Synthesis and Characterization of Schiff Base Derivatives Containing 2- Amino-1,3,4-Thiadiazole Ring

Yıl 2017, Cilt: 17 Sayı: 2, 460 - 468, 31.08.2017

Hakan Tahtacı

Öz

The compounds with thiadiazole and schiff base have an important place in heterocyclic chemistry. It is known for many years that these compounds show biological activities. It is also known that Schiff base and their derivatives have antienflamatuar, antidepressive, and antibacterial features besides that some derivatives are effective against herbicides and fungicides. Due to these features, compounds including Schiff bases and derivatives are highly studied in current researches. In the light of these significant data we obtained through the literature review, the main purpose of this study is to synthesize and characterize the various substituent groups including both thiadiazole and schiff bases with potential biological activities. Therefore, beginning from various nitrile derivatives (1a-c) and 5- amino-1,3,4-thiadiazole-2-thiol (5), primarily 2-amino-1,3,4-thiadiazol derivatives (2a-c, 7a-c) have been synthesized. Then these compounds have been reacted with various aldehyde derivatives (3a-c) to synthesize schiff base derivatives (4a-i, 8a-i). The structures of the synthesized compounds were elucidated using IR, 1 H NMR, 13C NMR, mass spectrometry and elemental analysis techniques.

Anahtar Kelimeler

Nitrile derivatives, 2-Amino-1, 3, 4, thiadiazole, Schiff base

2-Amino-1,3,4-Tiyadiazol Halkası İçeren Schiff Bazı Türevlerinin Sentezi ve Karakterizasyonu

Öz

Tiyadiazol ve schiff bazı içeren bileşikler heterosiklik kimyada önemli bir yere sahiptir. Bu bileşiklerin çeşitli biyolojik aktivite gösterdiği uzun yıllardır bilinmektedir. Schiff bazı ve bunların türevleri antienflammatuar, antidepresif, antibakteriyal özelliklerinin yanı sıra bazı türevlerinin herbisitlere ve fungisitlere karşıda etkin olduğu bilinmektedir. Bu özelliklerinden dolayı, günümüzde schiff bazlarını ve türevlerini içeren bileşikler üzerinde çokça çalışılmaktadır. Yapılan literatür araştırmaları ile elde ettiğimiz bu önemli veriler ışığında bu çalışmanın temel amacı, potansiyel biyolojik aktiviteye sahip tiyadiazol ve schiff bazlarını birlikte içeren çeşitli sübstitüe grupları sentezlemek ve karakterize etmektir. Bu amaç için çeşitli nitril türevlerinden (1a-c) ve 5-amino-1,3,4-tiyadiazol-2-tiyol (5)’den başlayarak öncelikle 2-amino-1,3,4-tiyadiazol türevleri (2a-c, 7a-c) sentezlendi. Daha sonra bu bileşikler çeşitli aldehit türevleri (3a-c) ile reaksiyona sokularak hedef bileşikler olan schiff bazı türevleri (4a-i, 8a-i) sentezlendi. Sentezlenen bileşiklerin yapıları IR, 1H NMR, 13C NMR, kütle spektrometresi ve elementel analiz teknikleri kullanılarak aydınlatıldı.

