Bazı Yeni Tiyofen-2,5 Dikarboksilik Asit bis-aril (alkil) amid Bileşiklerinin Antitümör ve Antibakteriyel Özelliklerinin İncelenmesi

Tiyofen türevli bileşikler, çeşitli farmakolojik aktiviteleri nedeniyle kimya, biyoloji ve farmakolojide ilgi uyandırır. Bu çalışma, tiyofen-2,5-dikarboksilik asit bis-aril (alkil) amid bileşiklerinin antitümör ve antibakteriyel aktivitesini araştırmayı amaçlamaktadır. Bu çalışmada, tüm bileşikler için antibakteriyel ve antitümör özellikleri in vitro ortamda belirlenmiştir. Sonuç olarak, hücre canlılığı deneyleri, bu bileşiklerin bazılarının in vitro anti-tümör aktivitesine sahip olduğunu göstermektedir. Ayrıca, bazı bileşiklerin etkili bir antibakteriyel aktiviteye sahip olduğu da bulunmuştur.

Investigation of Antitumor and Antibacterial Properties of Some New Thiophene-2,5-Dicarboxylic Acid bis-aryl (alkyl) amide Compounds

Thiophene-derived compounds are of interest in chemistry, biology and pharmacology because of theirvarious pharmacological activities This study aims to investigate the antitumor and antibacterial activity ofthiophene-2,5-dicarboxylic acid bis-aryl (alkyl) amide compounds. In this study, the properties of antibacterialand antitumor were determined in vitro media, for all compounds.As a result, cell viability experiments show that some of this compounds have effective in vitro antitumoractivity. In addition, it has also been found that some compounds have an effective antibacterial activity.

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  • Song P., Yao X., Zhong T., Zhang S., Guo Y., Ren W., Huang D., Duan XC., Yin YF., Zhang SS., Zhang X. The anti-tumor efficacy of 3-(2- Nitrophenyl) propionic acid-paclitaxel (NPPA-PTX): a novel paclitaxel bioreductive prodrug Oncotarget., 26 (2016) 48467-48480.
  • Munichandra Reddy S., Subba Rao D., Madhu K., Subramanyam Ch., Gnana Kumari P. & Naga Raju C. 2- (Benzo[d]thiazol-2-yl) phenyl-4- nitrophenyl alkyl/aryl substituted phosphoramidates: Synthesis, characterization and antimicrobial activity evaluation Phosphorus, Sulfur, and Silicon and the Related Elements, 193 (2018).
  • Babu YH., Vasu Govardhana RP., Suresh RC., Devendranath RC., Uma MDP. Synthesis and antimicrobial activity of novel 2‐alkyl/arylcarbamato‐ 6‐(1,1‐dimethylethyl)‐3‐cyclohexyl‐ 3,4‐dihydro‐2H‐1,3,2‐ benzoxazaphosphorine‐2‐oxides, Journal of Heterocyclic Chemistry, (2009).
  • Mashooq AB., Mohamed A.O., Ahmed MN., Mohamed MA., Hoong-Kun F. Synthesis and antitumor activity of 4- cyclohexyl/aryl-5-(pyridin-4- yl)-2,4- dihydro-3H-1,2,4-triazole-3-thione Med Chem Res., 24 (2014).
  • Mohamed G. G., Omar M. M., Hindy A. M. M., Spectrochimica Acta Part A, 62 (2005) 1140–1150
  • Diana P., Carbone A., Barraja P., Montalbano A., Martorana A., Dattolo G., Gia O., Viab L.D., Cirrincionea G., Synthesis and antitumor properties of 2,5-bis(3-indolyl)thiophenes: Analogues of marine alkaloid nortopsentin., Bioorganic & Medicinal Chemistry Letters 17 (2007) 2342– 2346.
