Synthesis, antimycobacterial, antiviral, antimicrobial activities, and QSAR studies of isonicotinic acid-1-(substituted phenyl)-ethylidene/cycloheptylidene hydrazides

Medicinal Chemistry Research

Volumn 21, Issue 8, 2012, Pages 1935-1952

  Judge, Vikramjeet ^a   Narasimhan, Balasubramanian ^b   Ahuja, Munish ^a   Sriram, Dharmarajan ^c   Yogeeswari, Perumal ^c   De Clercq, Erik ^d   Pannecouque, Christophe ^d   Balzarini, Jan ^d  

^a Guru Jambheswar University of Science and Technology   (India)

^b MAHARSHI DAYANAND UNIVERSITY   (India)

^c BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

^d REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antimicrobial; Antimycobacterial; Antiviral; Hydrazide derivatives; QSAR

Indexed keywords

ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTIMYCOBACTERIAL AGENT; ANTIVIRUS AGENT; BROMINE; CHLORIDE; CYTOSTATIC AGENT; FLUCONAZOLE; HYDRAZIDE DERIVATIVE; ISONIAZID; ISONICOTINIC ACID [1 (2,4 DICHLORO PHENYL) ETHYLIDENE] HYDRAZIDE; ISONICOTINIC ACID [1 (2,4 DIMETHOXY PHENYL) ETHYLIDENE] HYDRAZIDE; ISONICOTINIC ACID [1 (4 BROMO PHENYL) ETHYLIDENE] HYDRAZIDE; ISONICOTINIC ACID [1 (4 HYDROXY PHENYL) ETHYLIDENE] HYDRAZIDE; ISONICOTINIC ACID [1 (4 NITRO PHENYL) ETHYLIDENE] HYDRAZIDE; NORFLOXACIN; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BACILLUS SUBTILIS; CANDIDA ALBICANS; COXSACKIE VIRUS B4; CYTOTOXICITY; DNA VIRUS; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; IN VITRO STUDY; LIPOPHILICITY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PHYSICAL CHEMISTRY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RESPIRATORY SYNCYTIAL PNEUMOVIRUS; RNA VIRUS; STAPHYLOCOCCUS AUREUS; VESICULAR STOMATITIS VIRUS;

EID: 84866139573     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9705-2     Document Type: Article

References (58)

