Synthesis of certain pyrrole derivatives as antimicro-bial agents

Acta Pharmaceutica

Volumn 59, Issue 2, 2009, Pages 145-158

  Mohamed, Mosaad ^a   El Domany, Ramdan ^a   Abd El Hameed, Rania ^a  

^a Helwan University   (Egypt)

Author keywords

Antimicrobial activity; Pyrrole; Pyrrolopyrimidine

Indexed keywords

2 AMINO 1 (4 METHOXYPHENYL) 4,5 DIPHENYL 3 TETRAZOLO 1H PYRROLE DERIVATIVE; 2 AMINO 3 CARBAMOYL 1 (3 METHYLPHENYL) 4,5 DIPHENYL 1H PYRROLE DERIVATIVE; 2 AMINOPYRROLE 3 CARBONITRILE DERIVATIVE; 7 (3 METHYLPHENYL) 5,6 DIPHENYL 7H PYRROLO[2,3 D]PYRIMIDIN 4(3H) THIONE; 7 (4 METHOXYPHENYL) 5,6 DIPHENYL 7H PYRROLO[2,3 D]PYRIMIDIN 4(3H) ONE DERIVATIVE; AMOXICILLIN; ANTIINFECTIVE AGENT; AROMATIC AMINE; BENZOIN; FLUCONAZOLE; MALONONITRILE; N (3 CYANO 1 (2 METHYLPHENYL) 4,5 DIPHENYL 1H PYRROL 2 YL) ACETAMIDE DERIVATIVE; N (3 CYANO 1 (3 METHYLPHENYL)4,5 DIPHENYL 1H PYRROL 2 YL)ACETAMIDE DERIVATIVE; N [7 (2 METHYLPHENYL) 5,6 DIPHENYL 7H PYRROLO[2,3 D]PYRIMIDINE) N ARYL AMINE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLO[2,3 D]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; [2 AMINO 1 (2 METHYLPHENYL) 4,5 DIPHENYL 1H PYRROLE 3 CARBONITRILE DERIVATIVE;

ANTIMICROBIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM NEGATIVE INFECTION; GRAM POSITIVE BACTERIUM; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN;

EID: 67651154225     PISSN: 13300075     EISSN: None     Source Type: Journal    
DOI: 10.2478/v10007-009-0016-9     Document Type: Article

References (20)

