Skip to main content
SpringerLink
Log in

Synthesis, anti-microbial and anti-cancer evaluation study of 3-(3-benzofuranyl)-coumarin derivatives

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

Abstract

The series of 3-coumarin-substituted benzofuran derivatives 4a–4j have been synthesized under optimized experimental condition with excellent yields. All the isolated compounds were characterized and screened anti-microbiological and anti-cancer activity. The anti-microbiological results observed were extremely good against S. aureus, C. albicans and A. niger. The comparative docking studies with gyrase type IIA topoisomerase from mycobacterium tuberculosis docked with ligands and 4j have found lowest docked energy.

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
Scheme 2
Scheme 3
Scheme 4
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  • Amin KM, Abou-Seri SM, Awadallah FM, Eissa AAM, Hassan GS, Abdulla MM (2015) Synthesis and anticancer activity of some 8-substituted-7-methoxy-2H-chromen-2-one derivatives toward hepatocellular carcinoma HepG2 cells. Eur J Med Chem 90:221–231. doi:10.1016/j.ejmech.2014.11.027

    Article  CAS  PubMed  Google Scholar 

  • Avin BRV, Thirusangu P, Lakshmi Ranganatha V, Firdouse A, Prabhakar BT, Khanum SA (2014) Synthesis and tumor inhibitory activity of novel coumarin analogs targeting angiogenesis and apoptosis. Eur J Med Chem 75:211–221. doi:10.1016/j.ejmech.2014.01.050

    Article  Google Scholar 

  • Belluti F, Fontana G, Bo LD, Carenini N, Giommarelli C, Zunino F (2010) Design, synthesis and anticancer activities of stilbene-coumarin hybrid compounds: identification of novel proapoptotic agents. Bioorg Med Chem 18(10):3543–3550. doi:10.1016/j.bmc.2010.03.069

    Article  CAS  PubMed  Google Scholar 

  • Bigler L, Spirli C, Fiorotto R, Pettenazzo A, Duner E, Baritussio A, Follath F, Ha HR (2007) Synthesis and cytotoxicity properties of amiodarone analogues. Eur J Med Chem 42:861–867. doi:10.1016/j.ejmech.2006.12.031

    Article  CAS  PubMed  Google Scholar 

  • Bondock S, Khalifa W, Fadda AA (2011) Synthesis and antimicrobial activity of some new 4-hetarylpyrazole and furo[2,3-c]pyrazole derivatives. Eur J Med Chem 46:2555–2561. doi:10.1016/j.ejmech.2011.03.045

    Article  CAS  PubMed  Google Scholar 

  • Bouige A, Darmon A, Piton J, Roue M, Petrella S, Capton E, Forterre P, Aubry A, Mayer C (2013) Mycobacterium tuberculosis DNA gyrase possesses two functional GyrA boxes. Biochem J 455:285–294. doi:10.1042/BJ20130430

    Article  CAS  PubMed  Google Scholar 

  • China RB, Tiwari AK, Kumar AJ, Zehra Ali A, Agawane SB, Saidachary G, Madhusudana K (2010) a-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives. Bioorg Med Chem 18:358–365. doi:10.1016/j.bmc.2009.10.047

    Article  Google Scholar 

  • Corrie JET, Munasinghe VRN, Rettig W (2000) Synthesis and fluorescence properties of substituted 7-aminocoumarin-3-carboxylate derivatives. J Heteterocycl Chem 37:1447–1455. doi:10.1002/jhet.5570370608

    Article  CAS  Google Scholar 

  • Cragg GM, Newman DJ, Snader KM (1997) Natural products in drug discovery and development. J Nat Prod 60:52–60. doi:10.1021/np9604893

    Article  CAS  PubMed  Google Scholar 

  • DeLano WL (2002) The PyMOL molecular graphics system. DeLano Scientific, San Carlos, CA, USA. http://www.pymol.org

  • Deshpande AR, Paradkar MV (1990) Synthesis of 3-(3-benzofuranyl)coumarins. Synth Commun 20:809–816. doi:10.1080/00397919008052326

