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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 24
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Articles

Synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from (2S)-3-(benzyloxy)-2-[(tert-butoxycarbonyl) amino] propanoic acid and evaluation of anti-microbial activity

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Pages 3854-3864 | Received 03 Jul 2020, Published online: 11 Sep 2020

References

  • Ashraf, S. H.; Gaber, O. M.; Ahmed, A. A.; Ahmed, M. N.; Mohamed, A. A. Synthesis and anti-Bacterial Evaluation of Fused Pyrazoles and Schiff Bases. Synth. Commun. 2018, 48, 2761–2772. DOI: 10.1080/00397911.2018.1524492.
  • Khan, I.; Ali, S.; Hameed, S.; Rama, N. H.; Hussain, M. T.; Wadood, A.; Uddin, R.; Ul-Haq, Z.; Khan, A.; Ali, S.; Choudhary, M. I. Synthesis, Antioxidant Activities and Urease Inhibition of Some New 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives. Eur. J. Med. Chem. 2010, 45, 5200–5207. DOI: 10.1016/j.ejmech.2010.08.034.
  • Lee, J.; Lee, H.; Seo, H.; Son, E.; Lee, S.; Jung, M.; Lee, M.; Han, H.; Kim, J.; Kang, J.; et al. Novel C-Aryl Glucoside SGLT2 Inhibitors as Potential Antidiabetic Agents: 1,3,4-Thiadiazolylmethylphenyl Glucoside Congeners. Bioorg. Med. Chem. 2010, 18, 2178–2194. DOI: 10.1016/j.bmc.2010.01.073.
  • Li, P.; Shi, L.; Yang, X.; Yang, L.; Chen, X.; Wu, F.; Shi, Q.; Xu, W.; He, M.; Hu, Y.; et al. Design, Synthesis, and Antibacterial Activity Against Rice Bacterial Leaf Blight and Leaf Streak of 2,5-Substituted-1,3,4-Oxadiazole/Thiadiazole Sulfone Derivative. Bioorg. Med. Chem. Lett. 2014, 24, 1677–1680. DOI: 10.1016/j.bmcl.2014.02.060.
  • Liu, F.; Luo, X.; Song, B.; Bhadury, P.; Yang, S.; Jin, L.; Xue, W.; Hu, D. Synthesis and Antifungal Activity of Novel Sulfoxide Derivatives Containing Trimethoxyphenyl Substituted 1,3,4-Thiadiazole and 1,3,4-Oxadiazole Moiety. Bioorg. Med. Chem. 2008, 16, 3632–3640. DOI: 10.1016/j.bmc.2008.02.006.
  • Xu, W.; Li, S.; He, S.; Yang, S.; Li, X.; Li, P. Synthesis and Bioactivities of Novel Thioether/Sulfone Derivatives Containing 1,2,3-Thiadiazole and 1,3,4-Oxadiazole/Thiadiazole Moiety. Bioorg. Med. Chem. Lett. 2013, 23, 5821–5824. DOI: 10.1016/j.bmcl.2013.08.107.
  • Yusuf, M.; Khan, R.; Ahmed, B. Syntheses and Anti-Depressant Activity of 5-Amino-1, 3, 4-Thiadiazole-2-Thiol Imines and Thiobenzyl Derivatives. Bioorg. Med. Chem. 2008, 16, 8029–8034. DOI: 10.1016/j.bmc.2008.07.056.
  • Amir, M.; Kumar, H.; Javed, S. Non-carboxylic Analogues of Naproxen: Design, Synthesis, and Pharmacological Evaluation of some 1,3,4-Oxadiazole/Thiadiazole and 1,2,4-Triazole Derivatives. Arch. Pharm. 2007, 340, 577–585. DOI: 10.1002/ardp.200700065.
