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Bazı Yeni İsatin Türevlerinin Sentezi ve Yapılarının Aydınlatılması

Yıl 2019, , 67 - 70, 01.03.2019
https://doi.org/10.19113/sdufenbed.432261

Öz

Heterosiklik
halka sistemlerinde önemli bir rolü olan indol, önemli biyolojik etkiler
göstermektedir. Isatin (1H-indol-2,3-dion),
biyolojik özellikleri nedeniyle çok sayıda sentezde bir reaktif olarak
kullanılmıştır. Ayrıca, isatin, indol ve kinolin türevlerinin eldesinde ve
reaksiyonlarında kullanılan, bir heterosiklik halka sistemidir.  Bu çalışmada, iki yeni Schiff bazı
bileşikleri, 2-aminoantrasen ile isatin/5-nitro-isatinin reaksiyonuyla
sentezlendi. Sentezlenen bileşiklerin yapısı, IR, 1H-NMR, 13C-NMR
spektrumları ve Kütle analizi kullanılarak spektroskopik yöntemlerle
aydınlatıldı.

Kaynakça

  • [1] Pandeya, S.N., Smitha, S., Jyoti, M., Sridhar, S.K. 2005. Biological Activities of Isatin and Its Derivatives. Acta Pharm., 55(1),27-46.
  • [2] Vine, K.L., Matesic, L., Locke, J.M., Ranson, M., Skropeta, D. 2009. Cytotoxic and Anticancer Activities of Isatin and Its Derivatives: A Comprehensive Review from 2000-2008. Anticancer Agents in Med.Chem., 9(4), 397-414. DOI : 10.2174/1871520610909040397
  • [3] Phogat, P., Singh, P. 2015. A Mini Review on Central Nervous System Potential of Isatin Derivatives. Cent Nerv Syst Agents Med Chem.,15(1),28-31.
  • [4] Rawat P, Verma SM. 2016. Design and Synthesis of Chroman Derivatives with Dual Anti-Breast Cancer and Antiepileptic Activities. Drug Design, Development and Therapy, 10,2779-2788.
  • [5] Kahveci. B. 2005. Synthesis of 4-Amino-4,5-Dihydro-1H-1,2,4-Triazole-5-Ones and Their Isatin-3-Imine Derivatives. Molecules, 10, 376-382.
  • [6] Sridhar, S.K., Saravanan, M., Ramesh, A. 2001. Synthesis and Antibacterial Screening of Hydrazones, Schiff and Mannich Bases of Isatin Derivatives. Eur J Med Chem., 36(7-8),615-625.
  • [7] Shuttleworth, S.J., Nasturica, D., Gervais, C., Siddiqui, M.A., Rando, R.F., Lee, N. 2000. Parallel Synthesis of Isatin-Based Serine Protease İnhibitors. Bioorg Med Chem Lett., 20,10(22),2501-4.
  • [8] Hamaue, N., Minami, M., Hirafuji, M., Terado, M., Machida, M., Yamazaki, N., Yoshioka, M., Ogata, A., Tashiro, K. 1999. Isatin, an Endogenous MAO Inhibitor, as a New Biological Modulator. CNS Drug Reviews, 5(4), 331-346.
  • [9] Azizian,J., Mohammadi, M.K., Firuzi, O., Razzaghi-asl,N., Miri,R. 2012. Synthesis, Biological Activity and Docking Study of Some New Isatin Schiff Base Derivatives. Med. Chem Res., 21,3730-3740.
  • [10] El-Ossaily, Y. A., Zaki, R. M., Metwally, S. A. 2014. Investigation and Synthesis of Some Novel Spiro Heterocycles Related to Indoline Moiety. J. Sci. Res., 6(2), 293-307.
  • [11] Chinnasamy, R.P., Sundararajan, R., Govindaraj, S. 2010. Synthesis, Characterization, and Analgesic Activity of Novel Schiff Base of Isatin Derivatives. Journal of Advanced Pharmaceutical Technology & Research.,1(3),342-347. doi:10.4103/0110-5558.72428.
  • [12] Sharma, A., Rajyaguru, C., Upadhyay, J.M., Shah, M.K. 2013. Synthesis and Biological Activity of Some New Schiff Bases. Int. J. Chem. Sci.: 11(2), 2013, 981-988.
