Synthesis and antitumor properties of some new N-(5-R-benzyl-1,3-thiazol-2-yl)-4,5-dihydro-1H-imidazole-2-carboxamides
Keywords:
organic synthesis, thiazole, imidazole, anticancer activity
Abstract
New N-(5-R-benzyl-1,3-thiazol-2-yl)-2-morpholin-4-yl-2-oxoacetamides have been prepared in good yields via the reaction of N-(5-R-benzyl-1,3-thiazol-2-yl)-2-chloroacetamides with sulfur and morfoline. These compounds react with ethendiamine to form a series of novel N-[5-R-benzyl)-1,3-thiazol-2-yl]-4,5-dihydro-1H-imidazole-2-carboxamides with excellent yields. Anticancer activity screening of synthesized compounds was carried out within the framework of the Developmental Therapeutic Program of the National Cancer Institute's (DTP, NCI, Bethesda, Maryland, USA). It was shown that compounds are promising for new anticancer agents' search.
References
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Vukovic N., Sukdolak S., Solujic S., Milosevic T., 2008. Synthesis and antimicrobial evaluation of some novel 2-aminothiazole derivatives of 4-hydroxy-chromene-2-one. Arch Pharm., 341(8): 491-496. https://doi.org/ 10.1002/ardp.200700215.
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Available at: http://www.dtp.nci.nih.gov (Accessed 10 February 2019).
Yarovenko VN., Kosarev SA., Zavarzin IV., Krayushkin MM., 1999. Reactions of monothiooxamides with N-nucleophiles. Synthesis of 4,5-dihydroiidazole-2-carboxanilides. Russ Chem Bull., 71(4): 749–753. https://doi.org/10.1007/BF02496262
Zelisko NA., Atamanyuk DA., Ostapiuk YB., Bryhas AB., Matiychuk VS., Gzella AC., Lesyk RB., 2015. Synthesis of fused thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels-Alder reaction related tandem and domino processes. Tetrahedron Lett., 71(50): 9501-9508. https://doi.org/10.1016/j.tet.2015.10.019
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Akito T., Hiroyoshi S., Yukio M., Takatoshi I., Hisashi T, 1994. Antiplatelet agents based on cyclooxygenase inhibition without ulcerogenesis. evaluation and synthesis of 4,5-bis(4-methoxyphenyl)-2-substituted-thiazoles. J Med Chem., 37(8): 1189-1199. https://doi.org/10.1021/jm00034a017
Al-BalasQ, Anthony NG., Al-Jaidi B., Alnimr A., Abbott G., Brown AK., Taylor RC., Besra GS., McHugh TD., Gillespie SH., Johnson BF., Mackay SP., Coxon GD., 2009. Identification of 2-amino-thiazole-4-carboxylate derivatives active against mycobacterium tuberculosis H37rv and the beta-ketoacyl- acp synthase Mtfabh. PLoS One, 4(5): 5617-5621.
Beauchard A., Jaunet A., Murillo L., Baldeyrou B., Lansiaux A., Chérouvrier JR., Domon L., Picot L., Bailly C., 2009. Synthesis and antitumoral activity of novel thiazolobenzotriazole, thiazoloindolo[3,2-c]quinoline and quinolinoquinoline derivatives. Eur J Med Chem., 44(10): 3858-3865. https://doi.org/10.1016/j.ejmech.2009.04.012
Boyd MR., Paull KD., 1995. Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug Dev Res., 34: 91-109. https://doi.org/10.1002/ddr.430340203
Boyd MR., Teicher BA., 1997. In: cancer drug discovery and development. Humana Press, 2: 23-43.
