Araştırma Makalesi
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İsoindolsübstitüe-kalkon Türevlerine İyot Katalizli Tiyofenol Katılması

Yıl 2020, Cilt: 7 Sayı: 1, 161 - 169, 28.06.2020
https://doi.org/10.35193/bseufbd.721691

Öz

Kalkon ve isoindol türevleri önemli biyolojik aktivitelere sahip bileşiklerdir. Bu iki birimi aynı yapıda taşıyan hibrit moleküllerinde biyolojik aktivite gösterdikleri bilinmektedir. Ayrıca β-merkaptanlar bazı biyoaktif bileşiklerin sentezi için başlangıç materyali olarak kullanılmaktadırlar. Bu çalışmada, isoindolsübstitüe-kalkon türevlerine (3a-j) moleküler iyot katalizörlüğünde tiyofenol katılarak yeni β-merkapto karbonil bileşikleri, ((3aR,4S,7R,7aS)-2-(4-(3-(feniltiyo)-3-(aril)propanol)fenil)-3a,4,7,7a-tetrahidro-1H-4,7-metanisoindol-1,3(2H)-dion) (5a-j) yüksek verimler ile elde edildi. Elde edilen yeni bileşiklerin yapıları 1H-NMR, 13C-NMR, FT-IR ve Elementel Analiz spektroskopik yöntemleri kullanılarak aydınlatıldı.

Destekleyen Kurum

Gaziosmanpaşa Üniversitesi BAP Koordinatörlüğü ve TÜBİTAK tarafından desteklenmiştir.

Proje Numarası

GOÜ BAP (Proje No: 2015/117) ve TÜBİTAK (Proje No: 111T990)

Teşekkür

Gaziosmanpaşa Üniversitesi Bilimsel Araştırma Projeleri Koordinatörlüğü (Proje No: 2015/117) ve TÜBİTAK (Proje No: 111T990) tarafından desteklenmiştir.

