261
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

An Efficient One-Pot Synthesis of 6-Phenyl-3-(1H-Pyrazol-1-yl)-[1,2,4]Triazolo[3,4-b][1,3,4]Thiadiazole Derivatives and Their Antimicrobial Evaluation and Molecular Docking Studies

, , & ORCID Icon
Pages 4240-4254 | Received 21 Dec 2020, Accepted 30 Jan 2021, Published online: 11 Feb 2021

References

  • A. Iraji, A. Nouri, N. Edraki, S. Pirhadi, K. Mahsima, and K. Mehdi, “One-Pot Synthesis of Thioxo-Tetrahydropyrimidine Derivatives as Potent β-Glucuronidase Inhibitor, Biological Evaluation, Molecular Docking and Molecular Dynamics Studies,” Bioorganic & Medicinal Chemistry 28, no. 7 (2020): 115359
  • K. A. Frolov, V. V. Dotsenko, and S. G. Krivokolysko, “Mannich Reaction in the Synthesis of N, S-Containing Heterocycles. 15*. Multicomponent Cascade Synthesis of 3,4,6a,7,8,9,10,10a-Octahydro-2H,6H-Pyrimido[4',5':4,5]Pyrido[2,1-b][1,3,5]Thia(Selena)-Diazine Derivatives,” Chemistry of Heterocyclic Compounds 48, no. 10 (2013): 1555–61.
  • P. C. Jilloju, P. Shyam, A. Sanjeev, and R. R. Vedula, “Four-Component, One-Pot Synthesis of (E)-N-Benzylidene-3-(Benzylthio)-5-(3,5-Dimethyl-1H-Pyrazol-1-yl)-4H-1,2,4-Triazol-4-Amines and Their DNA Binding and Molecular Docking Studies,” Journal of Molecular Structure 1225, (2021): 129140.
  • P. C. Jilloju, M. Srikanth, S. V. Kumar, and R. R. Vedula, “One-Pot, Multi-Component Synthesis of Substituted 2-(6-Phenyl-7H-[1,2,4]Triazolo[3,4-b][1,3,4]Thiadiazin-3-yl)-2,3-Dihydrophthalazine-1,4-Diones,” Polycyclic Aromatic Compounds (2020): 1–12.
  • K. Gong, H. Wang, S. Wang, and X. Ren, “β-Cyclodextrin-Propyl Sulfonic Acid: A New and Eco-Friendly Catalyst for One-Pot Multi-Component Synthesis of 3,4-Dihydropyrimidones via Biginelli Reaction,” Tetrahedron 71, no. 29 (2015): 4830–4.
  • M. Krasavin, S. Tsirulnikov, M. Nikulnikov, V. Kysil, and A. Ivachtchenko, “Poorly Reactive 5-Piperazin-1-yl-1,3,4-Thiadiazol-2-Amines Rendered as Valid Substrates for Groebke–Black Burn Type Multi-Component Reaction,” Tetrahedron Letters 49, no. 36 (2008): 5241–3.
  • S. N. Murthy, B. Madhav, V. P. Reddy, and Y. V. D. Nageswar, “One-Pot Synthesis of 2-Amino-4H-Chromen-4-yl Phosphonate Derivatives Using β-Cyclodextrin as Reusable Catalyst in Water with Aldehydes and Isocyanides Using TMSCl as a Promoter,” Tetrahedron Letters 51, no. 28 (2010): 3649–53.
  • I. A. Ibarra, A. I. Jacome, and E. G. Zamora, “Synthesis of Polyheterocycles via Multicomponent reactions,” Organic & Biomolecular Chemistry 16, no. 9 (2018): 1402–18.
  • X. Zhao, A. Liao, F. Zhang, Q. Zhao, L. Zhou, J. Fan, Z. Zhang, Z. Wang, and Q. Wang, “Design, Synthesis, and Bioactivity of Nortopsentin Analogues Containing 1,2,4‐Triazole Moieties,” Journal of Heterocyclic Chemistry 57, no. 2 (2020): 761–7.
