Skip to main content

Advertisement

SpringerLink
Log in

Synthesis and evaluation of antimicrobial activity of 2-aminobenzothiazolomethyl naphthol derivatives

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript

Abstract

An efficient method is described for the synthesis of 2-aminobenzothiazolomethyl naphthol derivatives by one-pot three-component reaction of aldehydes, 2-naphthol, and 2-amino benzothiazole using triton X-100 as a catalyst in water with good yield. The synthesized compounds have been characterized by IR, 1H NMR, 13C NMR, and mass spectra. The synthesized compounds were screened for their antibacterial activity against gram-positive and gram-negative bacteria viz. Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella typhi, Escherichia coli, Bacillus cereus, and Providencia rettegeri and fungal activity against fungal strain such as Aspergillus niger, Aspergillus fumigatus, and Aspergillus flavus. Synthesized compounds exhibited MICs value between 3.25 and 12.5 μg/mL against bacterial strains and 6.25 and 12.5 μg/mL against fungal strains as shown in Tables 4 and 5, respectively. Derivatives 5c and 5h were equipotent activity as ciprofloxacin against E. coli and 5k against P. aeruginosa and B. cereus. Derivatives 5e, 5g, and 5k exhibited excellent antifungal activity against all tested fungal strains. Ciprofloxacin and fluconazole have been used as standard drugs for antibacterial and antifungal activity, respectively.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Bujdáková H, Múčková M (1994) Antifungal activity of a new benzothiazole derivative against Candida in vitro and in vivo. Int J Antimicrob Agents 4:303–308

    Article  PubMed  Google Scholar 

  • Crittenden JC, Trussell RR, Hand DW, Tchobanglouse G (2004) Water treatment principle and design, 2nd edn. John Wily and Sons, Hoboken

    Google Scholar 

  • Erian AW (1993) The chemistry of beta-enaminonitriles as versatile reagents in heterocyclic synthesis. Chem Rev 93:1991–2005

    Article  CAS  Google Scholar 

  • Heilmann J, Wasescha MR, Schmidt TJ (2001) The influence of glutathione and cysteine levels on the cytotoxicity of helenanolide type sesquiterpene lactones against KB cells. Bioorg Med Chem 9:2189–2194

    Article  CAS  PubMed  Google Scholar 

  • Hosseinian A, Shaterian HR (2012) NaHSO4·H2O catalyzed multicomponent synthesis of 1-benzothiazolylamino)methyl-2-naphthols under solvent-free conditions. Phosphorus Sulfur Silicon Relat Elem 187:1056–1063

    Article  CAS  Google Scholar 

  • Jin L, Song B, Zhang G, Xu R, Zhang S, Gao X, Hu D, Yang S (2006) Synthesis, X-ray crystallographic analysis, and antitumor activity of N-(benzothiazole-2-yl)-1-(fluorophenyl)-O, O-dialkyl-α-aminophosphonates. Bioorg Med Chem Lett 16(6):1537–1543

    Article  CAS  PubMed  Google Scholar 

  • Kamal A, Reddy KS, Khan MNA, Shetti RVCRNC, Ramaiah MJ, Pushpavalli SNCVL, Srinivas C, Bhadra MP, Chourasia M, Sastry GN, Juvekar A, Zingde S, Barkum M (2010) Synthesis, DNA-binding ability and anticancer activity of benzothiazole/benzoxazole–pyrrolo[2,1-c][1,4]benzodiazepine conjugates. Bioorg Med Chem 18(13):4747–4761

    Article  CAS  PubMed  Google Scholar 

  • Kumar A, Rao MS, Rao VK (2010a) Sodium dodesyl sulfate-assisted synthesis of 1-(benzothiazoloamino)-methyl-2-naphthol in water. Aust J Chem 63:1538–1540

    Article  CAS  Google Scholar 

  • Kumar A, Gupta MK, Kumar M (2010b) Non-ionic surfactant catalyzed synthesis of Betti base in water. Tetrahedron Lett 51:1582–1584

    Article  CAS  Google Scholar 

  • Lalitha MK (2004) Manual on antimicrobial susceptibility testing. Under the auspices of Indian Association of Medical Microbiologists

  • Malik JK, Soni H, Singhai AK (2013) Synthesis, characterization and evaluation for antifungal activity of substituted diaryl imidazo [2,1,b]-benzothiazole. J Pharm Res 7(1):39–46

    Article  CAS  Google Scholar 

  • Mitsuya H, Yarchoan R, Broder S (1990) Molecular targets for AIDS therapy. Science 249:1533–1544

    Article  CAS  PubMed  Google Scholar 

  • Mosman T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65(1–2):55–63

    Article  Google Scholar 

  • Ohanian A, Javanshir S, Heravi MM, Bamoharram FF (2009) One-pot synthesis of 2′-aminobenzothiazolomethylnaphtols in water catalyzed by Wells–Dawson heteropolyacid. In: 13th International electronic conference on synthetic organic chemistry, Nov. 1–30