Kaynakça

  • Rida, S. M., Labouta, I. M., Salama, H. M., Ghany, Y. S., El-Ghazzaui, E., Kader, O. (1986). Syntheses and in vitro antimicrobial evaluation of some benzimidazol-2-ylmethyl-thioureas, enzimidazol 2-ylacetyl thiosemicarbazides and products of their condensation with monochloroacetic acid. Pharmazie, 41, 475-478.
  • Bhat, A. R., Singh, D. (1988). Synthesis and biological activities of 4-thiazolidinones and dihydro-3-(2H)-thiophenones. Indian Journal of Pharmaceutical Sciences, 50, 169-171.
  • Pandeya, D., Nair, K. B. (1993). Bridged bis(4-thiazolidinones) and related compounds with antibacterial activity. Pharmazie, 48, 414-417.
  • Franchini, C., Muraglia, M., Corbo, F., Florio, M. A., Di Mola, A., Rosato, A., Matucci, R., Nesi, M., Van-Bambeke, F., Vitali, C. (2009). Synthesis and biological evaluation of 2-mercapto-1,3-benzothiazole derivatives with potential antimicrobial activity. Archiv der Pharmazie, 342, 605-613.
  • Cesur, N., Cesur, Z., Ergenc, N., Uzun, M., Kiraz, M., Kasimoglu, O., Kaya, D. (1994). Synthesis and antifungal activity of some 2-aryl-3-substituted 4-thiazolidinones. Archiv der Pharmazie, 327, 271-272.
  • Capan, G., Ulusoy, N., Ergenc, N., Kiraz, M. (1999). New 6-phenylimidazo[2,1-b]thiazole derivatives: synthesis and antifungal activity. Monatshefte für Chemie, 130, 1399-1407.
  • Bhatt, J. J., Shah, B. R., Shah, H. P., Trivedi, P. B., Undavia, N. K., Desai, N. C. (1994). Synthesis of anti-HIV, anticancer and antitubercular 4-oxo-thiazolidines, 2-imino-4-oxo-thiazolidines and their 5-arylidine derivatives. Indian Journal of Chemistry, 33B, 189-192.
  • Tandon, K.V., Chhor, R. B., Singh, R. V., Rai, S., Yadav, D. B. (2004). Design, synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antifungal and anticancer agents. Bioorganic & Medicinal Chemistry Letters, 14, 1079-1083.
  • Sheela, C. G., Augusti K. T. (1992). Antidiabetic effects of S-allyl cysteine sulphoxide isolated from garlic Allium sativum Linn. Indian Journal of Experimental Biology, 30, 523-526.
  • Mahmoodi, M., Aliabadi, A., Emami, S., Safavi, M., Rajabalian, S., Mohagheghi, M. A., Khoshzaban, A., Kermani, A. S., Lamei, N., Shafiee, A., Foroumadi, A. (2010). Synthesis and in-vitro Cytotoxicity of Polyfunctionalized 4-(2-Arylthiazol-4-yl)-4H-chromenes. Archiv der Pharmazie, 343, 411-416.
  • Katristzky, A. R., Button, M. A. (2001). Efficient syntheses of thiochromans via cationic cycloadditions. Journal of Organic Chemistry, 66, 5595-5600.
  • Ram, V. J., Agarwal, N., Saxena, A. S., Farhanullah, S., Sharon, A., Maulik, P. R. (2002). Carbanion induced synthesis of annulated unsymmetrical biaryls through ring transformation of 2H-pyran-2-one. Journal of the Chemical Society, Perkin Transactions 1, 1, 1426-1437.
  • Van-Vliet, L. A., Rodenhuis, N., Dijkstra, D., Wikström, H., Pugsley, T. A., Serpa, K. A., Meltzer, L. T., Heffner, T. G., Wise, L. D., Lajiness, M. E., Huff, R. M., Svensson, K., Sundell, S., Lundmark, M. (2000). Synthesis and pharmacological evaluation of thiopyran analogues of the dopamine D3 receptor-selective agonist (4aR,10bR)-(+)-trans-3,4,4a,10b-Tetrahydro-4-n-propyl-2H,5H-[1]benzopyrano [4,3-b]-1,4-oxazin-9-ol (PD 128907). Journal of Medicinal Chemistry, 43, 2871-2882.
  • Khatik, G. L., Kumar, R., Chakraborti, A. K. (2007). Magnesium Perchlorate as a New and Highly Efficient Catalyst for the Synthesis of 2,3-Dihydro-1,5-benzothiazepines. Synthesis, 4, 541-546.
  • Sharma, G., Kumar, R., Chakraborti, A. K. (2008). On water’ synthesis of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines catalysed by sodium dodecyl sulfate (SDS). Tetrahedron Letter, 49, 4269-4271.
  • Zielinska-Blajet, M., Kowalczyk, R., Skarzewski, J. (2005). Ring-closure reactions through intramolecularsubstitution of thiophenoxide by oxygen and nitrogen nucleophiles: simple stereospecific synthesis of 4,5-dihydroisoxazoles and 4,5-dihydropyrazoles. Tetrahedron, 61, 5235-5240.
  • Garg, S. K., Kumar, R., Chakraborti, A. K. (2005). Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for Michael addition of mercaptans to a,b-unsaturated carbonyl compounds. Tetrahedron Letter, 46, 1721-1724.
  • Cheng, S., Cromer, D. D. (2002). An alumina-catalyzed Michael addition of mercaptans to N-anilino-maleimides and its application to the solution-phase parallel synthesis of libraries. Tetrahedron Letters, 43, 1179-1181.
