Synthesis of Novel 1,2,3-Triazole-dihydro[3,2-c[chromenones as Acetylcholinesterase Inhibitors

Synthetic Communications

Volumn 45, Issue 20, 2015, Pages 2311-2318

  Saeedi, Mina ^a,b   Ansari, Shirin ^a   Mahdavi, Mohammad ^a   Sabourian, Reyhaneh ^b   Akbarzadeh, Tahmineh ^a,b   Foroumadi, Alireza ^a   Shafiee, Abbas ^a  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

1,2,3 triazole dihydro 3,2 c chromenones; Acetylcholinesterase; heterocycles

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 1,2,3 TRIAZOLE DIHYDRO[3,2 C]CHROMENONE DERIVATIVE; 2 AMINO 4 [4 [[4 [[1 (4 METYHYLBENZYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENYL] 5 OXO 4H,5H PYRANO[3,2 C]CHROMENE 3 CARBONITRILE; ACETYLCHOLINESTERASE; CHOLINESTERASE INHIBITOR; CHROMENE DERIVATIVE; RIVASTIGMINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84942984990     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2015.1077971     Document Type: Article

References (54)

1. Akselsen O. W., Odlo K., Cheng J.-J., Maccari G., Botta M., Hansen T. V. Synthesis, biological evaluation, and molecular modeling of 1,2,3-triazole analogs of combretastatin A-1. Bioorg. Med. Chem., 2012. 20:234-242
2. Ostrowski, T., Januszczyk, P., Cieslak, M., Kazmierczak-Baranska, J., Nawrot, B., Bartoszak-Adamska, E., Zeidler, J. 5-Ethynyl-1-β-d-ribofuranosyl-1 H-[1,2,3]triazole-4-carboxylic acid amide (ETCAR) and its analogues: Synthesis and cytotoxic properties. Bioorg. Med. Chem. 201 1, 19, 4386-4398.
3. Alvarez, R., Velázquez, S., San-Félix, A., Aquaro, S., De Clercq, E., Perno, C.-F., Karlsson, A., Balzarini, J., Camarasa, M. J. 1,2,3-Triazole-[2′,5′-bis-o-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3′-spiro-5″-(4″-amino-1″,2″-oxathiole2″,2″-dioxide) (TSAO) analogues: Synthesis and anti-HIV-1 activity. J. Med. Chem. 1994, 37, 4185-4194.
4. Cheng, H., Wan, J., Lin, M.-I., Liu, Y., Lu, X., Liu, J., Xu, Y., Chen, J., Tu, Z., Cheng, Y.-S. E., Ding, K. Design, synthesis, and in vitro biological evaluation of 1 H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents targeting virus nucleoprotein. J. Med. Chem. 2012, 55, 2144-2153.
5. Jordaõ, A. K., Ferreira, V. F., Lima, E. S., de Souza, M. C. B. V., Carlos, E. C. L., Castro, H. C., Geraldo, R. B., Rodrigues, C. R., Almeida, M. C. B., Cunha, A. C. Synthesis, antiplatelet, and in silico evaluations of novel N-substituted-phenylamino-5-methyl-1 H-1,2,3-triazole-4-carbohydrazides. Bioorg. Med. Chem. 2009, 17, 3713-3719.
6. Boechat, N., Ferreira, V. F., Ferreira, S. B., Ferreira, M. de L. G., da Silva, F. de C., Bastos, M. M., Costa, M. dos S., Lourenço, M. C. S., Pinto, A. C., Krettli, A. U., Aguiar, A. C., Teixeira, B. M., da Silva, N. V., Martins, P. R. C., Bezerra, F. A. F. M., Camilo, A. L. S., da Silva, G. P., Costa, C. C. P. Novel 1,2,3-triazole derivatives for use against mycobacterium tuberculosis H37Rv (ATCC 27294) strain. J. Med. Chem. 2011, 54, 5988-5999.
7. Lewis, W. G., Green, L. G., Grynszpan, F., Radić, Z., Carlier, P. R., Taylor, P., Finn, M. G., Sharpless, K. B. Click chemistry in situ: Acetylcholinesterase as a reaction vessel for the selective assembly of a femtomolar inhibitor from an array of building blocks. Angew. Chem., Int. Ed. Engl. 2002, 41, 1053-1057.
