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Design, characterization, in vitro antibacterial, antitubercular evaluation and structure–activity relationships of new hydrazinyl thiazolyl coumarin derivatives

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Abstract

Herein, we describe the synthesis of 11new thiazolyl coumarin derivatives and evaluation of their potential role as antibacterial and antituberculosis agents. The structures of the synthesized compounds were established by extensive spectroscopic studies (Fourier transform infrared spectroscopy, 1H-nuclear magnetic resonance, 13C-nuclear magnetic resonance, 2D-nuclear magnetic resonance and liquid chromatography–mass spectrometry) and elemental analysis. All synthesized compounds were assayed for their in vitro antibacterial activity against a few gram positive and gram negative bacteria and antituberculosis activity against Mycobacterium tuberculosis H37Rv ATCC 25618 by using colorimetric microdilution assay method. Nine derivatives showed moderate anti-bacterial and anti-tuberculosis activities against all the tested strains. The highest activity against all the pathogens including Mycobacterium tuberculosis was observed by compound 7c with MIC values ranging between 31.25–62.5 μg/mL, indicating that coumarin skeleton could indeed provide useful scaffold for the development of new anti-microbial drugs.

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References

  • Abdelgadir HA, Van Staden J (2013) Ethnobotany, ethnopharmacology and toxicity of Jatropha curcas L. (Euphorbiaceae): A review. S Afr J Bot 88:204–218

    Article  CAS  Google Scholar 

  • Arshad A, Osman H, Bagley MC, Lam CK, Mohamad S, Mohdzahariluddin AS (2011) Synthesis and antimicrobial properties of some new thiazolyl coumarin derivatives. Eur J Med Chem 46:3788–3794

    Article  CAS  PubMed  Google Scholar 

  • Arya V (2011) A review on anti-tubercular plants. Int J Phar Tech Res 3:872–80

    Google Scholar 

  • Atre S (2015) An urgent need for building technical capacity for rapid diagnosis of multidrug-resistant tuberculosis (MDR-TB) among new cases: A case report from Maharashtra, India. J Infect Public Health 8(5):502–505

    Article  PubMed  Google Scholar 

  • Azelmat J, Fiorito S, Taddeo VA, Genovese S, Epifano F, Grenier D (2015) Synthesis and evaluation of antibacterial and anti-inflammatory properties of naturally occurring coumarins. Phytochem Lett 13:399–405

    Article  CAS  Google Scholar 

  • Bjarnsholt T (2013) The role of bacterial biofilms in chronic infections. Acta Pathol Microbiol Immunol Scand 121(s136):1–58

    Article  Google Scholar 

  • Deribew A, Deribe K, Reda AA, Tesfaye M, Hailmichael Y, Maja T (2013) Do common mental disorders decline over time in TB/HIV co-infected and HIV patients without TB who are on antiretroviral treatment? BMC psychiatry 13(174):1–6

    Google Scholar 

  • Elhalim SA, Ibrahim IT (2015) Radioiodination of 2, 3-dimethyl-4H-furo [3, 2-c] coumarin and biological evaluation in solid tumor bearing mice. Appl Radiat Isot 95:153–158

    Article  Google Scholar 

  • Elmi OS, Jeab MZ, Abdullah SB, Hasan H, Zilafil BA, Naing NN (2016) Extensively drug-resistant mycobacterium tuberculosis in Kelantan east coast of Malaysia: first two cases. Clin Microbiol Newsl 38(5):40–42

    Article  Google Scholar 

  • Ghosh S, Indukuri K, Bondalapati S, Saikia AK, Rangan L (2013) Unveiling the mode of action of antibacterial labdane diterpenes from Alpinia nigra (Gaertn.) B. L. Burtt seeds. Eur J Med Chem 66:101–105