  • Lee, P. H., Ahn, H., Lee, K., Sung, S. Y., Kim, S. (2001). Studies on the reactions of -enones with allyl indium reagent; effects of TMSCI as promoter on regioselectivity. Tetrahedron Letters, 42, 37-39.
  • Jovanovic, B. Z., Misic, V. M., Marinkovic, A. D., Csanadi, J. (1999). 13C NMR spectra of pyridine chalcone analogs. Journal of Molecular Structure, 482-483, 371-374.
  • Ram V.J., Saxena A.S., Srivastava S., Chandra S. (2000). Oxygenated chalcones and bischalcones as potential antimalarial agents. Bioorganic & Medicinal Chemistry Letters, 10, 2159-2161.
  • Rolf, V.H., Wellinga, K. ve Grosscurt, C. (1978). 1-Phenylcarbamoyl-2-pyrazolines: a new class of insecticides. 2. Synthesis and insecticidal properties of 3,5-diphenyl-1-phenylcarbamoyl-2-pyrazolines. Journal of Agricultural and Food Chemistry, 26, 915-918.
  • Ankhiwala, M.D. (1990). Studies on flavonoids, part II: Synthesis and antimicrobial activity of 8-bromo-7-n-butoxy-6-nitroflavones, -flavonols, and flavanones. Journal of Indian Chemical Society, 67, 913-915.
  • Wu J.-H., Wang X.-H., Yi Y.-H. ve Lee K.-H. (2003). Anti-AIDS agents 54. A potent anti-HIV chalcone and flavonoids from genus Desmos. Bioorganic & Medicinal Chemistry Letters, 13, 1813-1815.
  • Kumar S.K., Erin H., Catherina P., Gurulingappa, H., Davidson, N. E. ve Khan, S. R. (2003). Design, synthesis, and evaluation of novel boronic-chalcone derivatives as antitumor agents. Journal of Medicinal Chemistry, 46, 2813-2815.
  • Buolamwını, J. K., Addo, J., Kamath, S., Patıl, S., Mason, D., Ores, M. (2005). Small molecule antagonists of the MDM2 oncoprotein as anticancer agents. Current Cancer Drug Targets, 5, 57-68.
  • Herencia, F., Ferrandiz, M. L., Ubeda, A., Dominguez, J. N., Charris, J. E., Lobo, G. M. ve Alcarez, M. J. (1998). Synthesis and anti-imflammatory activity of chalcone derivatives, Bioorganic & Medicinal Chemistry, 8, 1169-1174.
  • Satyanarayana, M., Tiwari, P., Tripathi, B. K., Srivastava, A. K., Pratap, R. (2004). Synthesis and antihyperglycemic activity of chalcone based aryloxypropanolamines. Bioorganic & Medicinal Chemistry, 12, 883-889.
  • Fayed, T. A., Awad, M. K. (2004). Dual emission of chalcone-analogue dyes emitting in the red region. Chemical Physics, 303, 317-326.
  • Gürdere, M. B., Özbek, O., Ceylan, M. (2016). Aluminum chloride–catalyzed C-alkylation of pyrrole and indole with chalcone and bis-chalcone derivatives. Synthetic Communications, 46, 322-331.
  • Ozbek, O., Usta, N. C., Gürdere, M B., Aslan, O. A., Budak, Y., Ceylan, M. (2017). Synthesis and antibacterial screening of novel 2-(4-(aryl) thiazol-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-ethanoisoindole-1,3(2H)-dione derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 192, 1153-1157.
  • Gilchrist, T. L. (1987). Heterocyclic Chemistry, 2. baskı, Harlow, Essex, England : Longman Scientific & Technical, Wiley, New York.
  • Sun, L., Tran, N., Liang C., Hubbard, S., Tang F., Lipson K., Schreck, R., Zhou Y., McMahon, G., Tang, C. (2000). Identification of substituted 3-[(4,5,6, 7-tetrahydro-1H-indol-2-yl)methylene]-1,3-dihydroindol-2-ones as growth factor receptor inhibitors for VEGF-R2 (Flk-1/KDR), FGF-R1, and PDGF-Rbeta tyrosine kinases. Journal of Medicinal Chemistry, 43(14), 2655-2663.
  • Kocyigit, U. M., Budak, Y., Gürdere, M. B., Tekin, Ş., Kul Köprülü, T., Ertürk, F., Özcan, K., Gülçin, I., Ceylan, M. (2017). Synthesis, characterization, anticancer, antimicrobial and carbonicanhydrase inhibition profiles of novel (3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl) acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives. Bioorganic Chemistry, 70, 118–125.
  • Budak, Y., Kocyigit, U. M., Gürdere, M. B., Özcan, K., Taslimi, P., Gülçin, İ., Ceylan, M. (2017). Synthesis and investigation of antibacterial activities and carbonic anhydrase and acetyl cholinesterase inhibition profiles of novel 4,5-dihydropyrazol and pyrazolyl-thiazole derivatives containing methanoisoindol-1,3-dion unit. Synthetic Communications, 47 (24), 2313–2323.
  • Ceylan, M., Gürdere, M. B., Karaman, İ., Gezegen, H. (2011). The synthesis and screening of the antimicrobial activity of some novel 3-(furan-2-yl)-1-(aryl)-3-(phenylthio)propan-1-one derivatives. Medicinal Chemistry Research, 20, 109-115.