8. Ranatunga, S., Tang, C.-H. A., Kang, C. W., Kriss, C. L., Kloppenburg, B. J., Hu, C.-C. A., Valle, J. R. D. Synthesis of novel tricyclic chromenone-based inhibitors of IRE-1 RNase activity. J. Med. Chem. 2014, 57, 4289-4301.
9. Nussbaumer, P., Lehr, P., Billich, A. 2-Substituted 4-(thio)chromenone 6-O-sulfamates: potent inhibitors of human steroid sulfatase. J. Med. Chem. 2002, 45, 4310-4320.
10. Cravotto, G., Nano, G. M., Palmisano, G., Tagliapietra, S. An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition. Tetrahedron Asymmetry 2001, 12, 707-709;
11. Manolov, I., Danchev, N. D. Synthesis, toxicological, and pharmacological assessment of some 4-hydroxycoumarin derivatives. Eur. J. Med. Chem. 1995, 30, 531-535;
12. Choure, R., Pitre, K. S. Structural modification of coumarin for its increased anticoagulation potency. Can. J. Chem., Eng. Technol. 2010, 1, 7-15.
13. Schio, L., Chatreaux, F., Klich, M. Tosylates in palladium-catalysed coupling reactions. Application to the synthesis of arylcoumarin inhibitors of gyrase B. Tetrahedron Lett. 2000, 41, 1543-1547;
14. Lad, H. B., Giri, R. R., Brahmbhatt, D. I. An efficient synthesis of some new 3-bipyridinyl substituted coumarins as potent antimicrobial agents. Chin. Chem. Lett. 2013, 24, 227-229.
15. Lacy, A., OKennedy, R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr. Pharm. Des. 2004, 10, 3797-3811.
16. Witaicenis, A., Seito, L. N., Chagas, A. S., Junior, L. D. A., Luchini, A. C., Rodrigues-Orsi, P., Cestari, S. H., Stasi, L. C. D. Antioxidant and intestinal anti-inflammatory effects of plant-derived coumarin derivatives. Phytomedicine 2014, 21, 240-246.
17. Mao, P. C.-M., Mouscadet, J. F., Leh, H., Christian, A., Hsu, L. Y. Chemical modification of coumarin dimer and HIV-1 integrase inhibitory activity. Chem. Pharm. Bull. 2002, 50, 1634-1637;
18. Yu, D., Suzuki, M., Xie, L., Morris-Natschke, S. L., Lee, K. H. Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Med. Res. Rev. 2003, 23, 322-345;
19. Olomola, T. O., Klein, R., Mautsa, N., Sayed, Y., Kaye, P. T. Synthesis and evaluation of coumarin derivatives as potential dual-action HIV-1 protease and reverse transcriptase inhibitors. Bioorg. Med. Chem. 2013, 21, 1964-1971.
20. Anand, P., Singh, B., Singh, N. A review on coumarins as acetylcholinesterase inhibitors for Alzheimers disease. Bioorg. Med. Chem. 2012, 20, 1175-1180;
21. Karatas, M. O., Alici, B., Cakir, U., Cetinkaya, E., Demir, D., Ergün, A., Gençer, N., Arslan, O. Synthesis and carbonic anhydrase inhibitory properties of novel coumarin derivatives. J. Enzyme Inhib. Med. Chem. 2013, 28, 299-304.
22. Kolb, H. C., Finn, M. G., Sharpless, K. B. Click chemistry: Diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
23. Jiang, Y., Kuang, C., Yang, Q. The use of calcium carbide in the synthesis of 1-monosubstituted aryl 1,2,3-triazole via click chemistry. Synlett 2009, 3163-3166.
24. Kolarovič, A., Schnürch, M., Mihovilovic, M. D. Tandem catalysis: From alkynoic acids and aryl iodides to 1,2,3-triazoles in one pot. J. Org. Chem. 2011, 76, 2613-2618.
