Synthesis, in vitro cytotoxicity, and anti-microbial studies of 1,4-bis(4-substituted-5-mercapto-1,2,4-triazol-3-yl)butanes

Medicinal Chemistry Research

Volumn 21, Issue 2, 2012, Pages 174-184

  Purohit, Madhusudan ^a   Mayur, Yergeri C ^b,c  

^a JSS COLLEGE OF PHARMACY   (India)

^b VL College of Pharmacy   (India)

^c Shri Vithal Education and Research Institute s   (India)

Author keywords

1,2,4 Triazoles; Anti microbial activity; Cytotoxicity; MTT assay

Indexed keywords

1,4 BIS[5 (CARBETHOXY METHYL))THIO 4 (3 TOLYL) 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (CARBETHOXY METHYL))THIO 4 (4 ETHOXYPHENYL) 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (CARBETHOXY METHYL))THIO 4 (4 TOLYL) 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (CARBETHOXY METHYL))THIO 4 BUTYL 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (CARBETHOXY METHYL))THIO 4 CYCLOHEXYL 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (CARBETHOXY METHYL))THIO 4 PHENYL 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (HYDRAZINOCARBONYLMETHYLTHIO) 4 3 TOLYL 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (HYDRAZINOCARBONYLMETHYLTHIO) 4 4 ETHOXYPHENYL 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (HYDRAZINOCARBONYLMETHYLTHIO) 4 4 TOLYL 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (HYDRAZINOCARBONYLMETHYLTHIO) 4 BUTYL 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (HYDRAZINOCARBONYLMETHYLTHIO) 4 CYCLOHEXYL 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (HYDRAZINOCARBONYLMETHYLTHIO) 4 PHENYL 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (N,N DIETHYLCARBAMOYL)THIO 4 (3 TOLYL) 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (N,N DIETHYLCARBAMOYL)THIO 4 (4 ETHOXYPHENYL) 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (N,N DIETHYLCARBAMOYL)THIO 4 (4 TOLYL) 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (N,N DIETHYLCARBAMOYL)THIO 4 (N BUTYL) 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (N,N DIETHYLCARBAMOYL)THIO 4 CYCLOHEXYL 1,2,4 TRIAZOL 3 YL]BUTANE; 1,4 BIS[5 (N,N DIETHYLCARBAMOYL)THIO 4 PHENYL 1,2,4 TRIAZOL 3 YL]BUTANE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CANCER CELL CULTURE; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED RADIATION; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PHARMACOPHORE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

EID: 84861856234     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9517-9     Document Type: Article

References (26)

