Discovery, Synthesis and Activity Evaluation of Novel Compounds Bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Moiety: A Review

Yıl 2019, Cilt: 2 Sayı: 2, 60 - 70, 06.09.2019

Efe Doğukan Dincel Nuray Ulusoy Güzeldemirci

https://doi.org/10.26650/JARHS2019-616357

Öz

Lately, much interest has been focused on the chemistry and the biological activity of fused heterocyclic compounds carrying nitrogen atoms because of their utility in various applications, and over the years N-bridged heterocyclic systems derived from 1,2,4-triazoles attracted the interest of researchers owing to the hopeful promise of their pharmacological activities such as antimicrobial, antifungal, molluscicidal, nematicidal, analgesic, anti-inflammatory, anticancer, phosphodiesterase 4 inhibitor, acetylcholinesterase, butyrylcholinesterases and alkaline phosphatase inhibitor. The fused ring of triazole and thiadiazines, named as triazolothiadiazines, represents a specific and important class of N-bridged heterocycles with their remarkable and wide range of biological activity and there are not enough studies that include the current developments associated with the new synthesis techniques and novel biological evaluation results of 1,2,4-triazolo[3,4-b][1,3,4] thiadiazine derivatives. In an attempt to overcome this deficiency in the literature, we deeply researched the literature and formed a review study about the discovery, synthesis and activity evaluation of new compounds bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine moiety within the years of 1996-2019. We aimed to provide scientists with a wide data resource about 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine derivatives, thus helping them perform a more organized and fertile drug discovery operation during their experimental studies. 

Anahtar Kelimeler

synthesis, biological activity, 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine

1,2,4-triazolo[3,4-b][1,3,4]tiyadiazin Artığı İçeren Yeni Bileşiklerin Keşfi, Sentezi ve Biyolojik Aktiviteleri: Bir Derleme

Öz

Son zamanlarda, geniş ölçekte çeşitlilik gösteren uygulamalardaki kullanımları nedeniyle azot atomu taşıyan kaynaşmış heterosiklik bileşiklerin kimyası ve biyolojik aktivitesi üzerine olan ilgi artmış ve yoğunlaşmıştır. Yıllar boyunca 1,2,4-triazollerden türetilen azot köprülü heterosiklik sistemler antimikrobiyal, antifungal, mollusisidal, nematisidal, analjezik, anti-inflamatuvar, antikanser, fosfodiesteraz-4 inhibitörü, asetilkolinesteraz, butirilkolinesteraz ve alkalen fosfataz inhibitörü gibi farklı biyolojik yönlerde, umut vadeden farmakolojik aktiviteler göstermiş ve buna bağlı olarak araştırmacıların ilgisini çekmiştir. Triazol ve tiyadiazin halkalarının kaynaşmasıyla oluşan triazolotiyadiazinler azot köprülü heterosiklik bileşikler arasında önemli ve dikkat çekici bir alt sınıfı oluşturmaktadır, buna karşın 1,2,4-triazolo[3,4-b][1,3,4]tiyadiazin türevlerinie ait güncel sentez teknikleri ve yeni biyolojik aktivite bulgularını içeren çalışmalar literatürde yeterli oranda bulunmamaktadır. Bu noktadan hareketle 1996-2019 tarih aralığını referans alarak 1,2,4-triazolo[3,4-b][1,3,4] tiyadiazin yapısı taşıyan yeni bileşiklerin keşfi, sentezi ve aktivite değerlendirmeleri ile ilişkili bir derleme çalışması yürütülmüştür. Araştırmacıların daha organize ve verimli bir ilaç keşif prosesi gerçekleştirmelerine yardımcı olmak amaçlanmıştır.