  • S. J. Gilani, S. A. Khan, and N. Siddiqui, “Synthesis and Pharmacological Evaluation of Condensed Heterocyclic 6-Substituted 1,2,4-Triazolo-[3,4-b]-1,3,4-Thiadiazole and 1,3,4-Oxadiazole Derivatives of Isoniazid,” Bioorganic & Medicinal Chemistry Letters 20, no. 16 (2010): 4762–5.
  • X. Cao, W. Wang, S. Wang, and L. Bao, “Asymmetric Synthesis of Novel Triazole Derivatives and Their in vitro antiviral activity and mechanism of action,” European Journal of Medicinal Chemistry 139 (2017) : 718–25.
  • S. A. El-Sebaey, “Recent Advances in 1,2,4-Triazole Scaffolds as Antiviral Agents,” ChemistrySelect 5 (2020): 11654–80.
  • Z. Rezaei, S. Khabnadideh, K. Pakshir, Z. Hossaini, F. Amiri, and E. Assadpour, “Design, Synthesis, and Antifungal Activity of Triazole and Benzotriazole Derivatives,” European Journal of Medicinal Chemistry 44, no. 7 (2009): 3064–7.
  • Krzysztof Sztanke, Tomasz Tuzimski, Jolanta Rzymowska, Kazimierz Pasternak, and Martyna Kandefer-Szerszeń, “Synthesis, Determination of the Lipophilicity, Anticancer and Antimicrobial Properties of Some Fused 1,2,4-Triazole Derivatives,” European Journal of Medicinal Chemistry 43, no. 2 (2008): 404–19.
  • Y. A. Al-Soud, M. N. Al-Dweri, and N. A. Al-Masoudi, “Synthesis, Antitumor and Antiviral Properties of Some 1,2,4-Triazole Derivatives,” Farmaco (Societa Chimica Italiana : 1989) 59, no. 10 (2004): 775–83.
  • M. F. El-Shehry, A. A. Abu-Hashem, and E. M. El-Telbani, “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, no. 5 (2010): 1906–11.
  • P. Haegler, L. Joerin, S. Krahenbuhl, and J. Bouitbir, “Hepatocellular Toxicity of Imidazole and Triazole Antimycotic Agents,” Toxicological Sciences : An Official Journal of the Society of Toxicology 157, no. 1 (2017): 183–95.
  • F. Gao, T. Wang, J. Xiao, and G. Huang, “Antibacterial Activity Study of 1,2,4-Triazole Derivatives,” European Journal of Medicinal Chemistry 173 (2019) : 274–81.
  • M. Yusuf, and S. Thakur, “Synthesis, Characterization & in Vitro Antimicrobial‐Antioxidant Studies of Novel N,1‐Diphenyl‐4,5‐Dihydro‐1H‐1,2,4‐Triazol‐3‐Amine Derivatives,” Journal of Heterocyclic Chemistry 56 (2019): 3403–13.
  • Y. Zhang, B. L. Wang, Y. Z. Zhan, L. Y. Zhang, Y. H. Li, and Z. M. Li, “Synthesis and Biological Activities of Novel 5-(Pyridine-3-yl)-1,2,4-Triazole Mannich Bases and Bis-Mannich Bases Containing Piperazine Moiety,” Chemical Journal of Chinese Universities 37 (2016): 1100–7.
  • J. X. Mu, Z. W. Zhai, C. X. Tan, J. Q. Weng, H. K. Wu, S. O. Duke, Y. G. Zhang, and X. H. Liu, “Synthesis and Herbicidal Activity of 1,2,4-Triazole Derivatives Containing a Pyrazole Moiety,”Journal of Heterocyclic Chemistry 56, no. 3 (2019): 968–71.
  • S. Zhang, Z. Xu, C. Gao, Q. C. Ren, L. Chang, Z. S. Lv, and L. S. Feng, “Triazole Derivatives and Their anti-Tubercular Activity,” European Journal of Medicinal Chemistry 138 (2017): 501–13.