1. Bajaj S, Sambi SS, Madan AK (2005) Prediction of anti-inflammatory activity of N-arylanthranilic acids: computational approach using refined Zagreb Indices. Croat Chem Acta 78(2):165-174
2. Balaban AT (1982) Highly discriminating distance-based topological index. Chem Phys Lett 89:399-404
3. Bayrak H, Demirbas A, Demirbas N, Karaoglu SA (2009a) Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities. Eur J Med Chem 44:4362-4366
4. Bayrak H, Demirbas A, Karaoglu SA, Demirbas N (2009b) Synthesis of some new 1,2,4-triazoles, their mannich and schiff bases and evaluation of their antimicrobial activities. Eur J Med Chem 44:1057-1066
5. Boojamra CG, Mackman RL, Markevitch DY, Prasad V, Ray AS, Douglas J, Grant D, Kim CU, Cihlar T (2008) Synthesis and anti-HIV activity of GS-9148 (20-Fd4AP), a novel nucleoside phosphonate HIV reverse transcriptase inhibitor. Bioorg Med Chem Lett 18:1120-1123
6. Cappucino JG, Sherman N (1999) Microbiology-a laboratory manual. Addison Wesley Longman Inc, California, p 263
7. Cruz-Monteagudo M, Gonzalez-Diaz H, Aguero-Chapin G, Santana L, Borges F, Dominguez ER, Podda G, Uriarte E (2007) Computational chemistry development of a unified free energy Markov model for the distribution of 1300 chemicals to 38 different environmental or biological systems. J Comput Chem 28(11):1909-1923
8. Dai J, Sun C, Han S, Wang L (1999) QSAR for polychlorinated compounds (PCOCs). I. Prediction of partition properties for PCOCs using quantum chemical parameters. Bull Environ Contam Toxicol 62:530-538
9. Emami S, Foroumadi A, Falahati M, Lotfali E, Rajabalian S, Ebrahimi FS, Shafiee A (2008) 2-Hydroxyphenacyl azoles and related azolium derivatives as antifungal agents. Bioorg Med Chem Lett 18:141-146
10. Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR (1998) Vogel's text book of practical organic chemistry. AddisonWesley Longman Inc, California, p 34
11. Furusjo E, Svenson A, Rahmberg M, Andersson M (2006) The importance of outlier detection and training set selection for reliable environmental QSAR predictions. Chemosphere 63:99-108
12. Golbraikh A, Tropsha A (2002) Beware of q2!. J Mol Graphics Model 20:269-276
13. Gonzalez-Diaz H, Prado-Prado FJ (2008) Unified QSAR and network-based computational chemistry approach to antimicrobials, part 1: multispecies activity models for antifungals. J Comput Chem 29(4):656-667
14. Gonzalez-Diaz H, Vilar S, Santana L, Uriarte E (2007) Medicinal chemistry and bioinformatics-current trends in drugs discovery with networks topological indices. Curr Top Med Chem 7(10):1015-1029
15. Gonzalez-Diaz H, Gonzalez-Diaz Y, Santana L, Ubeira FM, Uriarte E (2008) Networks and connectivity indices. Proteomics 8(4): 750-778
16. Guven OO, Erdogan T, Goker H, Yildiz S (2007) Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers. Bioorg Med Chem 17:2233-2236
17. Hansch C, Fujita T (1964) p-r- analysis. A method for the correlation of biological activity and chemical structure. J Am Chem Soc 86:1616-1626
18. Hansch C, Leo A, Unger SH, Kim KH, Nikaitani D, Lien EJ (1973) Aromatic substituent constants for structure-activity correlations. J Med Chem 16:1207-1216
19. Hatya SA, Aki-sener E, Tekiner-Gulbas B, Yildiz I, Temiz-Arpaci O, Yalcin I, Altanlar N (2006) Synthesis, antimicrobial activity and QSARs of new benzoxazine-3-ones. Eur J Med Chem 41: 1398-1404
20. Hyperchem 6.0 (1993) Hypercube, Inc., Florida
21. Ivanciuc O, Ivanciuc T, Cabrol-Bass D (2002) QSAR for dihydrofolate reductase inhibitors with molecular graph structural descriptors. J Mol Str (Theochem) 582:39-51
22. Johnson K, Schultz PG (1994) Mechanistic studies of the oxidation of isoniazid by catalase-eroxidase from Mycobacterium tuberculosis. J Am Chem Soc 116:7425-7426
23. Judge V, Narang R, Sharma D, Narasimhan B, Kumar P (2010) Hansch analysis for the prediction of antimycobacterial activity of ofloxacin derivatives. Med Chem Res. doi:10.1007/s00044-010-9400-8.
24. Kamal A, Reddy KS, Ahmed SK, Khan MNA, Sinha RK, Yadav JS, Arora SK (2006) Antitubercular agents. Part 3. Benzothiadiazine as novel scaffold for antimycobacterium activity. Bioorg Med Chem 14:650-658
25. Khasnobis S, Escuyer VE, Chatterjee D (2002) Emerging therapeutic targets in tuberculosis: post genomic era. Expert Opin Ther Targets 6(1):21-40
26. Kier LB, Hall LH (1976) Molecular connectivity in chemistry and drug research. Academic Press, New York
27. Kim YM, Farrah S, Baney RH (2007) Structure-antimicrobial activity relationship for silanols, a new class of disinfectants, compared with alcohols and phenols. Int J Antimicrob Agents 29:217-222
28. Kucukguzel I, Tatar E, Kucukguzel SG, Rollas S, De Clercq E (2008) Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy) methyl]-4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents. Eur J Med Chem 43:381-392
29. Kumar A, Narasimhan B, Kumar D (2007) Synthesis, antimicrobial, and QSAR studies of substituted benzamides. Bioorg Med Chem 15:4113-4124
30. Kumar D, Judge V, Narang R, Sangwan S, De Clercq E, Balzarini J, Narasimhan B (2010a) Benzylidene/2-chlorobenzylidene hydrazides: synthesis, antimicrobial activity, QSAR studies and antiviral evaluation. Eur J Med Chem 45:2806-2816