Anahtar Kelimeler

sentez, biyolojik aktivite, 1,2,4-triazolo[3,4-b][1,3,4]tiyadiazin

Kaynakça

• 1. Abdel-Wahab, B.F., Abdel-Aziz, H.A., Ahmed, E.M. (2009): Synthesis and antimicrobial evaluation of some 1,3-thiazole, 1,3,4-thiadiazole, 1,2,4-triazole, and 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazine derivatives including a 5-(benzofuran-2-yl)-1-phenylpyrazole moiety,  Monatshefte für Chemie-Chemical Monthly, 140(6): 601-605.
• 2. Ahmad, A., Varshney, H., Rauf, A., Sherwani, A., Owais, M. (2017): Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione, 1,2,4-triazol-3-thione and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives,  Arabian Journal of Chemistry, 10: 3347-3357.
• 3. Aytac, S.P., Tozkoparan, B., Kaynak, F.B., Aktay, G., Göktaş, Ö., Ünüvar, S. (2009): Synthesis of 3,6-disubstituted 7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines as novel analgesic/anti-inflammatory compounds, European Journal of Medicinal Chemistry, 44(11): 45284538.
• 4. Badr, S.M., Barwa, R.M. (2011): Synthesis of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles starting from 5-nitro-2-furoic acid and evaluation of their antimicrobial activity, Bioorganic & Medicinal Chemistry, 19(15): 4506-4512.
• 5. Baeeri, M., Foroumadi, A., Motamedi, M., YahyaMeymandi, A., Firoozpour, L., Ostad, S.N., Shafiee, A., Souzangarzadeh, S., Abdollahi, M. (2011): Safety and Efficacy of New 3,6‐diaryl‐7H‐[1,2,4]triazolo[3,4‐b] [1,3,4]thiadiazine Analogs as Potential Phosphodiesterase‐4 Inhibitors in NIH‐3T3 Mouse Fibroblastic Cells, Chemical Biology & Drug Design, 78(3): 438444.
• 6. El Shehry, M.F., Abu-Hashem, A.A., El-Telbani, E.M. (2010): Synthesis of 3-((2,4-dichlorophenoxy)methyl)-1,2,4-triazolo(thiadiazoles and thiadiazines) as anti-inflammatory and molluscicidal agents, European Journal of Medicinal Chemistry, 45(5): 19061911.
• 7. Ergenc, N., Ulusoy, N., Çapan, G., Sanis, G.Ö., Kiraz, M. (1996): Synthesis and Antimicrobial Properties of New 4‐(Alkylidene/arylidene)‐amino‐5‐(2‐furanyl)‐2, 4‐dihydro‐3H‐1,2,4‐triazole‐3‐thiones and 6‐Aryl‐3‐(2‐furanyl)‐7H‐1,2,4‐triazolo[3,4‐b][1,3,4] thiadiazines, Archiv der Pharmazie, 329(8‐9): 427430.
• 8. Holla, B.S., Rao, B.S., Sarojini, B.K., Akberali, P.M., Kumari, N.S. (2006): Synthesis and studies on some new fluorine containing triazolothiadiazines as possible antibacterial, antifungal and anticancer agents, European Journal of Medicinal Chemistry, 41(5): 657-663.
• 9. İlhan, E., Ergenç, N., Ulusoy, N., Ötük Sanış, G. (1996): Synthese und antimikrobielle Untersuchung einiger 4-Arylidenamino-3-(α,α-diphenyl-α-hydroxymethyl)-1,4-dihydro-5H-1,2,4-Triazol-5-thione und 6-Aryl-3-(α,α-diphenyl-α-hydroxymethyl)-7H-s-Triazolo[3,4-b][1,3,4]thiadiazine, Die Pharmazie, 51(2): 123-124.
• 10. Karabasanagouda, T., Adhikari, A.V., Shetty, N.S. (2007): Synthesis and antimicrobial activities of some novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines carrying thioalkyl and sulphonyl phenoxy moieties, European Journal of Medicinal Chemistry, 42(4): 521-529.
• 11. Karegoudar, P., Prasad, D.J., Ashok, M., Mahalinga, M., Poojary, B., Holla, B.S. (2008): Synthesis, antimicrobial and anti-inflammatory activities of some 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines bearing trichlorophenyl moiety, European Journal of Medicinal Chemistry, 43(4): 808-815.
• 12. Khan, I., Zaib, S., Ibrar, A., Rama, N.H., Simpson, J., Iqbal, J. (2014): Synthesis, crystal structure and biological evaluation of some novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines, European Journal of Medicinal Chemistry, 78: 167-177.
• 13. Mekala, R.V.R., Yata, M.R., Talagadadivi, R.P. (2014): Synthesis, characterizatıon and bilogical screening of some novel indole based 1,2,4-trıazolo 1,3,4 thiadiazines, Journal of Drug Delivery and Therapeutics, 4(2): 43-46.
• 14. Penta, S., Gadidasu, K.K., Basavoju, S., Rao, V.R. (2013): An efficient one-pot synthesis of pyrazolyl-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazin-6-yl)-2H-pyran-2-one derivatives via multicomponent approach and their potential antimicrobial and nematicidal activities, Tetrahedron Letters, 54(42): 5663-5666.
• 15. Pundeer, R., Kiran, V., Prakash, R., Bhatia, S.C., Sharma, C., Aneja, K.R. (2012): α,α-Dibromoacetophenones mediated synthesis of some new 7H-7alkoxy-3-alkyl/phenyl-6-aryl-s-triazolo[3,4-b][1,3,4] thiadiazines and their antimicrobial evaluation, Medicinal Chemistry Research, 21(12): 4043-4052.
• 16. Puthiyapurayil, P., Poojary, B., Buridipad, S.K. (2014): Synthesis, Characterization and Biological Evaluation of a Novel Series of 1,2,4‐triazolo-[3,4‐b]-1,3,4-thiadiazines Containing an Amide Linkage, Journal of Heterocyclic Chemistry, 51(S1): E55-E67.
• 17. Sahu, J.K., Ganguly, S., & Kaushik, A. (2014): Synthesis and antimicrobial activity of some novel fused heterocyclic 1,2,4-triazolo [3,4-b][1,3,4] thiadiazine derivatives, Journal of advanced pharmaceutical technology & research, 5(2): 90.
• 18. Sumangala, V., Poojary, B., Chidananda, N., Arulmoli, T., Shenoy, S. (2012): Facile synthesis, cytotoxic and antimicrobial activity studies of a new group of 6-aryl-3-[4-(methylsulfonyl)benzyl]-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines, European Journal of Medicinal Chemistry, 54: 59-64.