A Review of Heterocyclic Composites Compounds in Synthetic Strategies for Pyridine Derivatives
Keywords:
Heterocyclic Composites, Nitrogen, Pyridine Derivatives, Synthetic StrategiesAbstract
This review provides a comprehensive analysis of synthetic strategies employed in the preparation of pyridine derivatives, focusing on the intricate landscape of heterocyclic composite compounds. Pyridine, as a quintessential heterocycle, holds immense importance in medicinal chemistry, agrochemicals, and materials science, prompting continuous advancements in synthetic methodologies. The review encompasses an in-depth exploration of classical and contemporary synthetic routes for pyridine derivatives, emphasizing the key role played by diverse heterocyclic composites. the impact of heterocyclic composites on reaction selectivity and the diversification of pyridine derivatives, highlighting the significance of nitrogen-containing building blocks in these synthetic pathways.
Downloads
References
Pizzarello, S.; Huang,Y.; Becker, L.; Poreda, R.J.; Nieman, R.A.; Cooper G.; Williams, M. Science, 2001, 293,2236.
Ashry, E.S.H.; Ramadan, E, Kassem, A.A, Adv. Heterocycl. Chem., 2005,88, 1-3.
Ohnmacht, S.; West, R.; Parker, R.; Atkinson, J. Bioorg. Med. Chem., 2008, 16(16), 7631- 7631.
Naidu, K. A. Nutrition Journal, 2003, 2, 1.
Padayatty, S. J.; Katz, A.; Wang, Y.; Eck, P.; Kwon, O.; Lee, J. H.; Chen, S.; Corpe, C.; Dutta, A.; Dutta, S. K.; Levine, M. J. Am. Coll. Nutr. 2003, 22, 18-35
Phillips, A.P., Hantzsch's Pyridine Synthesis, Journal of the American Chemical Society 1949, 71, 4003-4007
Baumann, M.; Baxendale, I. R., An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles, Beilstein J. Org. Chem. 2013, 9, 2265–2319.
Koehn, C.J.; Elvehjem, C.A., Further Studies on the Concentration of the Anti-pellagra Factor, J. Biol. Chem., 1937, 118, 693
Farhanullah; Agarwal, N.; Goel, A.; Ram, V. J., Synthesis of aminonicotinonitriles and diaminopyridines through base-catalyzed ring transformation of 2H-pyran-2-ones, J. Org. Chem. 2003, 68, 2983.
Matolcsy, G.; Nádasy, M.; Andriska, V., Pesticide Chemistry, ElsevierAmsterdam 1988, 388
Henkel, T.; Brunne, R. M.; Müller, H.; Reichel, F., Statistical investigation into the structural complementarity of natural products and synthetic compounds, Angew. Chem., Int. Ed. Engl., 1999, 38, 643.
Santos, V. A. F. F. M.; Regasini, L. O.; Nogueira, C. R.; Passerini, G. D.; Martinez, I.; Bolzani, V. S.; Graminha, M. A. S.; Cicarelli, R. M. B.; Furlan M., J. Nat. Prod., 2012, 75, 991. Antiprotozoal Sesquiterpene Pyridine Alkaloids from Maytenus ilicifolia. J Nat Prod.; 2012, 75, 991–995.
Bull, J. A.; Mousseau, J. J.; Pelletier, G.; Charette, A. B., Synthesis of pyridine and dihydropyridine derivatives by regio- and stereoselective addition to Nactivated pyridines, Chem. Rev. 2012, 112, 2642.
Goetz, A. E.; Garg, N. K., Regioselective reactions of 3,4-pyridynes enabled by the aryne distortion model, Nature Chem., 2013, 5, 54
Henry, G. D., De novo synthesis of substituted pyridines, Tetrahedron, 2004, 60, 6043
Helal, M.; El-Awdan, S.; Salem, M.; Abd-elaziz, T.A.; Moahamed, Y.A.; ElSherif, A.A.; Mohamed, G.A.M., Synthesis, biological evaluation and molecular modeling of novel series of pyridine derivatives as anticancer, antiinflammatory and analgesic agents, Spectrochim Acta Part A Mol Biomol Spectrosc., 2015, 135, 764.
Nohara, A.; Ishiguro, T.; Ukawa, K.; Sugihara, H,; Maki, Y,; Sanno, YStudies on Antianaphylactic Agents. Synthesis of Antiallergic 5-Oxo-5H- [1]benzopyrano[2,3-b]pyridines.; . J. Med. Chem., 1985, 28, 559.
Lu, X.; Tang, J.; Cui, S.; Wan, B.; Franzblauc, S. G.; Zhang, T.; Zhang, X.; Ding, K., Pyrazolo[1,5-a]pyridine-3-carboxamide hybrids: Design, synthesis and evaluation of anti-tubercular activity, European J. Med. Chem., 2017, 125, 41.
