Synthesis, antitubercular and antimicrobial potential of some new thiazole substituted thiosemicarbazide derivatives
- 319 Downloads
The increase in antibiotic resistance due to multiple factors has warranted the need for search of new compounds which are active against multidrug resistant pathogens. In this context a small focused library of thiosemicarbazide derivatives of 2-arylthiazole-4-carbaldehyde, 4-methyl-2-arylthiazole-5-carbaldehyde and 1-(4-methyl-2-arylthiazol-5-yl) ethanone, (5a–l) has been synthesized. The title compounds were screened for inhibitory activity against Mycobacterium tuberculosis H37Ra (ATCC 25177) and Mycobacterium bovis Bacille Calmette Guerin (ATCC 35743) strains. The synthesized compounds, 5a–l were further assayed for their cytotoxic activity against the two human cancer cell lines, HeLa and human colon carcinoma 116 cell lines and showed no significant cytotoxic activity against these two cell lines at the maximum concentration evaluated. Further, the synthesized compounds were found to have potential antibacterial activity against Gram-negative bacteria, Escherichia coli, Pseudomonas flurescence and Gram-positive bacteria, Staphylococcus aureus, Bacillus subtilis. Most of the synthesized compounds showed moderate activity against fungal strain Candida albicans. This study provides valuable directions to our ongoing endeavor of rationally designing more potent antimycobacterial agent.
KeywordsThiosemicarbazide Thiazole Antitubercular activity Antimicrobial activity Cytotoxicity
Y.K.A. expresses her gratefulness to CSIR [File No. 08/590(0001)/2012-EMR-I] for the financial support. P.C.M. would like to thank University Grant Commission (UGC No. 42-355/2013(SR), New Delhi, India for the financial assistance and CSIR-NCL, Pune for supporting biological activity. Central Analysis facility, Savitribai Phule Pune University, Pune is also acknowledged for spectral analysis.
Compliance with ethical standards
Conflict of interest
The authors declare that they have no competing interests.
- Arora S, Agarwal S, Singhal S (2014) Anticancer activities of thiosemicarbazides / thiosemi-carbazones: a review. Int J Pharm Pharm Sci 6:34–41Google Scholar
- Inamdar GS, Pandya AN, Thakar HM, Sudarsanam V, Kachler S, Sabbadin D, Moro S, Klotz KN, Vasu KK (2013) New insight into adenosine receptors selectivity derived from a novel series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamides and furamides. Eur J Med Chem 63:924–934CrossRefPubMedGoogle Scholar
- Johnson M, Antonio T, Reith ME, Dutta AK (2012) Structure-activity relationship study of N6-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine analogues: development of highly selective D3 dopamine receptor agonists along with a highly potent D2/D3 agonist and their pharmacological characterization. J Med Chem 55(12):5826–5840CrossRefPubMedPubMedCentralGoogle Scholar
- Moglea PP, Meshramb RJ, Hesea SV, Kamblea RD, Kambleb SS, Gaccheb RN, Dawanea BS (2016) Synthesis and molecular docking studies of new series of bipyrazol-ylthiazol-ylidene-hydrazinecarbothioamide derivatives as potential antitubercular agents. MedChemCom 7:1405-1420Google Scholar
- Perkoviisć I, Butula I, Kralj M, Martin-Kleiner I, Balzarini J, Hadjipavlou-Litina D, Katsori AM, Zorc B (2012) Novel NSAID 1-acyl-4-cycloalkyl/arylsemicarbazides and 1-acyl-5-benzyloxy/hydroxyl carbamoylcarbazides as potential anticancer agents and antioxidants. Eur J Med Chem 51:227–238CrossRefGoogle Scholar
- Pitucha M, Wos´ M, Miazga-Karska M, Klimek K, Mirosław B, Pachuta-Stec A, Gładysz A, Ginalska G (2016) Synthesis, antibacterial and antiproliferative potential of somenew 1-pyridinecarbonyl-4-substituted thiosemicarbazidederivatives. Med Chem Res 25:1666–1677CrossRefPubMedPubMedCentralGoogle Scholar
- Salgın-Goksen U, Gokhan-Kelekci N, Goktas O, Koysal Y, Kılıc E, Isık S, Aktay G, Ozalp M (2007) 1-Acylthiosemicarbazides,1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic, anti-inflammatory and antimicrobial activities. Bioorg Med Chem 15:5738–5751CrossRefPubMedGoogle Scholar
- Tomasic T, Katsamakas S, Hodnik Z, Ilas J, Brvar M, Solmajer T, Montalvao S, Tammela P, Banjanac M, Ergovic G, Anderluh M, Masic LP, Kikelj D (2015) Discovery of 4,5,6,7-Tetrahydrobenzo[1,2-d]thiazoles as Novel DNA Gyrase Inhibitors Targeting the ATP-Binding Site. J Med Chem 58:5501–5521CrossRefPubMedGoogle Scholar
- Umadevi P, Deepti K, Srinath I, Vijayalakshmi G, Tarakaramji M (2012) Synthesis and in vitro antibacterial activity of some urea, thiourea and thiosemicarbazide derivatives. Int J Pharm Pharm Sci 4(3):379–383Google Scholar
- Yusufzai SK, Osman H, Khan MS, Mohamad S, Sulaiman O, Parumasivam T, Gansau JA, Johansah N, Noviany (2017) Design, characterization, in vitro antibacterial, antitubercular evaluation and structure–activity relationships of new hydrazinyl thiazolyl coumarin derivatives. Med Chem Res. doi: 10.1007/s00044-017-1820-2