How to cite this paper
Dhuda, G., Kapadiya, K., Ladwa, P & Modha, J. (2020). S-Methylene linkage comprising 1,3,4-oxadiazoles: synthesis, reaction optimization and in vitro anti-microbial potential.Current Chemistry Letters, 10(2), 109-118.
Refrences
1. Adil A., Othman M., and Sarah A. (2019) 1,3,4-Oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole derivatives as potential anti-bacterial agents. Arab. J. Chem., 12 (7) 1660-1675.
2. (a) Yang S. J., Lee S. H., Kwak H. J., and Gong Y. D. (2013) Regio selective Synthesis of 2-Amino-Substituted 1,3,4-Oxadiazole and 1, 3, 4-Thiadiazole Derivatives via Reagent-Based Cyclization of Thiosemicarbazide Intermediate. J. Org. Chem., 78 438-444. (b) Prezent M.A., and Baranin S.V. (2019) A convenient route to the 1,2,5-oxadiazole-substituted 1,2,4-triazolo[1,5-a]pyrimidine derivatives. Chem Heterocycl Comp., 55 1131–1134.
3. Badran M., Moneer A., Rafaat H., and El-Malah A. (2007) Synthesis and Anti-microbial Activity of Novel Quinoxaline Derivatives. J. Chin. Chem. Soc., 54 (2) 469-478.
4. Plech T., Wujec M., Siwek A., Kosikowska U., and Malm A. (2013) The effect of C-5 substituent on anti-bacterial activity. Med Chem Res., 22 2531.
5. Sun X., Hong Z., Liu M., Guo S., Yang D., Wang Y., Lan T., Gao L., Qi H., and Gong P. (2017) Design, synthesis, and biological activity of novel tetrahydropyrazolopyridone derivatives as FXa inhibitors with potent anticoagulant activity. Bioorg. Med. Chem., 25 (10) 2800-2810.
6. Mickevičius V., Vaickelionienė R., and Sapijanskaitė B. (2009) Synthesis of substituted 1,3,4-oxadiazole derivatives. Chem Heterocycl Comp., 45 215-218.
7. Stephens C., Tanious F., Kim, S., Wilson W., Schell W., Perfect J., Franzblau S., and Boykin D. (2001) Diguanidino and “Reversed” Diamidino 2,5-Diarylfurans as Antimicrobial Agents. J. Med. Chem., 44 (11) 1741-1748.
8. (a) Abd El-Meguid E., Awad H., and Anwar M. (2019) Synthesis of New 1,3,4-Oxadiazole-benzimidazole Derivatives as Potential Antioxidants and Breast Cancer Inhibitors with Apoptosis Inducing Activity. Russ. J. Gen. Chem., 89, 348-356. (b) Mohi El-Deen E., Mohamed N.A., El-Serwy W., Abdelghany T., and Nossier E., (2016) Synthesis, molecular docking and cytotoxicity evaluation of novel 1,2-disubstituted benzimidazole derivatives against liver and breast cancer cell lines. Res J Pharm Biol Chem Sci., 7, 1599-1615.
9. Singh A., Lohani M., and Parthsarthy R. (2013) Synthesis, Characterization and Anti-Inflammatory Activity of Some 1, 3,4 -Oxadiazole Derivatives. Iran. J. Pharm. Res., 12 (2) 319–323.
10. Zheng X., Li Z., Wang Y., Chen W., Huang Q., Liu C., and Song G. (2003) Synthesis and insecticidal activities of novel 2,5-disubstituted-1,3,4-oxadiazoles. J. Fluorine Chem., 123 163-169.
11. Almasirad A., Tabatabai S., Faizi M., Kebriaeezadeh A., Mehrabi N., Dalvandi A., and Shafiee, A. (2004) Synthesis and anticonvulsant activity of new 2-substituted-5- [2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles. Bioorg. Med.Chem. Lett., 24 6057-6059.
12. Mochona B., Qi X., Euynni S., Sikazwi D., Mateeva N., and Soliman K. (2016) Design and Evaluation of Novel Oxadiazole Derivatives as Potential Prostate Cancer Agents. Bioorg. Med.Chem. Lett., 26 (12) 2847-2851.
13. Kadi A., El-Brollosy N., Al-Deeb O., Habib E., Ibrahim T., and El-Emam A. (2007) Synthesis, anti-microbial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. Eur. J. Med. Chem., 42 235-242.
14. Ramazani A., and Souldozi A. (2008) Iminophosphorane-mediated one-pot synthesis of 1,3,4-oxadiazole derivatives. Arkivoc, 16 235-242.
15. Ramazani A., Ahmadi Y., and Tarasi R. (2011) Efficient One-Pot Synthesis of Disubstituted 1,3,4-Oxadiazole Derivatives from the Reaction of (N-Isocyanimino)triphenylphosphorane, Acetaldehyde, a Secondary Amine, and an Electron-Poor (E)-Cinnamic Acid. Heteroat. Chem., 22 (1) 79-84.
