Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2016 Nov;53(6):1871-1877.
doi: 10.1002/jhet.2501. Epub 2015 Sep 18.

Synthesis and Cytotoxic Evaluation of Pyrrole Hetarylazoles Containing Benzimidazole/Pyrazolone/1,3,4-Oxadiazole Motifs

Bereket Mochona  1 , Timothy Jackson  1 , DeCoria McCauley  1 , Elizabeth Mazzio  2 , Kinfe K Redda  2
Affiliations

Synthesis and Cytotoxic Evaluation of Pyrrole Hetarylazoles Containing Benzimidazole/Pyrazolone/1,3,4-Oxadiazole Motifs

Bereket Mochona et al. J Heterocycl Chem. 2016 Nov.

Abstract

Azomethine linked pyrrole bishetarylazoles containing benzimidazole/pyrazolone/1,3,4-oxadiazole were synthesized in satisfactory yields. Their structures were confirmed by IR, 1H-NMR, 13C-NMR and elemental analysis. Evaluation for the cytotoxic activities In vitro against a panel of breast cancer cell lines (MDA-AB-231, BT-474 and Ishikawa cells) revealed that the pyrrole-benzimidazole hybrids are more potent than the pyrazolone and 1,3,4-oxadiazole hybrids in all cell lines. Compound (9) displayed promising cytotoxicity against BT-474 cell line with IC50 values, 7.7 µM.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Reagents and Conditions: (i) 4-R-PhCH2Cl, K2CO3, Acetone, reflux, 8h (ii) N2H4. H2O 160°C, 5h (iii) ArCHO, EtOH, 60°C, 2h (iv) NaN3, DMSO, rt-50°C, 4h (v) NH4Cl, EtOH/H2O, Zn, reflux, 4h (vi) 10% Pd/C, H2, EtOH
Scheme 2
Scheme 2
Reagents and Conditions: (i) 2-pyrrole carboxaldehyde, EtOH, AcOH (iii) NaH/DMF, RC6H4CH2X
Scheme 3
Scheme 3
Reagents and Conditions: (i) 2-pyrrole carboxaldehyde, EtOH, AcOH (ii) NaH/DMF, RC6H4CH2X
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. Kumar V, Kaue K, Gupta GK, Sharma AK. Eur. J. Med. Chem. 2013;69:735–753. - PubMed
    1. Spasov A, L Yozhitsa I, Bugaeva LI, Amisimova VA. Pharm. Chem. J. 1999;33(5):232.
    1. Gaba Monika, Singh Sarbjot, Mohan Chander. Eur. J. Med. Chem. 2014;76(9):494. - PubMed
    1. Khokra SI, Choudhary D. Asian J. Biochem. Pharm. Res. 2011;3(1):476.
    1. Kharb R, ShaharYar M, Sharma PC. Mini Rev Med Chem. 2011;11(1):84. - PubMed

Publication types

LinkOut - more resources

  NODES
twitter 2