  • Zhang, K.; Wang, P.; Xuan, L.; Fu, X.; Jing, F.; Li, S.; Liu, Y.; Chen, B. Synthesis and Antitumor Activities of Novel Hybrid Molecules Containing 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Bearing Schiff Base Moiety. Bioorg. Med. Chem. Lett. 2014, 24, 5154–5156. DOI: 10.1016/j.bmcl.2014.09.086.
  • Tahghighi, A.; Babalouei, F. Thiadiazoles: The Appropriate Pharmacological Scaffolds with Leishmanicidal and Antimalarial Activities: A Review. Iran. J. Basic Med. Sci. 2017, 20, 613–622. DOI: 10.22038/IJBMS.2017.8828.
  • Mounika, K.; Anupama, B.; Pragathi, J.; Gyanakumari, C. Synthesis, Characterization and Biological Activity of a Schiff Base Derived from 3-Ethoxy Salicylaldehyde and 2-Amino Benzoic Acid and Its Transition Metal Complexes. J. Sci. Res. 2010, 2, 513–524. DOI: 10.3329/jsr.v2i3.4899.
  • Chaubey, A.; Pandeya, S. Synthesis & Anticonvulsant Activity (Chemo Shock) of Schiff and Mannich Bases of Isatin Derivatives with 2-Amino Pyridine (Mechanism of Action*). Int. J. PharmTech Res. 2012, 4, 590–598.
  • Aboul-Fadl, T.; Mohammed, F.; Hassan, E. Synthesis, Antitubercular Activity and Pharmacokinetic Studies of Some Schiff Bases Derived from 1-Alkylisatin and Isonicotinic Acid Hydrazide (INH). Arch. Pharm. Res. 2003, 26, 778–784. DOI: 10.1007/BF02980020.
  • Miri, R.; Razzaghi-Asl, N.; Mohammad, M. QM Study and Conformational Analysis of an Isatin Schiff Base as a Potential Cytotoxic Agent. J. Mol. Model. 2013, 19, 727–735. DOI: 10.1007/s00894-012-1586-x.
  • Sondhi, S.; Singh, N.; Kumar, A.; Lozach, O.; Meijer, L. Synthesis, Anti-inflammatory, Analgesic and Kinase (CDK-1, CDK-5 and GSK-3) Inhibition Activity Evaluation of Benzimidazole/Benzoxazole Derivatives and Some Schiff's Bases. Bioorg. Med. Chem. 2006, 14, 3758–3765. DOI: 10.1016/j.bmc.2006.01.054.
  • Chinnasamy, R.; Sundararajan, R.; Govindaraj, S. Synthesis, Characterization, and Analgesic Activity of Novel Schiff Base of Isatin Derivatives. J. Adv. Pharm. Technol. Res. 2010, 1, 342–347. DOI: 10.4103/0110-5558.72428.
  • Wei, D.; Li, N.; Lu, G.; Yao, K. Synthesis, Catalytic and Biological Activity of Novel Dinuclear Copper Complex with Schiff Base. Sci. China Ser. B. 2006, 49, 225–229. DOI: 10.1007/s11426-006-0225-8.
  • Avaji, P.; Kumar, C.; Patil, S.; Shivananda, K.; Nagaraju, C. Synthesis, Spectral Characterization, In-vitro Microbiological Evaluation and Cytotoxic Activities of Novel Macrocyclic bis Hydrazone. Eur. J. Med. Chem. 2009, 44, 3552–3559. DOI: 10.1016/j.ejmech.2009.03.032.
  • Venugopala, K.; Jayashree, B. Synthesis of Carboxamides of 2′-Amino-4′-(6-Bromo-3-Coumarinyl)Thiazole as Analgesic and Anti-Inflammatory Agents. Indian J. Heterocycl. Chem. 2003, 12, 307–310.
  • Foroumadi, A.; Rineh, A.; Emami, S.; Siavoshi, F.; Massarrat, S.; Safari, F.; Rajabalian, S.; Falahati, M.; Lotfali, E.; Shafiee, A. Synthesis and Anti-Helicobacter pylori Activity of 5-(Nitroaryl)-1,3,4-Thiadiazoles with Certain Sulfur Containing Alkyl Side Chain. Bioorg. Med. Chem. Lett. 2008, 18, 3315–3320. DOI: 10.1016/j.bmcl.2008.04.033.