Iodine-Catalyzed Addition of Thiophenol to Isoindolsubstitue Chalcones

Yıl 2020, Cilt: 7 Sayı: 1, 161 - 169, 28.06.2020
https://doi.org/10.35193/bseufbd.721691

Öz

Chalcone and isoindol derivatives possess significant biological activities. Also, ıt is known that hybrid molecules carrying these two units in the same structure show biological activity. In addition, -mercaptans are used as the starting material for the synthesis of some bioactive compounds. In this work, new β-mercapto carbonyl compounds (5a-j), (3aR,4S,7R,7aS)-2-(4-(3-(phenylthio)-3-(aryl)pyridyl)aminocarbonyl-propanol)phenyl)-3a,4,7,7a-tetrahydro-1H-7-methanoisoindole-1,3(2H)-dione), were obtained by molecular iodine-catalyzed addition of thiophenol to isoindol substituted chalcone derivatives (3a-j) in high yields. The structures of the obtained new compounds were clarified by 1H-NMR, 13C-NMR, FT-IR and Elemental Analysis spectroscopic methods.

Proje Numarası

GOÜ BAP (Proje No: 2015/117) ve TÜBİTAK (Proje No: 111T990)

Kaynakça

  • Rida, S. M., Labouta, I. M., Salama, H. M., Ghany, Y. S., El-Ghazzaui, E., Kader, O. (1986). Syntheses and in vitro antimicrobial evaluation of some benzimidazol-2-ylmethyl-thioureas, enzimidazol 2-ylacetyl thiosemicarbazides and products of their condensation with monochloroacetic acid. Pharmazie, 41, 475-478.
  • Bhat, A. R., Singh, D. (1988). Synthesis and biological activities of 4-thiazolidinones and dihydro-3-(2H)-thiophenones. Indian Journal of Pharmaceutical Sciences, 50, 169-171.
  • Pandeya, D., Nair, K. B. (1993). Bridged bis(4-thiazolidinones) and related compounds with antibacterial activity. Pharmazie, 48, 414-417.
  • Franchini, C., Muraglia, M., Corbo, F., Florio, M. A., Di Mola, A., Rosato, A., Matucci, R., Nesi, M., Van-Bambeke, F., Vitali, C. (2009). Synthesis and biological evaluation of 2-mercapto-1,3-benzothiazole derivatives with potential antimicrobial activity. Archiv der Pharmazie, 342, 605-613.
  • Cesur, N., Cesur, Z., Ergenc, N., Uzun, M., Kiraz, M., Kasimoglu, O., Kaya, D. (1994). Synthesis and antifungal activity of some 2-aryl-3-substituted 4-thiazolidinones. Archiv der Pharmazie, 327, 271-272.
  • Capan, G., Ulusoy, N., Ergenc, N., Kiraz, M. (1999). New 6-phenylimidazo[2,1-b]thiazole derivatives: synthesis and antifungal activity. Monatshefte für Chemie, 130, 1399-1407.
  • Bhatt, J. J., Shah, B. R., Shah, H. P., Trivedi, P. B., Undavia, N. K., Desai, N. C. (1994). Synthesis of anti-HIV, anticancer and antitubercular 4-oxo-thiazolidines, 2-imino-4-oxo-thiazolidines and their 5-arylidine derivatives. Indian Journal of Chemistry, 33B, 189-192.
  • Tandon, K.V., Chhor, R. B., Singh, R. V., Rai, S., Yadav, D. B. (2004). Design, synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antifungal and anticancer agents. Bioorganic & Medicinal Chemistry Letters, 14, 1079-1083.
  • Sheela, C. G., Augusti K. T. (1992). Antidiabetic effects of S-allyl cysteine sulphoxide isolated from garlic Allium sativum Linn. Indian Journal of Experimental Biology, 30, 523-526.
  • Mahmoodi, M., Aliabadi, A., Emami, S., Safavi, M., Rajabalian, S., Mohagheghi, M. A., Khoshzaban, A., Kermani, A. S., Lamei, N., Shafiee, A., Foroumadi, A. (2010). Synthesis and in-vitro Cytotoxicity of Polyfunctionalized 4-(2-Arylthiazol-4-yl)-4H-chromenes. Archiv der Pharmazie, 343, 411-416.
  • Katristzky, A. R., Button, M. A. (2001). Efficient syntheses of thiochromans via cationic cycloadditions. Journal of Organic Chemistry, 66, 5595-5600.