  • Padalkar VS, Borse BN, Gupta BD, Phatangare KR, Patil VS, Umape PG, Sekar N (2011) Synthesis and antimicrobial activity of novel 2-substituted benzimidazole, benzoxazole and benzothiazole derivatives. Arab J Chem. doi:10.1016/j.arabjc.2011.12.006

    Google Scholar 

  • Sahu PK, Sahu PK, Gupta SK, Thavaselvam D, Agarwal DD (2012) Synthesis and evaluation of antimicrobial activity of 4H-pyrimido[2,1-b] benzothiazole, pyrazole and benzylidene derivatives of curcumin. Eur J Med Chem 54:366–378

    Article  CAS  PubMed  Google Scholar 

  • Shaabani A, Rahmati A, Farhangi E (2007) Water promoted one-pot synthesis of 2′-aminobenzothiazolomethyl naphthols and 5-(2′-aminobenzothiazolomethyl)-6-hydroxyquinolines. Tetrahedron Lett 48:7291–7294

    Article  CAS  Google Scholar 

  • Singh MK, Tilak R, Nath G, Awasthi SK, Agarwal A (2013) Design, synthesis and antimicrobial activity of novel benzothiazole analogs. Eur J Med Chem. doi:10.1016/j.ejmech.2013.02.027

    PubMed Central  Google Scholar 

  • Solomon VR, Hu C, Lee H (2009) Hybrid pharmacophore design and synthesis of isatin–benzothiazole analogs for their anti-breast cancer activity. Bioorg Med Chem 17(21):7585–7592

    Article  CAS  PubMed  Google Scholar 

  • Sumana MN, Rajagopal V (2002) A study of dermatophytes and their in vitro antifungal sensitivity. Indian J Pathol Microbiol 45(2):169–172

    CAS  PubMed  Google Scholar 

  • Taylor EC, Mckillop A (1970) The chemistry of cyclic enaminonitriles and o-amino nitriles. Interscience, New York, p 415

    Google Scholar 

  • Tomi IHR, Tomma JH, Al-Daraji AHR, Al-Dujaili AH (2012) Synthesis, characterization and comparative study the microbial activity of some heterocyclic compounds containing oxazole and benzothiazole moieties. J Saudi Chem Soc. doi:10.1016/j.jscs.2012.04.010

    Google Scholar 

  • Wang Z, Shi XH, Wang J, ZhouT XuYZ, Huang TT, Li YF, Zhao YL, Yang L, Yang SY, Yu LT, Wei YQ (2011) Synthesis, structure–activity relationships and preliminary antitumor evaluation of benzothiazole-2-thiol derivatives as novel apoptosis inducers. Bioorg Med Chem Lett 21(4):1097–1101

    Article  CAS  PubMed  Google Scholar 

  • Yang L (2012) Trichloroisocyanuric acid, a new and efficient catalyst for the synthesis of 2′-aminobenzothiazolo-arylmethyl-2-naphthols. J Chem 9(4):2424–2428

    CAS  Google Scholar 

  • Yu Y, Guo H (2011) One-pot synthesis of 2′-aminobenzothiazolo-arylmethyl-2-naphthols in ionic liquid of [Hnmp]HSO4 under solvent-free conditions. Chin J Org Chem 31:96–100

    CAS  Google Scholar 

Download references

Acknowledgments

We are thankful to Director, Defense Research & Development Establishment, Gwalior-474002, Madhya Pradesh, India to conduct the facility of biological activity. This work is supported by a grant from the Graduate Studies and Scientific Research Agency (Grant no. 4.H.33) Salman bin Abdulaziz University, Alkharj, Saudi Arabia.

Author information

Authors and Affiliations

  1. School of Studies in Chemistry, Jiwaji University, Gwalior, 474011, Madhya Pradesh, India

    Pramod Kumar Sahu & Dau D. Agarwal

  2. Department of Industrial Chemistry, Jiwaji University, Gwalior, 474011, Madhya Pradesh, India

    Pramod Kumar Sahu, Praveen Kumar Sahu & Dau D. Agarwal

  3. Jagdishprasad Jhabarmal Tibrewala University, Jhunjhunu, 333001, Rajasthan, India

    Praveen Kumar Sahu & Dau D. Agarwal

  4. Microbiology Division, Defence Research Development Establishment, Jhansi Road, Gwalior, 474002, India

    D. Thavaselvam

  5. Department of Pharmaceutical Chemistry, College of Pharmacy, Salman bin Abdulaziz University, PO Box 173, Alkharj, 11942, Saudi Arabia

    Ahmed M. Alafeefy

Authors
  1. Pramod Kumar Sahu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Praveen Kumar Sahu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. Thavaselvam
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ahmed M. Alafeefy
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Dau D. Agarwal
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Pramod Kumar Sahu or Praveen Kumar Sahu.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sahu, P.K., Sahu, P.K., Thavaselvam, D. et al. Synthesis and evaluation of antimicrobial activity of 2-aminobenzothiazolomethyl naphthol derivatives. Med Chem Res 24, 725–736 (2015). https://doi.org/10.1007/s00044-014-1150-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-014-1150-6

Keywords

Search

Navigation