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Research Articles

In Vitro and in Vivo Antidiabetics Study of New Oxadiazole Derivatives Along with Molecular Docking Study

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Pages 6911-6926 | Received 14 Feb 2022, Accepted 19 Sep 2022, Published online: 12 Oct 2022

References

  • H. Gao, Y.-N. Huang, P.-Y. Xu, and J. Kawabata, “Inhibitory Effect on α-Glucosidase by the Fruits of Terminalia Chebula Retz,” Food Chemistry 105, no. 2 (2007): 628–34.
  • B. D. Walker, M. Kowalski, W. C. Goh, K. Kozarsky, M. Krieger, C. Rosen, L. Rohrschneider, W. A. Haseltine, and J. Sodroski, “Inhibition of Human Immunodeficiency Virus Syncytium Formation and Virus Replication by Castanospermine,” Proceedings of the National Academy of Sciences of the United States of America 84, no. 22 (1987): 8120–4.
  • E. Gallienne, T. Gefflaut, J. Bolte, and M. Lemaire, “Synthesis of New Nitrogen Analogues of Salacinol and Deoxynojirimycin and Their Evaluation as Glycosidase Inhibitors,” The Journal of Organic Chemistry 71, no. 3 (2006): 894–902.
  • J. E. Groopman, “Current Advances in the Diagnosis and Treatment of AIDS: An Introduction,” Reviews of Infectious Diseases 12, no. 5 (1990): 908–11.
  • N. Zitzmann, A. S. Mehta, S. Carrouée, T. D. Butters, F. M. Platt, J. McCauley, B. S. Blumberg, R. A. Dwek, and T. M. Block, “Imino Sugars Inhibit the Formation and Secretion of Bovine Viral Diarrhea Virus, a Pestivirus Model of Hepatitis C Virus: Implications for the Development of Broad Spectrum anti-Hepatitis Virus Agents,” Proceedings of the National Academy of Sciences of the United States of America 96, no. 21 (1999): 11878–82.
  • H. Gao and J. Kawabata, “α-Glucosidase Inhibition of 6-Hydroxyflavones. Part 3: Synthesis and Evaluation of 2, 3, 4-Trihydroxybenzoyl-Containing Flavonoid Analogues and 6-Aminoflavones as α-Glucosidase Inhibitors,” Bioorganic & Medicinal Chemistry 13, no. 5 (2005): 1661–71.
  • N. Asano, H. Kizu, K. Oseki, E. Tomioka, K. Matsui, M. Okamoto, and M. Baba, “N-Alkylated Nitrogen-in-the-Ring Sugars: conformational Basis of Inhibition of Glycosidases and HIV-1 Replication,” Journal of Medicinal Chemistry 38, no. 13 (1995): 2349–56.
  • O. Muraoka, K. Yoshikai, H. Takahashi, T. Minematsu, G. Lu, G. Tanabe, T. Wang, H. Matsuda, and M. Yoshikawa, “Synthesis and Biological Evaluation of Deoxy Salacinols, the Role of Polar Substituents in the Side Chain on the α-Glucosidase Inhibitory Activity,” Bioorganic & Medicinal Chemistry 14, no. 2 (2006): 500–9.
  • L. J. Scott, and C. M. Spencer, “Miglitol,” Drugs 59, no. 3 (2000): 521–49.
  • D. Kumar, S. Sundaree, E. O. Johnson, and K. Shah, “An Efficient Synthesis and Biological Study of Novel Indolyl-1, 3, 4-Oxadiazoles as Potent Anticancer Agents,” Bioorganic & Medicinal Chemistry Letters 19, no. 15 (2009): 4492–4.
  • Q.-Z. Zheng, X.-M. Zhang, Y. Xu, K. Cheng, Q.-C. Jiao, and H.-L. Zhu, “Synthesis, Biological Evaluation, and Molecular Docking Studies of 2-Chloropyridine Derivatives Possessing 1, 3, 4-Oxadiazole Moiety as Potential Antitumor Agents,” Bioorganic & Medicinal Chemistry 18, no. 22 (2010): 7836–41.
  • M. Amir, S. Javed, and H. Kumar, “Synthesis of Some 1, 3, 4-Oxadiazole Derivatives as Potential anti-Inflammatory Agents,” Indian Journal of Chemistry Section B 46 (2007): 1014–9.
