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Research Articles

Recent Progress on Fused Thiadiazines: A Literature Review

, ORCID Icon, &
Pages 2861-2893 | Received 23 Feb 2019, Accepted 11 Sep 2020, Published online: 30 Sep 2020

References

  • A. Achson, An Introduction to the Chemistry of Heterocyclic Compounds. 3rd ed. (India: Willy-Intersciences, 2009).
  • N. Campillo, C. García, P. Goya, I. Alkorta, and J. A. Páez, “Novel Bronchodilators: synthesis, Transamination Reactions, and Pharmacology of a Series of Pyrazino[2,3-c][1,2,6]Thiadiazine 2, 2-Dioxides,”Journal of Medicinal Chemistry 43, no. 22 (2000): 4219–27.
  • A. Martı́nez, A. I. Esteban, A. Herrero, C. Ochoa, G. Andrei, R. Snoeck, J. Balzarini, and E. De. Clercq, “Imidazothiadiazine Dioxides: synthesis and Antiviral Activity,” Bioorganic and Medicinal Chemistry 7, no. 8 (1999): 1617–23.
  • B. S. Holla, B. K. Sarojini, B. S. Rao, P. M. Akberali, N. S. Kumari, and V. Shetty, “Synthesis of Some Halogen-Containing 1,2,4-Triazolo-1,3,4-Thiadiazines and Their Antibacterial and Anticancer Screening Studies-Part I,” Farmaco (Societa Chimica Italiana: 1989) 56, no. 8 (2001): 565–70.
  • E. Arranz, J. A. Díaz, S. T. Ingate, M. Witvrouw, C. Pannecouque, J. Balzarini, E. De Clercq, and S. Vega, “Novel 1,1,3-Trioxo-2 H,4 H -Thieno[3,4- e ][1,2,4]Thiadiazine Derivatives as Non-Nucleoside Reverse Transcriptase Inhibitors That Inhibit Human Immunodeficiency Virus Type 1 Replication,” Journal of Medicinal Chemistry 41, no. 21 (1998): 4109–17.
  • M. E. Arranz, J. A. Díaz, S. T. Ingate, M. Witvrouw, C. Pannecouque, J. Balzarini, E. De Clercq, and S. Vega, “Synthesis and anti-HIV Activity of 1,1,3-Trioxo-2H,4H-Thieno[3,4-e][1,2,4]Thiadiazines (TTDs): A New Family of HIV-1 Specific Non-Nucleoside Reverse Transcriptase Inhibitors,” Bioorganic & Medicinal Chemistry 7, no. 12 (1999): 2811–22.
  • M. Witvrouw, M. E. Arranz, C. Pannecouque, R. Declercq, H. Jonckheere, J. C. Schmit, A. M. Vandamme, J. A. Diaz, S. T. Ingate, J. Desmyter, et al. “1,1,3-Trioxo-2H,4H-Thieno[3,4-e][1,2,4]Thiadiazine (TTD) Derivatives: A New Class of Nonnucleoside Human Immunodeficiency Virus Type 1 (HIV-1) Reverse Transcriptase Inhibitors with anti-HIV-1 Activity,” Antimicrobial Agents and Chemotherapy 42, no. 3 (1998): 618–23.
  • X. P. Hui, R. Z. Qiao, P. F. Xu, and Z. Y. Zhang, “Novel and Efficient Solid‐State Synthesis of 3‐Alkyl‐6‐Aryl‐ s ‐Triazolo[3,4‐ b ]‐1,3,4‐Thiadiazine Derivatives,” Synthetic Communications 36, no. 12 (2006): 1655–60.
  • V. V. Dabholkar, P. Naik, A. Karekar, and N. Shinde, “Synthesis and antimicrobial activity of novel 1,3,4-thiadiazine derivatives,” Der Pharma Chemica 5, no. 4 (2013): 161–5.
  • B. F. Abdel-Wahab, H. A. Abdel-Aziz, and E. M. Ahmed, “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, no. 6 (2009): 601–5.