25. Yamada, Y. M. A., Sarkar, S. M., Uozumi, Y. Amphiphilic self-assembled polymeric copper catalyst to parts per million levels: Click chemistry. J. Am. Chem. Soc. 2012, 134, 9285-9286.
26. Trkovnik, M., Ivezic, Z. Syntheses of some new coumarin-quinolone carboxylic acids. J. Heterocycl. Chem. 2000, 37, 137-141;
27. Mashraqui, S. H., Vashi, D., Mistry, H. D. Efficient synthesis of 3-substituted coumarins. Synth. Commun. 2004, 34, 3129-3134;
28. Matos, M. J., Vinã, D., Picciau, C., Orallo, F., Santana, L., Uriarte, E. A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors. Bioorg. Med. Chem. Lett. 2009, 19, 3268-3270.
29. Potdar, M. M., Mohile, S. S., Salunkhe, M. M. Coumarin syntheses via Pechmann condensation in Lewis acidic chloroaluminate ionic liquid. Tetrahedron Lett. 2001, 42, 9285-9287;
30. Santana, L., González-Diáz, H., Quezada, E., Uriarte, E., Yáñez, M., Vinã, D., Orallo, F. Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. J. Med. Chem. 2008, 51, 6740-6751.
31. Mali, R. S., Tilve, S. G. Useful synthesis of coumestans. Synth. Commun. 1990, 20, 1781-1791.
32. Mali, R. S., Joshi, P. P. Useful syntheses of prenylated-and pyrano-3-arylcoumarins. Synth. Commun. 2001, 31, 2753-2767.
33. Madkour, H. M. F. Synthesis and reactions of some 3-cyano-4-methylcoumarins. Heterocycles 1993, 36, 947-959.
34. Pokhodylo, N. T., Savka, R. D., Obushak, M. D. Synthesis of 3,4-dihydro-2 H-thiopyrans and thiopyrano[3,4-c[chromenes having a 1,2,3-triazole substituent by using thionylation-hetero-Diels-Alder domino reaction. Chem. Heterocycl. Compd. 2014, 50, 544-549.
35. Alizadeh, B. H., Saeedi, M., Dehghan, G., Foroumadi, A., Shafiee, A. Synthesis of some novel pyrano[2,3-f]chromenone derivatives. J. Iranian Chem. Soc. 2015, 12, 605-612;
36. Mahdavi, M., Foroughi, N., Saeedi, M., Karimi, M., Alinezhad, H., Foroumadi, A., Shafiee, A., Akbarzadeh, T. Synthesis of novel benzo[6,7][1,4]oxazepino[4,5-a]quinazolinone derivatives via transition-metal-free intramolecular hydroamination. Synlett 2014, 25, 385-388;
37. Asadi, M., Masoomi, S., Ebrahimi, S. M., Mahdavi, M., Saeedi, M., Ranjbar, P. R., Shafiee, A., Foroumadi, A. Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. Monatsh. Chem. 2014, 145, 497-504.
38. Mahdavi, M., Bialam, M., Saeedi, M., Jafarpour, F., Foroumadi, A., Shafiee, A. Efficient synthesis of 2-methylenethiazolo[2,3-b]quinazolinone derivatives. Synlett 2015, 26, 173-176;
39. Nahavandian, S., Allameh, S., Saeedi, M., Ansari, S., Mahdavi, M., Foroumadi, A., Shafiee, A. Novel 1,2,3,4-tetrahydroquinazolinones via reaction of 2-amino-N-substituted benzamides and dimethyl acetylenedicarboxylate. Helv. Chim. Acta 2015, 98, 1028-1033;
40. Saeedi, M., Goli, F., Mahdavi, M., Asadipour, A., Shafiee, A., Foroumadi, A. Efficient synthesis of novel thiazol-2-ylidene-amides using carbonylthiourea building blocks. J. Heterocycl. Chem. 2015, 52, 1150-1153.
41. Mohammadi-Khanaposhtani, M., Saeedi, M., Zafarghandi, N. S., Mahdavi, M., Sabourian, R., Razkenari, E. K., Alinezhad, H., Khanavi, M., Shafiee, A., Foroumadi, A., Akbarzadeh, T. Potent acetylcholinesterase inhibitors: Design, synthesis, biological evaluation and docking study of acridone linked to 1,2,3-triazole derivatives. Eur. J. Med. Chem. 2015, 92, 799-806;
