Design, synthesis and biological studies of tetrazole fused imidazopyridines

1. Musunuri S, Sreenivasulu R, Mak KK, Pichika MR, Rao MVB (2021) Synthesis of quinozilinium fluoroborate salts from harmine. Carbon Lett 31:297–30510.1007/s42823-020-00165-7 ↗

2. Alugubelli GR, Musunuri S, Sreenivasulu R, Rao MVB (2021) Synthesis of γ-carboline derivatives via indole-2,3-dienolate. Carbon Lett 31:1155–116110.1007/s42823-021-00238-1 ↗

3. Vargheese S, Dinesh M, Kavya KV, Pattappan D, Kumar RTR, Haldorai Y (2020) Triazine-based 2D covalent organic frame work derived nitrogen doped porous carbon for supercapacitor electrode. Carbon Lett 31:879–88610.1007/s42823-020-00190-6 ↗

4. Wu L, Chen X, Ding C, Wang P, Luo H (2023) Preparation and electrochemical performance of porous carbon derived from polypyrrole. Carbon Lett 33:443–45410.1007/s42823-022-00434-7 ↗

5. Velázquez-Olvera S, Salgado-Zamora H, Velázquez-Ponce M, Campos-Aldrete E, Reyes-Arellan A, Pérez-Gonzalez C (2012) Fluorescent property of 3-hydroxymethyl imidazo[1,2-a]pyridine and pyrimidine derivatives. Chem Cent J 6:8310.1186/1752-153X-6-83 ↗

6. El Kazzouli S, Griffon du Bellay A, Berteina-Raboin S, Delagrange P, Caignard DH, Guillaumet G (2011) Design and synthesis of 2-phenylimidazo[1,2-a]pyridines as a novel class of melatonin receptor ligands. Eur J Med Chem 46:4252–425710.1016/j.ejmech.2011.06.030 ↗

7. Enguehard-Gueiffier C, Gueiffier A (2007) Recent progress in the pharmacology of imidazo [1,2-a]pyridines. Minirev Med Chem 7:888–89910.2174/138955707781662645 ↗

8. Dahan-Farkas N, Langley C, Rousseau AL, Yadav DB, Davids H, de Koning CB (2011) 6-Substituted imidazo[1,2-a]pyridines: synthesis and biological activity against colon cancer cell lines HT-29 and Caco-2. Eur J Med Chem 46:4573–458310.1016/j.ejmech.2011.07.036 ↗

9. Chezal JM, Paeshuyse J, Gaumet V, Canitrot D, Maisonial A, Lartigue C, Gueiffier A, Moreau E, Teulade JC, Chavignon O, Neyts J (2010) Synthesis and antiviral activity of an imidazo[1,2-a]pyrrolo[2,3-c]pyridine series against the bovine viral diarrhea virus. Eur J Med Chem 45:2044–294710.1016/j.ejmech.2010.01.023 ↗

10. Al-Tel TH, Al-Qawasmeh RA, Zaarour R (2011) Design, synthesis and in vitro antimicrobial evaluation of novel Imidazo[1,2-a]pyridine and imidazo[2,1-b][1,3]benzo thiazole motifs. Eur J Med Chem 46:1874–188110.1016/j.ejmech.2011.02.051 ↗

11. Hamdouchi C, Ezquerra J, Vega JA, Vaquero JJ, Alvarez-Builla J, Heinz BA (1999) Short synthesis and anti-rhinoviral activity of imidazo[1,2-a]pyridines: the effect of acyl groups at 3-position. Bioorg Med Chem Lett 9:1391–139410.1016/S0960-894X(99)00193-6 ↗

12. Fisher MH, Lusi A (1972) Imidazo[1,2-a]pyridine anthelmintic and antifungal agents. J Med Chem 15:982–98510.1021/jm00279a026 ↗

