2000;35(1):45–50.
Search in Google Scholar Back to article
Fröhlich H, Zhao J, Täger T, Cebola R, Schellberg D, Katus HA, Grundtvig M, Hole T, Atar D, Agewall S, Frankenstein L. Carvedilol compared with metoprolol succinate in the treatment and prognosis of patients with stable chronic heart failure: carvedilol or metoprolol evaluation study. Circ Heart Fail. 2015;8(5):887–896.
Search in Google Scholar Back to article
Clemente-Moragón A, Martínez-Milla J, Oliver E, Santos A, Flandes J, Fernández I, Rodríguez-González L, Serrano del Castillo Ch, Ioan AM, López-Álvarez M, Gómez-Talavera S, Galán-Arriola C, Fuster V, Pérez-Calvo C, Ibáñez B. Metoprolol in critically ill patients with COVID-19. J Am Coll Cardiol. 2021;78(10):1001–1010.
Search in Google Scholar Back to article
de Groote P, Ennezat PV, Mouquet F. Bisoprolol in the treatment of chronic heart failure. Health Risk Manag. 2007;3(4):431–439.
Search in Google Scholar Back to article
Yasui T, Toru Oka T, Shioyama W, Oboshi M, Fujita M. Bisoprolol transdermal patch treatment for patients with atrial fibrillation after noncardiac surgery: A single-center retrospective study of 61 patients. SAGE Open Medicine. 2020;8: 2050312120907817.
Search in Google Scholar Back to article
Li Y, Jung NY, Yoo JC, Kim Y, Yi GS. Acebutolol, a cardioselective beta blocker, promotes glucose uptake in diabetic model cells by inhibiting JNK-JIP1 interaction. Biomol Ther (Seoul). 2018;26(5):458–463.
Search in Google Scholar Back to article
Baderkhan H, Wanhainen A, Stenborg A, Stattin EL, Björck M. Celiprolol treatment in patients with vascular Ehlers-Danlos syndrome. Eur J Vasc Endovasc Surg. 2021;61(2):326–331.
Search in Google Scholar Back to article
Barton AL, Moffet BS, Valdes SO, Miyake C, Kim JJ. Efficacy and safety of high-dose propranolol for the management of infant supraventricular tachyarrythmias. J Pediatr. 2015;166(1):115–118.
Search in Google Scholar Back to article
Bolin EH, Lang SM, Tang X, Collins RT. Propranolol versus digoxin in the neonate for supraventricular tachycardia (from the Pediatric Health Information System). Am J Cardiol. 2017;119(10):1605–1610.
Search in Google Scholar Back to article
Čižmáriková R, Valentová J, Némethy A. Propranolol as chiral agent. In: Propranolol: Medical uses, mechanisms of action and potential adverse effects. New York: Nova Science Publ.; 2015.
Search in Google Scholar Back to article
Čižmáriková R, Chudáčiková S, Valentová J, Némethy A. Synthesis and enantioseparation of derivatives of propranolol. Acta Fac Pharm Univ Comen. 2012;59:5–13.
Search in Google Scholar Back to article
Čižmáriková R, Habala L, Markuliak M, Valentová J. Survey of pharmacological activity and pharmacokinetics of selected β-adrenergic blockers in regard to their stereochemistry. Appl Sci. 2019;9:625.
Search in Google Scholar Back to article
Lee SB, Mai XL, Le TAT, Nguyen TNV, Kang JS, Mar W, Kim KH. Determination of nadolol enantiomers in human plasma using a coupled achiral-chiral high-performance liquid chromatography method. Anal Sci Technol. 2020;33(2):59–67.
Search in Google Scholar Back to article
Ogasawara H, Yoshida A, Fujio N, Konno S, Ishiko S. [Effect of topical levobunolol on retinal, optic nerve head, and choroidal circulation in normal volunteers]. Nippon Ganka Gakkai Zasshi. 1999;103(7):544–550.
Search in Google Scholar Back to article
Ishibashi T, Yokoi N, Kinoshita S. Comparison of the effects of topical levobunolol and timolol solution on the human ocular surface. Cornea 2003;22(8):709–715.
Search in Google Scholar Back to article
Sponer G, Borbe HO, Muller-Beckmann B, Freud P, Jakob, B. Naftopidil, a new adrenoceptor blocking agent with Ca(2+)-antagonistic properties: interaction with adrenoceptors. J Cardiovasc Pharmacol. 1992;20:1006–1013.
Search in Google Scholar Back to article
