Synthesis of Thiazole Derivatives as Antimicrobial Agents by Green Chemistry Techniques

Abstract

Amine (2) and (26) was obtained from the condensation of the corresponding amines with 3,4-difluoronitrobenzene. The reduction of nitro group produced the corresponding amines (3 and 27). The synthesis of esters (7, 12, 19, 28) was carried out from the treatment of the amines, 1, 3, 18, 27 with ethylbromoacetate, then these compounds were converted to the corresponding hydrazides (8, 13, 29) by the treatment with hydrazine hydrate. Triazole was obtained from the intramolecular cyclisation of the corresponding carbothioamide in basic media and this compound wad then converted to the morpholine-triazole-penicillin hybrid by a mannich reaction. The cyclocondensation of hydrazine carbothioamides (9b, 14, 21) or urea (4) with 2-bromo-1-(4-chlorophenyl) ethenone generated thiazole derivatives. On the other hand, the treatment of  4, 9b and 14 with ethyl bromoacetate yielded 4-oxo-1,3-thiazolidines (6, 11, 16). Three methods containing conventional, microwave and ultrasound mediated techniques were applied. Best results were assessed using microwave and ultrasounds promoted procedures. All the newly synthesized compounds were characterized on the basis of spectroscopic techniques, and they were screened for their antimicrobial activity. Some of them exhibited good-moderate activity on the test bacteria.

Keywords

• Antimicrobial activity,microwave,imidazole,morpholine,green chemistry

References

1. 1. Minbiole KPC, Jennings MC, Ator LE, Black JW, Grenier MC, LaDow JE, et al. From antimicrobial activity to mechanism of resistance: the multifaceted role of simple quaternary ammonium compounds in bacterial eradication. Tetrahedron 2016;72:3559–66.
2. 2. Yang H, Wang H-W, Zhu T-W, Yu L-M, Chen J-W, Wang L-X, et al. Syntheses and antibacterial activity of soluble 9-bromo substituted indolizinoquinoline-5,12-dione derivatives. Eur J Med Chem 2017;127:166–73.
3. 3. Kawai T, Kazuhiko I, Takaya N, Yamaguchi Y, Kishii R, Kohno Y, et al. Sulfonamide-based non-alkyne LpxC inhibitors as Gram-negative antibacterial agents. Bioorg Med Chem Lett 2017;27:1045–9.
4. 4. Yan S, Song L, Luan S, Xin Z, Du S, Shi H, et al. A hierarchical polymer brush coating with dual-function antibacterial capability. Colloids Surfaces B Biointerfaces 2017;150:250–60.
5. 5. Alagumuthu M, Arumugam S. Molecular docking, discovery, synthesis, and pharmacological properties of new 6-substituted-2-3-phenoxyphenyl. -4-phenyl quinoline derivatives; an approach to developing potent DNA gyrase inhibitors/antibacterial agents. Bioorg Med Chem 2017;25:1448–55.
6. 6. Jeankumar VU, Renuka J, Santosh P, Soni V, Sridevi JP, Suryadevara P, et al. Thiazole-aminopiperidine hybrid analogues: Design and synthesis of novel Mycobacterium tuberculosis GyrB inhibitors. Eur J Med Chem 2013;70:143–53.
7. 7. War JA, Srivastava SK, Srivastava SD. Design, synthesis and DNA-binding study of some novel morpholine linked thiazolidinone derivatives. SpectrochimActa Part A MolBiomolSpectrosc 2017;173:270–8.
8. 8. Padmavathi V, PremaKumari C, Venkatesh BC, Padmaja A. Synthesis and antimicrobial activity of amido linked pyrrolyl and pyrazolyl-oxazoles, thiazoles and imidazoles. Eur J Med Chem 2011;46:5317–26.