  • R. Saha, O. Tanwar, A. Marella, M. Mumtaz Alam, and M. Akhter, “Recent Updates on Biological Activities of Oxadiazoles,” Mini Reviews in Medicinal Chemistry 13, no. 7 (2013): 1027–46.
  • A. Zarghi, S. Hamedi, F. Tootooni, B. Amini, B. Sharifi, M. Faizi, et al, “Synthesis and Pharmacological Evaluation of New 2-Substituted-5-{2-[(2-Halobenzyl) Thio) Phenyl}-1, 3, 4-Oxadiazoles as Anticonvulsant Agents,” Scientia Pharmaceutica 76, no. 2 (2008): 185–201.
  • A. Zarghi, S. A. Tabatabai, M. Faizi, A. Ahadian, P. Navabi, V. Zanganeh, and A. Shafiee, “Synthesis and Anticonvulsant Activity of New 2-Substituted-5-(2-Benzyloxyphenyl)-1, 3, 4-Oxadiazoles,” Bioorganic & Medicinal Chemistry Letters 15, no. 7 (2005): 1863–5.
  • H. Chen, Z. Li, and J. Li, “Synthesis of 2-Pyrazoyl-5-Substituted-1, 3, 4-Oxadiazoles and Their Biological Activities,” Chemical Journal of Chinese Universities 21 (2000): 1520–3.
  • L. Jin, J. Chen, B. Song, Z. Chen, S. Yang, Q. Li, D. Hu, and R. Xu, “Synthesis, Structure, and Bioactivity of N′-Substituted Benzylidene-3, 4, 5-Trimethoxybenzohydrazide and 3-Acetyl-2-Substituted Phenyl-5-(3, 4, 5-Trimethoxyphenyl)-2, 3-Dihydro-1, 3, 4-Oxadiazole Derivatives,” Bioorganic & Medicinal Chemistry Letters 16, no. 19 (2006): 5036–40.
  • S.-J. Chao, X.-P. Hui, S. Li, Z.-Z. Qiu, P.-F. Xu, Z.-Y. Zhang, Q. Wang, and Z.-W. Guan, “Synthesis and Antibacterial Activities of Novel Biphenyltetrazole Derivatives Bearing 1, 3, 4‐Oxadiazole,” Journal of the Chinese Chemical Society 52, no. 3 (2005): 539–44.
  • M. R. Banday, R. H. Mattoo, and A. Rauf, “Synthesis, Characterization and anti-Bacterial Activity of 5-(Alkenyl)-2-Amino-and 2-(Alkenyl)-5-Phenyl-1, 3, 4-Oxadiazoles,” Journal of Chemical Sciences 122, no. 2 (2010): 177–82.
  • C.-J. Chen, B.-A. Song, S. Yang, G.-F. Xu, P. S. Bhadury, L.-H. Jin, D.-Y. Hu, Q.-Z. Li, F. Liu, W. Xue, et al, “Synthesis and Antifungal Activities of 5-(3, 4, 5-Trimethoxyphenyl)-2-Sulfonyl-1, 3, 4-Thiadiazole and 5-(3, 4, 5-Trimethoxyphenyl)-2-Sulfonyl-1, 3, 4-Oxadiazole Derivatives,” Bioorganic & Medicinal Chemistry 15, no. 12 (2007): 3981–9.
  • M. Kettles, S. R. Browning, T. S. Prince, and S. W. Horstman, “Triazine Herbicide Exposure and Breast Cancer Incidence: An Ecologic Study of Kentucky Counties,” Environmental Health Perspectives. 105, no. 11 (1997): 1222–7.
  • L. Hu, Z.-R. Li, Y. Li, J. Qu, Y.-H. Ling, J.-D. Jiang, and D. W. Boykin, “Synthesis and Structure − Activity Relationships of Carbazole Sulfonamides as a Novel Class of Antimitotic Agents against Solid Tumors,” Journal of Medicinal Chemistry 49, no. 21 (2006): 6273–82.
  • S. S. Abd El-Karim, M. M. Anwar, Y. M. Syam, M. A. Nael, H. F. Ali, and M. A. Motaleb, “Rational Design and Synthesis of New Tetralin-Sulfonamide Derivatives as Potent anti-Diabetics and DPP-4 Inhibitors: 2D & 3D QSAR, in Vivo Radiolabeling and Bio Distribution Studies,” Bioorganic Chemistry 81 (2018): 481–93.