  • Talath, S.; Gadad, A. Synthesis, Antibacterial and Antitubercular Activities of Some 7-[4-(5-Amino-[1,3,4]Thiadiazole-2-Sulfonyl)-Piperazin-1-yl] Fluoroquinolonic Derivatives. Eur. J. Med. Chem. 2006, 41, 918–924. DOI: 10.1016/j.ejmech.2006.03.027.
  • Menteşe, E.; Ülker, S.; Kahveci, B. Synthesis and Study of α-Glucosidase Inhibitory, *anti-Microbial and Antioxidant Activities of Some Benzimidazole Derivatives Containing Triazole, Thiadiazole, Oxadiazole, and Morpholine Rings. Chem. Heterocycl. Comp. 2015, 50, 1671–1682. DOI: 10.1007/s10593-015-1637-1.
  • Bagihalli, G.; Avaji, P.; Patil, S.; Badami, P. Synthesis, Spectral Characterization, *in Vitro Antibacterial, Antifungal and Cytotoxic Activities of Co(II), Ni(II) and Cu(II) Complexes with 1,2,4-Triazole Schiff Bases. Eur. J. Med. Chem. 2008, 43, 2639–2649. DOI: 10.1016/j.ejmech.2008.02.013.
  • Jarrahpour, A.; Khalili, D.; Clercq, E.; Salmi, C.; Brunel, J. Synthesis, Antibacterial, Antifungal and Antiviral Activity Evaluation of Some New bis-Schiff Bases of Isatin and their Derivatives. Molecules. 2007, 12, 1720–1730. DOI: 10.3390/12081720.
  • Asati, K.; Srivastava, S. Synthesis of 5-Arylidene-2-Aryl-3-(Benzotriazoloacetamidyl)-1, 3-Thiazolidin-4-Ones as Analegesic and Anti-Microbial Agents. Indian J. Chem. 2006, 45, 526–531.
  • Sharma, R.; Misra, G. P.; Sainy, J.; Chaturvedi, S. C. Synthesis and Biological Evaluation of 2-Amino-5-Sulfanyl-1, 3, 4-Thiadiazole Derivatives as Antidepressant, Anxiolytics and Anticonvulsant Agents. Med. Chem. Res. 2011, 20, 245–253. DOI: 10.1007/s00044-010-9308-3.
  • Sonwane, S.; Srivastava, S. Synthesis and Biological Significance of 2-Amino-4-Phenyl-1, 3-Thiazole Derivatives. Proc. Natl. Acad. Sci. 2008, 78A, 129–136.
  • Jalhan, S.; Jindal, A.; Gupta, A.; Hemraj, H. Synthesis, Biological Activities and Chemistry of Thiadiazole Derivatives and Schiff Bases. Asian J. Pharm. Clin. Res. 2012, 5, 199–208.
  • Mousa, M. Synthesis, Characterization and Evaluation of Anti-Bacterial Activity of 1, 3, 4-Thiadiazole Derivatives Containing Schiff Bases. J. Chem. Pharm. Res. 2017, 9, 196–200.
  • Naveen, M.; Shiva, K.; Chandan, S.; Prasad, N. Synthesis and Characterization of Thiadiazole Containing Schiff Base: Anti-Microbial Activity. Der Pharma Chemica 2014, 6, 10–14.
  • Pandey, A.; Rajavel, R.; Chandraker, R.; Dash, D. Synthesis of Schiff Bases of 2-Amino-5-Aryl-1, 3, 4-Thiadiazole and Its Analgesic, Anti-Inflammatory and Anti-Bacterial Activity. E-J. Chem. 2012, 9, 2524–2531. DOI: 10.1155/2012/145028.