  • [13] More, P.G., Bhalvankar, R.B., Pattar, S.C. 2001. Synthesis and Biological Activities of Schiff Bases of Aminothiazoles. J. Indian Chem. Soc., 78, 474-475.
  • [14] El-Masry, A.H., Fahmy, H.H., Abdelwahed, S.H.A. 2000. Synthesis and Antimicrobial Activity of Some New Benzimidazole Derivatives. Molecules, 5, 1429-1438.
  • [15] Baseer, M.A., Jadhav, V.D., Phule, R.M., Archana, Y.V., Vibhute, Y.B. 2000. Synthesis and Antimicrobial Activity of Some New Schiff Base. Orient. J. Chem., 16, 553-556.
  • [16] Pandeya, S.N., Sriram, D., Nath, G., Clercq, De E. 1999. Synthesis and Antimicrobial Activity of Schiff and Mannich Bases of Isatin and its Derivatives with Pyrimidine. IL Farmaco, 54, 624-628.
  • [17] Singh, W.M., Dash, B.C. 1988. Synthesis of Some New Schiff Bases containing Thiazole and Oxazole Nuclei and their Fungicidal Activity. Pesticides, 22, 33-37.
  • [18] Hodnett, E.M., Dunn, W. J. Structure-Antitumor Activity Correlation of Some Schiff Bases. 1970. J. Med. Chem., 13, 768-770.
  • [19] Hoeffkes, H.; Buettner, R.; Moeller,H. Ger.Offen. DE 4,211,450,1992 (CA 119: 278349c)
  • [20] Lang G., Cotteret, J. Eur.Pat.Appl. EP 497, 697 1192. (CA 117;P178123q)
  • [21] Lang G., Cotteret, J. Eur.Pat.Appl. EP 502,783 1992. (CA 117;P257972u)
  • [22] Lang G., Cotteret, J. US 5190564 1993. (CA 117:P178123q)
  • [23] Lang G., Cotteret, J. US 5261926 1993. (IBM intellectual property network)
  • [24] Lang G., Cotteret, J. US 5279616 1994. (CA 117: P257972u)
  • [25] Lang G., Cotteret, J. US 5340366 1994. (CA 117:P257972u)
  • [26] Lang G., Cotteret, J. Eur.Pat.Appl. EP 502, 784 1995. (CA 118:P11497y)
  • [27] Moeller,H.; Hoeffkes, H. WO 9424988 1994. (CA 122:P38518a)
  • [28] Moeller,H.; Hoeffkes, H. WO 9424989 1994 (CA 122: P16832w)
  • [29] Moeller,H.; Hoeffkes, H. WO 9524886 1995 (IBM intellectual property network)
  • [30] Moeller,H.; Hoeffkes, H. EP 695162 1996 (CA 122:P38518a)
  • [31] Moeller,H.; Hoeffkes, H. EP 695163 1996. (CA 122:P16832w)
  • [32] Moeller,H.; Hoeffkes, H. US 5611817 1997. (CA 122:P16832w)
  • [33] Moeller,H.; Hoeffkes, H. US 5616150 1997 (CA 122:P38518a)
  • [34] Moeller,H.; Hoeffkes, H. US 5743919 1998. (CA 123:P265783x)
  • [35] Moeller,H.; Hoeffkes, H. WO 9847472 1998. (CA 129: P347133y)
  • [36] Rosenbaum, G; Cotteret, J. US 4750908 1998. (CA 107:P120859m)
  • [37] Anderson, JS; Schultz, TM. US 4921503 1990. (CA 113:P217781s)
  • [38] Mueller, W. Swiss 580,673 1976. (CA 86:P6388e)
  • [39] Merlo,F; Bornengo, G Eur.Pat.Appl. 3,565 1979. (CA 92: P7839p)
  • [40] Upadhyay, RK.; Agarwal, N.; Mishra,G. Synthesis of Aryl-2-(Alpha-Hydroxy)Phenylketo-4-Thiazolidinones as Dyes. 1995. J. Indian Chem Soc., 72, 849.
  • [41] Layer, R.W. The Chemistry of Imines. 1963. Chem. Rev.,63,489-510.
  • [42] Silverstein, R.M. Spectrometric Identification of Organic Compounds, John Wiley&Sons, New York, 1998.
  • [43] Pretsch, E., Clerk, T., Seibl, J., Simon, W. Tables of Spectral Data For Structure Determination of Organic Compounds, Springer-Verlag, Berlin, 1983.