Alam, M.N.; Yu, J.Q.: Beale, P.; Turner, P.; Proschogo, N.; Huq, F. Crystal Structure, Antitumour and Antibacterial Activity of Imidazo[1, 2-α]pyridine Ligand Containing Palladium Complexes, Chem. Select, 2020, 5, 668.
Gouda, M. A.; Attia, E.; Helal, M. H.; and Salem, M. A., Recent Progress on Nicotinonitrile Scaffold-based Anticancer, Antitumor, and Antimicrobial Agents: A Literature Review, J. Heterocyclic Chem., 2018, 55, 2224.
Al‐Omar, M.A.; Amr, A.E.‐G.E.; Al‐Salahi, R.A., Anti-inflammatory, Analgesic, Anticonvulsant and Antiparkinsonian Activities of Some Pyridine Derivatives Using 2,6-Disubstituted Isonicotinic Acid Hydrazides, Arch. Pharm. Med. Chem., 2010, 343, 648.
Hamdy, N.A.; Kamel, G.M., Potent anti-inflammatory and analgesic activities of new derivatives of chalcone, pyridine, pyrazole, and isoxazole incorporated into 5,6,7,8-tetrahydronaphthalene, Egypt Pharmaceut J., 2012, 11, 22.
Tripathi, L.; Singh, R.; Stables, J.P., Design & synthesis of N‟-[substituted] pyridine-4-carbohydrazides as potential anticonvulsant agents‟, Eur. J. Med. Chem., 2011, 46,
Wei, L.; Tan, W.; Zhang, J.; Mi, Y.; Dong, F.; Li, Q.; Guo, Z., Synthesis, Characterization, and Antifungal Activity of Schiff Bases of Inulin Bearing Pyridine ring. Polymers, 2019, 11, 371.
Zhang, J.; Tan, W.; Mi, Y.; Luan, F.; Wei, L.; Li, Q.; Dong, F.; Guo, Z., Synthesis and Characterization of Inulin Derivatives Bearing Urea Groups with Promising Antifungal Activity; Starch, 2019, 71, 1800058
Tucker, J.A.; Allwine, D.A.; Grega, K.C.; Barbachyn, M.R.; Klock, J.L.; Adamski, J.L.; Brickner, S.J.; Hutchinson, D.K.; Ford, C.W.; Zurenko, G.E.; Conradi, R.A.; Burton, P.S.; Jensen, R.M., Piperazinyl oxazolidinone antibacterial agents containing a pyridine, diazene, or triazene heteroaromatic ring J. Med. Chem., 1998, 41, 3727.
Parikh, K.; Patel, R., Synthesis and Characterization of Some Cyanopyridine Compounds in Therapeutic Interest.; Int. J. ChemTech Res., 2009, 1, 581.
Bhadani, V.; Patel, P.; Purohit, H.; Purohit, D., Synthesis and Antimicrobial Screening 6-Aryl-2-(Amino/Methoxy)-4-[(4′-Difluoro Methoxy) (3′-Hydroxy) Phenyl] Nicotinonitrile, Int. Lett. Chem. Physics and Astronomy, 2015, 50, 35
Konda, S.G.; Khedkar, V.T.; Dawane, B.S.; Synthesis of some new 2-amino3-cyano-4-aryl-6-(1-napthyl amino)-pyridines as antibacterial agents, J. Chem. Pharm. Res., 2010, 2, 187.
El-Hashash, M.A.; Sherif, S.M.; Badawy, A.; Rashdan, H., Facial synthesis of some new pyrazolopyridine, barbituric and thiobarbituric acid derivatives with antimicrobial activities, Inter. J. Adv. Res., 2014, 2, 900.
Chavan, V.; Sonawane, S.; Shingare, M.; Karale, B., Synthesis, characterization, and biological activities of some 3,5,6-trichloropyridine derivatives, Chem. Heterocycl. Comp., 2006, 42, 625
Zav‟yalova, V.K.; Zubarev, A.A.; Shestopalov, A.M., Synthesis and reactions of 3-acetyl-6-methyl-2-(methylthio)pyridine. Russ Chem. Bull ., 2009, 58, 1939–1944.
Acharya, B.N.; Thavaselvam, B.D.; Kaushik, M.P., Synthesis and antimalarial evaluation of novel pyridine quinoline hybrids, Med Chem Res., 2008, 17, 487.
Marquez-Flores, Y.K., Campos-Aldrete, M.E., Salgado-Zamora, H., Acute and chronic anti-inflammatory evaluation of imidazo[1,2-a]pyridine carboxylic acid derivatives and docking analysis, Med. Chem. Res., 2012, 21, 3491.
Nigade, G.; Chavan, P.; Deodhar, M., Synthesis and analgesic activity of new pyridine-based heterocyclic derivatives.; Med. Chem. Res., 2010, 21.
