Design, synthesis, structural characterization by IR, 1H, 13C, 15N, 2D-NMR, X-ray diffraction and evaluation of a new class of phenylaminoacetic acid benzylidene hydrazines as pfenr Inhibitors

Chemical Biology and Drug Design

Volumn 81, Issue 6, 2013, Pages 715-729

  Samal, Ramanuj P ^a   Khedkar, Vijay M ^a   Pissurlenkar, Raghuvir R S ^a   Bwalya, Angela Gono ^b   Tasdemir, Deniz ^b,c   Joshi, Ramesh A ^d   Rajamohanan, P R ^d   Puranik, Vedavati G ^d   Coutinho, Evans C ^a  

^a BOMBAY COLLEGE OF PHARMACY   (India)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c NATIONAL UNIVERSITY OF IRELAND   (Ireland)

^d NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

ADMET; Docking; Enoyl ACP reductase; FabI; Hydrogen bonding; NMR; Phenylaminoacetic acid benzylidene hydrazine; Plasmodium falciparum; Plasmodium falciparum enoyl ACP reductase; QSAR; Recursive partitioning; X ray diffraction

Indexed keywords

BENZYLIDENE DERIVATIVE; GLYCINE DERIVATIVE; HYDRAZINE DERIVATIVE; OXIDOREDUCTASE INHIBITOR; PFENR INHIBITOR; TRICLOSAN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG DESIGN; DRUG SYNTHESIS; FATTY ACID SYNTHESIS; HYDROGEN BOND; MALARIA; MOLECULAR DOCKING; NITROGEN NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; X RAY DIFFRACTION;

PLASMODIUM FALCIPARUM;

EID: 84878349390     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12118     Document Type: Article

References (34)