    Article  CAS  PubMed  Google Scholar 

  • Gursoy A, Karali N (2003) Synthesis, characterization and primary antituberculosis activity evaluation of 4-(3-coumarinyl)-3-benzyl-4-thiazolin-2-one benzylidenehydrazones. Turk J Chem 27(5):545–52

    Google Scholar 

  • Hasanen JA (2012) Synthesis and mass spectra of some new 3-substituted coumarin derivatives. Der Pharma Chem 4:1923–1934

    CAS  Google Scholar 

  • Hummelova J, Rondevaldova J, Balastikova A, Lapcik O, Kokoska L (2014) The relationship between structure and in vitro antibacterial activity of selected isoflavones and their metabolites with special focus on antistaphylococcal effect of demethyltexasin. Lett Appl Microbiol 60:242–247

    Article  PubMed  Google Scholar 

  • Joshi JM (2011) Tuberculosis chemotherapy in the 21st century: Back to the basics. Lung India 28(3):193–200

    Article  PubMed  PubMed Central  Google Scholar 

  • Karatas MO, Olgundeniz B, Gunal S, Ozdemir I, Alici B, Cetinkaya E (2015) Synthesis, characterization and antimicrobial activities of novel silver (I) complexes with coumarin substituted N-heterocyclic carbene ligands. Bioorg Med Chem 24(4):643–650

    Article  PubMed  Google Scholar 

  • Kharb R, Shahar Yar M, Sharma PC (2011) New insights into chemistry and anti-infective potential of triazole scaffold. Curr Med Chem 18(21):3265–3297

    Article  CAS  PubMed  Google Scholar 

  • Kumar HN, Parumasivam T, Jumaat F, Ibrahim P, Asmawi MZ, Sadikun A (2014) Synthesis and evaluation of isonicotinoyl hydrazone derivatives as antimycobacterial and anticancer agents. Med Chem Res 23(1):269–279

    Article  Google Scholar 

  • Ma C, Case RJ, Wang Y, Zhang HJ, Tan GT, Van Hung N, Cuong NM, Franzblau SG, Soejarto DD, Fong HH, Pauli GF (2005) Anti-tuberculosis constituents from the stem bark of Micromelum hirsutum. Planta Med 71(3):261–267

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Mahato S, Singh A, Rangan L, Jana CK (2016) Synthesis, In silico studies and In vitro evaluation for antioxidant and antibacterial properties of diarylmethylamines: A novel class of structurally simple and highly potent pharmacophore. Eur J of Pharm Sci 88:202–209

    Article  CAS  Google Scholar 

  • Mannhold R, Kubinyi H, Timmerman H (2008) Lipophilicity in drug action and toxicology (Vol 4), Pliska V, Testa B, van de Waterbeemd H (eds). Wiley-VCH Verlag GmbH: 26 Sep

  • Matsuda K, Hattori S, Kariya R, Komizu Y, Kudo E, Goto H, Taura M, Ueoka R, Kimura S, Okada S (2015) Inhibition of HIV-1 entry by the tricyclic coumarin GUT-70 through the modification of membrane fluidity. Biochem Biophys Res Commun 457(3):288–294

    Article  CAS  PubMed  Google Scholar 

  • Muthukrishnan M, Mujahid M, Yogeeswari P, Sriram D (2011) Syntheses and biological evaluation of new triazole-spirochromone conjugates as inhibitors of Mycobacterium tuberculosis. Tetrahedron Lett 52(18):2387–2389

    Article  CAS  Google Scholar 

  • Nocentini A, Carta F, Ceruso M, Bartolucci G, Supuran CT (2015) Click-tailed coumarins with potent and selective inhibitory action against the tumor-associated carbonic anhydrases IX and XII. Bioorg Med Chem 23(21):6955–6966

    Article  CAS  PubMed  Google Scholar 

  • Patil SA, Prabhakara CT, Halasangi BM, Toragalmath SS, Badami PS (2015) DNA cleavage, antibacterial, antifungal and anthelmintic studies of Co (II), Ni (II) and Cu (II) complexes of coumarin Schiff bases: Synthesis and spectral approach. Spectrochim Acta A Mol Biomol Spectrosc 137:641–651

