Design and synthesis of novel N-benzylidenesulfonohydrazide inhibitors of murC and murD as potential antibacterial agents

Molecules

Volumn 13, Issue 1, 2008, Pages 11-30

  Frlan, Rok ^a   Kovač, Andreja ^a   Blanot, Didier ^b   Gobec, Stanislav ^a   Pečar, Slavko ^a,c   Obreza, Aleš ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b INSTITUTE FOR INTEGRATIVE BIOLOGY OF THE CELL I2BC   (France)

^c JO EF STEFAN INSTITUTE   (Slovenia)

Author keywords

Amidobenzaldehyde; Antibacterial; Hydrazide; Inhibitors; MurC; MurD

Indexed keywords

ENZYME INHIBITOR; ESCHERICHIA COLI PROTEIN; PEPTIDE SYNTHASE; POLYMER; PYRIDAZINE DERIVATIVE; RHODANINE; UDP N ACETYLMURAMOYL ALANINE SYNTHETASE; UDP N ACETYLMURAMOYLALANINE D GLUTAMATE LIGASE; UDP-N-ACETYLMURAMOYL-ALANINE SYNTHETASE; UDP-N-ACETYLMURAMOYLALANINE-D-GLUTAMATE LIGASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; ESCHERICHIA COLI; OXIDATION REDUCTION REACTION; SYNTHESIS;

CATALYSIS; ENZYME INHIBITORS; ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; OXIDATION-REDUCTION; PEPTIDE SYNTHASES; POLYMERS; PYRIDAZINES; RHODANINE;

EID: 38949165234     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13010011     Document Type: Article

References (25)