13. Moraski GC, Markley LD, Chang M, Cho S, Franzblau SG, Hwang CH, Boshoff H, Miller MJ (2012) Generation and exploration of new classes of antitubercular agents: the optimization of oxazolines, oxazoles, thiazolines, thiazoles to imidazo[1,2-a]pyridines and isomeric 5,6-fused scaffolds. Bioorg Med Chem 20:2214–222010.1016/j.bmc.2012.02.025 ↗

14. Kaminski JJ, Hilbert JM, Pramanik BN, Solomon DM, Conn DJ, Rizvi RK, Elliott AJ, Guzik H, Lovey RG (1987) Antiulcer agents. 2. Gastric antisecretory, cytoprotective, and metabolic properties of substituted imidazo[1,2-a]pyridines and analogs. J Med Chem 30:2031–204610.1021/jm00394a018 ↗

15. Ismail MA, Brun R, Wenzler T, Tanious FA, Wilson WD, Boykin DW (2004) Novel dicationic imidazo[1,2-a]pyridines and 5,6,7,8-Tetrahydro-imidazo[1,2-a]pyridines as antiprotozoal agents. J Med Chem 47:3658–366410.1021/jm0400092 ↗

16. Goodacre SC, Street LJ, Hallett DJ, Crawforth JM, Kelly S, Owens AP, Blackaby WP, Lewis RT, Stanley J, Smith AJ, Ferris P, Sohal B, Cook SM, Pike A, Brown N, Wafford KA, Marshall G, Castro JL, Atack JR (2006) Imidazo[1,2-a]pyrimidines as functionally selective and orally bioavailable GABAAα2/α3 binding site agonists for the treatment of anxiety disorders. J Med Chem 49:35–3610.1021/jm051065l ↗

17. Starr JT, Sciotti RJ, Hanna DL, Huband MD, Mullins LM, Cai H, Gage JW, Lockard M, Rauckhorst MR, Owen RM, Lall MS, Tomilo M, Chen H, McCurdy SP, Barbachyn MR (2009) 5-(2-Pyrimidinyl)-imidazo[1,2-a]pyridines are antibacterial agents targeting the ATPase domains of DNA gyrase and topoisomerase IV. Bioorg Med Chem Lett 19:5302–530610.1016/j.bmcl.2009.07.141 ↗

18. Emmitte KA, Wilson BJ, Baum EW, Emerson HK, Kuntz KW, Nailor KE, Salovich JM, Smith SC, Cheung M, Gerding RM, Stevens KL, Uehling DE, Mook RA, Moorthy GS, Dickerson SH, Hassell AM, Anthony Leesnitzer M, Shewchuk LM, Groy A, Rowand JL, Anderson K, Atkins CL, Yang J, Sabbatini P, Kumar R (2009) Discovery and optimization of imidazo[1,2-a]pyridine inhibitors of insulin-like growth factor-1 receptor (IGF-1R). Bioorg Med Chem Lett 19:1004–100810.1016/j.bmcl.2008.11.058 ↗

19. Warshakoon NC, Wu S, Boyer A, Kawamoto R, Sheville J, Bhatt RT, Renock S, Xu K, Pokross M, Zhou S, Walter R, Mekel M, Evdokimov AG, East S (2006) Design and synthesis of substituted pyridine derivatives as HIF-1α prolyl hydroxylase inhibitors. Bioorg Med Chem Lett 16:5616–562010.1016/j.bmcl.2006.08.026 ↗

20. Roelofs AJ, Hulley PA, Meijer A, Ebetino FH, Russell RGG, Shipman CM (2006) Selective inhibition of rab prenylation by a phosphonocarboxylate analogue of risedronate induces apoptosis, but not S-phase arrest, in human myeloma cells. Int J Cancer 119:1254–126110.1002/ijc.21977 ↗

21. Hamdouchi C, Zhong B, Mendoza J, Collins E, Jaramillo C, De Diego JE, Robertson D, Spencer CD, Anderson BD, Watkins SA, Zhang F, Brooks HB (2005) Structure-based design of a new class of highly selective aminoimidazo[1,2-a]pyridine-based inhibitors of cyclin dependent kinases. Bioorg Med Chem Lett 15:1943–194710.1016/j.bmcl.2005.01.052 ↗

