Synthesis and Antitubercular Activity of 2-(substituted phenyl/benzyl-amino)-6-(4-chlorophenyl)-5-(methoxycarbonyl)-4-methyl-3,6-dihydropyrimidin-1-ium Chlorides

Chemical Biology and Drug Design

Volumn 81, Issue 2, 2013, Pages 219-227

  Narayanaswamy, Venugopala K ^a   Nayak, Susanta K ^b   Pillay, Melendhran ^c   Prasanna, Renuka ^d   Coovadia, Yacoob M ^c   Odhav, Bharti ^a  

^a DURBAN UNIVERSITY OF TECHNOLOGY   (South Africa)

^b ISTITUTO ITALIANO DI TECNOLOGIA   (Italy)

^c INKOSI ALBERT LUTHULI CENTRAL HOSPITAL   (South Africa)

^d SRI KRISHNADEVARAYA UNIVERSITY   (India)

Author keywords

Anti TB activity; Cytotoxicity; Dihydropyrimidine; Single crystal X ray crystallography

Indexed keywords

2 (3 BROMO 4 FLUOROPHENYLAMINO) 6 (4 CHLOROPHENYL) 5 (METHOXYCARBONYL) 4 METHYL 3,6 DIHYDROPYRIMIDIN 1 IUM CHLORIDE; 2 (3 BROMOPHENYLAMINO) 6 (4 CHLOROPHENYL) 5 (METHOXYCARBONYL) 4 METHYL 3,6 DIHYDROPYRIMIDIN 1 IUM CHLORIDE; 2 (3 CHLORO 5 HYDROXYPHENYLAMINO) 6 (4 CHLOROPHENYL) 5 (METHOXYCARBONYL) 4 METHYL 3,6 DIHYDROPYRIMIDIN 1 IUM CHLORIDE; 2 (4 BROMOPHENYLAMINO) 6 (4 CHLOROPHENYL) 5 (METHOXYCARBONYL) 4 METHYL 3,6 DIHYDROPYRIMIDIN 1 IUM CHLORIDE; 6 (4 CHLOROPHENYL) 2 (2 HYDROXY 4 NITROPHENYLAMINO) 5 (METHOXYCARBONYL) 4 METHYL 3,6 DIHYDROPYRIMIDIN 1 IUM CHLORIDE; 6 (4 CHLOROPHENYL) 2 (2,4 DIMETHOXYBENZYLAMINO) 5 (METHOXYCARBONYL) 4 METHYL 3,6 DIHYDROPYRIMIDIN 1 IUM CHLORIDE; 6 (4 CHLOROPHENYL) 2 (4 CYANOPHENYLAMINO) 5 (METHOXYCARBONYL) 4 METHYL 3,6 DIHYDROPYRIMIDIN 1 IUM CHLORIDE; 6 (4 CHLOROPHENYL) 5 (METHOXYCARBONYL) 4 METHYL 2 [3 (TRIFLUOROMETHYLTHIO)PHENYLAMINO] 3,6 DIHYDROPYRIMIDIN 1 IUM CHLORIDE; ISONIAZID; KANAMYCIN; OFLOXACIN; RIFAMPICIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

AGAR DIFFUSION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; HYDROGEN BOND; INFRARED SPECTROSCOPY; MULTIDRUG RESISTANT TUBERCULOSIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PERIPHERAL BLOOD MONONUCLEAR CELL; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ANTITUBERCULAR AGENTS; BINDING SITES; EXTENSIVELY DRUG-RESISTANT TUBERCULOSIS; LEUKOCYTES, MONONUCLEAR; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; PYRIMIDINES; TUBERCULOSIS, MULTIDRUG-RESISTANT;

MYCOBACTERIUM TUBERCULOSIS;

EID: 84872338859     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12065     Document Type: Article

References (30)

