Synthesis and antimicrobial evaluation of some new N-pyridinium, quinolinium, and isoquinolinium sulfonate derivatives

Article abstract of DOI:10.1080/10426507.2016.1149850

1,3-propane- and/or 1,4-butane sultone (sultones are internal esters of hydroxyl sulfonic acid) are used as a chemical intermediate to introduce sulfopropyl and/or sulfobutyl groups into heterocyclic molecules and to confer water solubility and anionic ch

Full text of DOI:10.1080/10426507.2016.1149850

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Phosphorus, Sulfur, and Silicon and the Related Elements
ISSN: 1042-6507 (Print) 1563-5325 (Online) Journal homepage: http://www.tandfonline.com/loi/gpss20
Synthesis and antimicrobial evaluation of
some new N-pyridinium, quinolinium and
isoquinolinium sulfonate derivatives
Ahmed Ali Fadda, Rasha El-Demerdashi El-Mekawy & Mohammed Taha
AbdelAal
To cite this article: Ahmed Ali Fadda, Rasha El-Demerdashi El-Mekawy & Mohammed
Taha AbdelAal (2016): Synthesis and antimicrobial evaluation of some new N-pyridinium,
quinolinium and isoquinolinium sulfonate derivatives, Phosphorus, Sulfur, and Silicon and the
Related Elements, DOI: 10.1080/10426507.2016.1149850
To link to this article: http://dx.doi.org/10.1080/10426507.2016.1149850
Accepted author version posted online: 18
Feb 2016.
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Date: 04 April 2016, At: 03:59

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Synthesis and antimicrobial evaluation of some new N-pyridinium, quinolinium and
isoquinolinium sulfonate derivatives
Ahmed Ali Faddaa,*, Rasha El-Demerdashi El-Mekawyb,c, and Mohammed Taha AbdelAald
aDepartment of Chemistry, Faculty of Science, Mansoura University, El-Gomhoria Street,
Mansoura, 35516, Egypt
bPermanent Address: Department of Petrochemicals, Egyptian Petroleum Research Institute,
Nasr City, Cairo, Egypt
cPresent Address: Department of Chemistry, Faculty of Applied Science, Umm Al-Qura
University, Makkah Al Mukarrama, Saudi Arabia
dDepartment of Chemistry, Faculty of Science, Menofia University, Menofia, Egypt
*Corresponding author. Tel.: ‏20502265636; fax: ‏20502246781, (A.A. Fadda) E-mail address:
afadda50@yahoo.com
1,3-propane- and/or 1,4-butane sultone (sultones are internal esters of hydroxyl sulfonic
acid) are used as a chemical intermediate to introduce the sulfopropyl and/or sulfobutyl groups
into heterocyclic molecules and to confer water solubility and an anionic character to the
molecules. Therefore, the synthesis of three novel functionalized N-sulfonates are described.
These sulfonates containing pyridyl (2a-f), quinolyl (4a-m) and isoquinolyl (6a,b) functional
groups with potential biological activity. The synthesized quaternary ammonium salts 3-(2 or 4-
arylpyridinium-1-yl)propane or butane-1-sulfonate (2a-f), 3-(alkylquinolinium-1-yl)propane or
butane-1-sulfonate (4a-m) and
3-(alkylisoquinolinium-1-yl)propane or butane-1-sulfonate (6a,b) were screened for their
antimicrobial and antifungal activities. Among all tested compounds, it was found that
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compound 4-(4-carboxypyridinium-1-yl)butane-1-sulfonate (2f) showed high activity against
Gram-positive bacteria, Gram-negative bacteria and tested fungi. Most of the compounds
showed a moderate degree of antimicrobial activity. The structures of these compounds were
1
13
confirmed on the basis of their analytical and spectral data (IR, HNMR, CNMR spectroscopy
and mass spectral data).
Keywords
1,3-Propane sultone; 1,4-Butane sultone; Antibacterial; Antifungal; Pyridinium; Quinolinium;
Quaternary ammonium
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Introduction
The synthesis and characterization of pyridine and S-alkylpyridine derivatives has become a
main focus of this research group. This is because these derivatives have significant and versatile
biological and pharmacological activities, such as antimalarial [1], antiproliferative [2],
antimicrobial [3], inhibition of cyclin-dependent kinases [4], cardiovascular [5], antiviral [6] and
antileishmanial activities [7]. In addition, the quinoline ring system occurs in various natural
products, especially in alkaloids. The quinoline and isoquinoline [8] skeletons are one of the
privileged medicinal scaffolds that show a wide range of pharmaceutical activities. The presence
of quinoline framework of various pharmacologically active compounds with antiasthmatic [9],
antifungal [10], antimalarial [11], antiviral [12], antitumor [13], and anti-inflammatory [14]
activities continues to promote their synthetic efforts. Sulfoalkylic heterocyclic compounds are
widely used in the production of medicinal materials [15], various dyes [16], and in other areas.
Even though 1,3-propane sultone and 1,4-butane sultone, used for the synthesis of sulfoalkylic
heterocyclic compounds, have a high reactivity, they are also sensitive to hydrolysis and to the
influence of alkalis. Therefore, a water-free medium is essential for the synthesis of sulfonates;
however, they make the sulfoalkylation process more difficult and expensive. The sulfoalkyl
group has been used extensively to improve the aqueous solubility and otherwise enhance the
hydrophilicity of a variety of surfactants [17], dyes [18] nucleosides [19], proteins [20] and
polymers [21]. Compounds having a combination of pyridine derivatives with sulfopropyl and/
or sulfobutyl moieties are expected to possess interesting medicinal properties. Encouraged by
these reports and in continuation of our work in this field [22-26], we report here the synthesis of
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