  • P. Mikuš, D. Krajčiová, M. Mikulová, B. Horváth, D. Pecher, V. Garaj, S. Bua, A. Angeli, and C. T. Supuran, “Novel Sulfonamides Incorporating 1, 3, 5-Triazine and Amino Acid Structural Motifs as Inhibitors of the Physiological Carbonic Anhydrase Isozymes I, II and IV and Tumor-Associated Isozyme IX,” Bioorganic Chemistry 81 (2018): 241–52.
  • N. Buğday, F. Z. Küçükbay, H. Küçükbay, S. Bua, G. Bartolucci, J. Leitans, A. Kazaks, K. Tars, and C. T. Supuran, “Synthesis of Novel Dipeptide Sulfonamide Conjugates with Effective Carbonic Anhydrase I, II, IX, and XII Inhibitory Properties,” Bioorganic Chemistry 81 (2018): 311–8.
  • W. M. Eldehna, A. Nocentini, S. T. Al-Rashood, G. S. Hassan, H. M. Alkahtani, A. A. Almehizia, A. M. Reda, H. A. Abdel-Aziz, and C. T. Supuran, “Tumor-Associated Carbonic Anhydrase Isoform IX and XII Inhibitory Properties of Certain Isatin-Bearing Sulfonamides Endowed with in Vitro Antitumor Activity towards Colon Cancer,” Bioorganic Chemistry 81 (2018): 425–32.
  • M. Abdul Qadir, M. Ahmed, and M. Iqbal, “Synthesis, Characterization, and Antibacterial Activities of Novel Sulfonamides Derived through Condensation of Amino Group Containing Drugs, Amino Acids, and Their Analogues,” BioMed Research International 2015 (2015): 938486.
  • M. Taha, N. H. Ismail, S. Imran, M. H. Mohamad, A. Wadood, F. Rahim, S. M. Saad, A. U. Rehman, and K. M. Khan, “Synthesis, α-Glucosidase Inhibitory, Cytotoxicity and Docking Studies of 2-Aryl-7-Methylbenzimidazoles,” Bioorganic Chemistry 65 (2016): 100–9.
  • S. Imran, M. Taha, N. H. Ismail, S. M. Kashif, F. Rahim, W. Jamil, H. Wahab, and K. M. Khan, “Synthesis, in Vitro and Docking Studies of New Flavone Ethers as α‐Glucosidase Inhibitors,” Chemical Biology & Drug Design 87, no. 3 (2016): 361–73.
  • M. Taha, N. H. Ismail, S. Imran, A. Wadood, F. Rahim, S. M. Saad, K. M. Khan, and A. Nasir, “Synthesis, Molecular Docking and α-Glucosidase Inhibition of 5-Aryl-2-(6′-Nitrobenzofuran-2′-yl)-1, 3, 4-Oxadiazoles,” Bioorganic Chemistry 66 (2016): 117–23.
  • N. K. N. A. Zawawi, M. Taha, N. Ahmat, N. H. Ismail, A. Wadood, F. Rahim, and A. U. Rehman, “Synthesis, in Vitro Evaluation and Molecular Docking Studies of Biscoumarin Thiourea as a New Inhibitor of Aglucosidases Bioorg,” Bioorganic Chemistry 63 (2015): 36–44.
  • M. Taha, N. H. Ismail, K. Javaid, S. Imran, E. H. Anouar, A. Wadood, M. Ali, K. M. Khan, S. M. Saad, F. Rahim, et al, “Evaluation of 2-Indolcarbohydrazones as Potent α-Glucosidase Inhibitors, in Silico Studies and DFT Based Stereochemical Predictions,” Bioorganic Chemistry 63 (2015): 24–35.
  • M. Taha, N. H. Ismail, S. Imran, A. Wadood, F. Rahim, M. Ali, and A. U. Rehman, “Novel Quinoline Derivatives as Potent in Vitro α-Glucosidase Inhibitors: In Silico Studies and SAR Predictions,” MedChemComm 6, no. 10 (2015): 1826–36.
  • F. Rahim, F. Malik, H. Ullah, A. Wadood, F. Khan, M. T. Javid, M. Taha, W. Rehman, A. Ur Rehman, K. M. Khan, et al, “Isatin Based Schiff Bases as Inhibitors of α-Glucosidase: Synthesis, Characterization, in Vitro Evaluation and Molecular Docking Studies,” Bioorganic Chemistry 60 (2015): 42–8.