    Article  CAS  Google Scholar 

  • Evstropov AN, Yavorovskaya VE, Vorobev ES, Khudonogova ZP, Gritsenko LN, Shmidt EV, Medvedeva SG, Filimonov VD, Prishchep TP, Saratikov AS (1992) Synthesis and antiviral activity of antipyrine derivatives. Pharm Chem J 26(5):426–430. doi:10.1007/BF00772907

    Article  Google Scholar 

  • Fall Y, Santana L, Teijeira M, Uriarte E (1995) A convenient synthesis of benzofuran-3-acetic acid. Heterocycles 41(4):647–650. doi:10.3987/COM-94-6996

    Article  CAS  Google Scholar 

  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE (2009) Gaussian 09, Revision B.1, Gaussian, Inc., Wallingford

  • Fuganti C, Serra S (1998) A new approach to 2-aryl-7-alkoxy-benzofurans: synthesis of ailanthoidoi, a natural neolignan. Tetrahedron Lett 39:5609–5610. doi:10.1016/S0040-4039(98)01053-3

    Article  CAS  Google Scholar 

  • Jiang X, Liu W, Zhang W, Jiang F, Gao Z, Zhuang H, Lei F (2011) Synthesis and antimicrobial evaluation of new benzofuran derivatives. Eur J Med Chem 46:3526–3530. doi:10.1016/j.ejmech.2011.04.053

    Article  CAS  PubMed  Google Scholar 

  • Karatas F, Koca M, Kara H, Servi S (2006) Synthesis and oxidant properties of novel (5-bromobenzofuran-2-yl)(3-methyl-3-mesitylcyclobutyl)ketonethiosemicarbazone. Eur J Med Chem 41:664–669. doi:10.1016/j.ejmech.2006.01.003

    Article  CAS  PubMed  Google Scholar 

  • Khan IA, Kulkarni MV, Chung-Ming S (2005) One pot synthesis of oxygenated tri-heterocycles as anti-microbial agents. Eur J Med Chem 40:1168–1172. doi:10.1016/j.ejmech.2005.05.007

    Article  CAS  PubMed  Google Scholar 

  • Kirilmis C, Ahmedzade M, Servi S, Koca M, Kizirgil A, Kazaz C (2008) Synthesis and antimicrobial activity of some novel derivatives of benzofuran: part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives. Eur J Med Chem 43:300–308. doi:10.1016/j.ejmech.2007.03.023

    Article  CAS  PubMed  Google Scholar 

  • Koca M, Servi S, Kirilmis C, Ahmedzade M, Kazaz C, Ozbek B, Otuk G (2005) Synthesis and antimicrobial activity of some novel derivatives of benzofuran: part 1. Synthesis and antimicrobial activity of (benzofuran-2-yl)(3-phenyl-3-methylcyclobutyl) ketoxime derivatives. Eur J Med Chem 40:1351–1358. doi:10.1016/j.ejmech.2005.07.004

    Article  CAS  PubMed  Google Scholar 

  • Kulkarni MV, Patil VD (1981) Studies on coumarins. Arch Pharm 314:708. doi:10.1002/ardp.19813140810

    Article  CAS  Google Scholar 

  • Liu J, Jiang F, Jiang X, Zhang W, Liu J, Liu W, Lei F (2012) Synthesis and antimicrobial evaluation of 3-methanone-6-substitutedbenzofuran derivatives. Eur J Med Chem 54:879–886. doi:10.1016/j.ejmech.2012.05.013

    Article  CAS  PubMed  Google Scholar 

  • Manna K, Agrawal YK (2010) Design, synthesis, and antitubercular evaluation of novel series of 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1 pyrazolylcarbonyl-4-oxo-naphthyridin analogs. Eur J Med Chem 45:3831–3839. doi:10.1016/j.ejmech.2010.05.035