  • P. C. Jilloju, and R. R. Vedula, “A Facile One-Pot Three-Component Synthesis of Benzylideneamino-3,5-Dimethyl-1H-Pyrazoles,”Synthetic Communications 48, no. 14 (2018): 1739–46.
  • P. C. Jilloju, A. Vinaykumar, P. Shyam, and R. R. Vedula, “One-Pot, Multi-Component Cascade Reaction for the Synthesis of Various Aralkyl/Alkylthio-3,5-Dimethyl-1H-Pyrazolyl-4H-1,2,4-Triazol-4-Amineand Their Docking Studies,”Journal of Heterocyclic Chemistry 56, no. 3 (2019): 1012–9.
  • K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y. N. Mabkhot, F. A. Al-Aizari, and M. Ansar, “Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review,” Molecules 23, no. 1 (2018): 134–220.
  • R. Kamal, V. Kumar, R. Kumar, J. K. Bhardwaj, P. Saraf, P. Kumari, and V. Bhardwaj, “Design, Synthesis, and Screening of Triazolopyrimidine–Pyrazole Hybrids as Potent Apoptotic Inducers,”Archiv Der Pharmazie 350, no. 11 (2017): e1700137.
  • Adnan A. Bekhit, Manal N. Saudi, Ahmed M. M. Hassan, Salwa M. Fahmy, Tamer M. Ibrahim, Doaa Ghareeb, Aya M. El-Seidy, Sherry N. Nasralla, and Alaa El-Din A. Bekhit, “Synthesis, in Silico Experiments and Biological Evaluation of 1,3,4-trisubstituted Pyrazole Derivatives as Antimalarial Agents,” European Journal of Medicinal Chemistry 163 (2019) : 353–66.
  • H. M. Faidallah, M. M. Al-Mohammadi, K. Alamry, and K. A. Khan, “Synthesis and Biological Evaluation of Fluoropyrazolesulfonylurea and Thiourea Derivatives as Possible Antidiabetic Agents,” Journal of Enzyme Inhibition and Medicinal Chemistry 31, no. sup1 (2016): 157–63.
  • A. Ozdemir, M. D. Altıntop, Z. A. Kaplancikli, O. D. Can, U. D. Ozkay, and G. T. Zitouni, “Synthesis and Evaluation of New 1,5-diaryl-3-[4-(methyl-sulfonyl)phenyl]-4,5-dihydro-1H-pyrazole derivatives as potential antidepressant agents,” Molecules (Basel, Switzerland) 20, no. 2 (2015): 2668–84.
  • A. R. Sayed, S. M. Gomha, F. M. Abdelrazek, M. S. Farghaly, S. A. Hassan, and P. Metz, “Design, Efficient Synthesis and Molecular Docking of Some Novel Thiazolyl‐Pyrazole Derivatives as Anticancer Agents,” BMC Chemistry 13, no. 1 (2019): 1–13.
  • A. M. Vijesh, A. M. Isloor, P. Shetty, S. Sundershan, and H. K. Fun, “New Pyrazole Derivatives Containing 1,2,4-Triazoles and Benzoxazoles as Potent Antimicrobial and Analgesic Agents,” European Journal of Medicinal Chemistry 62 (2013): 410–5.
  • G. S. Hassan, D. E. A. Rahman, E. A. Abdelmajeed, R. H. Refaey, M. A. Salem, and Y. M. Nissan, “New Pyrazole Derivatives: Synthesis, anti-Inflammatory Activity, Cycloxygenase Inhibition Assay and Evaluation of mPGES,” European Journal of Medicinal Chemistry 171, (2019) : 332–42.
  • H. Chuang, L. C. S. Huang, M. Kapoor, Y. J. Liao, C. L. Yang, C. C. Chang, C. Y. Wu, J. R. Hwu, T. J. Huang, and M. H. Hsu, “Design and Synthesis of Pyridine-Pyrazole-Sulfonate Derivatives Aspotential anti-HBV Agents,” MedChemComm 7, no. 5 (2016): 832–6.
  • Y. Hu, C. Y. Li, X. M. Wang, Y. H. Yang, and H. L. Zhu, “1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry,” Chemical Reviews 114, no. 10 (2014): 5572–610.