  • Gharu, C. Green and Efficient Protocol for Synthesis of Schiff Bases and Hydroxyl Derivatives of 1, 3, 4-Thiadiazole Containing n-Phenyl Piperazine Moiety and Their Anti-Microbial and Antioxidant Potential. Res. J. Chem. Sci. 2014, 4, 43–47.
  • Hassan, F.; Hairunisa, N.; Mohammed, S.; Yousif, E. A Study on Antitumor Effect of 1, 3, 4-Thiadiazole Derivatives in Prostate and Breast Cancer Cell Lines (In Vitro). Preprints 2017, 2017030053. DOI: 10.20944/preprints201703.0053.v1.
  • Kemparajegowda; Hassan, A.; Nagarakere, C.; Rangappa, S.; Kempegowda, M.; Kanchugarakoppal, S. Efficient One‐Pot Synthesis of 3, 5‐Disubstituted 1, 3, 4‐Thiadiazole from Dithioesters under Mild Condition. Chem. Select. 2019, 4, 4611–4614. DOI: 10.1002/slct.201900630.
  • Lundberg, H.; Tinnis, F.; Selander, N.; Adolfsson, H. Catalytic Amide Formation from Non-*Activated Carboxylic Acids and Amines. Chem. Soc. Rev. 2014, 43, 2714–2742. DOI: 10.1039/c3cs60345h.
  • Hu, Y.; Li, C.; Wang, M.; Yang, H.; Zhu, L. 1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry. Chem. Rev. 2014, 114, 5572–5610. DOI: 10.1021/cr400131u.
  • Nagendra, G.; Lamani, R.; Narendra, N.; Sureshbabu, V. A Convenient Synthesis of 1, 3, 4-Thiadiazole and 1, 3, 4-Oxadiazole Based Peptidomimetics Employing Diacylhydrazines Derived from Amino Acids. Tetrahedron Lett. 2010, 51, 6338–6341. DOI: 10.1016/j.tetlet.2010.09.122.
  • Cui, N.; Li, S.; Hu, K.; Tian, H.; Jiang, Z.; Wang, Y.; Yan, J. Synthesis and Fungicidal Activity of Novel 2, 5-Disubstituted-1, 3, 4-Thiadiazole Derivatives Containing 5-Phenyl-2-Furan. Sci. Rep. 2016, 6, 20204. DOI: 10.1038/srep20204.
  • Zarei, M. One-Pot Synthesis of 1, 3, 4-Thiadiazoles Using Vilsmeier Reagent as a Versatile Cyclodehydration Agent. Tetrahedron. 2017, 73, 1867–1872. DOI: 10.1016/j.tet.2017.02.042.
  • Li, J.; Chen, S. Y.; Tao, S.; Wang, H.; Li, J. J.; Swartz, S.; Musial, C.; Hernandez, A. A.; Flynn, N.; Murphy, B. J.; et al. Design and Synthesis of Tetrazole-Based Growth Hormone Secretagogue: The SAR Studies of the O-Benzyl Serine Side Chain. Bioorg. Med. Chem. Lett. 2008, 18, 1825–1829. DOI: 10.1016/j.bmcl.2008.02.021.
  • Tang, J.; Liu, J.; Wu, F. Molecular Docking Studies and Biological Evaluation of 1,3,4-Thiadiazole Derivatives Bearing Schiff Base Moieties as Tyrosinase Inhibitors. Bioorg. Chem. 2016, 69, 29–36. DOI: 10.1016/j.bioorg.2016.09.007.
  • Kumar, N.; Kumar, M.; Chang, K.; Shah, K. Synthesis and Anticancer Activity of 5-(3-Indolyl)-1,3,4-Thiadiazoles. Eur. J. Med. Chem. 2010, 45, 4664–4668. DOI: 10.1016/j.ejmech.2010.07.023.
  • Staab, H. New Methods of Preparative Organic Chemistry IV. Syntheses Using Heterocyclic Amides (Azolides). Angew. Chem. Int. Ed. Engl. 1962, 1, 351–367. DOI: 10.1002/anie.196203511.

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