16. (a) Lu J., Jiang F., Lu A., and Zhang G. (2016) Linkers Having a Crucial Role in Antibody-Drug Conjugates. Int J Mol Sci., 17 561. (b) Krishna, C., Bhargavi, M., and Krupadanam, G. (2018) Design, Synthesis, and Cytotoxicity of Semisynthetic Betulinic Acid-1,2,4-Oxadiazole Amide Derivatives. Russ. J. Gen. Chem., 88 312–318.
17. Zhao T., Zhao Z., and Lu F. (2020) Two- and three-dimensional QSAR studies on hURAT1 inhibitors with flexible linkers: topomer CoMFA and HQSAR. Mol Divers., 24 141-154.
18. Cramer R., Patterson D., and Bunce J. (1988) Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc., 110 (18) 5959-5967.
19. Rayam P., Polkam N., Kummari B., Banothu V., Gandamalla D., Reddy N., and Anireddy J. (2019) Synthesis and Biological Evaluation of New Ibuprofen‐1,3,4‐oxadiazole‐1,2,3‐triazole Hybrids. J. Heterocycl. Chem., 56 (1) 296-305.
20. Jasiński, R. (2015) On the question of zwitterionic intermediates in 1,3-dipolar cycloadditions between hexafluoroacetone and sterically crowded diazocompounds. J. Fluor. Chem., 176 35-39.
21. Iyer, V., Gurupadayya B., Koganti V., Inturi B., and Chandan R. (2017) Design, synthesis and biological evaluation of 1,3,4-oxadiazoles as promising anti-inflammatory agents. Med Chem Res., 26 190–204.
22. Muhi-eldeen Z., Juma’a G., Al-kaissi, G., and Nouri L. (2008) Anti-microbial activity of some new oxadiazole derivatives. Jordan J. Chem., 3 (3) 233-243.
23. Wang S., Wang K., Kong X., Zhang S., Jiang G., Ji F. (2019) DMF as Methine Source: Copper‐Catalyzed Direct Annulation of Hydrazides to 1,3,4‐Oxadiazoles. Adv. Synth. Catal., 361 (17) 3986-3990.
24. de Oliveira C., Lira B., Barbosa-Filho J., Lorenzo J., and de Athayde-Filho P. (2012) Synthetic approaches and pharmacological activity of 1,3,4-oxadiazoles: a review of the literature from 2000-2012. Molecules, 17 (9) 10192-10231.
25. Kapadiya K., Kotadiya R., Kavadia K., Kothari R., Mehariya K., and Khunt R. (2015) Synthesis and Microbial Evaluation of Versatile Base Catalyzed Chiral Tetrahydrobenzofuran Derivatives via Multicomponent Reaction. Lett Drug Des Discov., 13 (6) 505-513.
2. (a) Yang S. J., Lee S. H., Kwak H. J., and Gong Y. D. (2013) Regio selective Synthesis of 2-Amino-Substituted 1,3,4-Oxadiazole and 1, 3, 4-Thiadiazole Derivatives via Reagent-Based Cyclization of Thiosemicarbazide Intermediate. J. Org. Chem., 78 438-444. (b) Prezent M.A., and Baranin S.V. (2019) A convenient route to the 1,2,5-oxadiazole-substituted 1,2,4-triazolo[1,5-a]pyrimidine derivatives. Chem Heterocycl Comp., 55 1131–1134.
3. Badran M., Moneer A., Rafaat H., and El-Malah A. (2007) Synthesis and Anti-microbial Activity of Novel Quinoxaline Derivatives. J. Chin. Chem. Soc., 54 (2) 469-478.
4. Plech T., Wujec M., Siwek A., Kosikowska U., and Malm A. (2013) The effect of C-5 substituent on anti-bacterial activity. Med Chem Res., 22 2531.
5. Sun X., Hong Z., Liu M., Guo S., Yang D., Wang Y., Lan T., Gao L., Qi H., and Gong P. (2017) Design, synthesis, and biological activity of novel tetrahydropyrazolopyridone derivatives as FXa inhibitors with potent anticoagulant activity. Bioorg. Med. Chem., 25 (10) 2800-2810.
6. Mickevičius V., Vaickelionienė R., and Sapijanskaitė B. (2009) Synthesis of substituted 1,3,4-oxadiazole derivatives. Chem Heterocycl Comp., 45 215-218.
7. Stephens C., Tanious F., Kim, S., Wilson W., Schell W., Perfect J., Franzblau S., and Boykin D. (2001) Diguanidino and “Reversed” Diamidino 2,5-Diarylfurans as Antimicrobial Agents. J. Med. Chem., 44 (11) 1741-1748.
8. (a) Abd El-Meguid E., Awad H., and Anwar M. (2019) Synthesis of New 1,3,4-Oxadiazole-benzimidazole Derivatives as Potential Antioxidants and Breast Cancer Inhibitors with Apoptosis Inducing Activity. Russ. J. Gen. Chem., 89, 348-356. (b) Mohi El-Deen E., Mohamed N.A., El-Serwy W., Abdelghany T., and Nossier E., (2016) Synthesis, molecular docking and cytotoxicity evaluation of novel 1,2-disubstituted benzimidazole derivatives against liver and breast cancer cell lines. Res J Pharm Biol Chem Sci., 7, 1599-1615.
