Green synthesis and antibacterial activity of chalcogenoesters

Article abstract of DOI:10.1007/s00706-020-02565-x

Abstract: Herein, we present a new variation for an eco-friendly methodology for the synthesis of chalcogenoester in good-to-excellent yields in a short time, with an easy work-up/purification step, and in a greenest methodology, affording the minimum gen

Full text of DOI:10.1007/s00706-020-02565-x

Monatshefte für Chemie - Chemical Monthly
https://doi.org/10.1007/s00706-020-02565-x
ORIGINAL PAPER
Green synthesis and antibacterial activity of chalcogenoesters
Rafael S. da Silva1 · Guerino B. Junior2 · Letiére C. Soares3 · Fernanda H. da Rosa1 · Bruno B. Ravanello1 ·
Luciano Dornelles1 · Victor dos S. Barboza4 · Rodrigo de A. Vaucher4 · Roberto C. V. Santos2 ·
Bernardo Baldisserotto2 · Oscar E. D. Rodrigues1
Received: 2 December 2019 / Accepted: 17 February 2020
© Springer-Verlag GmbH Austria, part of Springer Nature 2020
Abstract
Herein, we present a new variation for an eco-friendly methodology for the synthesis of chalcogenoester in good-to-excellent
yields in a short time, with an easy work-up/purifcation step, and in a greenest methodology, afording the minimum gen-
eration of solid and liquid waste, in comparison to that described in the literature. Additionally, some selected compounds
were evaluated as antimicrobial agents, showing moderate activity against a variety of microorganisms including the K.
pneumoniae, P. aeruginosa and also some selected fsh pathogenic bacteria.
Graphic abstract
Keywords Thermal diastereomerization · Photochemistry · Acidity · Fluorescence · Absorption
Introduction
Organochalcogen chemistry has been gaining considerable
attention due to a high number of publications involving this
class of compounds in diferent scientifc felds, including
Electronic supplementary material The online version of this
those of biochemistry [1, 2], chemistry [3] and materials [4].
Since chalcogen atoms have an important hole in oxidation
processes due to their chemical properties, as well as they
are present in the structure of some enzymes [5, 6], they are
often reported as a glutathione peroxidase mimic [7–9] even
as antitumor agents [10–14]. Regarding organochalcogen com-
pounds, chalcogenoesters ofer a wide variety of applications.
In organic synthesis, they have been used as a precursor of
the acyl radical [15] and acyl anions [16] as well as in the
synthesis of new materials, such as molecular conductors and
superconductors [17], molecular machines [18, 19], V-shaped
materials [20], and liquid crystals [21, 22]. Considering the
wide applications of chalcogenoesters, recently, there was an
article (https://doi.org/10.1007/s00706-020-02565-x) contains
supplementary material, which is available to authorized users.
* Oscar E. D. Rodrigues
rodriguesoed@gmail.com
1
Departamento de Química, Universidade Federal de Santa
Maria, Prédio 18, Santa Maria, RS 97105-900, Brazil
2
Departamento de Fisiologia e Farmacologia, Universidade
Federal de Santa Maria-UFSM, CCS, Santa Maria,
Rio Grande do Sul 97105-900, Brazil
3
Departamento de Química, Universidade Federal da Fronteira
Sul, Realeza, PR 85770-000, Brazil
4
Departamento de Microbiologia, Universidade Franciscana,
Santa Maria, RS 97010-032, Brazil
Vol.:(0123456789)
1 3