Chaban T., Klenina O., Harkov S., Ogurtsov V., Chaban I., Nektegaev I., 2017. Synthesis of some new N3 substituted 6-phenylazo-3Н-thiazolo[4,5-b]pyridin-2-ones as possible anti-inflammatory agents. Pharmacia, 64(4): 16-30. http://bsphs.org/wp-content/uploads/2018/02/Chaban.pdf
Chaban T., Klenina O., Chaban I., Ogurtsov V., Harkov S., Lelyukh M., 2018. Thiazolo[5,4-d]pyrimidines and thiazolo[4,5-d]pyrimidines: A review on synthesis and Pharmacological importance of their derivatives. Pharmacia, 65(2): 54-70. http://bsphs.org/wp-content/uploads/2018/08/Chaban.pdf
Chaban T., Ogurtsov V., Chaban I., Myrko I., Harkov S., Leluykh M., 2019. Synthesis of some new 4-iminothiazolidine-2-ones as possible antioxidants agents. Pharmacia, 66 (1): 27-32. https://doi.org/10.3897/pharmacia.66.e35131
Chaban TI., Ogurtsov VV., Matiychuk VS., Chaban IG., Demchuk IL., Nektegayev IA., 2019. Synthesis, anti-inflammatory and antioxidant activities of novel 3H-thiazolo[4,5-b]pyridines. Acta Chim. Slovenica, 66 (1): 103–111. https://doi.org/10.17344/acsi.2018.4570
Chaudhary M., Pareek D., Pareek PK., Kant R., Ojha KG., Pareek A., 2011. Synthesis of some new biologically active benzothiazole derivatives containing benzimidazole and imidazoline moieties. Bull Korean Chem Soc., 32(1): 131-136.
Chhabria MT., Patel S., Modi P., Brahmkshatriya PS., 2016. Thiazole: A review on chemistry, synthesis and therapeutic importance of its derivatives. Curr Top Med Chem., 16(26): 2841-2862. https://doi.org/10.2174/1568026616666160506130731
Choi MJ., Jung KH., Kim D., Lee H., Zheng HM., Park BH., Hong SW., Kim MH., Hong S., Hong SS., 2011. Anti-cancer effects of a novel compound HS-113 on cell growth, apoptosis, and angiogenesis in human hepatocellular carcinoma cells. Cancer Lett, 306(2): 190-196. https://doi.org/10.1016/j.canlet.2011.03.005
Edwards JA., Kemski MM., Rappleye CA., 2013. Identification of an aminothiazole with antifungal activity against intracellular histoplasmacapsulatum antimicrobial agents. Chemotherapy, 57(9): 4349-4359. https://doi.org/10.1128/AAC.00459-13
Finiuk NS., Hreniuh VP., Ostapiuk YuV., Matiychuk VS., Frolov DA., Obushak MD., Stoika RS., Babsky AM., 2017. Antineoplastic activity of novel thiazole derivatives. Biopolymers and Cell, 33(2): 135-146. http://dx.doi.org/10.7124/bc.00094B
Francieszek S., Tabin P., Tyacke RJ., Maconie A., Saczewski J., KornickaA., Nutt DJ., Hudson AL., 2006 2-(4,5-Dihydroimidazol-2-yl)benzimidazoles as highly selective imidazoline I2/adrenergic α2 receptor ligands. Bioorg Med Chem., 14(19): 6679-6685. https://doi.org/10.1016/j.bmc.2006.06.020
Gorak YuI., Obushak ND., Matiychuk VS., Lytvyn RZ., 2009. Synthesis of heterocycles from arylation products of unsaturated compounds: XVIII. 5-Arylfuran-2-carboxylic acids and their application in the synthesis of 1,2,4-thiadiazole, 1,3,4-oxadiazole, and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives. Russ J Org Chem., 45(4): 541-550. https://doi.org/10.1134/S1070428009040125
Holla BS., Malini KV., Rao BS., Sarojini BK., Kumari NS., 2003. Synthesis of some new 2,4-disubstitutedthiazoles as possible antibacterial and anti-inflammatory agents. Eur J Med Chem., 38(3): 313-318. https://doi.org/10.1016/S0223-5234(02)01447-2
