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

Year 2018, Volume: 39 Issue: 2, 357 - 365, 29.06.2018

Pelin Koparır , Akif Evren Parlak

https://doi.org/10.17776/csj.412145
Cited By: 1

Abstract

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.

Keywords

1-3-4 tiadiazol antioksidan aktivite radikal süpürücü aktivite biyolojik aktiviteler

References

  • [1]. Kandepu N.M., Mannich bases of chalcones and cyclohexanones as candidate cytotoxic agents, Ottawa: University of Saskatchewan,Thesis(Phd) (1999).
  • [2]. Palaska E., Antikanser ilaçlar, 2nd ed. Ankara: Hacettepe Üniversitesi Yayınları, (2004).
  • [3]. Durackova Z, Mendiola M.A., Sevilla M.T., Valent A., Bioelect. and Bioener., 48 (1999) 109-116.
  • [4]. Xia Y., Qu F., Wu Q. and Peng L., Synthesis of bitriazolyl compounds via huisgen reactions, Heterocycles, 65 (2005) 345-352.
  • [5]. Holla B.S., Poojary N., Rao B.S. and Shivananda M.K., New bis-amino mercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents, European Journal of Chemistry, 10 (2002) 1-7.
  • [6]. Molvi K.I., Mansuri M., Sudarsanam V., Patel M.M., Andrabi S.M.A. and Haque N., Synthesis anty-inflammatory, analgesic, and antioxidant activities of some tetrasubstitued thiophenes, Journal of Enzyme Inhibition and Medicinal Chemistry, 23 (2008) 829-838.
  • [7]. 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.
  • [8]. 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-tert-butyl-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.
  • [9]. 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.
  • [10]. 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.
  • [11]. 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.
  • [12]. 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.
  • [13]. Campaigne E. In Comprehensive Heterocyclic Chemistry; Katritzky A.R., Rees C.W., Eds.; Pergamon Press: Oxford, (1984) Vol. 2, pp 863–934.
  • [14]. 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.
  • [15]. 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.
  • [16]. 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.
  • [17]. 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.
  • [18]. 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.
  • [19]. Radwan M.A.A., Shehab M.A., El-Shenawy S. M., Monatsh Chem. 140 (2009) 445–450.
  • [20]. Jiao J., Fang H., Wang X., Guan P., Yuan Y., Xu W., European Journal of Medicinal Chemistry, 44 (2009) 4470–4476.
  • [21]. Stolic I., Miškovic K., Magdaleno A., Silber A. M., Piantanida I., Bajic M., Glavaš-Obrovac L., Bioorganic & Medicinal Chemistry 17 (2009) 2544–2554.
  • [22]. 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.
  • [23]. Parai M.K., Panda G., Chaturvedi V., Manjub Y.K., Sinhab S., Bioorganic & Medicinal Chemistry Letters, 18 (2008) 289–292.
  • [24]. Singh S., Athar F., Maurya M.R., Azam A., European Journal of Medicinal Chemistry, 41 (2006) 592–598.
  • [25]. Sharma S., Athar F., Maurya M.R., Azam A., European Journal of Medicinal Chemistry, 40 (2005) 1414–1419.
  • [26]. 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.
  • [27]. Koparır M., Cansız A., and Cetin A., Thiophene-2,5-dicarboxylic Acid Bis-aryl(alkyl) Amides Heteroatom Chemistry (2005) 16-6.
  • [28]. Offing O.E., Martelli S. Antibacterial Activity of Metal Complexes of Benzil and Benzoin Thiosemicarbazones, IL Farmaco., 49 (1994) 513-518.
  • [29]. 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.
  • [30]. 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.
  • [31]. Clinical Laboratory Standarts Institute (CLSI) M100-S23; Vol. 33 No.1, january 2013.
  • [32]. 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.
  • [33]. 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.
  • [34]. Mohamed G. G., Omar M. M., Hindy A. M. M., Spectrochimica Acta Part A, 62 (2005) 1140–1150.
  • [35]. 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).
  • [36]. 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).
  • [37]. 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).
  • [38]. 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.