1. S. Petruso, S. Bonanno, S. Caronna, M. Ciofalo, B. Maggio and D. Schillaci, A new synthesis of bioactive analogs of monodeoxypyoluteorin, J. Heterocyclic Chem. 31 (1994) 941-945.
2. M. V. Raimondi, S. Cascioferro, D. Schillaci and S. Petruso, Synthesis and antimicrobial activity of new bromine-rich pyrrole derivatives related to monodeoxypyoluteorin, Eur. J. Med. Chem. 41 (2006) 1439-1445; DOI 10.1016/j.ejmech.2006.0.009.
3. D. Schillaci, S. Petruso and V. Sciortino, 3,4,5,3,5-Pentabromo-2-(2- hydroxybenzoyl)pyrrole: a potential lead compound as anti-Gram-positive and anti-biofilm agent, Int. J. Antimicrob. Ag. 25 (2005) 338-340; DOI: 10.1016/j.ijantimicag.2004.11.014.
4. M. Biava, R. Fioravanti, G. C. Porretta, D. Deidda, C. Maullu and R. Pompei, New pyrrole derivatives as antimycobacterial agents analogs of BM 212, Bioorg. Med. Chem. Lett. 9 (1999) 2983-2988; DOI: 10.1016/s0960-894x(99)00510-7.
5. M. Biava, G. C. Porretta, D. Deidda, R. Pompei, A. Tafi and F. Manetti, Importance of the thio-morpholine introduction in new pyrrole derivatives as antimycobacterial agents analogues of BM 212, Bioorg. Med. Chem. 11 (2003) 515-520; DOI: 10.1016/s0968-0896(02)00455-8.
6. G. H. Jana, S. Jain, S. K. Arora and N. Sinha, Synthesis of some diguanidino 1-methyl-2,5-diaryl--1H-pyrroles as antifungal agents, Bioorg. Med. Chem. Lett. 15 (2005) 3592-3595; DOI: 10.1016/ j.bmcl.2005.05.080.
7. Y. Misumo, M. J. Ikehara, K. A. Watanabe, S. Suzuki and T. Itoh, Synthetic studies of potential antimetabolites. IX. The anomeric configuration of tubercidin, J. Org. Chem. 28 (1969) 3329-3331.
8. Q. Dang and J. E. Gomez-Galeno, An efficient synthesis of pyrrolo[2,3-d]pyrimidines via inverse electron demand Diels-Alder reactions of 2-amino-4-cyanopyrroles with 1,3,5-triazines, J. Org. Chem. 67 (2002) 8703-8705; DOI: 10.1021/jo026309d.
9. K. V. Rao, Structure of sangivamycin, J. Med. Chem. 11 (1968) 939-941; DOI: 10.1021/jm00311a005.
10. A. Gangjee, X. Lin and S. F. Queener, Design, synthesis, and biological evaluation of 2,4-diami-no-5-methyl-6-substituted-pyrrolo[2,3-d]pyrimidines as dihydrofolate reductase inhibitors, J. Med. Chem. 47 (2004) 3689-3692; DOI: 10.1021/jm0306327.
11. P. M. Traxler, P. Furet, H. Mett, E. Buchdunger, T. Meyer and N. Lydon, 4-(Phenylamino)pyr-rolopyrimidines: Potent and selective, ATP site directed inhibitors of the EGF-receptor protein tyrosine kinase, J. Med. Chem. 39 (1996) 2285-2290; DOI: 10.1021/jm960118j.
12. M. S. Mohamed, A. E. Rashad, M. E. A. Zaki and S. S. Fatahala, Synthesis and antimicrobial screening of some fused heterocyclic pyrroles, Acta Pharm. 55 (2005) 237-249.
13. H. J. Roth und K. Eger, Synthese von 2-Amino-3-cyano-pyrrolen, Arch. Pharm. 18 (1974) 179-185.
14. H. J. Roth und K. Eger, Synthese von pyrrolo[2,3-d]pyrimidinen, Arch. Pharm. 18 (1974) 252-258.
15. A. C. Gales, H. S. Sader and R. N. Jones, Urinary tract infection trends in Latin American hospitals: report from the SENTRY antimicrobial surveillance program, Diagn. Mic. Infec. Dis. 44 (1997-2000) 289-294.
16. A. Jorgensen, K. A. M. El-Bayouki and E. B. Pedersen, Phosphorus pentoxide in organic synthesis. XX: Synthesis of N-aryl-7H-pyrrolo[2,3-d] pyrimidin-4-amines, J. Heterocyclic Chem. 22 (1985) 859-863.
17. C. G. Dave and M. C. Shukla, Diethyl ethoxymethylenemalonate in triheterocycles: a new synthesis of pyrido[3,2-e]pyrimido[1,2-c]pyrimidines, J. Heterocyclic Chem. 34 (1997) 1805-1808.
18. C. G. Dave and R. D. Shah, Synthesis of 7H-tetrazolo[1,5-c]pyrrolo[3,2-e] pyrimidines and their reductive ring cleavage to 4-aminopyrrolo[2,3-d] pyrimidines, J. Heterocyclic Chem. 35 (1998) 1295-1300.
19. C. G. Dave, Synthesis and reactions of fluoroaryl substituted 2-amino-3-cyanopyrroles and pyrrolo[2,3-d]pyrimidines, J. Heterocyclic Chem. 36 (1999) 729-733.
20. G. F. Gad, R. A. El-Domany and H. M. Ashour, Antimicrobial susceptibility profile of Pseudomonas aeruginosa isolates in Egypt, J. Urol. 180 (2008) 176-181; DOI: 10.1016/j.juro.2008.03.081.