Jin, Y.; Rho, M.C.; Gajulapati, K.; Jung, H.Y.; Boovanahalli, S.K;, Lee, J.H.; Song, G.Y.; Choi, J.H.; Kim, Y.K.; Lee, K.; Choi, Y.,Synthesis of a Novel Series of Imidazo[1,2-α]pyridines as Acyl-CoA: Cholesterol Acyltransferase (ACAT) Inhibitors,Bull. Korean Chem. Soc., 2009, 30, 1297.
López-Martínez, M.; Salgado-Zamora, H.; San-Juan, E. R.; Zamudio, S.; Picazo, O.; Campos, M. E.; Naranjo-Rodriguez, E. B.,Anti-anxiety and sedative profile evaluation of imidazo[1,2-a]pyridine derivatives, Drug Dev. Res., 2010, 71, 371.
Cho, S. Y.; Kang, S. K.; Kim, S. S.; Cheon, H. G.; Choi, J. K.;Yum, E. K. Synthesis and SAR of benzimidazolederivatives containing oxycyclicpyridineas a gastric H+/K+-ATPase inhibitors, Bull. Korean Chem. Soc., 2001, 22, 1217.
Brown, F.C., 4-Thiazolidinones, Chem. Rev.1961, 61, 463.
Rao, A.; Balzarini, J.; Carbone, A.; Chimirri, A.; De Clercq, M., Synthesis of new 2,3-diaryl-1,3-thiazolidin-4-ones as anti-HIV agents.; Farmaco, 2004, 59, 33.
Rao, A.; Carbone, A.; Chimirri. A.; De Clercq. E.; Monforte, A.M.; Monforte, P.; Pannecouque, C.; Zappalà M., Farmaco., 2002, 57, 747. Synthesis and anti-HIV activity of 2,3-diaryl-1,3-thiazolidin-4-(thi)one derivatives. Il Farmaco, 2002, 57(9): 747–751
Rawal, R.K.; Tripathi, R.; Katti, S.B.; Pannecouque, C.; Synthesis and evaluation of 2-(2,6-dihalophenyl)-3-pyrimidinyl-1,3-thiazolidin-4-one analogues as anti-HIV-1 agents. Bioorganic & Medicinal Chemistry, 2007, 15(9): 3134–3142
Srivastava A.V.K.; Kumar, A., Synthesis of newer thiadiazolyl and thiazolidinonyl quinazolin-4(3H)-ones as potential anticonvulsant agents Eur. J. Med. Chem., 2002, 37, 873
Shiradkar, M.; Ghodke, M.; Bothara, K.; Bhandari, S. V.; Nikalje, A.; Kalyan, C.; Chakravarthy, A.; Desai, N.; Burange, P., Synthesis and anticonvulsant activity of clubbed thiazolidinone–barbituric acid and thiazolidinone–triazole derivatives.; Arkivoc, 2007, 14, 58.
Yanofsky, S. D.; Shen, E. S.; Holden, F.; Whitehorn, E.; Aguilar, B.; Tate, E.; Holmes, C. P.; Scheuerman, R.; MacLean, D.; Wu, M. M.; Frail, D. E.; López, F. J.; Winneker, R.; Arey, B. J.; Barrett, R. W., Allosteric Activation of the Follicle-stimulating Hormone (FSH) Receptor by Selective, Nonpeptide Agonists.; J. Biol. Chem., 2006, 19, 281
Gawrońska-Grzywacz, M.; Popiołek, Ł.; Natorska-Chomicka, D.; Piątkowska-Chmiel, I.; Izdebska, M.; Herbet, M.; Iwan, M.; Korga, A.; Dudka, J.; Wujec, M., Novel 2,3-disubstituted 1,3-thiazolidin-4-one derivatives as potential antitumor agents in renal cell adenocarcinoma, Oncol. Rep. 2019, 41, 693
Vazzana I.; Terranova, E.; Mattioli, F.; Sparatore, F., Aromatic Schiff Bases and 2,3-Disubstituted-1,3-thiazolidin-4-one Derivatives as Anti-Inflammatory Agents., Arkivoc, 2004, 5, 364
Kumar A.; Rajput, C.S.; Bhati, S.K., Synthesis of 3-[4′-(p-chlorophenyl)- thiazol-2′-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6- bromoquinazolin-4-ones as anti-inflammatory agent, Bioorg. Med. Chem., 2007, 15, 3089.
Altintas, H.; Ateş, Ö.; Birteksöz, S.; Ötük, G.; Uzun, M.; Satana, D., Synthesis of Mannich bases of some 2,5-disubstituted 4-thiazolidinones and evaluation of their antimicrobial activities, Turk. J. Chem., 2005, 29, 425
Desai, K.G.; Desai, K.R., A facile microwave enhanced synthesis of sulfurcontaining 5-membered heterocycles derived from 2-mercaptobenzothiazole over ZnCl2/DMF and antimicrobial activity evaluation, J. Sulphur Chem., 2006, 27, 315.
