Asian Journal of Research in Chemistry

Open Access Open Access  Restricted Access Subscription Access
Open Access Open Access Open Access  Restricted Access Restricted Access Subscription Access

1,2,3,4-Tetrahydroquinoline Derivatives and its Significance in Medicinal Chemistry


Affiliations
1 Department of Pharmaceutical Chemistry, Parul Institute of Pharmacy, Limda-391 760, Vadodara, Gujarat, India
     

   Subscribe/Renew Journal


1,2,3,4-Tetrahydroquinoline derivatives are the most important class of compounds in the pharmaceutical and agrochemical industries and play important role in the field of medicinal chemistry with so many Pharmacological activities such as anti-cancer, anti-diabetic, anti-parasitic, anti-inflammatory, anti-oxidant, adrenergic, anti-HIV, antialzheimer, anti-hyperlipidemic, activities. The tetrahydroquinoline ring containing system found in numerous biologically active natural products and pharmacologically relevant therapeutic agents and very common structure motif. Because of the significance of these scaffolds in medicinal chemistry, the development of some potent and important amalgams continues to be a very active field in development of a promising target for new drug development. 1,2,3,4-Tetrahydroquinoline is one such important part of pharmacophore and having different pharmacological activities. Here we have introduced different 1,2,3,4-tetrahydroquinoline derivatives which possess different biological activities depends on its types and position of substituted functional groups. This review is summarized to know about the chemistry of different 1,2,3,4-tetrahydroquinoline derivatives along with their pharmacological activities.

Keywords

1,2,3,4-tetrahydroquinoline, Anti-cancer, Anti-cancer, Anti-diabetic, Anti-parasitic, Antiinflammatory
Subscription Login to verify subscription
User
Notifications
Font Size


  • Alan RK and Stanislaw RBR. Recent progress in the synthesis of 1,2,3,4-tetrahydroquinolines. University of Florida. p. 15032-59.

  • Ke D, Judy FA, Jeffrey RD and Shaomeng W. An efficient synthesis of optically pure (S)-2-functionalized 1,2,3,4- tetrahydroquinoline. Tetrahedron Letters.45: 2004: 1027–9.

  • Raghuram RA. Novel tetrahydroquinolines as aromatase inhibitors. U.S. Patent 20100280070 A1, 2010.

  • Owen BW and Zionsville. Tetrahydroquinoline derivatives for the inhibition of osteoporosis, estrogen dependent breast cancer, endometriosis and uterine fibrosis. U.S. Patent 6962928 B2, 2005.

  • Abu TK, Deb Kumar D and Musawwer KMd. Ferric sulfate [Fe2(SO4)3xH2O]: an efficient heterogeneous catalyst for the synthesis of tetrahydroquinoline derivatives using povarov reaction. Tetrahedron Letters.52: 2011: 4539–42.

  • Saleh IA, Areej MAT, Ahmed MA, Mostafa M and Eman N. Discovering some novel tetrahydroquinoline derivatives bearing the biologically active sulfonamide moiety as a new class of antitumor agents. European Journal of Medicinal Chemistry.45: 2010: 1849–53.

  • Xia Y, Yang ZY, Xia P, Bastow KF, Tachibana Y, Kuo SC, et al. Synthesis and biological evaluation of 6,7,2,3,4-substituted- 1,2,3,4-tetrahydro-2-phenyl-4-quinolones as a new class of antimitotic antitumor agents. Journal of Medicinal Chemistry.41: 1998: 1155-62.

  • Ghosh S, Santulli RJ, Kinney WA, DeCorte BL, Liu L, Lewis JM, et al. 1,2,3,4-Tetrahydroquinoline-containing /3 integrin antagonists with enhanced oral bioavailability. Bioorganic Journal of Medicinal Chemistry Letters.14: 2004: 5937-41.

  • Hibi S, Kikuchi K, Yoshimura H, Nagai M, Tai K and Hida T. Syntheses and structure-activity relationships of novel retinoid x receptor agonists. Journal of Medicinal Chemistry.41: 1998: 3245-52.

  • Rauckman BS, Tidwell MY, Johnson JV and Roth B. 2, 4- Diamino-5-benzylpyrimidines and Analogues as Antibacterial Agents. 10. 2, 4-Diamino-5-(6-quinolylmethy1) - and - [(tetrahydro-6-quinoly1)methyl pyrimidine derivatives. Further Specificity Studies. Journal of Medicinal Chemistry.32: 1989: 1927-36.

  • Richard LB, Min T, Diana FC, Tien TD, Scott MT, Taghreed A, et al. Synthesis and biological activity of 1,2,3,4- tetrahydroquinolineAnd 3,4-(1h)-dihydroquinolin-2-one analogs of retinoic acid. Bioorganic and Medicinal Chemistry Letters.7: 1997: 2373-78.