Synthesis of Some New Isatin Derivatives and Identification of Their Structures

Yıl 2019, , 67 - 70, 01.03.2019
https://doi.org/10.19113/sdufenbed.432261

Öz

Indole,
which has an important role in heterocyclic ring systems, exhibits significant
biological effects. Isatin (1H-indole-2,3-dione)
has been used as a reagent in a large number of synthesis due to its biological
properties. In addition, it is a heterocyclic ring system used for obtaining and
other reactions of indole and quinoline derivatives. In this study, two new
Schiff base compounds were synthesized by the reaction of 2-aminoantracene with
an isatin/5-nitro-isatin. The structure of the synthesized compounds, were
elucidated by spectroscopic methods using IR, 1H-NMR, 13C-NMR
spectra and Mass analysis.

Kaynakça

  • [1] Pandeya, S.N., Smitha, S., Jyoti, M., Sridhar, S.K. 2005. Biological Activities of Isatin and Its Derivatives. Acta Pharm., 55(1),27-46.
  • [2] Vine, K.L., Matesic, L., Locke, J.M., Ranson, M., Skropeta, D. 2009. Cytotoxic and Anticancer Activities of Isatin and Its Derivatives: A Comprehensive Review from 2000-2008. Anticancer Agents in Med.Chem., 9(4), 397-414. DOI : 10.2174/1871520610909040397
  • [3] Phogat, P., Singh, P. 2015. A Mini Review on Central Nervous System Potential of Isatin Derivatives. Cent Nerv Syst Agents Med Chem.,15(1),28-31.
  • [4] Rawat P, Verma SM. 2016. Design and Synthesis of Chroman Derivatives with Dual Anti-Breast Cancer and Antiepileptic Activities. Drug Design, Development and Therapy, 10,2779-2788.
  • [5] Kahveci. B. 2005. Synthesis of 4-Amino-4,5-Dihydro-1H-1,2,4-Triazole-5-Ones and Their Isatin-3-Imine Derivatives. Molecules, 10, 376-382.
  • [6] Sridhar, S.K., Saravanan, M., Ramesh, A. 2001. Synthesis and Antibacterial Screening of Hydrazones, Schiff and Mannich Bases of Isatin Derivatives. Eur J Med Chem., 36(7-8),615-625.
  • [7] Shuttleworth, S.J., Nasturica, D., Gervais, C., Siddiqui, M.A., Rando, R.F., Lee, N. 2000. Parallel Synthesis of Isatin-Based Serine Protease İnhibitors. Bioorg Med Chem Lett., 20,10(22),2501-4.
  • [8] Hamaue, N., Minami, M., Hirafuji, M., Terado, M., Machida, M., Yamazaki, N., Yoshioka, M., Ogata, A., Tashiro, K. 1999. Isatin, an Endogenous MAO Inhibitor, as a New Biological Modulator. CNS Drug Reviews, 5(4), 331-346.
  • [9] Azizian,J., Mohammadi, M.K., Firuzi, O., Razzaghi-asl,N., Miri,R. 2012. Synthesis, Biological Activity and Docking Study of Some New Isatin Schiff Base Derivatives. Med. Chem Res., 21,3730-3740.
  • [10] El-Ossaily, Y. A., Zaki, R. M., Metwally, S. A. 2014. Investigation and Synthesis of Some Novel Spiro Heterocycles Related to Indoline Moiety. J. Sci. Res., 6(2), 293-307.
  • [11] Chinnasamy, R.P., Sundararajan, R., Govindaraj, S. 2010. Synthesis, Characterization, and Analgesic Activity of Novel Schiff Base of Isatin Derivatives. Journal of Advanced Pharmaceutical Technology & Research.,1(3),342-347. doi:10.4103/0110-5558.72428.
  • [12] Sharma, A., Rajyaguru, C., Upadhyay, J.M., Shah, M.K. 2013. Synthesis and Biological Activity of Some New Schiff Bases. Int. J. Chem. Sci.: 11(2), 2013, 981-988.