22. Kercher T, Rao C, Bencsik JR, Josey JA (2007) Diversification of the three-component coupling of 2-aminoheterocycles, aldehydes, and isonitriles: Efficient parallel synthesis of a diverse and drug like library of imidazo- and tetrahydroimidazo[1,2-a]heterocycles. J Comb Chem 9:1177–118710.1021/cc0700290 ↗

23. Katritzky AR, Xu YJ, Tu H (2003) Regiospecific synthesis of 3-substituted imidazo [1,2-a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[1,2-c]pyrimidine. J Org Chem 68:4935–493710.1021/jo026797p ↗

24. Langer SZ, Arbilla S, Benavides J, Scatton B (1990) Zolpidem and alpidem: two imidazo pyridines with selectivity for omega 1- and omega 3-receptor subtypes. Adv Biochem Psychopharmacol 46:61–72

25. Okubo T, Yoshikawa R, Chaki S, Okuyamac S, Nakazato A (2004) Design, synthesis and structure–affinity relationships of aryloxyanilide derivatives as novel peripheral benzodiazepine receptor ligands. Bioorg Med Chem 12:423–43810.1016/j.bmc.2003.10.050 ↗

26. Jain AN (2004) Ligand based structural hypotheses for virtual screening. J Med Chem 47:947–96110.1021/jm030520f ↗

27. Harrison TS, Keating GM (2005) Zolpidem: a review of its use in the management of insomnia. CNS Drugs 19:65–8910.2165/00023210-200519010-00008 ↗

28. Wiegand MH (2008) Antidepressants for the treatment of Insomnia. Drugs 68:2411–241710.2165/0003495-200868170-00001 ↗

29. Veron JB, Allouchi H, Gueiffier CE, Snoeck RE, Clercq D, Gueiffier A (2008) Influence of 6- or 8-substitution on the antiviral activity of 3-arylalkylthiomethylimidazo [1,2-a]pyridine against human cytomegalovirus (CMV) and varicella-zoster virus (VZV): part II. Bioorg Med Chem 16:9536–954510.1016/j.bmc.2008.09.027 ↗

30. Zubarev VY, Ostrovskii VA (2000) Methods for the synthesis of mono- and polynuclear NH-tetrazoles. Chem Het Comp 36:759–77410.1007/BF02256907 ↗

31. Romagnoli R, Baraldi PG, Salvador MK, Preti D, Tabrizi MA, Brancale A, Fu XH, Li J, Zhang SZ, Hamel E, Bortolozzi R, Basso G, Viola G (2012) Synthesis and evaluation of 1,5-disubstituted tetrazoles as rigid analogues of Combretastatin A-4 with potent antiproliferative and antitumor activity. J Med Chem 55:475–48810.1021/jm2013979 ↗

32. Luo Y-P, Gong Q, Chen Q, Yang G-F (2008) Synthesis and herbicidal activities of tetrazolinone derivatives containing oxime ether. Chin J Org Chem 28(9):1561–1565

33. Diwakar SD, Bhagwat SS, Shingare MS, Gill CH (2008) Substituted 3-((Z)-2-(4-nitro phenyl)-2-(1H-tetrazol-5-yl)vinyl)-4H-chromen-4-ones as novel anti-MRSA agents: synthesis, SAR, and in-vitro assessment. Bioorg Med Chem Lett 18:4678–468110.1016/j.bmcl.2008.07.007 ↗

34. Yeung KS, Qiu Z, Yang Z, Zadjura L, D’Arienzo CJ, Browning MR, Hansel S, Huang XS, Eggers BJ, Riccardi K, Lin PF, Meanwell NA, Kadow JF (2013) Inhibitors of HIV-1 attachment. Part 9: An assessment of oral prodrug approaches to improve the plasma exposure of a tetrazole-containing derivative. Bioorg Med Chem Lett 23:209–21210.1016/j.bmcl.2012.10.125 ↗