9. Singh A., Lohani M., and Parthsarthy R. (2013) Synthesis, Characterization and Anti-Inflammatory Activity of Some 1, 3,4 -Oxadiazole Derivatives. Iran. J. Pharm. Res., 12 (2) 319–323.
10. Zheng X., Li Z., Wang Y., Chen W., Huang Q., Liu C., and Song G. (2003) Synthesis and insecticidal activities of novel 2,5-disubstituted-1,3,4-oxadiazoles. J. Fluorine Chem., 123 163-169.
11. Almasirad A., Tabatabai S., Faizi M., Kebriaeezadeh A., Mehrabi N., Dalvandi A., and Shafiee, A. (2004) Synthesis and anticonvulsant activity of new 2-substituted-5- [2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles. Bioorg. Med.Chem. Lett., 24 6057-6059.
12. Mochona B., Qi X., Euynni S., Sikazwi D., Mateeva N., and Soliman K. (2016) Design and Evaluation of Novel Oxadiazole Derivatives as Potential Prostate Cancer Agents. Bioorg. Med.Chem. Lett., 26 (12) 2847-2851.
13. Kadi A., El-Brollosy N., Al-Deeb O., Habib E., Ibrahim T., and El-Emam A. (2007) Synthesis, anti-microbial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. Eur. J. Med. Chem., 42 235-242.
14. Ramazani A., and Souldozi A. (2008) Iminophosphorane-mediated one-pot synthesis of 1,3,4-oxadiazole derivatives. Arkivoc, 16 235-242.
15. Ramazani A., Ahmadi Y., and Tarasi R. (2011) Efficient One-Pot Synthesis of Disubstituted 1,3,4-Oxadiazole Derivatives from the Reaction of (N-Isocyanimino)triphenylphosphorane, Acetaldehyde, a Secondary Amine, and an Electron-Poor (E)-Cinnamic Acid. Heteroat. Chem., 22 (1) 79-84.
16. (a) Lu J., Jiang F., Lu A., and Zhang G. (2016) Linkers Having a Crucial Role in Antibody-Drug Conjugates. Int J Mol Sci., 17 561. (b) Krishna, C., Bhargavi, M., and Krupadanam, G. (2018) Design, Synthesis, and Cytotoxicity of Semisynthetic Betulinic Acid-1,2,4-Oxadiazole Amide Derivatives. Russ. J. Gen. Chem., 88 312–318.
17. Zhao T., Zhao Z., and Lu F. (2020) Two- and three-dimensional QSAR studies on hURAT1 inhibitors with flexible linkers: topomer CoMFA and HQSAR. Mol Divers., 24 141-154.
18. Cramer R., Patterson D., and Bunce J. (1988) Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc., 110 (18) 5959-5967.
19. Rayam P., Polkam N., Kummari B., Banothu V., Gandamalla D., Reddy N., and Anireddy J. (2019) Synthesis and Biological Evaluation of New Ibuprofen‐1,3,4‐oxadiazole‐1,2,3‐triazole Hybrids. J. Heterocycl. Chem., 56 (1) 296-305.
20. Jasiński, R. (2015) On the question of zwitterionic intermediates in 1,3-dipolar cycloadditions between hexafluoroacetone and sterically crowded diazocompounds. J. Fluor. Chem., 176 35-39.
21. Iyer, V., Gurupadayya B., Koganti V., Inturi B., and Chandan R. (2017) Design, synthesis and biological evaluation of 1,3,4-oxadiazoles as promising anti-inflammatory agents. Med Chem Res., 26 190–204.
22. Muhi-eldeen Z., Juma’a G., Al-kaissi, G., and Nouri L. (2008) Anti-microbial activity of some new oxadiazole derivatives. Jordan J. Chem., 3 (3) 233-243.
23. Wang S., Wang K., Kong X., Zhang S., Jiang G., Ji F. (2019) DMF as Methine Source: Copper‐Catalyzed Direct Annulation of Hydrazides to 1,3,4‐Oxadiazoles. Adv. Synth. Catal., 361 (17) 3986-3990.
24. de Oliveira C., Lira B., Barbosa-Filho J., Lorenzo J., and de Athayde-Filho P. (2012) Synthetic approaches and pharmacological activity of 1,3,4-oxadiazoles: a review of the literature from 2000-2012. Molecules, 17 (9) 10192-10231.
25. Kapadiya K., Kotadiya R., Kavadia K., Kothari R., Mehariya K., and Khunt R. (2015) Synthesis and Microbial Evaluation of Versatile Base Catalyzed Chiral Tetrahydrobenzofuran Derivatives via Multicomponent Reaction. Lett Drug Des Discov., 13 (6) 505-513.