  • B. S. Holla, B. Kalluraya, K. R. Sridhar, E. Drake, L. M. Thomas, K. K. Bhandary, and M. J. Levine, “Synthesis, Structural Characterization, Crystallographic Analysis and Antibacterial Properties of Some Nitrofuryl Triazolo[3,4-b]-1,3,4-Thiadiazines,” European Journal of Medicinal Chemistry 29, no. 4 (1994): 301–8.
  • J. Y. Jin, L. X. Zhang, X. X. Chen, A. J. Zhang, and H. L. Zhang, “Syntheses and Biological Activities of 6-Aryl-3-(3-Hydroxypropyl)-7H-1,2,4-Triazolo[3,4-b][1,3,4]Thiadiazines,” Molecules (Basel, Switzerland) 12, no. 3 (2007): 297–303.
  • J. Y. Jin, L. X. Zhang, A. J. Zhang, X. X. Lei, and J. H. Zhu, “Synthesis and Biological Activity of Some Novel Derivatives of 4-Amino-3-(D-Galactopentitol-1-yl)-5-Mercapto-1,2,4-Triazole,” Molecules (Basel, Switzerland) 12, no. 8 (2007): 1596–605.
  • P. Puthiyapurayil, B. Poojary, C. Chikkanna, and S. K. Buridipad, “Synthesis, Spectral Characterization and Biological Evaluation of a Novel Series of 6-Arylsubstituted-3-[2-(4-Substitutedphenyl)Propan-2-yl]-7H-[1,2,4]Triazolo[3,4-b][1,3,4]Thiadiazines,” European Journal of Medicinal Chemistry 57, (2012): 407–16.
  • T. Afrough, M. Bakavoli, and H. Eshghi, “Synthesis and Characterisation of New 3-Methyl-6-[1-(Pyrimidin-4-yl)Ethyl]-5 H -Pyrimido[5,4- e ][1,2,4]Triazolo[3,4- b ][1,3,4]Thiadiazine Derivatives,” Journal of Chemical Research 41, no. 7 (2017): 376–9.
  • M. Bakavoli, S. M. Seyedi, A. Shiri, S. Saberi, M. Gholami, and H. Sadeghian, “Synthesis of new derivatives of pyrimido [5, 4-e][1, 2, 4] triazolo [3, 4-b][1, 3, 4] thiadiazine and their enzyme inhibitory activity assessment on soybean 15-lipoxygenase,” Journal of Chemistry Research 37, no. 1 (2013): 48–50.
  • J. K. Sahu, S. Ganguly, and A. Kaushik, “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, no. 2 (2014): 90–5.
  • C. S. Reddy, D. C. Rao, V. Yakub, and A. Nagaraj, “Synthesis of Some Novel Bis[1, 2, 4]Triazolo[3, 4-b][1, 3, 4]Thiadiazine Derivatives for Antimicrobial Evaluation,” Acta Chimica Slovenica 58, no. 3 (2011): 582–9.
  • A. Ahmad, H. Varshney, A. Rauf, A. Sherwani, and M. Owais, “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, (2017): S3347–S3357.
  • B. Zhang, Y. H. Li, Y. Liu, Y. R. Chen, E. S. Pan, W. W. You, and P. L. Zhao, “Design, Synthesis and Biological Evaluation of Novel 1,2,4-Triazolo [3,4-b][1,3,4] Thiadiazines Bearing Furan and Thiophene Nucleus,” European Journal of Medicinal Chemistry 103, (2015): 335–42.
  • M. R. Shaaban and T. Fuchigami, “Electrolytic Partial Fluorination of Organic Compounds. Part 56: Highly Regioselective Anodic Mono- and Difluorination of s-Triazolo[3,4-b][1,3,4]Thiadiazine Derivatives,” Tetrahedron Letters 43, no. 2 (2002): 273–6.