  • K. S. Bhat, D. J. Prasad, B. Poojary, and B. S. Holla, “Synthesis of Some New 1,2,4-Triazolo[3,4-b]-Thiadiazole Derivatives Possible Anticancer Agents,” Phosphorus, Sulfur, and Silicon and the Related Elements 179, no. 8 (2004): 1595–603.
  • S. M. I. Badr, and R. M. Barwa, “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, no. 15 (2011): 4506–12.
  • D. H. Purohit, B. L. Dodiya, R. M. Ghetiya, P. B. Vekariya, and H. S. Joshi, “Synthesis and Antimicrobial Activity of Some New 1,3,4-Thiadiazoles and 1,3,4-Thiadiazines Containing 1,2,4-Triazolo Nucleus,” Acta Chimica Slovenica 58, no. 1 (2011): 53–9.
  • M. Amir, H. Kumar, and S. A. Javed, “Condensed Bridgehead Nitrogen Heterocyclic System: Synthesis and Pharmacological Activities of 1,2,4-Triazolo-[3,4-b]-1,3,4-Thiadiazole Derivatives of Ibuprofen and Biphenyl-4-Yloxy Acetic Acid,” European Journal of Medicinal Chemistry 43, no. 10 (2008): 2056–66.
  • M. Amir, H. Kumar, and S. A. Javed, “Synthesis and Pharmacological Evaluation of Condensed Heterocyclic 6-Substituted-1,2,4-Triazolo[3,4-b]-1,3,4-Thiadiazole Derivatives of Naproxen,” Bioorganic & Medicinal Chemistry Letters 17, no. 16 (2007): 4504–8.
  • A. R. Farghaly, E. D. Clercq, and H. El-Kashef, “Synthesis and Antiviral Activity of Novel [1,2,4]Triazolo[3,4-b][1,3,4]Thiadiazoles, [1,2,4]Triazolo[3,4-b][1,3,4]Thiadiazines and [1,2,4]Triazolo[3,4-b][1,3,4] Thiadiazepines,” Arkivoc 10 (2006) : 137–51.
  • J. Ramprasad, N. Nayak, U. Dalimba, P. Yogeeswari, and D. Sriram, “ One-pot Synthesis of New Triazole-Imidazo[2,1-b][1,3,4]Thiadiazole Hybrids Via Click Chemistry and Evaluation of Their Antitubercular Activity,”Bioorganic & Medicinal Chemistry Letters 25no. 19 (2015): 4169–73.
  • A. Aliabadi, “1,3,4-Thiadiazole Based Anticancer Agents,” Anti-Cancer Agents in Medicinal Chemistry 16, no. 10 (2016): 1301–14.
  • N. Polkam, P. Rayam, J. S. Anireddy, S. Yennam, H. S. Anantaraju, S. Dharmarajan, Y. Perumal, S. S. Kotapalli, R. Ummanni, and S. Balasubramanian, “Synthesis, in Vitro Anticancer and Antimycobacterial Evaluation of New 5-(2,5-Dimethoxyphenyl)-1,3,4-Thiadiazole-2-Amino Derivatives,” Bioorganic & Medicinal Chemistry Letters 25, no. 7 (2015): 1398–402.
  • K. M. Dawood, and T. A. Farghaly, “Thiadiazole Inhibitors: A Patent Review,” Expert Opinion on Therapeutic Patents 27, no. 4 (2017): 477–505.
  • K. Vaarla, and R. R. Vedula, “Synthesis of 6-(5-Methylisoxazol-3yl)-3-Alkyl Sulfanyl-[1,2,4]Triazolo-[3,4-b][1,3,4]Thiadiazoles,” Journal of Heterocyclic Chemistry 52, no. 6 (2015): 1614–7.
  • P. Shyam, N. Veerababu, and B. Manjula, “Green Synthesis of Silver Nanoparticles Using Leaf Extract Medicinally Potent Plant Saracaindica: A Novel Study,” Applied Nanoscience 6 (2016) : 747–53.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.