    Article  CAS  PubMed  Google Scholar 

  • Prakash R, Kumar D, Gupta VK, Jain S, Chauhan DS, Tiwari PK, Katoch VM (2016) Status of multidrug resistant tuberculosis (MDR-TB) among the Sahariya tribe of North Central India. J Infect Public Health 9(3):289–297

    Article  PubMed  Google Scholar 

  • Prasad R, Srivastava DK (2013) Multi drug and extensively drug-resistant TB (M/XDR-TB) management: Current issues. Clin Epidemiol Glob Health 1(3):124–128

    Article  Google Scholar 

  • Shaikh MH, Subhedar DD, Khan FA, Sangshetti JN, Shingate BB (2016) 1, 2, 3-Triazole incorporated coumarin derivatives as potential antifungal and antioxidant agents. Chin Chem Lett 2(27):295–301

    Article  Google Scholar 

  • Vazquez-Rodriguez S, Lopez RL, Matos MJ, Armesto-Quintas G, Serra S, Uriarte E, Santana L, Borges F, Crego AM, Santos Y (2015) Design, synthesis and antibacterial study of new potent and selective coumarin–chalcone derivatives for the treatment of tenacibaculosis. Bioorg Med Chem 23(21):7045–7052

    Article  CAS  PubMed  Google Scholar 

  • World Health Organisation Global Tuberculosis report 2015. http://www.who.int/tb/publications/global_report/gtbr15_main_text.pdf. Accessed 10 June 2016. WHO/ HTM/TB/2015

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Acknowledgements

The authors thank the School of Chemical Sciences, Universiti Sains Malaysia (USM) for providing necessary research facilities. The authors are also thankful to the School of Biological Sciences, USM and Faculty of Science and Natural Resources, University Malaysia Sabah for providing facilities for biological studies. Thanks are due to Malaysian Government and USM for the grant FRGS 203/PKIMIA/6711462 to conduct this work. Samina Khan Yusufzai thanks Graduate Assistance fellowship for financial support.

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Authors and Affiliations

  1. School of Chemical Sciences, Universiti Sains Malaysia, Minden, 11800, Penang, Malaysia

    Samina KhanYusufzai & Hasnah Osman

  2. Industrial Chemistry Programme, Faculty of Science and Natural Resources, Universiti Malaysia Sabah, 88400, Sabah, Malaysia

    Mohammad Shaheen Khan

  3. School of Biological Sciences, Universiti Sains Malaysia, Minden, 11800, Penang, Malaysia

    Suriyati Mohamad

  4. Bioresource, Paper and Coatings Technology Division, School of Industrial Technology, Universiti Sains Malaysia, Minden, 11800, Penang, Malaysia

    Othman Sulaiman

  5. School of Pharmaceutical Sciences, Universiti Sains Malaysia, Minden, 11800, Penang, Malaysia

    Thaigarajan Parumasivam

  6. Biotechnology Program, Faculty of Science and Natural Resources, Universiti Malaysia Sabah, 88400, Sabah, Malaysia

    Jualang Azlan Gansau & Norhaniza Johansah

  7. Department of Chemistry, Universitas Lampung, Bandar Lampung 35145, Lampung, Indonesia

    Noviany

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  1. Samina KhanYusufzai
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  2. Hasnah Osman
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  9. Noviany
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Correspondence to Hasnah Osman.

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KhanYusufzai, S., Osman, H., Khan, M.S. et al. Design, characterization, in vitro antibacterial, antitubercular evaluation and structure–activity relationships of new hydrazinyl thiazolyl coumarin derivatives. Med Chem Res 26, 1139–1148 (2017). https://doi.org/10.1007/s00044-017-1820-2

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