Cardioprotective activity of 2-substituted-1,3-oxazolidines on CaCl2-induced arrhythmias in isolated frog heart

V. Dinakaran, J.E. Mathew, M. Vanathi, P. Panneerselvam

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Sudden cardiac death is a primary cause of mortality in patients with cardiovascular diseases, is caused by the loss of regular cardiac rhythm. In the present study 1, 3-oxazolidines were synthesized and their physiochemical parameters like melting point, retardation factor were analyzed. All the compounds were screened for their antiarrhythmic activity by calcium chloride- induced arrhythmias in isolated frog heart at graded dose level. Compounds 4-[3-(2-furylmethyl)-4-phenyl-1,3-oxazolidin-2-yl]-2-methoxy phenol (8), 4-[3-(2-furylmethyl)-4-phenyl-1,3-oxazolidin-2-yl]phenol (9) and 2-(4-chlorophenyl)-3-(2-furylmethyl)-4-phenyl-1, 3-oxazolidine (10) showed very good negative chronotropic and inotropic effect by blocking the calcium entry. All other compounds showed moderate activity. Compounds containing 4-hydroxy and 3-methoxy, 4-hydroxy and 4-chloro substitutions were found to increase the antiarrhythmic activity.
Original languageEnglish
Pages (from-to)485-492
Number of pages8
JournalPharmacologyonline
Volume2
Publication statusPublished - 2008

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Anura
Cardiac Arrhythmias
Guaiacol
Calcium Chloride
Sudden Cardiac Death
Phenol
Freezing
Cardiovascular Diseases
Calcium
Mortality
oxazolidine

Cite this

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title = "Cardioprotective activity of 2-substituted-1,3-oxazolidines on CaCl2-induced arrhythmias in isolated frog heart",
abstract = "Sudden cardiac death is a primary cause of mortality in patients with cardiovascular diseases, is caused by the loss of regular cardiac rhythm. In the present study 1, 3-oxazolidines were synthesized and their physiochemical parameters like melting point, retardation factor were analyzed. All the compounds were screened for their antiarrhythmic activity by calcium chloride- induced arrhythmias in isolated frog heart at graded dose level. Compounds 4-[3-(2-furylmethyl)-4-phenyl-1,3-oxazolidin-2-yl]-2-methoxy phenol (8), 4-[3-(2-furylmethyl)-4-phenyl-1,3-oxazolidin-2-yl]phenol (9) and 2-(4-chlorophenyl)-3-(2-furylmethyl)-4-phenyl-1, 3-oxazolidine (10) showed very good negative chronotropic and inotropic effect by blocking the calcium entry. All other compounds showed moderate activity. Compounds containing 4-hydroxy and 3-methoxy, 4-hydroxy and 4-chloro substitutions were found to increase the antiarrhythmic activity.",
