Syntheses of hitherto unknown thiazole, ylidene and pyridinethione derivatives having a piperidin-1-yl moiety and their use as antimicrobial agents

Journal of the Chinese Chemical Society

Volumn 51, Issue 1, 2004, Pages 125-134

  El Gaby, Mohamed Sayed A ^a  

^a Assiut Branch   (Egypt)

Author keywords

Antimicrobial activity; Piperidin 1 yl; Pyridinethione; Thiazole; Ylidene

Indexed keywords

2 (1H BENZIMIDAZOL 2 YL) 3 [4 (PIPERIDIN 1 YL)PHENYL]ACRYLONITRILE; 2 AMINO 4 [4 (PIPERIDIN 1 YL)PHENYL] 3 ETHOXYCARBONYL 6 THIOXO 1,6 DIHYDROPYRIDINE 5 CARBONITRILE; 2 CYANO 3 DIMETHYLAMINOACRYLIC ACID[4 (PIPERIDIN 1 YL)BENZYLIDENYL]HYDRAZIDE; 2 CYANO 3 [4 (MORPHOLIN 4 YL)PHENYL]ACRYLAMIDE; 2 CYANO 3 [4 (PIPERIDIN 1 YL)PHENYL]THIOACRYLAMIDE; 2 [4 (MORPHOLIN 4 YL)BENZYLIDENYL]INDAN 1,3 DIONE; 2 [4 (MORPHOLIN 4 YL)BENZYLIDENYL]MALONONITRILE; 2 [4 (PIPERIDIN 1 YL)BENZYLIDENYL]INDAN 1,3 DIONE; 2 [4 (PIPERIDIN 1 YL)BENZYLIDENYL]MALONONITRILE; 2 [N' [4 (PIPERIDIN 1 YL)BENZYLIDENYL]HYDRAZINO] 4,5 DIHYDROTHIAZOL 4 ONE; 2 [N' [4 (PIPERIDIN 1 YL)BENZYLIDENYL]HYDRAZINO]NAPHTHO[2,3 D]THIAZOL 4,9 DIONE; 5 CYANO 2 METHYL 4 [4 (MORPHOLIN 4 YL)PHENYL] 6 THIOXO 1,6 DIHYDROPYRIDINE 3 CARBOXYLIC ACID ETHYL ESTER; 5 OXO 4 [4 (MORPHOLIN 4 YL)PHENYL] 2 THIOXO 2,5 DIHYDRO 1H INDENO[1,2 B]PYRIDINE 3 CARBONITRILE; 5 OXO 4 [4 (PIPERIDIN 1 YL)PHENYL] 2 THIOXO 2,5 DIHYDRO 1H INDENO[1,2 B]PYRIDINE 3 CARBONITRILE; 5 [4 (PIPERIDIN 1 YL)BENZYLIDENYL] 2 THIOXODIHYDROPYRIMIDINE 4,6 DIONE; 6 AMINO 4 METHYLSULFANYL 2 OXO 1 [[4 (PIPERIDIN 1 YL)BENZYLIDENYL]AMINO] 1,2 DIHYDROPYRIDINE 3,5 DICARBONITRILE; 6 AMINO 4 [4 (PIPERIDIN 1 YL)PHENYL] 2 THIOXO 1,2 DIHYDROPYRIDINE 3,5 DICARBONITRILE; ANTIINFECTIVE AGENT; CARBENOID; CYANOACETIC ACID[4 (MORPHOLIN 4 YL)BENZYLIDENYL]HYDRAZIDE; CYANOACETIC ACID[4 (PIPERIDIN 1 YL)BENZYLIDENYL]HYDRAZIDE; HYDRAZONE DERIVATIVE; N (4 METHYLTHIAZOL 2 YL) N' [4 (PIPERIDIN 1 YL)BENZYLIDENYL]HYDRAZINE; N (4 PHENYLTHIAZOL 2 YL) N' [4 (PIPERIDIN 1 YL)BENZYLIDENYL]HYDRAZINE; N (5 ETHOXYCARBONYL 4 METHYLTHIAZOL 2 YL) N' [4 (PIPERIDIN 1 YL)BENZYLIDENYL]HYDRAZINE; PIPERIDINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; [4 (PIPERIDIN 1 YL)BENZYLIDENYL]THIOSEMICARBAZIDE;

ANTIMICROBIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; SPECTROSCOPY;

EID: 2142713186     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200400020     Document Type: Article

References (25)