R. S. da Silva et al.
increase in the development of new and efective methodolo-
gies providing the desired products. Thereby, there is a large
number of protocols for synthesis of chalcogenoesters based
on metals including palladium complexes [23], samarium [24],
indium [25], mercury [26], bimetallic systems [27], and zinc
[28]. However, despite some protocols proved to be highly
efcient, they require a conventional purifcation step, which
generally employs a large volume of solvents and silica gel
which are normally discarded.
current critical situation that most hospitals around the world
have been facing.
Additionally, bacterial multi-resistance is also a problem
in aquaculture. Intensifcation in fsh production led to an
increase in density, generating stress and infectious diseases
and consequently, increasing the use of antimicrobial agents
[40]. These diseases are mainly caused by Gram-negative
bacteria, such as Aeromonas hydrophila, A. veronii [41], and
Citrobacter freundii [42]. As well as Raoltella ornithino-
lytica is a Gram-negative bacillus that produces histamines,
which leads to poisoning by ingestion of contaminated fsh
[43]. Overuse of antimicrobials led to an increase of bacte-
rial resistance, residues in the aquatic environment and in
the fsh meat, generating a public health problem [44]. With
increasingly resistant microorganisms coupled with limited
therapeutic options, it is essential that research studies aim
at the development of new classes of antimicrobial drugs,
especially to combat resistant microorganisms.
Therefore, research on the development of methodologies
that enhance the environment-friendly nature of chemical
processes is currently a subject of great interest, mainly in
synthetic organic chemistry [29, 30]. In this intend, the prepa-
ration of chalcogenoesters using a greener approach, as using
ionic liquids (ILs) or solid-phase reactions has been described
in the literature [31, 32]. However, for a real account, all syn-
thetical steps must be considered, including the purifcation
process and the toxicity of chemicals involved. In this context,
the E factor, which is defned as the real amount of waste pro-
duced during a transformation and measured by the total mass
of waste according to the mass ratio of the desired product,
represents a valuable tool for the evaluation of the laboratory
chemical synthesis processes, considering the total amount of
residue generated, as shown in Fig. 1 [33, 34].
Therefore, we report a new variant of a low-cost and
highly eco-friendly methodology for the synthesis of chal-
cogenoesters. The desired esters were obtained in good-to-
excellent yields in a short reaction time, with an easy work-
up/purifcation step and a lower E factor, compared with
similar protocols (Fig. 2).
In what concerns the importance of antimicrobial activ-
ity, there were 52.8 Mio. deaths globally in 2010 and infec-
tious diseases were among the main causes. These illnesses
are represented primarily by lower respiratory infections
(2.8 Mio.), neonatal disorders (2.2 Mio.), diarrheal disease
(1.4 Mio.), tuberculosis (1.2 Mio.), measles (0.13 Mio.), and
tetanus (0.06 Mio.) [35]. In the beginning of this decade,
Enterobacteriaceae, which produces Klebsiella pneumoniae
carbapenemase (KPC), was reported in the USA and subse-
quently worldwide. These KPC-producing bacteria are pre-
dominantly involved in systemic and nosocomial infections
[36]. The emergence of these multi-drug-resistant bacteria is,
therefore, of concern, since antimicrobial treatment options
are very restricted, because this enzyme leads to decreased
susceptibility or even resistance to virtually all β-lactam drugs
[37]. The few therapeutic options available are limited to the
polymyxins, which are drugs with high nephro and neuro-
toxic potential [38]. Another microorganism of high clinical
importance is Pseudomonas aeruginosa, which is one of the
leading nosocomial pathogens. The increasing frequency of
multi-drug-resistant P. aeruginosa strains severely limits the
number of efective antimicrobials against infections caused
by this pathogen [39]. These are the only two examples of the
The antimicrobial activity of the compounds obtained
against Gram-positive and Gram-negative bacteria, includ-
ing K. pneumoniae, P. aeruginosa and fsh pathogenic bac-
teria was investigated. It should be noted that the present
protocol represents a ‘greener’ variant aimed at improving
a traditional methodology for the preparation of chalcog-
enoesters and consists of a simple molecular building blocks
for new antimicrobial compounds.
Results and discussion
Synthesis of the chalcogenoesters
To synthesize the chalcogenoesters, diphenyl diselenide
was diluted in acetone followed by the addition of four
m
m
products
E
(
)
-factor
reactants
-
=
m products
Fig. 2 General synthesis scheme
Fig. 1 E-factor calculation, m (mass)
1 3