  • X. Lei, L. Zhang, A. Zhang, X. Ye, and J. Xiong, “1H and 13C NMR Spectral Characterization of Some Novel 7H-1,2,4-Triazolo[3, 4-b] [1,3,4] Thiadiazine Derivatives,” Magnetic Resonance in Chemistry: MRC 45, no. 3 (2007): 265–8.
  • A. A. Hassan, Y. R. Ibrahim, and A. M. Shawky, “Indazole, Oxathiadiazole, and Thiadiazine Derivatives from Thiosemicarbazides,” Journal of Sulfur Chemistry 28, no. 2 (2007): 211–22.
  • M. Igei, M. Bakavoli, A. Shiri, Z. Ebrahimpour, H. Azizollahi, H. Beyzaei, and M. Moghaddam-Manesh, “Synthesis of Some New Pyrimido[4,5-e]Tetrazolo[5,1-b][1,3,4]Thiadiazine Derivatives via an S–N Type Smiles Rearrangement and Their Antibacterial Evaluation,” Journal of Chemical Research 40, no. 10 (2016): 628–32.
  • M. Nikpour, M. Bakavoli, M. Rahimizadeh, A. J. Sabbaghian, and M. R. Bigdeli, “Convenient Synthesis of New Pyrimido[4,5-e][1,3,4]Thiadiazine Derivatives,” Mendeleev Communications 18, no. 5 (2008): 284–5.
  • V. V. Dotsenko, S. G. Krivokolysko, E. B. Rusanov, and V. P. Litvinov, “The Mannich Reaction in the Synthesis of N,S-Containing Heterocycles,” Russian Chemical Bulletin 56, no. 7 (2007): 1437–40.
  • S. Sert‐Ozgur, B. C. Tel, E. I. Somuncuoglu, I. Kazkayasi, M. Ertan, and B. Tozkoparan, “Design and Synthesis of 1,2,4-Triazolo[3,2- b ]-1,3,5-Thiadiazine Derivatives as a Novel Template for Analgesic/anti-Inflammatory Activity,” Archiv Der Pharmazie 350, no. 7 (2017): e1700052.
  • S. Bondock, A. E. G. Tarhoni, and A. A. Fadda, “Facile Route to Novel Pyrazolo[3,4- d ]Pyrimidine, Imidazo[1,2- b ] Pyrazole, Pyrazolo[3,4- d ][1,2,3]Triazine, Pyrazolo[1,5- c ][1,3,5]Triazine and Pyrazolo[1,5- c ][1,3,5]Thiadiazine Derivatives,” Journal of Heterocyclic Chemistry 52, no. 2 (2015): 346–51.
  • V. V. Dotsenko, S. G. Krivokolysko, A. N. Chernega, and V. P. Litvinov, “Synthesis and Structure of Pyrido [2, 1-b][1, 3, 5] thiadiazine Derivatives,” In Doklady Chemistry 389, no. 4/6 (2003): 92–96.
  • X. Liu, R. Yan, N. Chen, W. Xu, M. T. Molina, and S. Vega, “Regioselective Synthesis of Novel N2- and N4-Substituted 7-Methylpyrazolo[4,5-e][1,2,4]Thiadiazines,” Molecules (Basel, Switzerland) 11, no. 11 (2006): 827–36.
  • X. Y. Liu, R. Z. Yan, N. G. Chen, and W. F. Xu, “Regioselective Synthesis and anti-HIV Activity of the Novel 2- and 4-Substituted Pyrazolo[4,5-e][1,2,4]Thiadiazines,” Chinese Chemical Letters 18, no. 2 (2007): 137–40.
  • X. Liu, N. Chen, R. Yan, W. Xu, M. Teresa Molina, and S. Vega, “Regioselective Synthesis of the Novel N4-Substituted Pyrazolo[4,5-e][1,2,4]Thiadiazines as Potent HIV-1 NNRTIs,” Heterocycles 68, no. 6 (2006): 1225–32.
