Synthesis and Characterization of N-Substituted Tetrahydroiso-quinoline Derivatives via a Pictet-Spengler Condensation
DOI:
https://doi.org/10.6000/1929-5030.2014.03.03.5Keywords:
Tetrahydroisoquinoline, Pictet-Spengler reaction, Imine, Trifluoroacetic acid.Abstract
Synthesis of N-substituted 1,2,3,4 –tetrahydroisoquinoline derivatives and bis-isoquinoline has been carried out via a Pictet-Spengler condensation. Tetrahydroisoquinolines were obtained from 2-(3',4'-dimethoxyphenyl) ethylamine in four steps. The entire synthesized compounds were characterized by IR, 1H NMR and mass spectral data.
References
[1] Locher C, Peerzada N Synthesis of some N-methyl-1,2,3,4- tetrahydroisoquinolines by Friedel–Crafts cyclisation using benzotriazole auxiliary. Chem Soc Perkin Trans 1 1999; 179- 84. http://dx.doi.org/10.1039/a807543c
[2] He Y, Nikulin VI, Vansal SS, Feller DR, Miller DD. Synthesis and human -adrenoceptor activity of 1-(3,5-diiodo-4- methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol derivatives in vitro. J Med Chem 2000; 43: 591-8. http://dx.doi.org/10.1021/jm990463j
[3] Lees GJ. Pharmacology of AMPA/kainate receptor ligands and their therapeutic potential in neurological and psychiatric disorders. Drugs 2000; 59: 33-78. http://dx.doi.org/10.2165/00003495-200059010-00004
[4] Lin Z, Kabada PK. Molecular targets for the rational design of antiepileptic drugs and related neuroprotective agents. Med Res Rev 1997; 17: 537-72. http://dx.doi.org/10.1002/(SICI)1098- 1128(199711)17:63.0.CO;2-2
[5] Rogawski MA, Donevan SD. AMPA receptors in epilepsy and as targets for antiepileptic drugs. Adv Neurol 1999; 79: 947- 63. http://www.ncbi.nlm.nih.gov/pubmed/10514878
[6] Gitto R, Barreca ML, De Luca L, et al. Discovery of a novel and highly potent noncompetitive AMPA receptor antagonist. J Med Chem 2003; 46: 197-00. http://dx.doi.org/10.1021/jm0210008
[7] Kaur J, Ghosh NN, Chandra R. Synthesis and antispasmodic activity evaluation of bis-(papaverine) analogues. Chem Pharm Bull 2004; 52: 316-21. http://dx.doi.org/10.1248/cpb.52.316
[8] Chandra R, Kaur J, Talwar A, Ghosh NN. Synthesis and antispasmodic effect of aryl substituted N-carbamoyl/ thiocarbamoyl isoquinolines. Arkivoc 2001; (viii): 129-35. http://dx.doi.org/10.3998/ark.5550190.0002.814
[9] Kaur J, Ghosh NN, Talwar A, Chandra R. Synthesis of NSubstituted Piperazinyl Carbamoyl and Acetyl Derivatives of Tetrahydropapaverine: Potent Antispasmodic Agents. Chem Pharm Bull 2002; 50: 1223-8. http://dx.doi.org/10.1248/cpb.50.1223
[10] Kitamura M, Hsiao Y, Otha M, et al. General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAPruthenium(I1) complexes. J Org Chem 1994; 59: 297-310. http://dx.doi.org/10.1021/jo00081a007
[11] Scott JD, Williams RM. Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics. Chem Rev 2002; 102: 1669-730. http://dx.doi.org/10.1021/cr010212u
[12] Iwasa K, Moriyasu M, Tachibana Y, et al. Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents. Bioorg Med Chem 2001; 9: 2871-4. http://dx.doi.org/10.1016/S0968-0896(01)00154-7
[13] Minor DL, Wyrick SD, Charifson PS, Watts VJ, Nichols DE, Mailman RB. Synthesis and molecular modeling of 1-phenyll,2,3,4-tetrahydroisoquinolines and related 5,6,8,9-tetrahydro- 13bH-dibenzo
[a,h]quinolizineass D1 dopamine antagonists. J Med Chem 1994; 37: 4317-28. http://dx.doi.org/10.1021/jm00051a008
[14] Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase1 . J Nat Prod 1991; 54: 143-54. http://dx.doi.org/10.1021/np50073a012
[15] Pham VC, Ma J, Thomas SJ, Xu Z, Hecht SM. Alkaloids from alangium javanicum and alangium grisolleoides that mediate Cu2+-dependent DNA strand scission. J Nat Prod 2005; 68: 1147-52. http://dx.doi.org/10.1021/np058013j
[16] Oku N, Matsunaga S, van Soest RWM, Fusetani N. Renieramycin J, a highly cytotoxic tetrahydroisoquinoline alkaloid, from a marine sponge Neopetrosia sp1 . J Nat Prod 2003; 66: 1136-9. http://dx.doi.org/10.1021/np030092g
[17] Naito R, Yonetoku Y, Okamoto Y, Toyoshima A, Ikeda K, Takeuchi M. Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists1 . J Med Chem 2005; 48: 6597-606. http://dx.doi.org/10.1021/jm050099q
[18] Castro L, Ball RG, Broughton HB, et al. Controlled modification of acidity in cholecystokinin B receptor antagonists: N-(1,4-Benzodiazepin-3-yl)-N -
[3-(tetrazol-5- ylamino)phenyl]ureas. J Med Chem 1996; 39: 842-9. http://dx.doi.org/10.1021/jm9506736
[19] Nakamura S, Tanaka M, Taniguchi T, Uchiyama M, Ohwada T. Stereoselectivity of superacid-catalyzed pictet-spengler cyclization reactions. Org Lett 2003; 5: 2087-90. http://dx.doi.org/10.1021/ol034526a
[20] Cox ED, Cook JM. The Pictet-Spengler condensation: a new direction for an old reaction. Chem Rev 1995; 95: 1797-842. http://dx.doi.org/10.1021/cr00038a004
[21] Semple G, Ryder H, Rooker DP, et al. (3R)-N-(1-(tertButylcarbonylmethyl)-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4- benzodiazepin-3-yl)-N’-(3-(methylamino)phenyl)urea (YF476): A potent and orally active gastrin/CCK-B antagonist. J Med Chem 1997; 40: 331-41. http://dx.doi.org/10.1021/jm960669+
[22] March J. Advanced Organic Chemistry: Reactions, Mechanisms and Structure. New York: John Wiley & Sons, 4th ed 1992.
[23] Larghi EL, Amongero M, Bracca ABJ, Kaufman TS. The intermolecular Pictet-Spengler condensation with chiral carbonyl derivatives in the stereoselective syntheses of optically active isoquinoline and indole alkaloids. Arkivoc 2005; (vii): 98-153. http://dx.doi.org/10.3998/ark.5550190.0006.c09
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2014-09-18
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How to Cite
Synthesis and Characterization of N-Substituted Tetrahydroiso-quinoline Derivatives via a Pictet-Spengler Condensation. (2014). Journal of Applied Solution Chemistry and Modeling, 3(3), 169-174. https://doi.org/10.6000/1929-5030.2014.03.03.5