Anahtar Kelimeler

Nitril türevleri; 2-Amino-1, 3, 4-tiyadiazol, Schiff bazı

Kaynakça

• Al-Abdullah, E. S., Al-Tuwaijri, H. M., Hassan, H. M., Al-Alshaikh, M. A., Habib, E. E., El-Emam, A. A., 2015. Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl) carbothioamide Derivatives. Molecules,20(5), 8125-8143.
• Anbazhagan, R., Sankaran, K., 2013. Syntheses, spectral characterization, single crystal X-ray diffraction and DFT computational studies of novel thiazole derivatives. Journal of Molecular Structure, 1050, 73-80.
• Bharti, S. K., Nath, G., Tilak, R., Singh, S., 2010. Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2, 4-disubstituted thiazole ring. European Journal of Medicinal Chemistry, 45(2), 651-660.
• Bondock, S., El-Azab, H., Kandeel, E. E. M., Metwally, M. A. 2013. Efficient synthesis of new functionalized 2-(hetaryl) thiazoles. Synthetic Communications, 43(1), 59-71.
• Dhahagani, K., Kumar, S. M., Chakkaravarthi, G., Anitha, K., Rajesh, J., Ramu, A., Rajagopal, G., 2014. Synthesis and spectral characterization of Schiff base complexes of Cu (II), Co (II), Zn (II) and VO (IV) containing 4-(4-aminophenyl) morpholine derivatives: Antimicrobial evaluation and anticancer studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 117, 87-94.
• Er, M., Isildak, G., Tahtaci, H., Karakurt, T., 2016. Novel 2-amino-1, 3, 4-thiadiazoles and their acyl derivatives: Synthesis, structural characterization, molecular docking studies and comparison of experimental and computational results. Journal of Molecular Structure, 1110, 102-113.
• Güzeldemirci, N. U., Küçükbasmacı, Ö., 2010. Synthesis and antimicrobial activity evaluation of new 1, 2, 4-triazoles and 1, 3, 4-thiadiazoles bearing imidazo [2,1-b] thiazole moiety. European Journal of Medicinal Chemistry, 45(1),63-68.
• Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M., El-Emam A. A., 2007. Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. European Journal of Medicinal Chemistry, 42(2), 235-242.
• Kadi, A. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M., El-Emam A. A., 2010. Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1,3,4-thiadiazole derivatives. European Journal of Medicinal Chemistry, 45(11), 5006-5011.
• Khedr, A. M., Marwani, H. M., 2012. Synthesis, spectral, thermal analyses and molecular modeling of bioactive Cu (II)-complexes with 1, 3, 4-thiadiazole Schiff base derivatives. Their catalytic effect on the cathodic reduction of oxygen, International Journal of Electrochemical Science,7, 10074-10093.
• Kumar, G. S., Prasad, Y. R., Mallikarjuna, B., Chandrashekar, S., 2010. Synthesis and pharmacological evaluation of clubbed isopropylthiazole derived triazolothiadiazoles, triazolothiadiazines and mannich bases as potential antimicrobial and antitubercular agents. European Journal of Medicinal Chemistry, 45(11), 5120-5129.
• Liu, H., Wu, R., Sun, Y., Ye, Y., Chen, J., Luo, X., Shen, X., Liu, H., 2014. Identification of novel thiadiazoloacrylamide analogues as inhibitors of dengue-2 virus NS2B/NS3 protease. Bioorganic & Medicinal Chemistry, 22(22),6344-6352.
• Matysiak, J., Malinski, Z., 2007. 2-(2, 4-dihydroxyphenyl)-1, 3, 4-thiadiazole analogues: Antifungal activity in vitro against Candida species. Russian Journal of Bioorganic Chemistry, 33(6), 594-601.
• Nagesh, G., Mruthyunjayaswamy, B., 2015. Synthesis, characterization and biological relevance of some metal (II) complexes with oxygen, nitrogen and oxygen (ONO) donor Schiff base ligand derived from thiazole and 2-hydroxy-1-naphthaldehydeJournal of Molecular Structure, 1085, 198-206.
• Rostom, S. A., El-Ashmawy, I. M., El Razik, H. A. A., Badr, M. H., Ashour, H. M., 2009. Design and synthesis of some thiazolyl and thiadiazolyl derivatives of antipyrine as potential non-acidic anti-inflammatory, analgesic and antimicrobial agents. Bioorganic & Medicinal Chemistry, 17(2), 882-895.
• Sancak, K., Ünver, Y., Er, M., 2007. Synthesis of 2-Acylamino, 2-Aroylamino and ethoxycarbonyl imino-1,3,4-thiadiazoles as antitumor agents. Turkish Journal of Chemistry,31, 125-134.
• Siddiqui, N., Ahsan, W., 2011. Synthesis, anticonvulsant and toxicity screening of thiazolyl-thiadiazole derivatives. Medicinal Chemistry Research,20(2), 261-268.
• Zarei, S. A., Piltan, M., Hassanzadeh, K., Akhtari, K., Cinčić, D., 2015. Synthesis, characterization, crystal structure and predicting the second-order optical nonlinearity of a new dicobalt (III) complex with Schiff base ligand. Journal of Molecular Structure, 1083, 82-87.