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A Novel Efficient Synthetic Strategy for (±)Carvedilol, an Antihypertensive Drug


Affiliations
1 Department of Chemistry, JNT University, Anantapuram, Andhra Pradesh, India
2 Department of Chemistry, KL University, Vaddeswaram ,Guntur - 522502, A.P, India
3 Department of Chemistry, Krishna University, Machilipatnam - 521 001, India
     

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A New and alternate simple synthetic strategy of carvedilol, -adrenergic blocking agent and its analogs, The key step in this approach is synthesis of 3-(9H-carbazol-4-yloxy)-2-hydroxypropyl 4-methylbenzenesulfonate, it is wished to report towards synthesis of Carvedilol this approach is more efficient , improved overall yield, easy process and to avoid the process impurities.

Keywords

β,-adrenergic Blocking Agents, Antihypertensive Efficacy Drug Suzuki Coupling, Regioselective Tosylation, Cyclisation, Yields
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  • Main B G, Tucker H, In Medicinal Chemistry: the role of Organic chemistry in Drug Research of -blockers: Roberts S M and Price B J, Eds, Academic Press: London, 1985.
  • Howe R, Crowther A F, Stephenson J S, Rao B S , Smith L H, J Med Chem, 1968, 11, 1000.
  • Crowther A F ,Smith L H, J Med Chem, 1968, 11, 1009. 4. Howe R , Rao B S, J Med Chem, 1968, 11, 1118 .
  • (a) Powell J R, Wainer I W, Drayer D E, Drug stereochemistry Analytical Methods and Pharmacology, Dekker M, USA, 1988; (b) Connolly M E, Kersting F, Bollery C T, Prog Cardiovas Dis, 1976, 19, 203.
  • (a) Rabkin R, Stables D P, Levin N W & Suzman M M, Am J Cardiol, 1966, 18, 370; (b) Bestermann E M M , Friedlander D H, Postgrad Med J, 1965, 41, 526; (c) Ross E J, Prichard B N C, Kaufmann L, Robertson A I G , Harries B J, Br Med J, 1967, 191; (d) Prichard B N C ,Gillam P M S, Br Med J, 1964, 725; (e) Geroge C F, Prescriber’s Journal 1974,14,93; (f) Sandler G , Pistevos A C, Br Med J, 1971, 254.
  • (a) Gas D , Kregar M, Ann Inter Med, 1970, 70, 985; (b) Granville-Grossmann P , Turner P, Lancet, 1966, 788; (c) Grosz H J, Lancet, 1972, 564; (d) Hadden D R, Montogomery D A, Shanks R G , Weaver J A, Lancet, 1968, 852; (e) Morelli H F, Ann Inter Med, 1973, 78, 913; (f) Owen D A L , Marsden C D, Lancet, 1965, 1259; (g) Weber R B , Reinmuth O M, Neurology, 1972, 22, 366; (h) Young R R, Gowen J H , Shahani B T, N Engl J Med, 1975, 293, 950.
  • Nakamura, K.; Kusano, K.; Nakamura, Y.; Kakishita, M.; Ohta, K.; Nagase, S.; Yamamoto, M.; Miyaji, K.; Saito, H.; Morita, H.; Emori, T.; Matsubara, H.; Toyokuni, S.; Ohe, T. Carvedilol decreases elevated oxidative stress in human failing myocardium. Circulation 2002, 105, 2867–2871.
  • Kukin, L. M.; Kalman, J.; Charney, H. R.; Levy, K. D.; Buchholz-Varley, C.; Ocampo, N. O. Prospective, randomized comparison of effect of long-term treatment with metoprolol or carvedilol on symptoms, exercise, ejection fraction, and oxidative stress in heart failure. Eng. C Circulation, 1999, 99, 2645–2651.
  • (a) Fritz W, Wolfgang K, Max T, Gisbert S, Egon R , Karl D, DE 2,815,926 A1, Oct 18, 1979,Chem Abstr, 1979, 92, P128716e. (b) Anand Kumar B, RamanVysabhattar, amadasu G, Mukkanti K and Madhusudhan G ; Org. Chem. Ind. J, 2010, 6, 70-73.(c) Madhusudhan G, Anand Kumar B, Hintamani U S, Narasimha Rao M, Udaykiran D, Suresh T, Kiran Kumar V and Mukkanti K; Ind. J. Chem. 49B, 2010, 606-610.
  • Jan Bergman and Benjamin Pelcman, Pure and Appl. Chem., 1990,Vol. 62, No. 10, pp. 1967-1976, , Printed in Great Britain.
  • (a) Gabriella Egri, Attila Kolbert, József Bálint, Elemér Fogassy, Lajos Novák and László Poppe, Tetrahedron: Asymmetry 1998, 9, 271–283 (b) Hirokazu Maeda, Takashi Kikui, Yohji Nakatsuji, and Mitsuo Okahara. J. Org. Chem. 1982, 47, 5167- 5171.
  • (a) Chorom Kim, Ji Eun Keum, Sang Hee Yu, and Soo Y.Ko
  • Bull. Korean Chem. Soc. 2009, Vol. 30, No. 7, 1671.(b) Boyapati M. Choudary,
  • Naidu S. Chowdari and Mannepalli L. Kantam, Tetrahedron 2000, 56, 7291–7298. (c) Michael J. Martinelli, Naresh K. Nayyar, Eric D.Moher, Ulhas P. Dhokte, Joseph M. Pawlak, and Rajappa Vaidyanathan, Organic Letters,1999,1, 3447-3450
  • Stewart H, Can J Res, sect B, 27, 1949 , 740

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  • A Novel Efficient Synthetic Strategy for (±)Carvedilol, an Antihypertensive Drug

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Authors

M Yedukondalu
Department of Chemistry, JNT University, Anantapuram, Andhra Pradesh, India
R Sridhar
Department of Chemistry, KL University, Vaddeswaram ,Guntur - 522502, A.P, India
M.V Basaveswara Rao
Department of Chemistry, Krishna University, Machilipatnam - 521 001, India

Abstract


A New and alternate simple synthetic strategy of carvedilol, -adrenergic blocking agent and its analogs, The key step in this approach is synthesis of 3-(9H-carbazol-4-yloxy)-2-hydroxypropyl 4-methylbenzenesulfonate, it is wished to report towards synthesis of Carvedilol this approach is more efficient , improved overall yield, easy process and to avoid the process impurities.

Keywords


β,-adrenergic Blocking Agents, Antihypertensive Efficacy Drug Suzuki Coupling, Regioselective Tosylation, Cyclisation, Yields

References