31. Kumar P, Narasimhan B, Yogeeswari P, Sriram D (2010b) Synthesis and antitubercular activities of substituted benzoic acid N0-(substituted benzylidene/furan-2-ylmethylene)-N-(pyridine-3-carbonyl)-hydrazides. Eur J Med Chem 45:6085-6089
32. Lather V, Madan AK (2005) Topological models for the prediction of anti-HIV activity of dihydro (alkylthio) (napthylmethyl) oxopyrimidines. Bioorg Med Chem 13:1599-1604
33. Maccari R, Ottana R, Monforte F, Vigorita MG (2002) In vitro antimycobacterial activities of 20-monosubstituted isonicotinohydrazides and their cyanoborane adducts. Antimicrob Agents Chemother 46(2):294-299
34. MamoloMG, Zampieri D, Falagiani V, Vio L, Fermeglia M, Ferrone M, Pricl S, Banfi E, Scialino G (2004) Antifungal and antimycobacterial activity of new N1-[1-aryl-2-(1H-Imidazol-1-yl and 1H-1,2, 4-triazol-1-yl)-ethylidene]-yridine- 2-carboxamidrazone derivatives: a combined experimental and computational approach. ARKIVOC v:231-250
35. Mandloi D, Joshi S, Khadikar PV, Khosla N (2005) QSAR study on the antibacterial activity of some sulfa drugs: building blockers of Mannich bases. Bioorg Med Chem Lett 15:405-411
36. Masunari A, Tavares LC (2007) A new class of nifuroxazide analogues: synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug resistant Staphylococcus aureus. Bioorg Med Chem Lett 15:4229-4236
37. Narasimhan B, Judge V, Narang R, Ohlan S, Ohlan R (2007) Quantitative structure-activity relationship studies for prediction of antimicrobial activity of synthesized 2,4-hexadienoic acid derivatives. Bioorg Med Chem Lett 17:5836-5845
38. National Committee for Clinical Laboratory Standards (1995) Antimycobacterial susceptibility testing for Mycobacterium tuberculosis. Proposed standard M24-T. National Committee for Clinical Laboratory Standards, Villanova, Pa
39. Pauwels R, Balzarini J, Baba M, Snoeck R, Schols D, Herdewijn P, Desmyter J, De Clercq E (1988) Rapid and automated tetrazolium based colorimetric assay for detection of anti-HIV compounds. J Virol Methods 20:309-322
40. Pharmacopoeia of India (2007) Vol. I, Controller of Publications. Ministry of Health Department, Government of India, New Delhi, p 37
41. Pinheiro AAC, Borges RS, Santos SL, Alves CN (2004) A QSAR study of 8.O.40-neolignans with antifungal activity. J Struct Mol (Theochem) 672:215-219
42. Prado-Prado FJ, Gonzalez-Diaz H, Vega OMDL, Ubeira FM, Chou KC (2008) First multi-tasking QSAR model for Input-Coded prediction, structural back-rojection, and complex networks clustering of antiprotozoal compounds. Bioorg Med Chem 16(11):5871-5880
43. Randic M (1975) Characterization of molecular branching. J Am Chem Soc 97:6609-6615
44. Randic M (1993) Comparative regression analysis. Regressions based on a single descriptor. Croat Chem Acta 66:289-312
45. Rodriguez-Arguelles MC, Lopez-Silva EC, Sanmartin J, Pelagatti P, Zani F (2007) Copper complexes of imidazole-2-, pyrrole-2-and indol-3-carbaldehyde thiosemicarbazones: inhibitory activity against fungi and bacteria. J Inorg Biochem 101:138-147
46. Sahu KK, Ravichandran V, Mourya VK, Agrawal RK (2007) QSAR analysis of caffeoyl naphthalene sulfonamide derivatives as HIV-1 integrase inhibitors. Med Chem Res 15:418-430
47. Sbardella G, Mai A, Artico M, Setzu MG, Poni G, Colla PL (2004) New 6-nitroquinolones: synthesis and antimicrobial activities. IL Farmaco 59:463-471
48. Shahar Yar M, Siddiqui AA, Ali MA (2007) Synthesis and antimycobacterial activity of novel heterocycles. J Serb Chem Soc 72(1):5-11
49. Sharma P, Rane N, Gurram VK (2004) Synthesis and QSAR studies of pyrimido[4,5-d] pyrimidine-2,5-dione derivatives as potential antimicrobial agents. Bioorg Med Chem Lett 14:4185-4190
50. Sharma P, Kumar A, Sharma M (2006) Synthesis and QSAR studies on 5-[2-(2-methylprop-1-enyl)-1Hbenzimidazol-1yl]-4,6-diphenyl-yrimidin-2-(5H) -thione derivatives as antibacterial. Eur J Med Chem 41:833-840
51. Shoeb HA, Bowman BU Jr, Ottolenghi AC, Merola AJ (1985) Peroxidase mediated oxidation of isoniazid. Antimicrob Agents Chemother 27:399-403
52. Sortino M, Delgado P, Jaurez S, Quiroga J, Abonia R, Insuasey B, Rodero MN, Garibotto FM, Enriz RD, Zacchino SA (2007) Synnthesis and antifungal activity of (Z)-5-arylidenerhodanines. Bioorg Med Chem Lett 15:484-494
53. SPSS For Windows Version 10.05 (1999) SPSS Inc. Bangalore India
54. Bangalore, India Sriram D, Yogeeswari P, Dhakla P, Senthilkumar P, Banerjee D (2007) N-Hydroxythiosemicarbazones: synthesis and antitubercular activity. Bioorg Med Chem Lett 17:1888-1891
55. Tripathi RP, Saxena N, Tiwari VK, Verma SS, Chaturvedi V, Manju YK, Srivastva AK, Gaikwad A, Sinha S (2006) Synthesis and antitubercular activity of substituted phenylmethyl-and pyridylmethyl amines. Bioorg Med Chem 4:8186-8196
56. TSAR 3D Version 3.3 (2000), Oxford Molecular Limited
57. Wiener H (1947) Structural determination of paraffin boiling points. J Am Chem Soc 69:17-20
58. Zhang P, Heym B, Allen B, Young D, Cole ST (1992) The catalaseperoxidase gene and isoniazid resistance to Mycobacterium tuberculosis. Nature 358:591-593