42. Mohammadi-Khanaposhtani, M., Mahdavi, M., Saeedi, M., Sabourian, R., Safavi, M., Khanavi, M., Foroumadi, A., Shafiee, A., Akbarzadeh, T. Design, synthesis, biological evaluation, and docking study of acetylcholinesterase inhibitors: New acridone-1,2,4-oxadiazole-1,2,3-triazole hybrids. Chem. Biol. Drug. Des. In press. doi: 10.1111/cbdd.12609;
43. Mohammadi-Khanaposhtani, M.; Safavi, M., Sabourian, R., Mahdavi, M., Pordeli, M., Saeedi, M., Ardestani, S. K., Foroumadi, A., Shafiee, A., Akbarzadeh, T. Design, synthesis, in vitro cytotoxic activity evaluation, and apoptosis-induction study of new 9(10H)-acridinone-1,2,3-triazoles. Mol. Divers. In press. doi: 10.1007/s11030-015-9616-0.
44. Rayatzadeh, A., Saeedi, M., Mahdavi, M., Rezaei, Z., Sabourian, R., Mosslemin, M. H., Akbarzadeh, T., Foroumadi, A., Shafiee, A. Synthesis and evaluation of novel oxoisoindolines derivatives as acetylcholinesterase inhibitors. Monatsh. Chem. 2015, 146, 637-643;
45. Rahmani-Nezhad, S., Khosravani, L., Saeedi, M., Divsalar, K., Firoozpour, L., Pourshojaei, Y., Sarrafi, Y., Nadri, H., Moradi, A., Mahdavi, M., Shafiee, A., Foroumadi, A. Synthesis and evaluation of coumarin-resveratol hybrids as 15-lipoxygenase inhibitors. Synth. Commun. 2015, 45, 751-759;
46. Esmati, N., Foroughian, M., Saeedi, M., Mahdavi, M., Khoshneviszadeh, M., Firuzi, O., Tanideh, N., Edraki, N., Miri, R., Shafiee, A., Foroumadi, A. Synthesis and cytotoxic activity of some novel dihyrobenzo[h]pyrano[3,2-c]chromene derivatives. J. Heterocycl. Chem. 2015, 52, 97-104.
47. Berchtold, N. C., Cotman, C. W. Evolution in the conceptualization of dementia and Alzheimers disease: Greco-Roman period to the 1960s. Neurobiol. Aging 1998, 19, 173-189.
48. Mao, F., Huang, L., Luo, Z. H., Liu, A. Q., Lu, C. J., Xie, Z. Y., Li, X. S. O-Hydroxyl-or o-amino benzylamine-tacrine hybrids: multifunctional biometals chelators, antioxidants, and inhibitors of cholinesterase activity and amyloid-β aggregation. Bioorg. Med. Chem. 2012, 20, 5884-5892.
49. Zhou, X., Wang, X. B., Wang, T., Kong, L. Y. Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues. Bioorg. Med. Chem. 2008, 16, 8011-8021.
50. Tang, H., Zhao, H. T., Zhong, S. M., Wang, Z. Y., Chen, Z. F., Liang, H. Novel oxoisoaporphine-based inhibitors of acetyl-and butyrylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation. Bioorg. Med. Chem. Lett. 2012, 22, 2257-2261.
51. Bolognesi, M. L., Cavalli, A., Valgimigli, L., Bartolini, M., Rosini, M., Andrisano, V., Recanatini, M., Melchiorre, C. Multi-target-directed drug design strategy: From a dual binding site acetylcholinesterase inhibitor to a trifunctional compound against Alzheimers disease. J. Med. Chem. 2007, 50, 6446-6449.
52. Miyamae, Y., Kurisu, M., Murakami, K., Han, J., Isoda, H., Irie, K., Shigemori, H. Protective effects of caffeoylquinic acids on the aggregation and neurotoxicity of the 42-residue amyloid β-protein. Bioorg. Med. Chem. 2012, 20, 5844-5849.
53. Scarpini, E., Scheltens, P., Feldman, H. Treatment of Alzheimers disease: Current status and new perspectives. Lancet Neurol. 2003, 2, 539-547.
54. Ellman, G. L., Courtney, K. D., Andres Jr., V., Feather-Stone, R. M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7, 88-95.