author = "V. Dinakaran and J.E. Mathew and M. Vanathi and P. Panneerselvam",
note = "Cited By :2 Export Date: 10 November 2017 Correspondence Address: Dinakaran, V.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal 576 104 Karnataka, India; email: sdvachu@gmail.com Chemicals/CAS: calcium chloride, 10043-52-4; gum arabic, 9000-01-5 References: Morgan, P.H., Mathison, Arrhythmias and antiarrhythmic drugs: Mechanism of action and structure-activity relationships (1976) J Pharm Sci, 65 (4), pp. 467-482; Burger's, Medicinal Chemistry and drug discovery, Churchill Livingstone, London (1997) Therapeutic agents, 4, pp. 75-88. , 5th edition; Kamlesh, S., Kishwar, S., Anwar, S., Stereo selective formation of steroidal (6R)-spiro oxazolidines (2003) Indian J Chem, 42 B, pp. 2866-2868; James, R.G., William, R.P., Toni-Jo, P., Richard, C.T., Stereo divergent synthesis of sulfoxide containing antibiotics (2000) Tetrahedron Lett, 41, pp. 4301-4305; Heong, S.O., Hoh-Gyu, H., Seung, H.C., Deok-Chan, H., Solid phase synthesis of 1,3-oxazolidine derivatives (2000) Tetrahedron Lett, 41, pp. 5069-5072; Chengzhi, Y., Yongying, J., Longqin, H., A facile synthesis of 2-oxazolidinones via Hofmann rearrangement mediated by bis (trifluoroacetoxy) iodo benzene (2001) Tetrahedron Lett, 42, pp. 1449-1452; Biju Kumar, G., Shah, A.C., Derivatives of (R) and (S)-2-amino-butanol as possible anti-arrhythmics (1996) Indian J. Chem, 35 (B), pp. 79-82; Chalina, E., Dantchev, D., Georgiev, A., Mitova, K., Syntheses and pharmacological activities of 5-(cycloalkoxymethyl) oxazolidines and N-substituted derivatives (1986) Archiv der Pharmazie, 319 (7), pp. 598-603; Upthagrove, A.L., Nelson, W.L., Carbinolamines, imines and oxazolidines from fluorinated propranolol analogs (2001) Drug metabolism and Disposition, 29 (8), pp. 1114-1122; Santhan, P.R., Venkataratnam, R.V., Single pot reductive amination of aromatic aldehyde to N-arylamines (1996) Indian J Chem, 35 B, pp. 1199-1200; Atsushi, A., Satoru, M., Convenient procedure for reduction of aminoacids to aminoalcohols: Use of NaBH4-H2SO4 (1992) Tetrahedron Lett, 33, pp. 5517-5618; Burn, J.H., (1952) Practical pharmacology Blackwell, pp. 1-7. , Scientific publications, London; Muralidharan, A., Dhananjayan, R., Cardiac stimulant activity of Ocimum basilicum Linn. extracts (2004) Indian J Pharmacol, 36, pp. 163-166; Bhosale, S.H., Bodhankar, S.L., Kulkami, M.B., Kulkami, B.A., Pharmacological studies of isomeric juglones on the isolated frog heart (1999) Indian J Pharmacol, 31, pp. 222-224",
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issn = "1827-8620",
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}