35. Bertinaria M, Shaikh MA, Buccellati C (2012) Designing multitarget anti-inflammatory agents: chemical modulation of the Lumiracoxib structure toward dual thromboxane antagonists–COX-2 inhibitors. Chem Med Chem 7:1647–166010.1002/cmdc.201200272 ↗

36. Gundugola AS, Chandra KL, Perchellet EM, Waters AM, Perchellet JPH, Rayat S (2010) Synthesis and antiproliferative evaluation of 5-oxo and 5-thio derivatives of 1,4-diaryl tetrazoles. Bioorg Med Chem Lett 20:3920–392410.1016/j.bmcl.2010.05.012 ↗

37. Trecant C, Dlubala A, George P, Pichat P, Ripoche I, Troin Y (2011) Synthesis and biological evaluation of analogues of M6G. Eur J Med Chem 46:4035–404110.1016/j.ejmech.2011.05.076 ↗

38. Andres-Gil JI, Alcazar-Vaca MJ, Pastor-Fernandez J, Drinkenburg WHIM, Langlois XJM, Oyarzabal-Santamarina J, Vega-Ramiro JA (2006) Preparation of triazolone, tetrazolone and imidazolone derivatives for use as alpha 2C-adrenoreceptor antagonists. EP569512006067139

39. Shaw-Reid CA, Miller MD, Hazuda DJ, Ferrer M, Sur SM, Summa V, Lyle TA, Kinzel O, Pescatore G, Muraglia E, Orvieto F, Williams PD (2005) Preparation of tetrazolyl derivatives as HIV reverse transcriptase inhibitors. U.S. 16671 2005115147

40. Cirino G, Mirone V, Ignarro LJ, Del Soldato P (2004) EP 50779 2004043443

41. Janssens FE, Sommen FM, Surleraux DLNG, Leenaerts JE, Van Roosbroeck YEM (1997) EP 46609716440

42. Shih TL, Candelore MR, Cascieri MA, Chiu SHL, Colwell LF, Deng L, Feeney WP, Forrest MJ, Hom GJ, MacIntyre DE, Miller RR, Stearns RA, Strader CD, Tota L, Wyvratt MJ, Fisher MH, Weber AE (1999) L-770,644: a potent and selective human β3 adrenergic receptor agonist with improved oral bioavailability. Bioorg Med Chem Lett 9:1251–125410.1016/S0960-894X(99)00182-1 ↗

43. Lee PY, Chang WN, Lu CH, Lin MW, Cheng BC, Chien CC, Chang C, Chang HW (2003) Clinical features and in vitro antimicrobial susceptibilities of community-acquired Klebsiella pneumoniae meningitis in Taiwan. Antimicrobial Agents Chem other 51:957–96210.1093/jac/dkg158 ↗

44. Thorn CF, Oshiro C, Marsh S, Hernandez-Boussard T, McLeod H, Klein TE, Altman RB (2011) Doxorubicin pathways: pharmacodynamics and adverse effects. Pharmacogenet Genom 21:440–44610.1097/FPC.0b013e32833ffb56 ↗

45. Verma A, Kaur B, Venugopal S, Wadhwa P, Sahu S, Kaur P, Kumar D, Sharma A (2022) Tetrazole: a privileged scaffold for the discovery of anticancer agents. Chem Biol Drug Des 100:419–44210.1111/cbdd.14103 ↗

46. Yu Y, Han Y, Zhang F, Gao Z, Zhu T, Dong S, Ma M (2020) Design, synthesis, and biological evaluation of Imidazo[1,2-a]pyridine derivatives as novel PI3K/mTOR dual inhibitors. J Med Chem 63:3028–304610.1021/acs.jmedchem.9b01736 ↗

47. Gkeka P, Papafotika A, Christoforidis S, Cournia Z (2015) Exploring a non-ATP pocket for potential allosteric modulation of PI3Kα. J Phys Chem B 119:1002–101610.1021/jp506423e ↗