9. 9. Chen W, Deng X-Y, Li Y, Yang L-J, Wan W-C, Wang X-Q, et al. Synthesis and cytotoxic activities of novel hybrid 2-phenyl-3-alkylbenzofuran and imidazole/triazole compounds. Bioorg Med Chem Lett 2013;23:4297–302.
10. 10. Wang K, Xu W, Liu Y, Zhang W, Wang W, Shen J, et al. Design and synthesis of imidazole and triazole derivatives as Lp-PLA2 inhibitors and the unexpected discovery of highly potent quaternary ammonium salts. Bioorg Med Chem Lett 2013;23:1187–92.
11. 11. Yurttaş L, Duran M, Demirayak Ş, Gençer HK, Tunalı Y. Synthesis and initial biological evaluation of substituted 1-phenylamino-2-thio-4,5-dimethyl-1H-imidazole derivatives. Bioorg Med Chem Lett 2013;23:6764–8.
12. 12. Wen S-Q, Jeyakkumar P, Avula SR, Zhang L, Zhou C-H. Discovery of novel berberineimidazoles as safe antimicrobial agents by down regulating ROS generation. Bioorg Med Chem Lett 2016;26:2768–73.
13. 13. Rathore A, Sudhakar R, Ahsan MJ, Ali A, Subbarao N, Jadav SS, et al. In vivo anti-inflammatory activity and docking study of newly synthesized benzimidazole derivatives bearing oxadiazole and morpholine rings. BioorgChem 2017;70:107–17.
14. 14. Tereshchenko AD, Myronchuk JS, Leitchenko LD, Knysh I V., Tokmakova GO, Litsis OO, et al. Synthesis of 3-oxadiazolyl/triazolyl morpholines: Novel scaffolds for drug discovery. Tetrahedron 2017;73:750–7.
15. 15. Surendra Kumar R, Moydeen M, Al-Deyab SS, Manilal A, Idhayadhulla A. Synthesis of new morpholine-connected pyrazolidine derivatives and their antimicrobial, antioxidant, and cytotoxic activities. Bioorg Med Chem Lett 2017;27:66–71.
16. 16. Doan P, Karjalainen A, Chandraseelan JG, Sandberg O, Yli-Harja O, Rosholm T, et al. Synthesis and biological screening for cytotoxic activity of N-substituted indolines and morpholines. Eur J Med Chem 2016;120:296–303.
17. 17. Gadekar PK, Roychowdhury A, Kharkar PS, Khedkar VM, Arkile M, Manek H, et al. Design, synthesis and biological evaluation of novel azaspiro analogs of linezolid as antibacterial and antitubercular agents. Eur J Med Chem 2016;122:475–87.
18. 18. Micheli F, Cremonesi S, Semeraro T, Tarsi L, Tomelleri S, Cavanni P, et al. Novel morpholine scaffolds as selective dopamine DA. D3 receptor antagonists. Bioorganic Med Chem Lett 2016;26:1329–32.
19. 19. Zhao Z, Pissarnitski DA, Josien HB, Bara TA, Clader JW, Li H, et al. Substituted 4-morpholine N-arylsulfonamides as ??-secretase inhibitors. Eur J Med Chem 2016;124:36–48.
20. 20. Desai NC, Rajpara KM, Joshi V V. Microwave induced synthesis of fluorobenzamides containing thiazole and thiazolidine as promising antimicrobial analogs. J Fluor Chem 2013;145:102–11.
21. 21. Zhao Z, Shi Z, Liu M, Liu X. Microwave-assisted synthesis and in vitro antibacterial activity of novel steroidal thiosemicarbazone derivatives. Bioorg Med Chem Lett 2012;22:7730–4.
22. 22. Mamaghani M, Loghmanifar A, Taati MR. An efficient one-pot synthesis of new 2-imino-1,3-thiazolidin-4-ones under ultrasonic conditions. UltrasonSonochem 2011;18:45–8.
23. 23. Hossein Nia R, Mamaghani M, Tabatabaeian K, Shirini F, Rassa M. An expeditious regioselective synthesis of novel bioactive indole-substituted chromene derivatives via one-pot three-component reaction. Bioorganic Med Chem Lett 2012;22:5956–60.
24. 24. Martinez-Guerra E, Gude VG. Synergistic effect of simultaneous microwave and ultrasound irradiations on transesterification of waste vegetable oil. Fuel 2014;137:100–8.
25. 25. Mahmoodi NO, Shoja S, Tabatabaeian K, Sharifzadeh B. Ultrasound-promoted one-pot five-components synthesis of biologically active novel bis6-alkyl or phenyl-2-phenylpyrimidine-4-yl. oxy. alkane or methyl benzene derivatives. UltrasonSonochem 2015;23:31–6.
26. 26. Chen B-H, Li J-T, Chen G-F. Efficient synthesis of 2,3-disubstituted-2,3-dihydroquinazolin-41H. -ones catalyzed by dodecylbenzenesulfonic acid in aqueous media under ultrasound irradiation. UltrasonSonochem 2015;23:59–65.
27. 27. Nyborg WL. Biological effects of ultrasound: Development of safety guidelines. Part II: General review. Ultrasound Med Biol 2001;27:301–33.
28. 28. Mentese MY, Bayrak H, Uygun Y, Mermer A, Ulker S, Karaoglu SA, et al. Microwave assisted synthesis of some hybrid molecules derived from norfloxacin and investigation of their biological activities. Eur J Med Chem 2013;67:230–42.
29. 29. Ceylan S, Bektas H, Bayrak H, Demirbas N, Alpay-Karaoglu S, Ülker S. Syntheses and biological activities of new hybrid molecules containing different heterocyclic moieties. Arch Pharm Weinheim. 2013;346:743–56.
30. 30. Mentese M, Demirci S, Ozdemir SB, Demirbas A, Ulker S, Demirbas N. Microwave assisted synthesis and antimicrobial activity evaluation of new heterofunctionalizednorfloxacine derivatives. Lett Drug Des Discov 2016;13:1076–90.
31. 31. Weatherburn MW. Phenol-hypochlorite reaction for determination of ammonia. Anal Chem 1967;39:971–4.