  • Süleymanoğlu N., Ustabaşı R., Alpaslan Y.B., Ünver Y., Turan M., Sancak K., Synthesis, spectroscopic characterization, calculational studies and in vitro antitumoral activity of 4-(3- (1H-imidazol-1-yl)propyl)-(thiophen-2- ylmethyl)-1H-1,2,4-triazol-5(4H)-one., Journal of Molecular Structure 989 (2011) 101–108.
  • Clinical Laboratory Standarts Institute (CLSI) M100-S23; Vol. 33 No.1, january 2013.
  • Kumammoto T., Toyooka K., Nishida M., Kuwahara H., Yashimura Y., Kawada J., Kubota S., Effect of 2,4- Dihydro-3H-1,2,4- Triazole-3 –Thiones and Thiosemicarbazones on lodide Uptake by The Mause Thyroid , The Relationship Between Their Structure and Antithyroid Activity., Chem. Pharm. Bull., 38 (1990) 2595-2596
  • Ferrari B.M., Capacchi S., Pelosi G., Reffo G., Tarasconi P., Albertini R., Pinelli S., Lungni P., Synthesis, Structural Characterization and Biological Activity of Helicin Thiosemicarbazone Monohydrate and a Copper (II) Complex of Salicylaldehyde Thiosemicarbazone, Inorganica Chimica Acta, (1999) 286, 134-141.
  • Offing O.E., Martelli S. Antibacterial Activity of Metal Complexes of Benzil and Benzoin Thiosemicarbazones, IL Farmaco., 49 (1994) 513-518.
  • Koparır M., Cansız A., and Cetin A., Thiophene-2,5-dicarboxylic Acid Bisaryl( alkyl) Amides Heteroatom Chemistry (2005) 16-6.
  • Garcia-Tojal J., Garcia-Orad A., Serra J. L., Pizarro J.L., Lezama L., Arriortua M.I., Rojo T., Inorg. J., Biochem, 75 (1999) 45–54.
  • Sharma S., Athar F., Maurya M.R., Azam A., European Journal of Medicinal Chemistry, 40 (2005) 1414– 1419
  • Singh S., Athar F., Maurya M.R., Azam A., European Journal of Medicinal Chemistry, 41 (2006) 592–598.
  • Parai M.K., Panda G., Chaturvedi V., Manjub Y.K., Sinhab S., Bioorganic & Medicinal Chemistry Letters, 18 (2008) 289–292.
  • Romagnoli R., Baraldi P. G., Carrion M. D., Cara C. L., Cruz-Lopez O., Iaconinoto M. A., Preti D., Shryock J.C., Moorman A.R., Vincenzi F., Varani K., Borea P. A., J. Med. Chem., 51 (2008)5875–5879.
  • Stolic I., Miškovic K., Magdaleno A., Silber A. M., Piantanida I., Bajic M., Glavaš-Obrovac L., Bioorganic & Medicinal Chemistry 17 (2009) 2544– 2554.
  • Jiao J., Fang H., Wang X., Guan P., Yuan Y., Xu W., European Journal of Medicinal Chemistry, 44 (2009) 4470– 4476.
  • Radwan M.A.A., Shehab M.A., El- Shenawy S. M., Monatsh Chem. 140 (2009) 445–450.
  • Romagnoli R., Baraldi P.G., Carrion M. D., Cara C. L., Cruz-Lopez O., Preti D., Fruttarolo F., Pavani M.G., Tabrizi M.A., Tolomeo M., Grimaudo S., Cristina A. D., Balzarini J., Hadfield J. A., Brancale A., Hamel E., J. Med. Chem, 50 (2007) 2273–2277.
  • Romagnoli R., Baraldi P.G., Carrion M. D., Cara C. L., Cruz-Lopez O., Preti D., Tolomeo M., Grimaudo S., Cristina A.D., Zonta N., Balzarini J., Brancale A., Sarkar T., Hamel E., Bioorganic & Medicinal Chemistry 16 (2008) 5367– 5376.