    Article  CAS  PubMed  Google Scholar 

  • Manna K, Agrawal YK (2011) Potent in vitro and in vivo antitubercular activity of certain newlysynthesized indophenazine 1,3,5-trisubstituted pyrazoline derivatives bearing benzofuran. Med Chem Res 20:300–306. doi:10.1007/s00044-010-9322-5

    Article  CAS  Google Scholar 

  • Manolov I, Danchev ND (1995) Synthesis, toxicological and pharmacological assessment of some 4-hydroxycoumarin derivatives. Eur J Med Chem Chim Ther 30(6):531–536. doi:10.1016/0223-5234(96)88266-3

    Article  CAS  Google Scholar 

  • Olmedo D, Sancho R, Bedoya LM, Lopez-Perez JL, del-Olmo E, Munoz E, Alcami J, Gupta MP, Feliciano AS (2012) 3-Phenylcoumarins as inhibitors of HIV-1 replication. Molecules 17:9245–9257. doi:10.3390/molecules17089245

    Article  CAS  PubMed  Google Scholar 

  • Parekh S, Bhavsar D, Savant M, Thakrar S, Bavishi A, Parmar M, Vala H, Radadiya A, Pandya N, Serly J, Molnar J, Shah A (2011) Synthesis of some novel benzofuran-2-yl(4,5-dihyro-3,5-substituted diphenylpyrazol-1-yl) methanones and studies on the antiproliferative effects and reversal of multidrug resistance of human MDR1-gene transfected mouse lymphoma cells in vitro. Eur J Med Chem 46:1942–1948. doi:10.1016/j.ejmech.2011.02.045

    Article  CAS  PubMed  Google Scholar 

  • Pochet L, Doucet C, Schynts M, Thierry N, Boggeto N, Pirotte B, Liang KY, Masereel B, Pde Tulio, Delarge J, Reboud-Ravaux M (1996) Esters and amides of 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid as inhibitors of r-chymotrypsin: significance of the “aromatic” nature of the novel ester-type coumarin for strong inhibitory activity. J Med Chem 39:2579–2585. doi:10.1021/jm960090b

    Article  CAS  PubMed  Google Scholar 

  • Quezada E, Delogu G, Picciau C, Santana L, Podda G, Borges F, Garcia-Morales V, Vina D, Orallo F (2010) Synthesis and vasorelaxant and platelet antiaggregatory activities of a new series of 6-halo-3-phenylcoumarins. Molecules 15:270–279. doi:10.3390/molecules15010270

    Article  CAS  PubMed  Google Scholar 

  • Rajanarendar E, Reddy KG, Krishna SR, Shireesha B, Reddy YN, Rajam MV (2013) Design, synthesis, antimicrobial, anti-inflammatory, and analgesic activity of novel dihydrobenzo furo[3,2-e]isoxazolo[4,5-b]azepin-5(5aH)-ones. Med Chem Res 22:6143–6153. doi:10.1007/s00044-013-0598-0

    Article  CAS  Google Scholar 

  • Ritchie DW, Venkatraman V (2010) Ultra-fast FFT protein docking on graphics processors. Bioinformatics 26:2398. doi:10.1093/bioinformatics/btq444

    Article  CAS  PubMed  Google Scholar 

  • Saberi MR, Vinh TK, Yee SW, Griffiths BJN, Evans PJ, Simons C (2006) Potent CYP19 (aromatase) 1-[(benzofuran-2-yl)(phenylmethyl)pyridine, -imidazole, and -triazole inhibitors: synthesis and biological evaluation. J Med Chem 49:1016–1022. doi:10.1021/jm0508282

    Article  CAS  PubMed  Google Scholar 

  • Sashidhara KV, Palnati GR, Avula SR, Abdhesh K (2012) Efficient and general synthesis of 3-aryl coumarins using cyanuric chloride. Synlett 23:611–621. doi:10.1055/s-0031-1290344

    Article  CAS  Google Scholar 

  • Sashidhara KV, Avula SR, Sharma K, Palnati GR, Bathula SR (2013) Discovery of coumarinemonastrol hybrid as potential antibreast tumor-specific agent. Eur J Med Chem 60:120–127. doi:10.1016/j.ejmech.2012.11.044