  • Ram, V. J., Agarwal, N., Saxena, A. S., Farhanullah, S., Sharon, A., Maulik, P. R. (2002). Carbanion induced synthesis of annulated unsymmetrical biaryls through ring transformation of 2H-pyran-2-one. Journal of the Chemical Society, Perkin Transactions 1, 1, 1426-1437.
  • Van-Vliet, L. A., Rodenhuis, N., Dijkstra, D., Wikström, H., Pugsley, T. A., Serpa, K. A., Meltzer, L. T., Heffner, T. G., Wise, L. D., Lajiness, M. E., Huff, R. M., Svensson, K., Sundell, S., Lundmark, M. (2000). Synthesis and pharmacological evaluation of thiopyran analogues of the dopamine D3 receptor-selective agonist (4aR,10bR)-(+)-trans-3,4,4a,10b-Tetrahydro-4-n-propyl-2H,5H-[1]benzopyrano [4,3-b]-1,4-oxazin-9-ol (PD 128907). Journal of Medicinal Chemistry, 43, 2871-2882.
  • Khatik, G. L., Kumar, R., Chakraborti, A. K. (2007). Magnesium Perchlorate as a New and Highly Efficient Catalyst for the Synthesis of 2,3-Dihydro-1,5-benzothiazepines. Synthesis, 4, 541-546.
  • Sharma, G., Kumar, R., Chakraborti, A. K. (2008). On water’ synthesis of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines catalysed by sodium dodecyl sulfate (SDS). Tetrahedron Letter, 49, 4269-4271.
  • Zielinska-Blajet, M., Kowalczyk, R., Skarzewski, J. (2005). Ring-closure reactions through intramolecularsubstitution of thiophenoxide by oxygen and nitrogen nucleophiles: simple stereospecific synthesis of 4,5-dihydroisoxazoles and 4,5-dihydropyrazoles. Tetrahedron, 61, 5235-5240.
  • Garg, S. K., Kumar, R., Chakraborti, A. K. (2005). Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for Michael addition of mercaptans to a,b-unsaturated carbonyl compounds. Tetrahedron Letter, 46, 1721-1724.
  • Cheng, S., Cromer, D. D. (2002). An alumina-catalyzed Michael addition of mercaptans to N-anilino-maleimides and its application to the solution-phase parallel synthesis of libraries. Tetrahedron Letters, 43, 1179-1181.
  • Lee, P. H., Ahn, H., Lee, K., Sung, S. Y., Kim, S. (2001). Studies on the reactions of -enones with allyl indium reagent; effects of TMSCI as promoter on regioselectivity. Tetrahedron Letters, 42, 37-39.
  • Jovanovic, B. Z., Misic, V. M., Marinkovic, A. D., Csanadi, J. (1999). 13C NMR spectra of pyridine chalcone analogs. Journal of Molecular Structure, 482-483, 371-374.
  • Ram V.J., Saxena A.S., Srivastava S., Chandra S. (2000). Oxygenated chalcones and bischalcones as potential antimalarial agents. Bioorganic & Medicinal Chemistry Letters, 10, 2159-2161.
  • Rolf, V.H., Wellinga, K. ve Grosscurt, C. (1978). 1-Phenylcarbamoyl-2-pyrazolines: a new class of insecticides. 2. Synthesis and insecticidal properties of 3,5-diphenyl-1-phenylcarbamoyl-2-pyrazolines. Journal of Agricultural and Food Chemistry, 26, 915-918.
  • Ankhiwala, M.D. (1990). Studies on flavonoids, part II: Synthesis and antimicrobial activity of 8-bromo-7-n-butoxy-6-nitroflavones, -flavonols, and flavanones. Journal of Indian Chemical Society, 67, 913-915.
  • Wu J.-H., Wang X.-H., Yi Y.-H. ve Lee K.-H. (2003). Anti-AIDS agents 54. A potent anti-HIV chalcone and flavonoids from genus Desmos. Bioorganic & Medicinal Chemistry Letters, 13, 1813-1815.
  • Kumar S.K., Erin H., Catherina P., Gurulingappa, H., Davidson, N. E. ve Khan, S. R. (2003). Design, synthesis, and evaluation of novel boronic-chalcone derivatives as antitumor agents. Journal of Medicinal Chemistry, 46, 2813-2815.