1. Annoura, H.; Nakanishi, K.; Uesugi, M.; Fukunaga, A.; Imajo, S.; Miyajima, A.; Tamura-Horikawa, Y.; Tamura, S. Bioorg. Med. Chem. 2002, 10, 371.
2. Contreras, J.; Parrot, I.; Sippl, W.; Rival, Y. M.; Wermuth, G. G. J. Med. Chem. 2001, 4, 2707.
3. Pikul, S.; Ohler, N. E.; Ciszewski, G.; Laufersweiler, M. C.; Almstead, N. G.; De, B.; Natchus, M. G.; Hsieh, L. C.; Janusz, M. J.; Peng, S. X.; Branch, T. M.; King, S. L.; Taiwo, Y. O.; Mieling, G. E. J. Med. Chem. 2001, 44, 2499.
4. Winn, M.; Reilly, E. B.; Liu, G.; Huth, J. R.; Jae, H.; Freeman, J.; Pei, Z.; Xin, Z.; Lynch, J.; Kester, J.; Geldern, T. W.; Leitza, S.; Devries, P.; Dickinson, R.; Mussatto, D.; Okasinski, G. F. J. Med. Chem. 2001, 44, 4393.
5. Hu, B.; Ellingboe, J.; Han, S.; Largis, E.; Mulvey, R.; Oliphant, A.; Sun, F.; Tillett, J. J. Med. Chem. 2001, 44, 1456.
6. Bhagwat, S.; Palanki, M.; Erdman, P.; Double-day, M.; Sato, H. PCT Int. Appl. WO 01, 40, 187 (Cl. CO7D213/55). Jun 2001, US Appl. 450, 245. 29 Nov 1999. [Chem. Abstr. 2001, 135(3), 33643w].
7. Xiaoqiang He, J.; Honigschmidt, N. A.; Kohn, T. J.; Rocco, V. P.; Spinazze, P. G.; Takeuchi, K. PCT Int. Appl. WO 01, 46, 179 (Cl. CO7D409/04). 28 Jun 2001, US Appl. PV 172. 20 Dec 1999. [Chem. Abstr. 2001, 135(6), 76799u].
8. Magdolen, P.; Zahradnik, P.; Foltinova, P. Pharmazie. 2000, 55, 803.
9. Brown, W.; Walpole, C. PCT Int. Appl. WO 01, 46, 263 (Cl. CO7K211/58). 28 Jun 2001, SE Appl. 1999/4, 675. 20 Dec 1999. [Chem. Abstr. 2001, 135(6), 76802q].
10. El-Gaby, M. S. A.; Gaber, A. M.; Atalla, A. A.; Abd Al-Wahab, K. A. IL Farmaco. 2002, 57, 613.
11. El-Gaby, M. S. A.; Micky, J. A.; Taha, N. M.; El-Sharief, M. A. M. Sh. J. Chin. Chem. Soc. 2002, 49, 407.
12. El-Gaby, M. S. A.; Micky, J. A.; Taha, N. M.; El-Sharief, M. A. M. Sh. Acta Chim. Solv. 2002, 49, 159.
13. El-Gaby, M. S. A.; Ammar, Y. A.; El-Sharief, A. M. Sh.; Zahran, M. A.; Khames, A. A. Heteroatom Chem. 2002, 13(7), 611.
14. El-Gaby, M. S. A.; Atalla, A. A.; Gaber, A. M.; Abd Al-Wahab, K. A. IL Farmaco. 2000, 55, 596.
15. El-Gaby, M. S. A. Phosphorus, Sulfur and Silicon. 2000, 156, 157.
16. Gale, D. J.; Wilshire, J. F. K. Aust. J. Chem. 1970, 23, 1063.
17. Habib, N. S.; El-Hawash, S. A. Pharmazie. 1997, 52, 594.
18. Peseke, K.; Quincoces, J. Pharmazie. 1981, 36, 534.
19. Krauze, A.; Germane, S.; Eberlins, O.; Sturms, I.; Klusa, V.; Duburs, G. Eur. J. Med. Chem. 1999, 34, 301.
20. Guerrera, F.; Salemo, L.; Sarva, M. C.; Siracusa, M. A. IL Farmaco. 1993, 48, 1725.
21. Abbas, A. A.; Elneairy, M. A. A.; Mabkhot, Y. N. J. Chem. Research (S) 2001, 124; J. Chem. Research (M). 2001, 411.
22. Abbas, A. A.; Elneairy, M. A. A.; Mabkhot, Y. N. J. Chem. Research (S) 2001, 124; J. Chem. Research (M). 2001, 411.
23. Mekheimer, R.; Mohamed, N. H.; Sadek, K. U. Bull. Chem. Soc. Jpn. 1997, 70, 1625.
24. Carrod, L. P.; Grady, F. D. Antibiotics and Chemotherapy. 3rd ed.: Churchill Livingestone: Edinburgh. 1972, 477.
25. Courvalin, P. Interpretive Reading Antimicrobial Susceptibility Tests. Am. Soc. Microbial. New. 1992, 85, 368.