    Article  CAS  PubMed  Google Scholar 

  • Shastri LA, Ghate MD, Kulkarni MV (2004) Dual fluorescence and biological evaluation of paracetamol esters from 4-bromomethyl coumarins. Indian J Chem 43B:2416–2422

    CAS  Google Scholar 

  • Shu YZ (1998) Recent natural products based drug development: a pharmaceutical industry perspective. J Nat Prod 61:1053–1071. doi:10.1021/np9800102

    Article  CAS  PubMed  Google Scholar 

  • Singhapol C, Pal D, Czapiewski R, Porika M, Nelson G, Saretzki GC (2013) mitochondrial telomerase protects cancer cells from nuclear DNA damage and apoptosis. PLoS ONE 8(1):e52989. doi:10.1371/journal.pone.0052989

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Sun WC, Gee KR, Haugland PR (1998) Synthesis of novel fluorinated coumarins: excellent UV-light excitable fluorescent dyes. Bioorg Med Chem Lett 8:3107–3110. doi:10.1016/S0960-894X(98)00578-2

    Article  CAS  PubMed  Google Scholar 

  • Taksande K, Borse DS, Lokhande P (2010) Facile metal-free synthesis of 3-aryl-4-substituted coumarins from O-hydroxy carbonyl compounds. Synth Commun 40:2284–2290. doi:10.1080/00397910903222082

    Article  CAS  Google Scholar 

  • Vazquez R, Riveiro ME, Vermeulen M, Alonso E, Mondillo C, Facorro G, Piehl L, Gomez N, Moglioni A, Fernandez N, Baldi A, Shayo C, Davio C (2012) Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the d-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action. Bioorg Med Chem 20:5537–5549. doi:10.1016/j.bmc.2012.07.043

    Article  CAS  PubMed  Google Scholar 

  • Wang C, Wu C, Zhu J, Miller RH, Wang Y (2011) Design, synthesis, and evaluation of coumarin-based molecular probes for imaging of myelination. J Med Chem 54:2331–2340. doi:10.1021/jm101489w

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Xu X, Zhang Y, Qu D, Jiang T, Li S (2011) Osthole induces G2/M arrest and apoptosis in lung cancer A549 cells by modulating PI3 K/Akt pathway. J Exp Clin Cancer Res 30:33. doi:10.1186/1756-9966-30-33

    Article  PubMed Central  PubMed  Google Scholar 

  • Yu D, Suzuki M, Xie L, Morris-Natschke SL, Lee KH (2003) Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Med Res Rev 23(3):322–345. doi:10.1002/med.10034

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

We acknowledge the University Grant Commission (UGC) and Department of Science and Technology (DST) and also UGC-UPE New Delhi, for the financial support. Authors also thank to USIC KU Dharwad for single-crystal X-ray analysis.

Author information

Authors and Affiliations

  1. Department of Chemistry, Karnatak University, Dharwad, Karnataka, 580 003, India

    Bahubali M. Chougala, Samundeeswari L. Shastri, Megharaja Holiyachi & Lokesh A. Shastri

  2. P.G. Department of Biochemistry, CPGS-Jain University, 18/3, 9th Main Jayanagar 3rd Block, Bangalore, Karnataka, 560011, India

    Sunil S. More & K. V. Ramesh

Authors
  1. Bahubali M. Chougala
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Samundeeswari L. Shastri
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Megharaja Holiyachi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lokesh A. Shastri
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sunil S. More
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. K. V. Ramesh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Lokesh A. Shastri.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 4553 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chougala, B.M., Shastri, S.L., Holiyachi, M. et al. Synthesis, anti-microbial and anti-cancer evaluation study of 3-(3-benzofuranyl)-coumarin derivatives. Med Chem Res 24, 4128–4138 (2015). https://doi.org/10.1007/s00044-015-1449-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-015-1449-y

Keywords

Search

Navigation