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Synthesis of N-Mannich bases from 5-((4-methylpiperazin-1-yl)methyl)-1,3,4-oxadiazole-2-thiol

Yıl 2023, Cilt: 12 Sayı: 1, 146 - 150, 22.03.2023
https://doi.org/10.17798/bitlisfen.1205608

Öz

Methyl (4-methylpiperazin-1-yl)acetate (2) were synthesized by the condensation of compound (1) with ethyl bromoacetate in basic media. aThe synthesis of acid hydrazide derivatives (3) was brought about as a result of the reaction between a compound (2) and hydrazine hydrate. In the absence of basic conditions, the reaction of 2-(4-methylpiperazin-1-yl)acetohydrazide (3) with carbon disulfide resulted in the formation of 5-((4-methylpiperazin-1-yl)methyl)-1,3,4-oxadiazole-2-thiol (4). aThe reactions of (4) with different primary and secondary amines in the presence of formaldehyde led to the formation of the corresponding Mannich bases (5a-f).

Kaynakça

  • [1] S. G. Subramaniapillai, J Chem Sci 2013, 125, 467.
  • [2] G. Roman, Eur J Med Chem 2015, 89, 743.
  • [3] J. R. Dimmock, P. Kumar, Curr Med Chem 1997, 4, 1.
  • [4] A. V. Bogdanov, A. M. Vazykhova, N. R. Khasiyatullina, D. B. Krivolapov, A. B. Dobrynin, A. D. Voloshina, V. F. Mironov, V. F., Chem Heterocycl Comp 2016, 52, 25.
  • [5] S. George, R. Chkraborty, M. Parameswaran, A. Rajan, T. K. Ravi, J Heterocycl Chem 2015, 52, 211.
  • [6] H. Guo, Eur J Med Chem 2019, 164, 678.
  • [7] S. Shen, X. Sun, Y. Liu, B. Chen, R. Jin, H. Ma, J Heterocycl Chem 2015, 52, 1296.
  • [8] T. R. Bal, B. Anand, P. Yogeeswari, D. Sriram, Bioorg Med Chem Lett 2005, 15, 4451.
  • [9] T. Aboul‐Fadl, F. A. S. Bin‐Jubair, Int J Res Pharm. Sci 2010, 1,113.
  • [10] Chen, G.; Ning,Y.; Zhao, W.; Zhang,Y.; Zhang, Y.; Hao,X.; Wang, Y.; Mu, S. Lett Drug Des Discov 2016, 13, 395.
  • [11] Kushwaha,N.; Kaushik, D. J Applied Pharm Sci 2016, 6, 159.
  • [12] L. Pan, X. Li, C. Gong, H. Jin, Qin. B. Microbial Pathogenesis 2016, 95, 186.
  • [13] A. M. Alanazi, A. S. El‐Azab, I. A. Al‐Suwaidan, K. H. ElTahir, Y. A. Asiri, N. I. Abdel‐Aziz, A. Abdel‐Aziz, Eur J Med Chem 2015, 92, 115.
  • [14] S. Arti Kumar, D. Pathak, Int J Pharm Tech Res 2011, 3, 2104.
  • [15] P. S. Nayab, M. Irfan, M. Abid, M. Pulaganti, C. Nagaraju, S. K. Chitta, Luminescence 2017, 32, 298.
  • [16] R. Bamnela, S. P. Shrivastava, Indian J Chem 2014, 53B, 1128.
  • [17] D. Sachan, J. P. Singh, D. Sachan, S. Gangwar, Amer J Pharm Tech Res 2012, 2, 491.
  • [18] Y., Uygun Cebeci, Ş., Ceylan, N., Demirbaş, S., Alpay Karaoğlu, Microwave-assisted Synthesis of Novel Mannich Base and Conazole Derivatives Containing Biologically Active Pharmacological Groups, Letters in Drug Design & Discovery, 2021, 18, 1-15.
  • [19] H., Bayrak, A., Demirbas, N., Demirbas, S., Alpay-Karaoglu, Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities. Eur. J.Med. Chem. 2009, 44, 1057–1066.
  • [20] A., Demirbas, S., Ceylan, N., Demirbas, Synthesis of some new five membered heterocycles, a facile synthesis of oxazolidinones. J. Heterocycl. Chem. 2007, 44, 1271–1280.
  • [21] N., Demirbaş, R., Uğurluoğlu, Synthesis of novel 4-alkylidene- and 4-alkylamino-5-oxo-4,5- dihydro-[1,2,4]triazole derivatives and investigation of their antitumor activities. Turk. J. Chem. 2004, 28, 559–571.
  • [22] H., Bayrak, A., Demirbas, S., Alpay Karaoğlu, N., Demirbaş, Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities, European Journal of Medicinal Chemistry 44 (2009) 1057-1066
Yıl 2023, Cilt: 12 Sayı: 1, 146 - 150, 22.03.2023
https://doi.org/10.17798/bitlisfen.1205608