  • Romina JP, Sabrina L, Adriana BP, Reto B and María RM. Synthesis, stereoselectronic characterization and anti-parasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4- tetrahydroquinolines. Bioorganic & Medicinal Chemistry. 18: 2010: 142 –150.

  • Angela P, Sonia P, Tiziana G, Adele I, Marcello G and Antonella DD. Synthesis of 2-ferrocenylquinoline derivatives and evaluation of their anti-malarial activity. Journal of Organometallic Chemistry.716: 2012: 216-21.

  • Smith HC, Cavanaugh CK, Friz JL, Thompson CS, Saggers JA, Michelotti EL, et al. Synthesis and SAR of cis-1-Benzoyl-1,2,3,4- tetrahydroquinoline ligands for control of Gene Expression in Ecdysone Responsive Systems. Bioorganic and Medicinal Chemistry Letter.13: 2003: 1943-46.

  • Vivek JB, Kasey R, Christophe L, Verlinde MJ, Wesley CV and Michael HG. 2-Oxotetrahydroquinoline based anti-malarial with high potency and metabolic stability. Journal of Medicinal Chemistry.51: 2008: 384–7.

  • Cecile P, Jerome G, Daniel-Henri C, Nathalie H, Bart S, Marie- Claude, et al.4,4-Dimethyl-1,2,3,4-tetrahydroquinoline-based PPARa/c agonists, Part I: Synthesis and pharmacological evaluation. Bioorganic and Medicinal Chemistry Letter.18: 2008: 1617–22.

  • Romano DF, Giuseppe A, Barbara B and Daniele D. Chiral tetrahydroquinoline derivatives as potent anti-hyperalgesic agents in animal models of sustained inflammation and chronic neuropathic pain. Bioorganic and Medicinal Chemistry Letter.17: 2007: 1176–80.

  • Jayasree V. Tetrahydroquinoline derivatives having selective activity retinoid x receptors. EP 1354878 B1, 1999.

  • Steven LR, Robert IH, Andrew RH, Mark EA, Peter MS, Dale EM, et al. Tetrahydroquinoline glucocorticoid receptor agonists: Discovery of a 3-hydroxyl for improving receptor selectivity. Bioorganic and Medicinal Chemistry Letter.21: 2011: 168–71.

  • Tomihiro N, Yasuhiro H, Toshifumi S and Tomoki S. Antioxidant activity of the fused heterocyclic compounds, 1,2,3,4- tetrahydroquinolines, and related compounds-effect of orthosubstituents. Polymer Degradation and Stability.79: 2003: 225– 30.

  • Alina B and Janusz S. Comparative analysis of cytotoxic, genotoxic and anti-oxidant effects of 2,2,4,7-tetramethyl-1,2,3,4- tetrahydroquinoline and ethoxyquin on human lymphocytes. Chemico-Biological Interaction. 162: 2006: 70–80.

  • Neeraj S, Kuldeep KR and Anil KS. Substituted 1,2,3,4- tetrahydroquinolin-6-yloxypropanes as 3-adrenergic receptor agonists: Design, synthesis, biological evaluation and pharmacophore modelling. Bioorganic and Medicinal Chemistry. 17: 2009: 830–47.

  • Jing Z, Peng Z, Jingde W, Zhenyu L, Yan J, Weiying G, et al. Synthesis and biological evaluation of novel 5-alkyl-2-arylthio-6- ((3,4-dihydroquinolin-1(2H)-yl)methyl)pyrimidin-4(3H)-ones as potent non-nucleosideHIV-1 reverse transcriptase inhibitors. Bioorganic and Medicinal Chemistry.19: 2011: 4366–76.

  • Dai SS, John JL, Elizabeth T, BangLW, Mary BY, Kenneth DA, et al. Substituted tetrahydroquinolines as potent allosteric inhibitors of reverse transcriptase and its key mutants. Bioorganic and Medicinal Chemistry Letter.19: 2009: 5119–23.

  • Tao G, Huizhong G, Doug WH, Laura LR, Tara MS, Biji J et al. Design, synthesis, and evaluation of tetrahydroquinoline and pyrrolidinesulfonamidecarbamates as -secretase inhibitors. Bioorganic and Medicinal Chemistry Letter.17: 2007: 3010–13.

  • Leeson PD, Carling RW, Moore KW, Moseley AM, Smith JD, Stevenson G, et al. 4-Amido-2-carboxytetrahydroquinolines- Structure-Activity Relationships for Antagonism at the Glycine Site of the NMDA Receptor. Journal of Medicinal Chemistry.35: 1992: 1954-68.