Kirsten R, Breidert M, Nelson K, Heine A, Rosenkranz S, Erdeg B, Niebch G, Borbe HO, Siebert-Weigel M, Respondek J. Naftopidil inhibits 5-hydroxytryptamine-induced platelet aggregation and 5-hydroxytryptamine uptake in platelets of healthy volunteers. Eur J Clin Pharmacol. 1994;46:271–274.
Search in Google Scholar Back to article
de Groot AA, Mathy MJ, van Zwieten PA, Peters SLM. Antioxidant activity of nebivolol in the rat aorta. J Cardiovasc Pharmacol. 2004;43(1):148–153.
Search in Google Scholar Back to article
Gomes A, Costa D, Lima JL, Fernandes E. Antioxidant activity of β-blockers: an effect mediated by scavenging reactive oxygen and nitrogen species? Bioorg Med Chem. 2006;14(13):4568–4577.
Search in Google Scholar Back to article
Wendi M, Book MD. Carvedilol a nonselective beta blocking agent with antioxidant properties. Heart Failure 2002;8(3):129–191.
Search in Google Scholar Back to article
Kalíková K, Martínková M, Schmid MG, Tesařová E. Cellulose tris-(3,5-dimethylphenylcarbamate)-based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography: comparison with HPLC. J Sep Sci. 2018;41:1471–1478.
Search in Google Scholar Back to article
Li M, Jiang Z, Di X, Song Y. Enantiomeric separation of six beta-adrenergic blockers on Chiralpak IB column and identification of chiral recognition mechanisms by molecular docking technique. Biomed Chromatogr. 2020;34:e4803.
Search in Google Scholar Back to article
Yang Y, Wang Y, Bao Z, Yang Q, Zhang Z, Ren Q. Progress in the enantioseparation of β-blockers by chromatographic methods. Molecules 2021;26(2):468.
Search in Google Scholar Back to article
Bruchatá K, Čižmáriková R, Hroboňová K, Lehotay J, Kyselová Z. Syntéza a štúdium enantioseparácie niektorých potenciálnych β-blokátorov aryloxyaminopropanolového typu metódou HPLC s použitím makrocyklických antibiotík ako chirálnych selektorov. Acta Fac Pharm Univ Comen. 2006;53:68–75.
Search in Google Scholar Back to article
Pocrnić M, Ansorge M, Dovhunová M, Habinovec I, Tesařová E, Galić N. Chiral separation of beta-blockers by HPLC and determination of bisoprolol enantiomers in surface waters. Arh Hig Rada Toksikol. 2020;71:56–62.
Search in Google Scholar Back to article
Nazareth C, Pereira S. A review on chiral stationary phases for separation of chiral drugs. eIJPPR 2020;10(3):77–91.
Search in Google Scholar Back to article
Srivastava S, Bhandari K, Shankar G, Singh HK, Saxena AK. Synthesis, anorexigenic activity and QSAR of substituted aryloxypropanolamines. Med Chem Res. 2004;3(8–9):631–642.
Search in Google Scholar Back to article
Fagerstroem A, Nilsson M, Isaksson R. New propranolol analogues: Binding and chiral discrimination by cellobiohydrolase Ce17A. Org Biomol Chem. 2006;4(16):3067–3076.
Search in Google Scholar Back to article
Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Rad Biol Med. 1999;26(9):1231–1237.
Search in Google Scholar Back to article
Malík I, Stanzel L, Csöllei J, Čurillová J. The in vitro antioxidant properties of 2-alkoxyphenylcarbamic acid derivatives containing a 4′-(substituted phenyl)piperazin-1′-yl moiety determined by the 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) derived radical cation (ABTS•+) and ferric reducing antioxidant power (FRAP) assays. Indonesian J Pharm. 2017;28(1):1–9.
Search in Google Scholar Back to article
Čižmáriková R, Markuliak M, Habala L, Valentová J, Bilková A. Synthesis, antimicrobial and antiradical activity of (3-alkoxymethyl-4-hydroxyphenyl)propan-1-ones intermediates of biologically active compounds and activity comparison with 3-(alkoxymethyl)-4-(alkylamino-2-hydroxypropoxyphenyl) alkanones type of beta-blockers. Eur J Pharm Sci. 2020;67:34–44.
Search in Google Scholar Back to article
Čižmáriková R, Valentová J, Habala L, Konušová L. Synthesis, antioxidative activity and enantioseparation of aryloxyaminopropanols derived from 3-methylphenol – bevantolol, toliprolol and a pyrazolidine derivative (in slovak) Farm Obzor 2021;8–9:137–143.
Search in Google Scholar Back to article

Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol

Abstract

Paradigm

My account