  • Queiroz M.R.R., Ferreira I. C. F. R., Gaetano Y.D., Kirsch G., Calhelhab R.C., Estevinhob L. M., Bioorganic & Medicinal Chemistry, 14 (2006) 6827– 6831.
  • Pinto E., Queiroz M.J.R.P., Vale-Silva L.A., Oliveira J.F., Begouin A., Jeanne- Marie Begouin JM., Kirsch G., Bioorganic & Medicinal Chemistry, 16 (2008) 8172–8177.
  • Ronald K.R., Jefery B.P., In ComprehensiveHeterocyclic Chemistry II;Katritzky A.R., Rees C.W., Scriven E. F. V., Eds.; Pergamon Press: Oxford, (1996) Vol. 2, pp 679–729.
  • Campaigne E. In Comprehensive Heterocyclic Chemistry; Katritzky A.R., Rees C.W., Eds.; Pergamon Press: Oxford, (1984) Vol. 2, pp 863– 934.
  • Christophe S.G., Caubere C.K., Renard P., Pfeiffer B., Pierre A., Leonce S., Caubera P., Bioorganic and Med. Chem. Let, 10 (2000) 2589-91.
  • Blanco J.M., Caamano O., Fernandez F., Mera X.G., Hergueta A.R., Lopez C., Borgez J.E.R., Balzarini J., de Clercq E., Chem. Pharm. Bull, 47 (1999) 1314-1317.
  • Kulandasamy R., Adhikari A.V. and Stables J.P., A new class of anticonvulsants possesing 6 Hz activity: 3,4-Dialkyloxy thiophene bishydrazones, European Journal of Medicinal Chemistry, 44 (2009) 4376- 4384
  • Khanfar M.A., Hill R.A., Kaddoumi A. and El Sayed K.A., Discovery of novel GSK-3β ,nhibitors with potent in vitro and in vivo activities and excellent brain permeability using combined ligand- and structure-based virtual screening, Journal of Medicinal Chemistry, 53 (2010) 8534–8545.
  • Mullican M.D., Wilson M.W., Conner D.T., Kostlan C.R., Schrier D.J. and Dyer R. D., Desing of 5-(3,5-di-tertbutyl- 4-hydroxyphenyl)-1,3,4- oxadiazoles and 1,2,4-triazoles as Orally-Active, Nonuleerogenic Antiinflammatory agents, Journal of Medicinal Chemistry, 36 (1939) 1090- 1099.
  • Lesyk R., Vladzimirska O., Holota S., Zaprutko L. and Gzella A., New 5- substituted thiazolo[3,2-b](1,2,4)- triazole-6-ones: Synthesis and antycancer evaluation, European Journal of Medicinal Chemistry, 42 (2007) 641-648.
  • Molvi K.I., Mansuri M., Sudarsanam V., Patel M.M., Andrabi S.M.A. and Haque N., Synthesis antyinflammatory, analgesic, and antioxidant activities of some tetrasubstitued thiophenes, Journal of Enzyme Inhibition and Medicinal Chemistry, 23 (2008) 829-838.
  • Holla B.S., Poojary N., Rao B.S. and Shivananda M.K., New bis-amino mercaptotriazoles and bistriazolothiadiazoles as possible anticancer agents, European Journal of Chemistry, 10 (2002) 1-7.
  • Xia Y., Qu F., Wu Q. and Peng L., Synthesis of bitriazolyl compounds via huisgen reactions, Heterocycles, 65 (2005) 345-352.
  • Durackova Z, Mendiola M.A., Sevilla M.T., Valent A., Bioelect. and Bioener., 48 (1999) 109-116.
  • Palaska E., Antikanser ilaçlar, 2nd ed. Ankara: Hacettepe Üniversitesi Yayınları, (2004).
  • Kandepu N.M., Mannich bases of chalcones and cyclohexanones as candidate cytotoxic agents, Ottawa: University of Saskatchewan,Thesis(Phd) (1999).