1. Patricia J.C., Glenn P.M., David S.R., Tracy L.D., Beverly M, Angela M.S., Delaina P.H., Lauren S.C., Bonnie B.P., James E.P. (2011) Molecular detection of mutations associated with first- and second-line drug resistance compared with conventional drug susceptibility testing of Mycobacterium tuberculosis. Antimicrob Agents Chemother;55:2032-2041.
2. Velayati A.A., Masjedi M.R., Farnia P., Tabarsi P., Ghanavi J., Ziazarifi A.H., Hoffner S.E. (2009) Emergence of new forms of totally drug-resistant tuberculosis bacilli: super extensively drug resistant tuberculosis or totally drug-resistant strains in iran. Chest;136:420-425.
3. Keertan D., Karen S., Alimuddin Z., Motasim B., Elizabeth M.S., Liesl P.S., Paul W. et al. (2010) Early treatment outcomes and HIV status of patients with extensively drug-resistant tuberculosis in South Africa: a retrospective cohort study. Lancet;375:1798-1807.
4. Yee D., Valiquette C., Pelletier M., Parisien I., Rocher I., Menzies D. (2003) Incidence of serious side effects from first-line antituberculosis drugs among patients treated for active tuberculosis. Am J Respir Crit Care Med;167:1472-1477.
5. Baker M.A., Lin H.H., Chang H.Y., Murray M.B. (2012) The risk of tuberculosis disease among persons with diabetes mellitus: a prospective cohort study. Clin Infect Dis;54:818-825.
6. Oliver K.C. (1993) 100Years of the biginelli dihydropyrimidine synthesis. Tetrahedron;49:6937-6963.
7. Oliver K.C. (2000) Biologically active dihydropyrimidones of the Biginelli-type - a literature survey. Eur J Med Chem;35:1043-1052.
8. Hurst E.W., Hull R. (1960) Two new synthetic substances active against viruses of the psittacosis-lymphogranuloma-trachoma group. J Med Chem;3:215-229.
9. Mayer T.U., Kapoor T.M., Haggarty S.J., King R.W., Schreiber S.L., Mitchison T.J. (1999) Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen. Science;29:5441.
10. Karnail S.A., Brian N.S., Steven E.U., David M.F., Suzanne M., Anders H., Brian C.O. (1991) Dihydropyrimidine calcium channel blockers. 3. 3-Carbamoyl-4-aryl-1, 2, 3, 4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents. J Med Chem;34:806-811.
11. Amit R.T., Vimal R.B., Bipin H.D., Dipti K.D., Vipul B.K., Viresh H.S. (2010) Novel dihydropyrimidines as a potential new class of antitubercular agents. Bioorg Med Chem Lett;20:6100-6102.
12. Wael A.E.S., Ibrahim F.N., Adel A.H., Abdel R. (2009) C-Furyl glycosides, II: synthesis and antimicrobial evaluation of C-furyl glycosides bearing pyrazolines, isoxazolines, and 5, 6-dihydropyrimidine-2(1H)-thiones. Monatsh Chem;140:365-370.
13. Sushilkumar S.B., Devanand B.S. (2003) Synthesis and anti-inflammatory activity of some 2-amino-6-(4-substituted aryl)-4-(4-substituted phenyl)-1, 6-dihydropyrimidine-5-yl-acetic acid derivatives. Acta Pharm;53:223-229.
14. Jauk B., Pernat T., Kappe C.O. (2000) Design and synthesis of a conformationally rigid mimic of the dihydropyrimidine calcium channel modulator SQ 32, 926. Molecules;5:227-239.
15. Then R.L. (2004) Antimicrobial dihydrofolate reductase inhibitors - achievements and future options: review. J Chemother;16:3-12.
16. Venugopala K.N., Jayashree B.S. (2008) Microwave-induced synthesis of schiff bases of aminothiazolyl bromocoumarins as antibacterials. Indian J Pharm Sci;70:88-91.
17. Neithnadka P.R., Venugopala K.N., Thavendran G., Manuprasad B.K., Sheena S., Pirama N.A. (2010) Design, synthesis, characterization, and anti-bacterial activity of {5-chloro-2-[(3-substitutedphenyl-1, 2, 4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanones. Eur J Med Chem;45:2677-2682.
18. Ranjith P.K., Karickal R.H., Susanta K.N., Row T.N.G., Rajeesh P., Rishikesan R., Suchetha K.N. (2012) Design, synthesis of some new (2-aminothiazol-4-yl)methylester derivatives as possible antimicrobial and antitubercular agents. Eur J Med Chem;49:172-182.
19. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev;46:3-26.
20. Tim M. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods;65:55-63.
21. Sheldrick G.M. (2008) A short history of SHELX. Acta Crystallogr A;64:112-122.
22. Macrae C.F., Bruno I.J., Chisholm J.A., Edgington P.R., McCabe P., Pidcock E., Rodriguez-Monge L. et al. (2008) Mercury CSD 2.0 - new features for the visualization and investigation of crystal structures. J Appl Crystallogr;41:466-470.
23. Farrugia L.J. (1997) ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI). J Appl Crystallogr;30:565.
24. Yoshikuni O., Mayumi T., Kenichi S. (2001) Inhibitory activity of quinolones against DNA gyrase of Mycobacterium tuberculosis. J Antimicrob Chemother;47:447-450.
25. Middlebrook G., Reggiards Z., Tigertt W.D. (1977) Automable radiometric detection of growth of Mycobacterium tuberculosis in selective media. Am Rev Respir Dis;115:1067-1069.
26. Nayak S.K., Venugopala K.N., Chopra D., Vasu S., Row T.N.G. (2010) Effect of substitution on molecular conformation and packing features in a series of aryl substituted ethyl-6-methyl-4-phenyl-2-thioxo-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylates. CrystEngComm;12:1205-1216.
27. Sunil S.L., Nayak S.K., Hathwar V.R., Chopra D., Row T.N.G. (2012) Chapter 3 role of fluorine in weak interactions in co-crystals. Chapter 3 role of fluorine in weak interactions in co-crystals. The Royal Society of Chemistry; p. 29-43.
28. Nayak S.K., Sathishkumar R., Row T.N.G. (2010) Directing role of functional groups in selective generation of C-H[small pi] interactions: in situ cryo-crystallographic studies on benzyl derivatives. CrystEngComm;12:3112-3118.
29. Nishio M. (2011) The CH/[small pi] hydrogen bond in chemistry. Conformation, supramolecules, optical resolution and interactions involving carbohydrates. Phys Chem Chem Phys;13:13873-13900.
30. Naseer M.M., Hameed S. (2012) Layer-by-layer assembly of supramolecular hexagonal blocks driven by CH-[small pi] and [small pi]-[small pi] interactions. CrystEngComm;14:4247-4250.