  • M. Taha, N. H. Ismail, M. S. Baharudin, S. Lalani, S. Mehboob, K. M. Khan, S. Yousuf, S. Siddiqui, F. Rahim, M. I. Choudhary, et al, “Synthesis Crystal Structure of 2-Methoxybenzoylhydrazones and Evaluation of Their α-Glucosidase and Urease Inhibition Potential,” Medicinal Chemistry Research 24, no. 3 (2015): 1310–24.
  • K. M. Khan, F. Rahim, A. Wadood, N. Kosar, M. Taha, S. Lalani, A. Khan, M. I. Fakhri, M. Junaid, W. Rehman, et al, “Synthesis and Molecular Docking Studies of Potent α-Glucosidase Inhibitors Based on Biscoumarin Skeleton,” European Journal of Medicinal Chemistry 81 (2014): 245–52.
  • M. Taha, N. H. Ismail, S. Imran, A. Wadood, M. Ali, F. Rahim, A. A. Khan, and M. Riaz, “Novel Thiosemicarbazide–Oxadiazole Hybrids as Unprecedented Inhibitors of Yeast α-Glucosidase and in Silico Binding Analysis,” RSC Advances 6, no. 40 (2016): 33733–42.
  • F. Rahim, H. Ullah, M. T. Javid, A. Wadood, M. Taha, M. Ashraf, A. Shaukat, M. Junaid, S. Hussain, W. Rehman, et al, “Synthesis, in Vitro Evaluation and Molecular Docking Studies of Thiazole Derivatives as New Inhibitors of α-Glucosidase,” Bioorganic Chemistry 62 (2015): 15–21.
  • F. Rahim, K. Ullah, H. Ullah, A. Wadood, M. Taha, A. Ur Rehman, I. Uddin, M. Ashraf, A. Shaukat, W. Rehman, et al, “Triazinoindole Analogues as Potent Inhibitors of α-Glucosidase: Synthesis, Biological Evaluation and Molecular Docking Studies,” Bioorganic Chemistry 58 (2015): 81–7.
  • S. Imran, M. Taha, N. H. Ismail, S. M. Kashif, F. Rahim, W. Jamil, M. Hariono, M. Yusuf, and H. Wahab, “Synthesis of Novel Flavone Hydrazones: In-Vitro Evaluation of α-Glucosidase Inhibition, QSAR Analysis and Docking Studies,” European Journal of Medicinal Chemistry 105 (2015): 156–70.
  • W. D. Seo, J. H. Kim, J. E. Kang, H. W. Ryu, M. J. Curtis-Long, H. S. Lee, M. S. Yang, and K. H. Park, “Sulfonamide Chalcone as a New Class of α-Glucosidase Inhibitors,” Bioorganic & Medicinal Chemistry Letters 15, no. 24 (2005): 5514–6.
  • T. Tagami, K. Yamashita, M. Okuyama, H. Mori, M. Yao, and A. Kimura, “Molecular Basis for the Recognition of Long-Chain Substrates by Plant α-Glucosidases,” The Journal of Biological Chemistry 288, no. 26 (2013): 19296–303.
  • H. A. Abuelizz, R. E. Dib, M. Marzouk, E.-H. Anouar, Y. A. Maklad, H. N. Attia, and R. Al-Salahi, “Molecular Docking and Anticonvulsant Activity of Newly Synthesized Quinazoline Derivatives,” Molecules 22, no. 7 (2017): 1094.
  • H. Ullah, F. Rahim, M. Taha, R. Hussain, N. Tabassum, A. Wadood, M. Nawaz, A. Mosaddik, S. Imran, Z. Wahab, et al, “Aryl-Oxadiazole Schiff Bases: Synthesis, α-Glucosidase in Vitro Inhibitory Activity and Their in Silico Studies,” Arab J Chem 13, no. 4 (2020): 4904–15.
  • M. Taha, S. Imran, M. Salahuddin, N. Iqbal, F. Rahim, N. Uddin, A. Shehzad, R. Khalid Farooq, M. Alomari, K. Mohammed Khan, et al, “Evaluation and Docking of Indole Sulfonamide as a Potent Inhibitor of α-Glucosidase Enzyme in Streptozotocin–Induced Diabetic Albino Wistar Rats,” Bioorganic Chemistry 110 (2021): 104808.
  • M. Salahuddin, S. S. Jalalpure, and N. B. Gadge, “Antidiabetic Activity of Aqueous Bark Extract of Cassia Glauca in Streptozotocin-Induced Diabetic Rats,” Canadian Journal of Physiology and Pharmacology 88, no. 2 (2010): 153–60.

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