1. Davidson E.A., Gowda D.C. (2001) Glycobiology of Plasmodium falciparum. Biochimie;83:601-604.
2. Yeung S., Socheat D., Moorthy V.S., Mills A.J. (2009) Artemisinin resistance on the Thai-Cambodian border. Lancet;374:1418-1419.
3. Schofield L. (2007) Rational approaches to developing an anti-disease vaccine against malaria. Microbes Infect;9:784-791.
4. VanBuskirk K.M., O'Neill M.T., De La Vega P., Maier A.G., Krzych U., Williams J., Dowler M.G. et al. (2009) Preerythrocytic, live-attenuated Plasmodium falciparum vaccine candidates by design. Proc Natl Acad Sci USA;106:13004-13009.
5. Kappe S.H., Vaughan A.M., Boddey J.A., Cowman A.F. (2010) That was then but this is now: malaria research in the time of an eradication agenda. Science;328:862-866.
6. Vaughan A.M., O'Neill M.T., Tarun A.S., Camargo N., Phuong T.M., Aly A.S., Cowman A.F., Kappe S.H. (2009) Type II fatty acid synthesis is essential only for malaria parasite late liver stage development. Cell Microbiol;11:506-520.
7. Yu M., Kumar T.R., Nkrumah L.J., Coppi A., Retzlaff S., Li C.D., Kelly B.J. et al. (2008) The fatty acid biosynthesis enzyme FabI plays a key role in the development of liver-stage malarial parasites. Cell Host Microbe;4:567-578.
8. Heath R.J., White S.W., Rock C.O. (2001) Lipid biosynthesis as a target for antibacterial agents. Prog Lipid Res;40:467-497.
9. Smith S. (1994) The animal fatty acid synthase: one gene, one polypeptide, seven enzymes. FASEB J;8:1248-1259.
10. Singh A.P., Surolia N., Surolia A. (2009) Triclosan inhibit the growth of the late liver-stage of Plasmodium. IUBMB Life;61:923-928.
11. Pidugu L.S., Kapoor M., Surolia N., Surolia A., Suguna K. (2004) Structural basis for the variation in triclosan affinity to enoyl reductases. J Mol Biol;343:147-155.
12. Freundlich J.S., Anderson J.W., Sarantakis D., Shieh H.M., Yu M., Valderramos J.C., Lucumi E., Kuo M., Jacobs W.R. Jr, Fidock D.A, Schiehser G.A, Jacobus D.P, Sacchettini J.C. (2005) Synthesis, biological activity, and X-ray crystal structural analysis of diaryl ether inhibitors of malarial enoyl acyl carrier protein reductase. Part 1: 4'-substituted triclosan derivatives. Bioorg Med Chem Lett;15:5247-5252.
13. Mishra S., Karmodiya K., Parasuraman P., Surolia A., Surolia N. (2008) Design, synthesis, and application of novel triclosan prodrugs as potential antimalarial and antibacterial agents. Bioorg Med Chem;16:5536-5546.
14. Perozzo R., Kuo M., Sidhu A.S., Valiyaveettil J.T., Bittman R., Jacobs W.R. Jr, Fidock D.A., Sacchettini J.C. (2002) Structural elucidation of the specificity of the antibacterial agent triclosan for malarial enoyl acyl carrier protein reductase. J Biol Chem;277:13106-13114.
15. Khedkar V., Verma J., Coutinho E. (2009) Small-molecule screening techniques in drug discovery. Biobytes;4:4-7.
16. Kitchen D.B., Decornez H., Furr J.R., Bajorath J. (2004) Docking and scoring in virtual screening for drug discovery: methods and applications. Nat Rev Drug Discov;3:935-949.
17. Friesner R.A., Banks J.L., Murphy R.B., Halgren T.A., Klicic J.J., Mainz D.T., Repasky M.P., Knoll E.H., Shelley M., Perry J.K., Shaw D.E., Francis P., Shenkin P.S. (2004) Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem;47:1739-1749.
18. Halgren T.A., Murphy R.B., Friesner R.A., Beard H.S., Frye L.L., Pollard W.T., Banks J.L. (2004) Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. J Med Chem;47:1750-1759.
19. Ramamurthy B., Bhatt M.V. (1989) Synthesis and antitubercular activity of N-(2-naphthyl)glycine hydrazide analogues. J Med Chem;32:2421-2426.
20. Jain A.G., Gupta P., Ganesan G., Pande A., Malhotra R. (2007) Rapid solvent-free synthesis of aromatic hydrazides under microwave irradiation. Def Sci J;57:267-270.
21. Awasthi S.R., Gupta P., Rao A., Ganesan K., Malhotra R. (2007) Synthesis, characterization and spectral studies of various newer long chain aliphatic acid (2-hydroxy benzylidene and 1H-indol-3-ylmethylene) hydrazides as mosquito para-pheromones. J Korean Chem Soc;51:506-512.
22. Blower P., Fligner M., Verducci J., Bjoraker J. (2002) On combining recursive partitioning and simulated annealing to detect groups of biologically active compounds. J Chem Inf Comput Sci;42:393-404.
23. Strobl C., Malley J., Tutz G. (2009) An introduction to recursive partitioning: rationale, application, and characteristics of classification and regression trees, bagging, and random forests. Psychol Methods;14:323-348.
24. Choi S.Y., Shin J.H., Ryu C.K., Nam K.Y., No K.T., Park Choo H.Y. (2006) The development of 3D-QSAR study and recursive partitioning of heterocyclic quinone derivatives with antifungal activity. Bioorg Med Chem;14:1608-1617.
25. Young S.S., Hawkins D.M. (2004) Using recursive partitioning analysis to evaluate compound selection methods. Methods Mol Biol;275:317-334.
26. Rusinko A. 3rd, Young S.S., Drewry D.H., Gerritz S.W. (2002) Optimization of focused chemical libraries using recursive partitioning. Comb Chem High Throughput Screen;5:125-133.
27. Mamatha N., Murtuja S.B., Varaprasad B.F.M., Reddy L.V., Bhattacharya A., Helliwell M., Mukherjee A.K., Beevi S.S., Mangamoori L.N., Mukkanti K., Pal S. (2010) Naproxen and ibuprofen based acyl hydrazone derivatives: synthesis, structure analysis and cytotoxicity studies. J Chem Pharm Res;2:393-409.
28. Ershov A.Y., Lagoda I.V., Yakimovich S.I., Pakal'nis V.V., Zerova I.V., Dobrodumov A.V., Shamanin V.V. (2009) Tautomerism and conformational isomerism of mercaptoacetylhydrazones of aliphatic and aromatic aldehydes. Russ J Org Chem;45:660-666.
29. Palla G., Giovanni P., Domiano P. (1986) Conformational behaviour an E/Z isomerization of N-Acyl and N-aroylhydrazones. Tetrahedron;42:3649-3654.
30. Hübschle C.B., Sheldrick G.M., Dittrich B.J. (2011) ShelXle: a Qt graphical user interface for SHELXL. J Appl Crystallogr;44:1281-1284.
31. Tasdemir D., Lack G., Brun R., Ruedi P., Scapozza L., Perozzo R. (2006) Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids. J Med Chem;49:3345-3353.
32. Tasdemir D., Topaloglu B., Perozzo R., Brun R., O'Neill R., Carballeira N.M., Zhang X., Tonge P.J., Linden A., Rüedi P. (2007) Marine natural products from the Turkish sponge Agelas oroides that inhibit the enoyl reductases from Plasmodium falciparum, Mycobacterium tuberculosis and Escherichia coli. Bioorg Med Chem;15:6834-6845.
33. Zmuidinavicius D., Japertas P., Petrauskas A., Didziapetris R. (2003) Progress in toxinformatics: the challenge of predicting acute toxicity. Curr Top Med Chem;3:1301-1314.
34. Ghose A.K.V., Viswanadhan V.N., Wendolowski J.J. (1998) Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: an analysis of ALOGP and CLOGP methods. J Phys Chem;102A:3762.