Khalil A., Edwards JA., Rappleye CA., Tjarks W., 2015. Design, synthesis, and biological evaluation of aminothiazole derivatives against the fungal pathogens Histoplasmacapsulatum and Cryptococcus neoformans. Bioorg Med Chem., 23(3): 532-547. https://doi.org/10.1016/j.bmc.2014.12.006
Klenina O., Chaban T., Zimenkovsky B., Harkov S., Ogurtsov V., Chaban I., Myrko I., 2017. Qsar modeling for antioxidant activity of novel N3substituted 5,7-dimethyl-3Н-thiazolo[4,5-b]pyridin-2-ones. Pharmacia, 64(4): 49-71. http://bsphs.org/wp-content/uploads/2018/02/Klenina.pdf
Krasavin M., Karapetian R., Konstantinov I., Gezentsvey Y., Bukhryakov K., Godovykh E., Soldatkina O., Lavrovsky Y., Sosnov AV., Gakh AA., 2009. Discovery and potency optimization of 2-amino-5-arylmethyl-1,3-thiazole derivatives potential therapeutic agents for prostate cancer. Arch Pharm., 342(7): 420-427. https://doi.org/10.1002/ardp.200800201
Lozynska L., Tymoshuk O., Chaban T., 2015. Spectrophotometric studies of 4-[n’-(4-imino-2-oxo-thiazolidin-5-ylidene)-hydrazino]-benzenesulfonic acid as a reagent for the determination of Palladium. Acta Chim Slovenica, 62 (1): 159-167. https://doi.org/10.17344/acsi.2014.866
Matiichuk VS., Potopnyk MN., Obushak MD., 2008. Molecular design of pyrazolo[3,4-d]pyridazines. Russ J Org Chem., 44(9): 1352-1361. https://doi.org/10.1134/S1070428008090182
Nevagi RJ., 2014. Biological and medicinal significance of 2-aminothiazoles. Pharm Lett., 6 (5): 134-150. https://www.scholarsresearchlibrary.com/articles/biological-and-medicinal-significance-of-2aminothiazoles.pdf
Obushak ND., Matiichuk VS., Vasylyshin RY., Ostapiuk YuV., 2004. Heterocyclic syntheses on the basis of arylation products of unsaturated compounds 3-aryl-2-chloropropanals as reagents for the synthesis of 2-amino-1,3-thiazole derivative. Russ J Org Chem., 40(3): 383-389. https://doi.org/10.1023/B:RUJO.0000034976.75646.85
Obushak ND., Gorak YuI., Matiychuk VS., Lytvyn RZ., 2008. Synthesis of heterocycles based on arylation products of unsaturated compounds: XVII. Arylation of 2-acetylfuran and synthesis of 3-R-6-(5-aryl-2-furyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines. Russ J Org Chem., 44 (11): 1689-1694. https://doi.org/10.1134/S1070428008110213
Obushak MD., Matiychuk VS., Turytsya VV., 2009. A new approach to the synthesis of 3,4-dihydroisocoumarin derivatives. Tetrahedron Lett., 50(45): 6112-6115. https://doi.org/10.1016/j.tetlet.2009.08.024
Obushak ND., Lesyuk AI., Gorak YI., Matiychuk VS., 2009. Mechanism of Meerwein arylation of furan derivatives. Russ J Org Chem., 45(9): 1388-1394. https://doi.org/10.1134/S1070428009090103
Ostapiuk YVA., Obushak MD., Matiychuk VS., Naskrent MB., Gzella AK., 2012. A convenient method for the synthesis of 2-[(5-benzyl-1,3-thiazol-2-yl)imino]-1,3-thiazolidin-4-one derivatives. Tetrahedron Lett., 53 (5): 543-545. https://doi.org/10.1016/j.tetlet.2011.11.093
Ostapiuk YV., Frolov DA., Vasylyschyn RY., Matiychuk VS., 2018. Synthesis and antitumor activities of new N-(5-benzylthiazol-2-yl)-2-(heteryl-5-ylsulfanyl)-acetamides. Biopolymers and Cell, 34(1): 59–71. https://doi.org/10.7124/bc.000971
Pokhodylo N., Shyyka O., Matiychuk V., 2014. Synthesis and anticancer activity evaluation of new 1,2,3-triazole-4-carboxamide derivatives. Med Chem Res., 23(5): 2426-2438. https://doi.org/10.1007/s00044-013-0841-8
Rostom S., 2006. Synthesis and in vitro antitumor evaluation of some indeno[1,2-c]pyrazol(in)es substituted with sulfonamide, sulfonylurea(-thiourea) pharmacophores, and some derived thiazole ring systems. Bioorg Med Chem., 14 (19): 6475-6485. https://doi.org/10.1016/j.bmc.2006.06.020