  • P. Zhan, R. Z. Yan, X. Y. Liu, C. Pannecouque, M. Witvrouw, E. De Clercq, M. T. Molina, and S. Vega, “Synthesis and anti-HIV Activity of Novel 2,4-Disubstituted-7-Methyl-1,1,3-Trioxo-2H,4H-Pyrazolo[4,5-e][1,2,4]Thiadiazine Derivatives,” Drug Discoveries & Therapeutics 5, no. 6 (2011): 279–85.
  • M. E. Arranz, S. Vega, and J. A. Díaz, “Synthesis of Hetero[1,2,4]Thiadiazine 1,1-Dioxides,” Heterocycles 45, no. 9 (1997): 1767–74.
  • A. F. Kornahrens, A. B. Cognetta, I. I. I. D. M. Brody, M. L. Matthews, B. F. Cravatt, and D. L. Boger, “Design of Benzoxathiazin-3-One 1,1-Dioxides as a New Class of Irreversible Serine Hydrolase Inhibitors: Discovery of a Uniquely Selective PNPLA4 Inhibitor,” Journal of the American Chemical Society 139, no. 20 (2017): 7052–61.
  • B. Pirotte, R. Ouedraogo, P. De Tullio, S. Khelili, F. Somers, S. Boverie, L. On Dupont, J. Fontaine, J. Damas, and P. Lebrun, “3-Alkylamino-4H-Pyrido[2,3-e]-1,2,4-Thiadiazine 1,1-Dioxides Structurally Related to Diazoxide and Pinacidil as Potassium Channel Openers Acting on Vascular Smooth Muscle Cells: Design, Synthesis, and Pharmacological Evaluation,” Journal of Medicinal Chemistry 43, no. 8 (2000): 1456–66.
  • B. Pirotte, T. Podona, O. Diouf, P. De Tullio, P. Lebrun, L. Dupont, F. Somers, J. Delarge, P. Morain, P. Lestage, et al. “4H-1,2,4-Pyridothiadiazine 1,1-Dioxides and 2,3-Dihydro-4H-1,2, 4-Pyridothiadiazine 1,1-Dioxides Chemically Related to Diazoxide and Cyclothiazide as Powerful Positive Allosteric Modulators of (R/S)-2-Amino-3-(3-Hydroxy-5-Methylisoxazol-4-yl)Propionic Acid Receptors: Design, Synthesis, Pharmacology, and Structure-Activity Relationships,” Journal of Medicinal Chemistry 41, no. 16 (1998): 2946–59.
  • J. Sławiński, A. Pogorzelska, B. Żołnowska, T. Laskowski, and P. Sowiński, “Synthesis and Structure Determination of 2,3-Diaryl-9,9-Dioxo-1 H -9-Thia-1,4,4a,7,10-Pentaazaphenanthrene-2-Ols,” Tetrahedron 69, no. 41 (2013): 8675–9.
  • J. Sławiński, A. Grzonek, B. Żołnowska, and A. Kawiak, “Synthesis of Novel Pyrido[4,3-e][1,2,4]Triazino[3,2-c][1,2,4]Thiadiazine 6,6-Dioxide Derivatives with Potential Anticancer Activity,” Molecules 21, no. 1 (2015): 41–56.
  • G. García‐Muñoz, R. Madronero, C. Ochoa, M. Stud, and W. Pfleiderer, “Synthesis of Purine-like Ring Systems Derived from 1,2,6-Thiadiazine 1,1-Dioxide,” Journal of Heterocyclic Chemistry 13, no. 4 (1976): 793–6.
  • C. Ochoa, A. Herrero, J. Antonio Páez, M. Martínez-Ripoll, C. Foces-Foces, and F. Hernadez Cano, “A New Route for the Synthesis of 6-Substitutes Imidazo[4-5,c]-1,2,6-Thiadiazine 2,2-Dioxides: NMR Study and Crystal Structure of a Complex with Dimethylformamide,” Heterocycles 26, no. 12 (1987): 3123–33.

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