Öz

Kaynakça

  • [1] S. G. Subramaniapillai, J Chem Sci 2013, 125, 467.
  • [2] G. Roman, Eur J Med Chem 2015, 89, 743.
  • [3] J. R. Dimmock, P. Kumar, Curr Med Chem 1997, 4, 1.
  • [4] A. V. Bogdanov, A. M. Vazykhova, N. R. Khasiyatullina, D. B. Krivolapov, A. B. Dobrynin, A. D. Voloshina, V. F. Mironov, V. F., Chem Heterocycl Comp 2016, 52, 25.
  • [5] S. George, R. Chkraborty, M. Parameswaran, A. Rajan, T. K. Ravi, J Heterocycl Chem 2015, 52, 211.
  • [6] H. Guo, Eur J Med Chem 2019, 164, 678.
  • [7] S. Shen, X. Sun, Y. Liu, B. Chen, R. Jin, H. Ma, J Heterocycl Chem 2015, 52, 1296.
  • [8] T. R. Bal, B. Anand, P. Yogeeswari, D. Sriram, Bioorg Med Chem Lett 2005, 15, 4451.
  • [9] T. Aboul‐Fadl, F. A. S. Bin‐Jubair, Int J Res Pharm. Sci 2010, 1,113.
  • [10] Chen, G.; Ning,Y.; Zhao, W.; Zhang,Y.; Zhang, Y.; Hao,X.; Wang, Y.; Mu, S. Lett Drug Des Discov 2016, 13, 395.
  • [11] Kushwaha,N.; Kaushik, D. J Applied Pharm Sci 2016, 6, 159.
  • [12] L. Pan, X. Li, C. Gong, H. Jin, Qin. B. Microbial Pathogenesis 2016, 95, 186.
  • [13] A. M. Alanazi, A. S. El‐Azab, I. A. Al‐Suwaidan, K. H. ElTahir, Y. A. Asiri, N. I. Abdel‐Aziz, A. Abdel‐Aziz, Eur J Med Chem 2015, 92, 115.
  • [14] S. Arti Kumar, D. Pathak, Int J Pharm Tech Res 2011, 3, 2104.
  • [15] P. S. Nayab, M. Irfan, M. Abid, M. Pulaganti, C. Nagaraju, S. K. Chitta, Luminescence 2017, 32, 298.
  • [16] R. Bamnela, S. P. Shrivastava, Indian J Chem 2014, 53B, 1128.
  • [17] D. Sachan, J. P. Singh, D. Sachan, S. Gangwar, Amer J Pharm Tech Res 2012, 2, 491.
  • [18] Y., Uygun Cebeci, Ş., Ceylan, N., Demirbaş, S., Alpay Karaoğlu, Microwave-assisted Synthesis of Novel Mannich Base and Conazole Derivatives Containing Biologically Active Pharmacological Groups, Letters in Drug Design & Discovery, 2021, 18, 1-15.
  • [19] H., Bayrak, A., Demirbas, N., Demirbas, S., Alpay-Karaoglu, Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities. Eur. J.Med. Chem. 2009, 44, 1057–1066.
  • [20] A., Demirbas, S., Ceylan, N., Demirbas, Synthesis of some new five membered heterocycles, a facile synthesis of oxazolidinones. J. Heterocycl. Chem. 2007, 44, 1271–1280.
  • [21] N., Demirbaş, R., Uğurluoğlu, Synthesis of novel 4-alkylidene- and 4-alkylamino-5-oxo-4,5- dihydro-[1,2,4]triazole derivatives and investigation of their antitumor activities. Turk. J. Chem. 2004, 28, 559–571.
  • [22] H., Bayrak, A., Demirbas, S., Alpay Karaoğlu, N., Demirbaş, Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities, European Journal of Medicinal Chemistry 44 (2009) 1057-1066
Toplam 22 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Araştırma Makalesi
Yazarlar

Yıldız Uygun Cebecı 0000-0001-7949-0329

Erken Görünüm Tarihi 23 Mart 2023
Yayımlanma Tarihi 22 Mart 2023
Gönderilme Tarihi 16 Kasım 2022
Kabul Tarihi 9 Mart 2023
Yayımlandığı Sayı Yıl 2023 Cilt: 12 Sayı: 1

Kaynak Göster

IEEE Y. Uygun Cebecı, “Synthesis of N-Mannich bases from 5-((4-methylpiperazin-1-yl)methyl)-1,3,4-oxadiazole-2-thiol”, Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, c. 12, sy. 1, ss. 146–150, 2023, doi: 10.17798/bitlisfen.1205608.



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