1. Al-Soud YA, Al-Masoudi NA (2004) DNA directed alkylating agents: Synthesis, antitumor activity of DNA affinity of bis N,N′ trisubstituted 1,2,4-triazolo-piperazins. Il Farmaco 59:41-46. doi: 10.1016/j.farmac.2003.08. 006 (Pubitemid 38134283)
2. Antonini I, Santoni S, Lucciarini R et al (2008) Synthesis and antitumor evaluation of bis aza-anthracene-9,10-diones and bis aza-anthrapyrazole-6-ones. J Med Chem 51:997-1006. doi: 10.1021/jm7013937 (Pubitemid 351304708)
3. Badran MM, Abouzid KAM, Hussein MHM (2003) Synthesis of certain substituted quinoxalines as antimicrobial agents (part II). Arch Pharm Res 26:107-113 (Pubitemid 43086228)
4. Berghot MA (2001) Facile synthesis and biological evaluation of heterocyclic compounds containing Diazepam. Arch Pharm Res 24:263-269 (Pubitemid 33703571)
5. Brana MF, Castellano JM, Perron D et al (1997) Chromophore modified bis-naphthalimides: synthesis and anti tumor activity of bis-dibenz(d,h) isoquinolin-1,3-diones. J.Med Chem 40:449-454. doi:10.1021/jm960295k (Pubitemid 27080023)
6. Clemons M, Coleman RE, Verma S (2004) Aromatase inhibitors in the adjuvent setting; bringingthe gold to a standard? Cancer Treat Rev 30:325-332. doi:10.1016/j.ctrv.2004.03.004 (Pubitemid 38735701)
7. Coro J, Perez R, Rodriguez H et al (2005) Synthesis and antiprotozoan evaluation of new alkyl-linked bis(2-thioxo-[1,3,5]thiadiazinan- 3-yl) carboxylic acids. Bioorg Med Chem 13:3413-3421.doi:10.1016/j.bmc.2005.03.009 (Pubitemid 40545796)
8. Dabholkar VV, Ansari FY (2008) Synthesis and biological studies of bis (thiadiazole/triazole) by sonication. Acta Pol Pharm Drug Res 65:521-526
9. Denny WA (2003) Synthetic DNA targeted chemotherapeutic agents and related tumor activated prodrugs. In: Abraham DJ (ed) Bergers medicinal chemistry and drug discovery, vol 5, 6th edn. Wiley-Interscience Hoboken, Hoboken, pp 74-75
10. Gamage SA, Spicer JA, Atwell GJ et al (1999) Structure activity relationships for substituted bis(acridine 4-carboxamides): a new class of anticancer agents. J Med Chem 42:2383-2393. doi: 10.1021/jm980687m (Pubitemid 29305172)
11. Ghorab MM, El-Sharief AMS, Ammar YA et al (2000) Synthesis and radiation stability of novel biologically active sulfur compounds derived from 1, 2-bis(4-amino-5-mercapto-s-triazol-3-yl)ethane. Il Farmaco 55:354-361. doi:10.1016/S0014-827X(00)00051-3
12. Gulerman NN, Dogan HN, Rollas S et al (2001) Synthesis and structure elucidation of some new thioether derivatives of 1,2,4-triazoline-3-thiones and their antimicrobial activities. Il Farmaco 56:953-958. doi:10.1016/S0014- 827X(01)01167-3 (Pubitemid 34019225)
13. Holla BS, Gonsalves R, Shenoy S (1998) Studies on some N-bridged heterocycles derived from bis (4-amino 5-mercapto, 1,2,4 triazol-3-yl)alkanes. ILFarmaco 53:574-578. doi:10.1016/S0014-827X(98)00068-8 (Pubitemid 29084045)
14. Holla BS, Gonsalves R, Shenoy S (2000) Synthesis and anti bacterial studies of a new series of 1,2-bis (1,3,4-oxadiazol-2-yl) ethanes and 1,2 bis (4-amino-1,2,4 triazolo-3-yl)ethanes. Eur J Med Chem 35:267-271
15. Holla BS, Poojary KN, Rao BS et al (2002) New bis-amino mercapto triazoles and bis triazolo thiadiazoles as possible anticancer agents. Eur J Med Chem 37:511-517
16. Mahmoud Omar T (1997) Synthesis of new xanthenone derivatives of expected antibilharzial activity. Arch Pharm Res 20:602-609
17. Manjula SN, Noolvi NM, Parihar KV et al (2009) Synthesis and antitumor activity of optically active thiourea and their 2-amino benzothiazole derivatives: a novel class of anti cancer agents. Eur J Med Chem 44:2923-2929. doi:10.1016/j.ejmech.2008.12.002
18. Molinari A, Ojeda C, Oliva A et al (2009) Synthesis and cytotoxic evaluation of 6-(3-pyrazolylpropyl) derivatives of 1,4-naphthohydroquinone-1,4- diacetate. Arch Pharm Chem Life Sci 342:591-599. doi:10.1002/ardp.200900041
19. Pomarnacka E, KornickaA(2001) Synthesis and in vitro anticancer and anti-HIV evaluation of new 2-mercapto benzenesulfonamides. Il Farmaco 56:571-577. doi:10.1016/S0014-827X(01)01095-3 (Pubitemid 32727928)
20. Purohit MN, Pujar GV, Manohar KV et al (2006) Synthesis and antimicrobial activity of 4-substituted-5-mercapto 3-carboxamido triazoles. Indian J Heterocyclic Chem 16:93-94
21. Remers WA (2004) Antineoplastic agents. In: Block JH, Beale JM (eds) Wilson and Giswald's text book of organic medicinal and pharmaceutical chemistry, 11th edn. Lippincott Williams and Wilkins, p 397
22. Rewcastle GW, Denny WA, Baguley BC (1987) Potential anti tumor agents 51. Synthesis and anti tumor activity of substituted phenazine 1-carboxamides. J Med Chem 30:843-851. doi: 10.1021/jm00388a017 (Pubitemid 17119530)
23. Rostom SAF, Ashour HMA, El Razik HAA (2009) Synthesis and biological evaluation of some novel poly substituted pyrimidine derivatives as potential anti microbial and anti cancer agents. Arch Pharm Chem Life Sci 342:299-310. doi:10.1002/ardp.200800223
24. Sondhi SM, Jain S, Dinodia M et al (2007) One pot synthesis of pyrimidine and bispyrimidine derivatives and their evaluation for anti-inflammatory and analgesic activities. Bioorg Med Chem 15:3334-3344. doi:10.1016/j.bmc.2007.03. 028 (Pubitemid 46529272)
25. Spicer JA, Gamage SA, Rewcastle GW et al (2000) Bis(phenazine 1-carboxamide): structure activity relationships for a new class of dual topoisomerase I/II directed anti cancer drugs. J Med Chem 43:1350-1358. doi:10.1021/jm990423f (Pubitemid 30212576)
26. Yong P, Yang Q, Quin X (2005) Novel DNA bis-intercalators of isoquiolino-[4,5-bc]-acridones: design, synthesis and evaluation of cytotoxic activity. Tetrahedron 61:11895-11901. doi:10.1016/j.tet.2005.09.065 (Pubitemid 41635247)