  • [13] More, P.G., Bhalvankar, R.B., Pattar, S.C. 2001. Synthesis and Biological Activities of Schiff Bases of Aminothiazoles. J. Indian Chem. Soc., 78, 474-475.
  • [14] El-Masry, A.H., Fahmy, H.H., Abdelwahed, S.H.A. 2000. Synthesis and Antimicrobial Activity of Some New Benzimidazole Derivatives. Molecules, 5, 1429-1438.
  • [15] Baseer, M.A., Jadhav, V.D., Phule, R.M., Archana, Y.V., Vibhute, Y.B. 2000. Synthesis and Antimicrobial Activity of Some New Schiff Base. Orient. J. Chem., 16, 553-556.
  • [16] Pandeya, S.N., Sriram, D., Nath, G., Clercq, De E. 1999. Synthesis and Antimicrobial Activity of Schiff and Mannich Bases of Isatin and its Derivatives with Pyrimidine. IL Farmaco, 54, 624-628.
  • [17] Singh, W.M., Dash, B.C. 1988. Synthesis of Some New Schiff Bases containing Thiazole and Oxazole Nuclei and their Fungicidal Activity. Pesticides, 22, 33-37.
  • [18] Hodnett, E.M., Dunn, W. J. Structure-Antitumor Activity Correlation of Some Schiff Bases. 1970. J. Med. Chem., 13, 768-770.
  • [19] Hoeffkes, H.; Buettner, R.; Moeller,H. Ger.Offen. DE 4,211,450,1992 (CA 119: 278349c)
  • [20] Lang G., Cotteret, J. Eur.Pat.Appl. EP 497, 697 1192. (CA 117;P178123q)
  • [21] Lang G., Cotteret, J. Eur.Pat.Appl. EP 502,783 1992. (CA 117;P257972u)
  • [22] Lang G., Cotteret, J. US 5190564 1993. (CA 117:P178123q)
  • [23] Lang G., Cotteret, J. US 5261926 1993. (IBM intellectual property network)
  • [24] Lang G., Cotteret, J. US 5279616 1994. (CA 117: P257972u)
  • [25] Lang G., Cotteret, J. US 5340366 1994. (CA 117:P257972u)
  • [26] Lang G., Cotteret, J. Eur.Pat.Appl. EP 502, 784 1995. (CA 118:P11497y)
  • [27] Moeller,H.; Hoeffkes, H. WO 9424988 1994. (CA 122:P38518a)
  • [28] Moeller,H.; Hoeffkes, H. WO 9424989 1994 (CA 122: P16832w)
  • [29] Moeller,H.; Hoeffkes, H. WO 9524886 1995 (IBM intellectual property network)
  • [30] Moeller,H.; Hoeffkes, H. EP 695162 1996 (CA 122:P38518a)
  • [31] Moeller,H.; Hoeffkes, H. EP 695163 1996. (CA 122:P16832w)
  • [32] Moeller,H.; Hoeffkes, H. US 5611817 1997. (CA 122:P16832w)
  • [33] Moeller,H.; Hoeffkes, H. US 5616150 1997 (CA 122:P38518a)
  • [34] Moeller,H.; Hoeffkes, H. US 5743919 1998. (CA 123:P265783x)
  • [35] Moeller,H.; Hoeffkes, H. WO 9847472 1998. (CA 129: P347133y)
  • [36] Rosenbaum, G; Cotteret, J. US 4750908 1998. (CA 107:P120859m)
  • [37] Anderson, JS; Schultz, TM. US 4921503 1990. (CA 113:P217781s)
  • [38] Mueller, W. Swiss 580,673 1976. (CA 86:P6388e)
  • [39] Merlo,F; Bornengo, G Eur.Pat.Appl. 3,565 1979. (CA 92: P7839p)
  • [40] Upadhyay, RK.; Agarwal, N.; Mishra,G. Synthesis of Aryl-2-(Alpha-Hydroxy)Phenylketo-4-Thiazolidinones as Dyes. 1995. J. Indian Chem Soc., 72, 849.
  • [41] Layer, R.W. The Chemistry of Imines. 1963. Chem. Rev.,63,489-510.
  • [42] Silverstein, R.M. Spectrometric Identification of Organic Compounds, John Wiley&Sons, New York, 1998.
  • [43] Pretsch, E., Clerk, T., Seibl, J., Simon, W. Tables of Spectral Data For Structure Determination of Organic Compounds, Springer-Verlag, Berlin, 1983.
Toplam 43 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Makaleler
Yazarlar