Satish P., Woodgett J., 2008. Glycogen synthase kinase-3 and cancer: good cop, bad cop. Cancer cell, 14(5): 351-353. https://doi.org/ 10.1016/j.ccr.2008.10.013
Schiedel M., Rumpf T., Karaman B., Lehotzky A., Oláh J., Gerhardt S., Ovádi J., Sippl W., Einsle O., Jung M., 2016. Aminothiazoles as potent and selective sirt 2 inhibitors: a structure-activity relationship study. J Med Chem., 59(4): 1599-1612. https://doi.org/10.1021/acs.jmedchem.5b01517
Servi S., Genc M., Guer S., Koca M., 2005. The synthesis and antimicrobial activity of some new methyl N-arylthiocarbamates, dimethyl N-aryldithiocarbonimidates and 2-arylamino-2-imidazolines. Eur J Med Chem., 40(7): 687-693. https://doi.org/10.1016/j.ejmech.2005.02.002
Shoemaker RH., 2006. The NC I60 human tumour cell line anticancer drug screen. Nature Revievs Cancer, 6: 813-823. https://doi.org/10.1038/nrc1951
Tymoshuk O., Oleksiv L., Khvalbota L., Chaban T., Patsay I., 2019. Spectrophotometric determination of ru(iv) using 5-hydroxyimino-4-imino-1,3-thiazolidin-2-one as a novel analytical reagent. Acta Chim Slovenica, 66(1): 62–69. http://dx.doi.org/10.17344/acsi.2018.4570
Venkatachalam TK., Sudbeck EA., Mao C., Uckun FM., 2001. Anti-hiv activity of aromatic and heterocyclic thiazolylthiourea compounds. Bioorg Med Chem Lett., 11(4): 523-528. https://doi.org/10.1016/S0960-894X(01)00011-7
Vukovic N., Sukdolak S., Solujic S., Milosevic T., 2008. Synthesis and antimicrobial evaluation of some novel 2-aminothiazole derivatives of 4-hydroxy-chromene-2-one. Arch Pharm., 341(8): 491-496. https://doi.org/ 10.1002/ardp.200700215.
Wilkes MC., Lavrik PB., Freenplate J., 1991. Synthesis of n-benzoyl-n-alkyl-2-aminothiazoles: helio this vires censproin secticides. Journal of Agricultural Food Chemistry, 39(9): 1652-1657. https://doi.org/10.1021/acs.jafc.6b02032
Available at: http://www.dtp.nci.nih.gov (Accessed 10 February 2019).
Yarovenko VN., Kosarev SA., Zavarzin IV., Krayushkin MM., 1999. Reactions of monothiooxamides with N-nucleophiles. Synthesis of 4,5-dihydroiidazole-2-carboxanilides. Russ Chem Bull., 71(4): 749–753. https://doi.org/10.1007/BF02496262
Zelisko NA., Atamanyuk DA., Ostapiuk YB., Bryhas AB., Matiychuk VS., Gzella AC., Lesyk RB., 2015. Synthesis of fused thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels-Alder reaction related tandem and domino processes. Tetrahedron Lett., 71(50): 9501-9508. https://doi.org/10.1016/j.tet.2015.10.019
Zubkov FI., Ershova JD., Zaytsev VP., Obushak MD., Matiychuk VS., Sokolova EA., Khrustalev VN., Varlamov AV., 2010. The first example of an intramolecular Diels-Alder furan (IMDAF) reaction of iminium salts and its application in a short and simple synthesis of the isoindolo[1,2-a]isoquinoline core of the jamtine and hirsutine alkaloids. Tetrahedron Lett., 51 (52): 6822-6824. https://doi.org/10.1016/j.tetlet.2010.10.046
Published
2020-08-19
How to Cite
Ya Horishny, V., V Drapak, I., I Chaban, T., V Ostapiuk, Y., & S Matiychuk, V. (2020). Synthesis and antitumor properties of some new N-(5-R-benzyl-1,3-thiazol-2-yl)-4,5-dihydro-1H-imidazole-2-carboxamides. Indonesian Journal of Pharmacy, 31(3), 150-160. https://doi.org/10.22146/ijp.596
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