  • Buolamwını, J. K., Addo, J., Kamath, S., Patıl, S., Mason, D., Ores, M. (2005). Small molecule antagonists of the MDM2 oncoprotein as anticancer agents. Current Cancer Drug Targets, 5, 57-68.
  • Herencia, F., Ferrandiz, M. L., Ubeda, A., Dominguez, J. N., Charris, J. E., Lobo, G. M. ve Alcarez, M. J. (1998). Synthesis and anti-imflammatory activity of chalcone derivatives, Bioorganic & Medicinal Chemistry, 8, 1169-1174.
  • Satyanarayana, M., Tiwari, P., Tripathi, B. K., Srivastava, A. K., Pratap, R. (2004). Synthesis and antihyperglycemic activity of chalcone based aryloxypropanolamines. Bioorganic & Medicinal Chemistry, 12, 883-889.
  • Fayed, T. A., Awad, M. K. (2004). Dual emission of chalcone-analogue dyes emitting in the red region. Chemical Physics, 303, 317-326.
  • Gürdere, M. B., Özbek, O., Ceylan, M. (2016). Aluminum chloride–catalyzed C-alkylation of pyrrole and indole with chalcone and bis-chalcone derivatives. Synthetic Communications, 46, 322-331.
  • Ozbek, O., Usta, N. C., Gürdere, M B., Aslan, O. A., Budak, Y., Ceylan, M. (2017). Synthesis and antibacterial screening of novel 2-(4-(aryl) thiazol-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-ethanoisoindole-1,3(2H)-dione derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 192, 1153-1157.
  • Gilchrist, T. L. (1987). Heterocyclic Chemistry, 2. baskı, Harlow, Essex, England : Longman Scientific & Technical, Wiley, New York.
  • Sun, L., Tran, N., Liang C., Hubbard, S., Tang F., Lipson K., Schreck, R., Zhou Y., McMahon, G., Tang, C. (2000). Identification of substituted 3-[(4,5,6, 7-tetrahydro-1H-indol-2-yl)methylene]-1,3-dihydroindol-2-ones as growth factor receptor inhibitors for VEGF-R2 (Flk-1/KDR), FGF-R1, and PDGF-Rbeta tyrosine kinases. Journal of Medicinal Chemistry, 43(14), 2655-2663.
  • Kocyigit, U. M., Budak, Y., Gürdere, M. B., Tekin, Ş., Kul Köprülü, T., Ertürk, F., Özcan, K., Gülçin, I., Ceylan, M. (2017). Synthesis, characterization, anticancer, antimicrobial and carbonicanhydrase inhibition profiles of novel (3aR,4S,7R,7aS)-2-(4-((E)-3-(3-aryl) acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives. Bioorganic Chemistry, 70, 118–125.
  • Budak, Y., Kocyigit, U. M., Gürdere, M. B., Özcan, K., Taslimi, P., Gülçin, İ., Ceylan, M. (2017). Synthesis and investigation of antibacterial activities and carbonic anhydrase and acetyl cholinesterase inhibition profiles of novel 4,5-dihydropyrazol and pyrazolyl-thiazole derivatives containing methanoisoindol-1,3-dion unit. Synthetic Communications, 47 (24), 2313–2323.
  • Ceylan, M., Gürdere, M. B., Karaman, İ., Gezegen, H. (2011). The synthesis and screening of the antimicrobial activity of some novel 3-(furan-2-yl)-1-(aryl)-3-(phenylthio)propan-1-one derivatives. Medicinal Chemistry Research, 20, 109-115.
Toplam 36 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Yakup Budak 0000-0001-7108-5548

Ahmet Doğan Çakır 0000-0002-2233-5069

Oğuz Özbek 0000-0001-5185-9681

Meliha Burcu Gürdere 0000-0003-4285-5528

Mustafa Ceylan 0000-0002-9184-4385

Proje Numarası GOÜ BAP (Proje No: 2015/117) ve TÜBİTAK (Proje No: 111T990)
Yayımlanma Tarihi 28 Haziran 2020
Gönderilme Tarihi 17 Nisan 2020
Kabul Tarihi 11 Mayıs 2020
Yayımlandığı Sayı Yıl 2020 Cilt: 7 Sayı: 1

Kaynak Göster

APA Budak, Y., Çakır, A. D., Özbek, O., Gürdere, M. B., vd. (2020). İsoindolsübstitüe-kalkon Türevlerine İyot Katalizli Tiyofenol Katılması. Bilecik Şeyh Edebali Üniversitesi Fen Bilimleri Dergisi, 7(1), 161-169. https://doi.org/10.35193/bseufbd.721691