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 Mar 9;21(3):326.
doi: 10.3390/molecules21030326.

Hydrazonoyl Chlorides as Precursors for Synthesis of Novel Bis-Pyrrole Derivatives

Nabila Abdelshafy Kheder  1
Affiliations

Hydrazonoyl Chlorides as Precursors for Synthesis of Novel Bis-Pyrrole Derivatives

Nabila Abdelshafy Kheder. Molecules. .

Abstract

A convenient synthesis of some novel bis-pyrrole derivatives via hydrazonoyl halides is described. Antimicrobial evaluation of some selected examples of the synthesized products was carried out. The bis-pyrrole derivative having chloro substituents showed good activity against all of the used microbes. The molecular docking of the bis-pyrrole derivatives was performed by the Molecular Operating Environment (MOE) program.

Keywords: antibacterial activity; antifungal activity; bis-pyrrole; hydrazonoyl halides; molecular docking.

PubMed Disclaimer

Conflict of interest statement

The author declares that there is no conflict of interests regarding the publication of this paper.

Figures

Scheme 1
Scheme 1
Synthesis of diethyl 1,1′-(ethane-1,2-diyl)bis(2,5-dimethyl-4-(phenylazo)-1H-pyrrole-3-carboxylate) (5a).
Scheme 2
Scheme 2
Synthesis of bis-pyrrole derivatives 5b–e.
Figure 1
Figure 1
Docking of compound 5a into E. coli Enoyl reductase Enzyme (PDB ID: 1LXC) showing arene-cation interaction between Phe203 and the phenyl ring.
Figure 2
Figure 2
Docking of compound 5b into E. coli Enoyl reductase Enzyme (PDB ID: 1LXC).
Figure 3
Figure 3
Docking of compound 5c into E. coli Enoyl reductase Enzyme (PDB ID: 1LXC) showing arene-cation interaction with Lys163 and hydrogen bond with Phe 203.
Figure 4
Figure 4
Docking of compound 5d into E. coli Enoyl reductase Enzyme (PDB ID: 1LXC) showing hydrogen bond with Asn155.
Figure 5
Figure 5
Docking of compound 5e into E. coli Enoyl reductase Enzyme (PDB ID: 1LXC) showing hydrogen bond with Phe203.
See this image and copyright information in PMC

References

    1. Mabkhot Y.N., Barakat A., Al-Majid A.M., Alshahrani S., Yousuf S., Choudhary M.I. Synthesis, reactions and biological activity of some new bis-heterocyclic ring compounds containing sulphur atom. Chem. Cent. J. 2013;7:112–120. doi: 10.1186/1752-153X-7-112. - DOI - PMC - PubMed
    1. Kumar R., Panwar H. Synthesis and pharmacological evaluation: antimicrobial, anti-inflammatory, analgesic, ulcerogenic properties of several bis-heterocyclic derivatives. Indonesian J. Pharm. 2015;26 doi: 10.14499/indonesianjpharm26iss1pp1. - DOI
    1. Bhanu Prakash T., Dinneswara Reddy G., Padmaja A., Padmavathi V. Synthesis and antimicrobial activity of amine linked bis- and tris-heterocycles. Eur. J. Med. Chem. 2014;82:347–354. - PubMed
    1. Tripathi A., Fornabaio M., Kellogg G.E., Gupton J.T., Gewirtz D.A., Yeudall W.A., Vega N.E., Mooberry S.L. Docking and hydropathic scoring of polysubstituted pyrrole compounds with antitubulin activity. Bioorg. Med. Chem. 2008;16:2235–2242. doi: 10.1016/j.bmc.2007.11.076. - DOI - PMC - PubMed
    1. Micheli F., di Fabio R., Cavanni P., Rimland J.M., Capelli A.M., Chiamulera C., Corsi M., Corti C., Donati D., Feriani A., et al. Synthesis and pharmacological characterisation of 2,4-dicarboxy-pyrroles as selective non-competitive mGluR1 antagonists. Bioorg. Med. Chem. 2003;11:171–183. doi: 10.1016/S0968-0896(02)00424-8. - DOI - PubMed

MeSH terms

LinkOut - more resources