1. Hiramatsu, K.; Okuma, K.; Ma, X.X.; Yamamoto, M.; Hori, S.; Kapi, M. New trends in Staphylococcus aureus infections: glycopeptide resistance in hospital and methicillin resistance in the community. Curr. Opin. Infect. Dis. 2002, 15, 407-413.
2. Herrero, I.A.; Issa, N.C.; Patel R. Nosocomial spread of linezolid-resistant, vancomycin-resistant Enterococcus faecium. N. Engl. J. Med. 2002, 346, 867-869.
3. Jana, S.; Deb, J.K. Molecular targets for design of novel inhibitors to circumvent aminoglycoside resistance. Curr. Drug Targ. 2005, 6, 353-361.
4. van Heijenoort, J. Recent advances in the formation of the bacterial peptidoglycan monomer unit. Nat. Prod. Rep. 2001, 18, 503-519.
5. El Zoeiby, A.; Sanschagrin, F.; Levesque, R.C. Structure and function of the Mur enzymes: development of novel inhibitors. Mol. Microbiol. 2003, 47, 1-12.
6. Mengin-Lecreulx, D.; Flouret, B.; van Heijenoort, J. Cytoplasmic steps of peptidoglycan synthesis in Escherichia coli. J. Bacteriol. 1982, 151, 1109-1117.
7. Sim, M.M.; Ng, S.B.; Buss, A.D.; Crasta, S.C.; Goh, K.L.; Lee, S.K. Benzylidene rhodanines as novel inhibitors of UDP-N-acetylmuramate/L- alanine ligase. Bioorg. Med. Chem. Lett. 2002, 12, 697-699.
8. Cukurovali, A.; Yilmaz, I.; Gur, S.; Kazaz, C. Synthesis, antibacterial and antifungal activity of some new thiazolylhydrazone derivatives containing 3-substituted cyclobutane ring. Eur. J. Med. Chem. 2006, 41, 201-207.
9. Ersan, S.; Nacak, S.; Berkem, R. Synthesis and antimicrobial activity of N-[(alpha-methyl)benzylidene]-(3-substituted-1,2,4-triazol-5-yl-thio) acetohydrazides. Farmaco 1998, 53, 773-776.
10. El-Gaby, M.S.A.; Atalla, A.A.; Gaber, A.M.; Abd Al-Wahab K.A. Studies on aminopyrazoles: antibacterial activity of some novel pyrazoles. Farmaco 2000, 55, 596-602.
11. Rollas, S., Gulerman, N.; Erdeniz, H. Synthesis and antimicrobial activity of some new hydrazones of 4-fluorobenzoic acid hydrazide and 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines. Farmaco 2002, 57, 171-174.
12. Vicini, P.; Zani, F.; Cozzini, P; Doytchinova, I. Hydrazones of 1,2-benzisothiazole hydrazides: synthesis, antimicrobial activity and QSAR investigations. Eur. J. Med. Chem. 2002, 37, 553-564.
13. Islam, A.M.; Abdel-Halim, A.M.; Salama, M.A. Synthesis of some naphthalene sulfonohydrazides and related compounds of potential biological activity. Egypt. J. Chem. 1987, 29, 405-431.
14. Guibé-Jampel, E.; Wakselman, M. p-Nitrobenzyl side-chain protection for solid-phase synthesis. Synth. Commun. 1982, 12, 219-223.
15. Wu, X.; Hu, L. Amide bond formation from selenocarboxylates and aromatic azides. Tetrahedron Lett. 2005, 46, 8401-8405.
16. Folkes, A.; Roe, M.B.; Sohal, S.; Golec, J.; Faint, R.; Brooks, T.; Charlton, P. Synthesis and in vitro evaluation of a series of diketopiperazine inhibitors of plasminogen activator inhibitor-1. Bioorg. Med. Chem. Lett. 2001, 11, 2589-2592.
17. Feng, B.Y.; Shelat, A.; Doman, T.N.; Guy, R.K.; Shoichet, B.K.: High-throughput assays for promiscuous inhibitors. Nat. Chem. Biol. 2005, 1, 146-148.
18. Wagner, G.; Eppner, B. Synthesis of 2-(4-amidinophenyl)-benzofuran, -benzoxazole and -benzothiazole as well as of 2-(4-amidinobenzyl)benzoxazole. Pharmazie 1980, 35, 285-288.
19. Mukkala, V.M.; Helenius, M.; Hemmila, I.; Kankare, J.; Takalo, H. Development of luminescent europium(III) and terbium(III) chelates of 2,2′:6′,2″-terpyridine derivatives for protein labeling. Helv. Chim. Acta 1993, 76, 1361-1378.
20. Sanders, G.M.; Van Dijk, M.; Van Veldhuizen, A.; Van der Plas, H.C.; Hofstra, U.; Schaafsma, T.J. Studies on the conformation of 5,15- diarylporphyrins with (arylsulfonyl)oxy substituents. J. Org. Chem. 1988, 53, 5272-5281.
21. Morgenstern, O.; Richter, P. Synthesis and reactivity of 3-methyl-2-thioxo-1,2-dihydro-3H-1,3,4-benzotriazepine. Wissen. Z. Ernst-Moritz-Arndt-Univ. Greifswald, Math.-Nat. 1988, 37, 34-37.
22. Flamigni, L.; Ventura, B.; Tasior, M.; Gryko, D.T. Photophysical properties of a new, stable corrole-porphyrin dyad. Inorg. Chim. Acta 2007, 360, 803-813.
23. Liger, D.; Masson, A.; Blanot, D.; van Heijenoort, J.; Parquet, C. Over-production, purification and properties of the uridine-diphosphate- N-acetylmuramate:L-alanine ligase from Escherichia coli. Eur. J. Biochem. 1995, 230, 80-87.
24. Auger, G.; Martin, L.; Bertrand, J.; Ferrari, P.; Fanchon, E.; Vaganay, S.; Pétillot, Y.; van Heijenoort, J.; Blanot, D.; Dideberg, O. Large-scale preparation, purification, and crystallization of UDP-N-acetylmuramoyl-L-alanine: D-glutamate ligase from Escherichia coli. Prot. Express. Purif. 1998, 13, 23-29.
25. Lanzetta, P.A.; Alvarez, L.J.; Reinach, P.S.; Candia, O. An improved assay for nanomole amounts of inorganic phosphate. Anal. Biochem. 1979, 100, 95-97.