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

Year 2018, Volume: 39 Issue: 2, 357 - 365, 29.06.2018

Pelin Koparır , Akif Evren Parlak

https://doi.org/10.17776/csj.412145
Cited By: 1

Abstract

Thiophene-derived compounds are of
interest in chemistry, biology and pharmacology because of their various
pharmacological activities This study aims to investigate the antitumor and
antibacterial activity of
thiophene-2,5-dicarboxylic acid bis-aryl (alkyl) amide compounds. In this study, the properties of
antibacterial and 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 antitumor activity. In
addition, it has also been found that some compounds have an effective
antibacterial activity

Keywords

Thiophene-derived compounds antibacterial activity antimicrobial activities antitumor activity cancer

References

  • [1]. Kandepu N.M., Mannich bases of chalcones and cyclohexanones as candidate cytotoxic agents, Ottawa: University of Saskatchewan,Thesis(Phd) (1999).
  • [2]. Palaska E., Antikanser ilaçlar, 2nd ed. Ankara: Hacettepe Üniversitesi Yayınları, (2004).
  • [3]. Durackova Z, Mendiola M.A., Sevilla M.T., Valent A., Bioelect. and Bioener., 48 (1999) 109-116.
  • [4]. Xia Y., Qu F., Wu Q. and Peng L., Synthesis of bitriazolyl compounds via huisgen reactions, Heterocycles, 65 (2005) 345-352.
  • [5]. Holla B.S., Poojary N., Rao B.S. and Shivananda M.K., New bis-amino mercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents, European Journal of Chemistry, 10 (2002) 1-7.
  • [6]. Molvi K.I., Mansuri M., Sudarsanam V., Patel M.M., Andrabi S.M.A. and Haque N., Synthesis anty-inflammatory, analgesic, and antioxidant activities of some tetrasubstitued thiophenes, Journal of Enzyme Inhibition and Medicinal Chemistry, 23 (2008) 829-838.
  • [7]. 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.
  • [8]. 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-tert-butyl-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.
  • [9]. 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.
  • [10]. 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.
  • [11]. 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.
  • [12]. 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.
  • [13]. Campaigne E. In Comprehensive Heterocyclic Chemistry; Katritzky A.R., Rees C.W., Eds.; Pergamon Press: Oxford, (1984) Vol. 2, pp 863–934.
  • [14]. 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.
  • [15]. 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.
  • [16]. 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.
  • [17]. 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.
  • [18]. 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.
  • [19]. Radwan M.A.A., Shehab M.A., El-Shenawy S. M., Monatsh Chem. 140 (2009) 445–450.
  • [20]. Jiao J., Fang H., Wang X., Guan P., Yuan Y., Xu W., European Journal of Medicinal Chemistry, 44 (2009) 4470–4476.
  • [21]. Stolic I., Miškovic K., Magdaleno A., Silber A. M., Piantanida I., Bajic M., Glavaš-Obrovac L., Bioorganic & Medicinal Chemistry 17 (2009) 2544–2554.
  • [22]. 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.
  • [23]. Parai M.K., Panda G., Chaturvedi V., Manjub Y.K., Sinhab S., Bioorganic & Medicinal Chemistry Letters, 18 (2008) 289–292.
  • [24]. Singh S., Athar F., Maurya M.R., Azam A., European Journal of Medicinal Chemistry, 41 (2006) 592–598.
  • [25]. Sharma S., Athar F., Maurya M.R., Azam A., European Journal of Medicinal Chemistry, 40 (2005) 1414–1419.
  • [26]. 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.
  • [27]. Koparır M., Cansız A., and Cetin A., Thiophene-2,5-dicarboxylic Acid Bis-aryl(alkyl) Amides Heteroatom Chemistry (2005) 16-6.
  • [28]. Offing O.E., Martelli S. Antibacterial Activity of Metal Complexes of Benzil and Benzoin Thiosemicarbazones, IL Farmaco., 49 (1994) 513-518.
  • [29]. 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.
  • [30]. 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.
  • [31]. Clinical Laboratory Standarts Institute (CLSI) M100-S23; Vol. 33 No.1, january 2013.
  • [32]. 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.
  • [33]. 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.
  • [34]. Mohamed G. G., Omar M. M., Hindy A. M. M., Spectrochimica Acta Part A, 62 (2005) 1140–1150.
  • [35]. 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).
  • [36]. 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).
  • [37]. 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).
  • [38]. 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.
There are 38 citations in total.

Details

Primary Language English
Journal Section Natural Sciences
Authors

Pelin Koparır

Akif Evren Parlak

Publication Date June 29, 2018
Submission Date April 3, 2018
Acceptance Date May 22, 2018
Published in Issue Year 2018Volume: 39 Issue: 2

Cite

APA Koparır, P., & Parlak, A. E. (2018). Investigation of Antitumor and Antibacterial Properties of Some New Thiophene-2,5-Dicarboxylic Acid bis-aryl (alkyl) amide Compounds. Cumhuriyet Science Journal, 39(2), 357-365. https://doi.org/10.17776/csj.412145

Cited By

Synthesis, X-ray structure, antimicrobial activity, DFT and molecular docking studies of N-(thiophen-2-ylmethyl)thiophene-2-carboxamide
Acta Crystallographica Section C Structural Chemistry
https://doi.org/10.1107/S2053229622006283