İnci Selin Doğan 0000-0003-4949-1747

Gökçe Gül Bölek Bu kişi benim

Bahittin Kahveci 0000-0001-7394-0552

Yayımlanma Tarihi 1 Mart 2019
Yayımlandığı Sayı Yıl 2019

Kaynak Göster

APA Doğan, İ. S., Bölek, G. G., & Kahveci, B. (2019). Synthesis of Some New Isatin Derivatives and Identification of Their Structures. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 23, 67-70. https://doi.org/10.19113/sdufenbed.432261
AMA Doğan İS, Bölek GG, Kahveci B. Synthesis of Some New Isatin Derivatives and Identification of Their Structures. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. Mart 2019;23:67-70. doi:10.19113/sdufenbed.432261
Chicago Doğan, İnci Selin, Gökçe Gül Bölek, ve Bahittin Kahveci. “Synthesis of Some New Isatin Derivatives and Identification of Their Structures”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 23, Mart (Mart 2019): 67-70. https://doi.org/10.19113/sdufenbed.432261.
EndNote Doğan İS, Bölek GG, Kahveci B (01 Mart 2019) Synthesis of Some New Isatin Derivatives and Identification of Their Structures. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 23 67–70.
IEEE İ. S. Doğan, G. G. Bölek, ve B. Kahveci, “Synthesis of Some New Isatin Derivatives and Identification of Their Structures”, Süleyman Demirel Üniv. Fen Bilim. Enst. Derg., c. 23, ss. 67–70, 2019, doi: 10.19113/sdufenbed.432261.
ISNAD Doğan, İnci Selin vd. “Synthesis of Some New Isatin Derivatives and Identification of Their Structures”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 23 (Mart 2019), 67-70. https://doi.org/10.19113/sdufenbed.432261.
JAMA Doğan İS, Bölek GG, Kahveci B. Synthesis of Some New Isatin Derivatives and Identification of Their Structures. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. 2019;23:67–70.
MLA Doğan, İnci Selin vd. “Synthesis of Some New Isatin Derivatives and Identification of Their Structures”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, c. 23, 2019, ss. 67-70, doi:10.19113/sdufenbed.432261.
Vancouver Doğan İS, Bölek GG, Kahveci B. Synthesis of Some New Isatin Derivatives and Identification of Their Structures. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. 2019;23:67-70.

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