Review


DOI :10.26650/JARHS2019-616357   IUP :10.26650/JARHS2019-616357    Full Text (PDF)

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

Efe Doğukan DincelNuray Ulusoy Güzeldemirci

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.

DOI :10.26650/JARHS2019-616357   IUP :10.26650/JARHS2019-616357    Full Text (PDF)

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

Efe Doğukan DincelNuray Ulusoy Güzeldemirci

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. 


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References

  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar

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APA

Dincel, E.D., & Ulusoy Güzeldemirci, N. (2019). Discovery, Synthesis and Activity Evaluation of Novel Compounds Bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Moiety: A Review. Journal of Advanced Research in Health Sciences, 2(2), 60-70. https://doi.org/10.26650/JARHS2019-616357


AMA

Dincel E D, Ulusoy Güzeldemirci N. Discovery, Synthesis and Activity Evaluation of Novel Compounds Bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Moiety: A Review. Journal of Advanced Research in Health Sciences. 2019;2(2):60-70. https://doi.org/10.26650/JARHS2019-616357


ABNT

Dincel, E.D.; Ulusoy Güzeldemirci, N. Discovery, Synthesis and Activity Evaluation of Novel Compounds Bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Moiety: A Review. Journal of Advanced Research in Health Sciences, [Publisher Location], v. 2, n. 2, p. 60-70, 2019.


Chicago: Author-Date Style

Dincel, Efe Doğukan, and Nuray Ulusoy Güzeldemirci. 2019. “Discovery, Synthesis and Activity Evaluation of Novel Compounds Bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Moiety: A Review.” Journal of Advanced Research in Health Sciences 2, no. 2: 60-70. https://doi.org/10.26650/JARHS2019-616357


Chicago: Humanities Style

Dincel, Efe Doğukan, and Nuray Ulusoy Güzeldemirci. Discovery, Synthesis and Activity Evaluation of Novel Compounds Bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Moiety: A Review.” Journal of Advanced Research in Health Sciences 2, no. 2 (Sep. 2025): 60-70. https://doi.org/10.26650/JARHS2019-616357


Harvard: Australian Style

Dincel, ED & Ulusoy Güzeldemirci, N 2019, 'Discovery, Synthesis and Activity Evaluation of Novel Compounds Bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Moiety: A Review', Journal of Advanced Research in Health Sciences, vol. 2, no. 2, pp. 60-70, viewed 6 Sep. 2025, https://doi.org/10.26650/JARHS2019-616357


Harvard: Author-Date Style

Dincel, E.D. and Ulusoy Güzeldemirci, N. (2019) ‘Discovery, Synthesis and Activity Evaluation of Novel Compounds Bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Moiety: A Review’, Journal of Advanced Research in Health Sciences, 2(2), pp. 60-70. https://doi.org/10.26650/JARHS2019-616357 (6 Sep. 2025).


MLA

Dincel, Efe Doğukan, and Nuray Ulusoy Güzeldemirci. Discovery, Synthesis and Activity Evaluation of Novel Compounds Bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Moiety: A Review.” Journal of Advanced Research in Health Sciences, vol. 2, no. 2, 2019, pp. 60-70. [Database Container], https://doi.org/10.26650/JARHS2019-616357


Vancouver

Dincel ED, Ulusoy Güzeldemirci N. Discovery, Synthesis and Activity Evaluation of Novel Compounds Bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Moiety: A Review. Journal of Advanced Research in Health Sciences [Internet]. 6 Sep. 2025 [cited 6 Sep. 2025];2(2):60-70. Available from: https://doi.org/10.26650/JARHS2019-616357 doi: 10.26650/JARHS2019-616357


ISNAD

Dincel, EfeDoğukan - Ulusoy Güzeldemirci, Nuray. Discovery, Synthesis and Activity Evaluation of Novel Compounds Bearing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Moiety: A Review”. Journal of Advanced Research in Health Sciences 2/2 (Sep. 2025): 60-70. https://doi.org/10.26650/JARHS2019-616357



TIMELINE


Submitted23.01.2019
Accepted10.06.2019
Published Online06.09.2019

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