  • Carling RW, Leeson PD, Moseley AM, Baker R, Foster AC, Grimwood S, et al. 2-Carboxytetrahydroquinolines, Conformational and stereochemical requirements for antagonism of the glycine site on the NMDA receptor. Journal of Medicinal Chemistry.35: 1992: 1942-58.

  • Theodros A, Thomas AB, John WC, William JG, Henry SG, Hubert BJ, et al. Tetrahydroquinoline sulfonamides as -secretase inhibitors. Bioorganic and Medicinal Chemistry Letter.17: 2007: 205–07.

  • Thomas AR, Ellen SM, Patricia DP, Maria Y, Keith TD and Gee- Hong K. Design and synthesis of potent inhibitors of cholesteryl ester transfer protein (CETP) exploiting a 1,2,3,4- tetrahydroquinoline platform. Bioorganic and Medicinal Chemistry Letter.19: 2009: 2456–60.

  • Paul DM. 4-protected –amino-2-substituted- 1, 2, 3, 4- tetrahydroquinolines as intermediates for CEPT inhibitors. European Patent 1607 389 A1, 1999.

  • Koutnikova H. Modulaton of Nuclear Receptor Activity. WO 2004/ 072042 A2, 2004.

  • Yuzo M, Tsuzuki R, Akira M, Toru Y, Yoko Y, Isao Y, et al. Novel Potassium Channel Openers. Part 4:y Transformation of the 1,4-Benzoxazine Skeleton into 1,4-Benzothiazine, 1,2,3,4- Tetrahydroquinoline, 1,2,3,4-Tetrahydroquinoxaline, Indoline, and 1,5-Benzoxazepine. Bioorganic and Medicinal Chemistry Letter.8: 2000: 393-04.

  • Baldh H. Tetrahydroquinoline Derivatives as STAT6- Modulators, Preparation and use thereof. U.S. Patent 7030246 B2, 2006.

  • Bell MR, Zalay AW, Osterlin R, Schange P and Potts GO. Basic Eters of 1-(p-Hydroxy phenyl)-2-phenyl-1,2,3,4- tetrahydroquinoline and 1-(p-Hydroxyphenyl)-2-phenylindole. Journal of Medicinal Chemistry.13: 1970: 664-68.

  • Issac M, Slassi A, O Brien A, Edwards L, MacLean N, Bueschkens D, et al. Pyrrolo[3,2,1-ij]quinoline derivatives, a 5- HT2c Receptor agonist with selectivity over the 5-HT2a receptor: potential therapeutic applications for epilepsy and obesity. Bioorganic and Medicinal Chemistry Letter.10: 2000: 917-21.

  • Jack DS, Michael WM, Sarah WL, Sue IL, Henry AV, Liwu H, et al. Tetrahydroquinoline sulfonamides as vasopressin 1b receptor anatgonists. Bioorganic and Medicinal Chemistry Letter.19: 2009: 6018–602.


Abstract Views: 691

PDF Views: 8




  • 1,2,3,4-Tetrahydroquinoline Derivatives and its Significance in Medicinal Chemistry

Abstract Views: 691  |  PDF Views: 8

Authors

Prafulla M Sabale
Department of Pharmaceutical Chemistry, Parul Institute of Pharmacy, Limda-391 760, Vadodara, Gujarat, India
Pratik Patel
Department of Pharmaceutical Chemistry, Parul Institute of Pharmacy, Limda-391 760, Vadodara, Gujarat, India
Prabhjot Kaur
Department of Pharmaceutical Chemistry, Parul Institute of Pharmacy, Limda-391 760, Vadodara, Gujarat, India

Abstract


1,2,3,4-Tetrahydroquinoline derivatives are the most important class of compounds in the pharmaceutical and agrochemical industries and play important role in the field of medicinal chemistry with so many Pharmacological activities such as anti-cancer, anti-diabetic, anti-parasitic, anti-inflammatory, anti-oxidant, adrenergic, anti-HIV, antialzheimer, anti-hyperlipidemic, activities. The tetrahydroquinoline ring containing system found in numerous biologically active natural products and pharmacologically relevant therapeutic agents and very common structure motif. Because of the significance of these scaffolds in medicinal chemistry, the development of some potent and important amalgams continues to be a very active field in development of a promising target for new drug development. 1,2,3,4-Tetrahydroquinoline is one such important part of pharmacophore and having different pharmacological activities. Here we have introduced different 1,2,3,4-tetrahydroquinoline derivatives which possess different biological activities depends on its types and position of substituted functional groups. This review is summarized to know about the chemistry of different 1,2,3,4-tetrahydroquinoline derivatives along with their pharmacological activities.

Keywords


1,2,3,4-tetrahydroquinoline, Anti-cancer, Anti-cancer, Anti-diabetic, Anti-parasitic, Antiinflammatory

References