Cardioprotective activity of 2-substituted-1,3-oxazolidines on CaCl2-induced arrhythmias in isolated frog heart. / Dinakaran, V.; Mathew, J.E.; Vanathi, M.; Panneerselvam, P.

In: Pharmacologyonline, Vol. 2, 2008, p. 485-492.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Cardioprotective activity of 2-substituted-1,3-oxazolidines on CaCl2-induced arrhythmias in isolated frog heart

AU - Dinakaran, V.

AU - Mathew, J.E.

AU - Vanathi, M.

AU - Panneerselvam, P.

N1 - Cited By :2 Export Date: 10 November 2017 Correspondence Address: Dinakaran, V.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal 576 104 Karnataka, India; email: sdvachu@gmail.com Chemicals/CAS: calcium chloride, 10043-52-4; gum arabic, 9000-01-5 References: Morgan, P.H., Mathison, Arrhythmias and antiarrhythmic drugs: Mechanism of action and structure-activity relationships (1976) J Pharm Sci, 65 (4), pp. 467-482; Burger's, Medicinal Chemistry and drug discovery, Churchill Livingstone, London (1997) Therapeutic agents, 4, pp. 75-88. , 5th edition; Kamlesh, S., Kishwar, S., Anwar, S., Stereo selective formation of steroidal (6R)-spiro oxazolidines (2003) Indian J Chem, 42 B, pp. 2866-2868; James, R.G., William, R.P., Toni-Jo, P., Richard, C.T., Stereo divergent synthesis of sulfoxide containing antibiotics (2000) Tetrahedron Lett, 41, pp. 4301-4305; Heong, S.O., Hoh-Gyu, H., Seung, H.C., Deok-Chan, H., Solid phase synthesis of 1,3-oxazolidine derivatives (2000) Tetrahedron Lett, 41, pp. 5069-5072; Chengzhi, Y., Yongying, J., Longqin, H., A facile synthesis of 2-oxazolidinones via Hofmann rearrangement mediated by bis (trifluoroacetoxy) iodo benzene (2001) Tetrahedron Lett, 42, pp. 1449-1452; Biju Kumar, G., Shah, A.C., Derivatives of (R) and (S)-2-amino-butanol as possible anti-arrhythmics (1996) Indian J. Chem, 35 (B), pp. 79-82; Chalina, E., Dantchev, D., Georgiev, A., Mitova, K., Syntheses and pharmacological activities of 5-(cycloalkoxymethyl) oxazolidines and N-substituted derivatives (1986) Archiv der Pharmazie, 319 (7), pp. 598-603; Upthagrove, A.L., Nelson, W.L., Carbinolamines, imines and oxazolidines from fluorinated propranolol analogs (2001) Drug metabolism and Disposition, 29 (8), pp. 1114-1122; Santhan, P.R., Venkataratnam, R.V., Single pot reductive amination of aromatic aldehyde to N-arylamines (1996) Indian J Chem, 35 B, pp. 1199-1200; Atsushi, A., Satoru, M., Convenient procedure for reduction of aminoacids to aminoalcohols: Use of NaBH4-H2SO4 (1992) Tetrahedron Lett, 33, pp. 5517-5618; Burn, J.H., (1952) Practical pharmacology Blackwell, pp. 1-7. , Scientific publications, London; Muralidharan, A., Dhananjayan, R., Cardiac stimulant activity of Ocimum basilicum Linn. extracts (2004) Indian J Pharmacol, 36, pp. 163-166; Bhosale, S.H., Bodhankar, S.L., Kulkami, M.B., Kulkami, B.A., Pharmacological studies of isomeric juglones on the isolated frog heart (1999) Indian J Pharmacol, 31, pp. 222-224

PY - 2008

Y1 - 2008

N2 - Sudden cardiac death is a primary cause of mortality in patients with cardiovascular diseases, is caused by the loss of regular cardiac rhythm. In the present study 1, 3-oxazolidines were synthesized and their physiochemical parameters like melting point, retardation factor were analyzed. All the compounds were screened for their antiarrhythmic activity by calcium chloride- induced arrhythmias in isolated frog heart at graded dose level. Compounds 4-[3-(2-furylmethyl)-4-phenyl-1,3-oxazolidin-2-yl]-2-methoxy phenol (8), 4-[3-(2-furylmethyl)-4-phenyl-1,3-oxazolidin-2-yl]phenol (9) and 2-(4-chlorophenyl)-3-(2-furylmethyl)-4-phenyl-1, 3-oxazolidine (10) showed very good negative chronotropic and inotropic effect by blocking the calcium entry. All other compounds showed moderate activity. Compounds containing 4-hydroxy and 3-methoxy, 4-hydroxy and 4-chloro substitutions were found to increase the antiarrhythmic activity.

AB - Sudden cardiac death is a primary cause of mortality in patients with cardiovascular diseases, is caused by the loss of regular cardiac rhythm. In the present study 1, 3-oxazolidines were synthesized and their physiochemical parameters like melting point, retardation factor were analyzed. All the compounds were screened for their antiarrhythmic activity by calcium chloride- induced arrhythmias in isolated frog heart at graded dose level. Compounds 4-[3-(2-furylmethyl)-4-phenyl-1,3-oxazolidin-2-yl]-2-methoxy phenol (8), 4-[3-(2-furylmethyl)-4-phenyl-1,3-oxazolidin-2-yl]phenol (9) and 2-(4-chlorophenyl)-3-(2-furylmethyl)-4-phenyl-1, 3-oxazolidine (10) showed very good negative chronotropic and inotropic effect by blocking the calcium entry. All other compounds showed moderate activity. Compounds containing 4-hydroxy and 3-methoxy, 4-hydroxy and 4-chloro substitutions were found to increase the antiarrhythmic activity.

M3 - Article

VL - 2

SP - 485

EP - 492

JO - Pharmacologyonline

JF - Pharmacologyonline

SN - 1827-8620

ER -