Synthesis and antimicrobial evaluation of some new thiophene derivatives

Synthetic Communications

Volumn 40, Issue 11, 2010, Pages 1658-1669

  Khalil, A M ^a   Berghot, M A ^a   Abd El Ghani, Ghada E ^a   Gouda, M A ^a  

^a Mansoura University   (Egypt)

Author keywords

Ampicillin; Antimicrobial evaluation; Thiazolidine; Thiazolidinone; Thiophene; Thiophene derivatives

Indexed keywords

2 (2 CYANO 2 CYCLOHEXYLIDENEACETYLAMINO) 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 (2 CYANO 2 CYCLOPENTYLIDENEACETYLAMINO) 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 (2 CYANO 3 THIOPHEN 2 YLACRYLOYLAMINO) 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 (2 CYANOACETYLAMINO) 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 [(2 AMINO 5,6 DIHYDRO 4H CYCLOHEXA[B]THIOPHENE 3 CARBONYL)AMINO] 4,5,6,7 TETRAHYDRO BENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 [(2 AMINO 5,6 DIHYDRO 4H CYCLOPENTA[B]THIOPHENE 3 CARBONYL)AMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 [(5 ACETYL 4 AMINO 2 PHENYLAMINOTHIOPHENE 3 CARBONYL)AMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 [(5 BENZOYL 4 AMINO 2 PHENYLAMINOTHIOPHENE 3 CARBONYL)AMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 [2 (4 OXO 4,5 DIHYDROTHIAZOL 2 YL)ACETYLAMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 [2 CYANO 2 (3,4 DIPHENYL 3H THIAZOL 2 YLIDENE)ACETYLAMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 [2 CYANO 2 (4 METHYL 3 PHENYL 3H THIAZOL 2 YLIDENE)ACETYLAMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 [2 CYANO 2 (4 OXO 3 PHENYLTHIAZOLIDIN 2 YLIDENE)ACETYLAMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2 [2 CYANO 2 (4 TOLYLHYDRAZONO)ACETYLAMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXYLIC ACID AMIDE; 2 [3 (4 CHLOROPHENYL) 2 CYANOACRYLOYLAMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXAMIDE; 2,4 THIAZOLIDINEDIONE DERIVATIVE; 4 AMINO 3 PHENYL 2 THIOXO 2,3 DIHYDROTHIAZOLE 5 CARBOXYLIC ACID (3 CARBAMOYL 4,5,6,7 TETRAHYDROBENZO[B]THIOPHEN 2 YL)AMIDE; 4 THIAZOLIDINONE DERIVATIVE; ALDEHYDE; AMPICILLIN; HYDRAZONE DERIVATIVE; MORPHOLINE; SULFUR; THIOGLYCOLIC ACID; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS THURINGIENSIS; BOTRYTIS FABAE; DRUG STRUCTURE; DRUG SYNTHESIS; FUSARIUM OXYSPORUM; INFRARED SPECTROSCOPY; KLEBSIELLA PNEUMONIAE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77952030634     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903161652     Document Type: Article

References (31)

1. Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. 2-Aminothiophenes by the Gewald reaction. J. Heterocycl. Chem. 1999, 36, 333.
2. Baraldi, P. G.; Zaid, A. Z.; Lampronti, I.; Fruttarolo, F. F.; Pavani, M. G.; Tabrizi, M. A.; Shryock, J. C. S.; Leung, E.; Romagnoli, R. Synthesis and biological effects of a new series of 2-amino-3-benzoylthiophenes as allosteric enhancers of A1-adenosine receptor. Bioorg. Med. Chem. Lett. 2000, 10(17), 1953-1957.
3. Mohan, S.; Saravanan, J. Synthesis, characterization, and antibacterial activity of some Schiff bases of 2-amino-3-(N-tolyl carboxamido)-4,5 pentamethylene thiophenes. Asian J. Chem. 2003, 15(2), 625.
4. Malherbe, P.; Masciadri, R.; Norcross, R. D.; Ratni, H.; Thomas, A. W. Preparation of thienopyridines as GABAB allosteric enhancers for treating CNS disorders. PCT Int. Appl. World Patent, 2006, 063732.
5. Barnes, D. M.; Haight, A. R.; Hameury, T.; Mclaughlin, M. A.; Mei, J.; Tedrow, J. S.; Dalla, R. T. J. New conditions for the synthesis of thiophenes via the Knoevenagel= Gewald reaction sequence: Application to a multi-targeted kinase inhibitor. Tetrahedron 2006, 62(49), 11311-11319.
6. Vaghasiya, S. J.; Dodiya, D. K.; Trivedi, A. R.; Surani, J. J.; Shah, V. H. Synthesis and biological screening of some novel pyrazolo[3,4:4,5]thieno[2,3- d]primidin-8-ones via a Gewald reaction. Arkivoc 2008, 12, 1-8.
7. Seck, P.; Thomae, D.; Kirsch, G. Synthesis of substituted amino-cycloalkyl [b]thieno-[3,2-e]pyridine. J. Heterocycl. Chem. 2008, 45(3), 853-857.
8. Gewald, K.; Schinke, E.; Boettcher, H. Heterocycles from CH-acidic nitriles, VIII: 2-Aminothiophenes from methylene-active nitriles, carbonyl compounds, and sulfur. Chem. Ber. 1966, 99(1), 94-100.
9. Sauter, F.; Stanetty, P.; Schrom, E. Novel basically substituted pyrimidines and ben-zothienopyrimidines. Arch. Pharm. 1977, 310(4), 337-343.
10. Haugwitz, R. D.; Narayanan, V. L. Enol betaines of benzimidazoles. U.S. Patent 3,879,414, 1975
11. Chem. Abstr. 1975, 83, 131592f.
12. Devani, M. B.; Shishoo, C. J.; Pathak, U. S.; Parikh, S. H.; Radhakrishnan, A. V.; Padhya, A. C. Synthesis and pharmacological properties of some 4-amino-5-substituted thiazole-2(3H)-thiones and thiazolo[4,5-d]pyrimidine- 7(6H)-one-2(3H)-thiones. Arzneim-Forsch. 1977, 27(9), 1652-1655.
13. Ruschig, H.; Koenig, J.; Dittmar, W.; Klatt, P.; Duewel, D. 2,6-Dioxocyclohexane-carboxanilides and 2,6-dioxo-thiocyclohexane- carboxanilides. Ger. Offen Patent, 2,039,466, 1972;
14. Chem. Abstr. 1972, 76, 140270g.
15. Abdou, N. A.; Amin, F. M. Synthesis and biological activity of certain 5-mercapto-3-(3-pyridyl)-4H-1,2,4-triazole derivatives. Mansoura J. Pharm. Sci. 1990, 6(2), 25-29.
16. Durant, G. J.; Emmett, J. C.; Ganellin, C.; Prain, H. D. 1-[[2-Methylthiolethyl]amino]-1-aminoethylenes. Ger. Offen. Patent 2,423,813, 1974;
17. Chem. Abstr. 1975, 82, 170943.
18. Dubenko, R. G.; Gorbenko, E. F.; Pel'kis, P. S. Studies in a series of arylhydrazones of substituted glyoxylic acids, XXV: Arylamides of benzoyl carbamoyl: Thiacetic acid in the Japp-Klingemann reaction. Zh. Org. Khim. 1979, 15(7), 1483-1488.
19. Dubenko, R. G.; Konysheva, V. D.; Pel'kis, P. S. Study of arylhydrazones of glyoxylic acid derivatives, XXVIII: Ethyl cyanopyruvate reaction with aryl isothiocyanates. Zh. Org. Khim. 1981, 17(3), 490-499.
20. Dubenko, R. G.; Gorbenko, E. F.; Pel'kis, P. S.; Lozinskii, M. O. Study of a series of arylhydrazones of glyoxylic acid derivatives, XXIX: Arylamides of 2,4-dinitrophenyl-(acetyl)thioacetic acid in a reaction with aryldiazonium salts. Zh. Org. Khim. 1981, 17(8), 1704-1710.
21. Dubenko, R. G.; Konysheva, V. D.; Pel'kis, P. S.; Lozinskii, M. O. Studies of arylhydra-zones of substituted glyoxylic acid, XXX: Reaction of arylamides of diacylthioacetic acid with aryl diazonium salts. Zh. Org. Khim. 1982, 18(12), 2501-2504.
22. Dubenko, R. G.; Konysheva, V. D.; Gorbenko, E. F.; Pel'kis, P. S. Research on aryl hydrazones of glyoxylic acid derivatives, XXII: Arylamides of carboxycarbamoyl-thioacetic acid in the Japp-Klingemann reaction. Zh. Org. Khim. 1976, 12(3), 553-554.
23. Mohareb, R. M.; Sherif, M. One-pot synthesis of polyfunctionally substituted 2,3-dihydrothiazoles and thiazolidinones. Arch. Pharm. 1991, 324(8), 469-471.
24. Mohareb, R. M.; Sherif, S. M.; Abdel Aal, F. A. M.; Sayed, N. I. A. One-pot synthesis of polyfunctionally substituted 2,3-dihydrothiasoles and thiazolidinones. Liebigs Ann. Chem. 1990, 11, 1143-1146.
25. Behringer, H.; Weber, D. 2,5-Diamino-3,4-diazo-6a-thiathiophthalene derivatives of a quasi-aromatic heterocycle. Chem. Ber. 1964, 97, 2567-2582.
26. Fadda, A. A.; Abdel-Latif, E.; El-Mekawy, R. E. Synthesis and molluscicidal activity of some new thiophene, thiadiazole, and pyrazole derivatives. Eur. J. Med. Chem. 2008, 1-7.
27. Rida, S. M.; Ashour, F. A.; El-Hawash, S. A. M.; El-Semary, M. M.; Badr, M. H.; Shalaby, M. A. Synthesis of some novel benzoxazole derivatives as anticancer, anti-HIV-1, and antimicrobial agents. Eur. J. Med. Chem. 2005, 40(9), 949-959.
28. Rida, S. M.; Habib, N. S.; Badawey, E. A. M.; Fahmy, H. T. Y.; Ghozlan, H. A. Synthesis and biological investigations of some new thiazolylbenzimidazoles and benzimidazolyl-thiazolo[3,2-a]pyridines. Arch. Pharm. (Weinheim) 1995, 328, 325.
29. Elnagdi, M. H.; Khalifa, M. A.; Ibraheim, M. K. I.; Elmoghayar, M. R. The reaction of nitriles with mercaptoacetic acid: A new synthesis of thiazole derivatives. J. Heterocycl. Chem. 1981, 18, 877.
30. Badawey, E. A. M.; Hazzaa, A. A.; Rida, S. M.; Fahmy, H. T. Y. Assessment of anti-HIV activity of some benzimidazolylthiazoles. Arch. Pharm (Weinheim) 1992, 325, 565.
31. Cruickshank, R.; Duguid, J. P.; Marion, B. P.; Swain, R. H. A. Medicinal Microbiology, 12th ed. Churchill Livingstone: London, 1975; vol.2, pp. 196-202.