Synthesis of Pyrazole and Thiophene Derivatives Together with their Antitumor Evaluations
DOI:
https://doi.org/10.12970/2308-8044.2015.03.02.3Keywords:
Pyrazole, thiophene, tetrahydrobenzo[b]thiophene, cytotoxicity.Abstract
The reaction of cyclohexanone, cyanoacetylhydrazine and elemental sulfur gave the 4,5,6,7-tetrahydrobenzo[b]thiophene derivative 3. The latter compound was used as the key starting material for the synthesis of pyrazoles, thiazole derivatives. The newly synthesized products were screening against the three cancer cell lines namely the human tumor cell lines, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), and SF-268 (CNS cancer) and the human normal cell line the normal fibroblast WI 38. The results showed that compounds 7a and 19c were the most potent compounds among the tested compounds.
References
Sultana SS, Antony SA, Balachandran C. Thiophene and benzodioxole appended thiazolyl-pyrazoline compounds: Microwave assisted synthesis, antimicrobial and molecular docking studies. Bioorg Med Chem Lett 2015; 25: 2753-7. http://dx.doi.org/10.1016/j.bmcl.2015.05.033
Magd-El-Din AA, Atta SMS, Abd-El-All AS Galal SA, Abdalah MM. New synthesis of tetrahydrobenzo[4,5]thieno[2,3d] pyrimidine derivatives and Schiff bases derived from 2-aminotetrahydro benzothiophenes and hetarylcar-boxaldehydes studies on their antitumor and antimicrobial activities. World J Chem 2009; 4: 112-7.
Soliman R, Habib NS, El-Tombary AA, El-Hawash SAM, Shaaban OG. Synthesis of tetrahydrobenzothieno[2,3-d]pyrimidine and tetrahydrobenzothieno[3,2-e][1,2,4]triazolo [4,3-c]pyrimidine derivatives as potential antimicrobial agents. Sci Pharm 2009; 77: 755-73. http://dx.doi.org/10.3797/scipharm.0904-17
Sayyedeh Shadfar Pourpanah SS, Sayyed Mostafa Habibi-Khorassani SM, Mehdi Shahraki M. Fructose-catalyzed synthesis of tetrahydrobenzo[b]pyran derivatives: Investi-gation of kinetics and mechanism. Chinese J of Catalysis 2015; 36: 757-63. http://dx.doi.org/10.1016/S1872-2067(14)60302-8
Elmegeed GA, Wardakhan WW, Younis M, Louca NA. Synthesis and antimicrobial evaluation of some novel cholestane heterocyclic derivatives. Arch Pharm 2004; 337: 140-7. http://dx.doi.org/10.1002/ardp.200300825
Behbehani H, Ibrahim HM, Makhseed S, Elnagdi MH, Mahmoud H. 2-Aminothiophenes as building blocks in heterocyclic synthesis: Synthesis and antimicrobial evaluation of a new class of pyrido[1,2-a]thieno[3,2-e]pyrimidine, quinoline and pyridin-2-one derivatives. Eur J Med Chem 2012; 52: 51-65. http://dx.doi.org/10.1016/j.ejmech.2012.03.004
Angell RM, Atkinson FL, Brown MJ, et al. N-(3-Cyano-4,5,6,7-tetrahydro-1-benzothien-2-yl)amides as potent, selective, inhibitors of JNK2 and JNK3. Bioorg Med Chem Lett 2007; 17: 1296-1301. http://dx.doi.org/10.1016/j.bmcl.2006.12.003
Cohen SM, Duffy JL, Miller C, et al. Direct observation (NMR) of the efficacy of glucagon receptor antagonists in murine liver expressing the human glucagon receptor. Bioorg Med Chem 2006; 14: 1506-17. http://dx.doi.org/10.1016/j.bmc.2005.10.008
Gouda MA, Berghot MA, El-Ghani GF, Elattar KM, Khalil AE. Chemistry of 2-aminothiophene-3-carboxamide and related compounds. Turk J Chem 2011; 35: 815 - 37.
Silva WL, De Lima CA, Galdino SL, Pitta IR, De Simone CA. 2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile, Acta Crystallogr 2011; 67: O3161-U3836.
Abu-Hashem AA, Abu-Zied KM, El-Shehry, MF. Synthetic utility of bifunctional thiophene derivatives and antimicrobial evaluation of the newly synthesized agents. Monatsh Chem 2011; 142: 539-45. http://dx.doi.org/10.1007/s00706-011-0456-z
Wang T, Huang XG, Liu J, et al. An Efficient One-Pot Synthesis of Substituted 2-aminothiophenes via three-component Gewald reaction catalyzed by L-Proline. Synlett 2010; 1351-4. http://dx.doi.org/10.1002/chin.201040097
Fujita M, Seki T, Ikeda N. Synthesis and bioactivities of novel bicyclic thiophenes and 4,5,6,7-tetrahydrothieno[2,3-c]pyridines as inhibitors of tumor necrosis factor-α (TNF-α) production. Bioorg Med Chem Lett 2002; 12: 1897-1990. http://dx.doi.org/10.1016/S0960-894X(02)00332-3
Feroci M, Chiarotto I, Rossi L, Inesi A. Activation of elemental sulfur by electrogenerated cyanomethyl anion: synthesis of substituted 2-aminothiophenes by the Gewald reaction. Adv Synth Catal 2008; 350: 2740-6. http://dx.doi.org/10.1002/adsc.200800503
Castanedo GM, Sutherlin DP. Synthesis of tetrasubstituted thiophenes on solid-support using the Gewald reaction. Tetrahedron Lett 2001; 42: 7181-4. http://dx.doi.org/10.1016/S0040-4039(01)01470-8
Xian-Gui H, Jia L, Jiangmeng R, Tao W, Weidong C, Bu-Bing Z. A facile and practical one-pot synthesis of multisubstituted 2-aminothiophenes via imidazole-catalyzed Gewald reaction. Tetrahedron 2011; 67: 6202-5. http://dx.doi.org/10.1016/j.tet.2011.06.061
William CS, Maxwell ZS, James M. A Solvent-Free, One-step, one-pot Gewald reaction for alkyl-aryl ketones via mechanochemistry. Appl Sci 2014; 4: 171-9. http://dx.doi.org/10.3390/app4020171
Tormyshev VM, Trukhin DV, Rogozhnikova OY, Mikhalina TV, Troitskaya TI, Flinn A. Aryl alkyl ketones in a one-pot Gewald synthesis of 2-aminothiophenes. Synlett 2006; 2559-64. http://dx.doi.org/10.1055/s-2006-951484