Green synthesis and antibacterial activity of chalcogenoesters
equivalents of zinc dust (Zn0) as the reducing agent and
1 cm3 of hydrochloric acid (HCl) 1 M. After 5 min, a com-
plete disappearance of the yellow coloration was observed,
indicating total reduction of diselenide. p-toluoyl acyl chlo-
ride was then added and the reaction was monitored by thin-
layer chromatography (TLC). After 30 min, a precipitate
was visible and the consumption of the starting material was
confrmed by TLC. Aiming at the development of a ‘green’
work-up, 5 cm3 of 0.1 M HCl was added to the reaction ves-
sel, forcing the precipitation of the desired product. A fltra-
tion under vacuum was then carried out, leading to a mixture
of the desired product and metallic zinc. Subsequently, the
residual selenol was removed by the HCl solution, avoid-
ing the oxidation of selenol in the presence of the product.
The mixture with the chalcogenoester and zinc was fnally
diluted in acetone and fltered. The solvent was removed
under vacuum, afording the pure product. To evaluate the
scope of the methodology, a variety of dichalcogenides con-
taining electron-withdrawing and donating groups as well
as diferent acyl chlorides were employed. The results are
summarized in Table 2.
The infuence of the substituent attached to the aromatic
ring of the acyl chloride was also studied. In a general view,
the protocol was not sensible to electronic efects (Table 1,
compounds 1–4) with a slight decrease in the yield observed
in compound 4 when t-Bu group in para position was
employed (Table 1, compound 4). Furthermore, the infu-
ence by groups attached to the aromatic ring of selenium
moiety was investigated. It was possible to observe that
strong electron-donating groups afect the dichalcogenide
cleavage step. For instance, compound 5 required the longest
time to allow the cleavage of dichalcogenium bond compar-
ing to other substituted diselenides, probably due to Se–Se
Table 2 Values of minimal inhibitory concentration of compounds 1,
2, 6, 9, and 10 in mg/cm3
Compound Gram-positive bacte- Gram-negative bacterial strains
rial strains
S. aureus L. mono- K. pneumoniae P. aeruginosa
cytogenes
The synthesized chalcogenoesters were obtained in good-
to-excellent yields, with selenium species providing the
respective compounds in better yields comparing to those
bearing the sulfur moiety. This result is probably due to the
higher nucleophilicity of the selenium atom (Se) compared
with sulfur (S).
1
2
6
9
1.17
0.58
–
–
–
0.58
0.58
–
0.58
1.17
0.58
–
0.58
–
0.58
0.29
–
0.58
1.17
10
–
Table 1 Results obtained for the chalcogenoester-synthesized 1–12
Entry
Comp
Reagents
Waste
Product
E factor
Yield/%a
References
Y
Ar
R
1
2
3
4
5
6
7
8
1
4-Me-C6H4
4-NO2-C6H4
2-Cl-C6H4
C6H5
C6H5
C6H5
C6H5
2-OMe-C6H4
4-Me-C6H4
4-Cl-C6H4
C6H5
4-Cl-C6H4
4-Cl-C6H4
4-OMe-C6H4
4-Cl-C6H4
4-Cl-C6H4
Se
Se
Se
Se
Se
Se
Se
S
S
S
S
S
3.65
3.68
3.67
3.69
3.68
3.66
3.68
3.63
3.63
3.67
3.66
3.65
182.56
3.38
3.39
3.37
3.44
3.41
3.38
3.38
3.39
3.41
3.40
3.41
3.43
182.34
0.264
0.290
0,292
0.250
0.271
0.280
0.294
0.233
0.218
0.270
0.245
0.223
0.223
12.82
11,68
11.56
13.76
12.58
12.07
11.51
14.55
15.65
12.60
13.94
15.38
817.67
96
95
99
79
89
97
95
90
83
92
85
79
79
[47]
[25]
[48]
[48]
–
[49]
[47]
[50]
[51]
[52]
–
2
3
4
4-t-Bu-C6H4
4-Me-C6H4
4-Me-C6H4
4-Me-C6H4
4-NO2-C6H4
4-Me-C6H4
4-NO2-C6H4
4-NO2-C6H4
2-Cl-C6H4
5b
6
7
8
9
9
10
11
12
13c
10
11
12
12
–
2-Cl-C6H4
S
aProduct isolated direct from the reaction and characterized by 1H NMR, 13C NMR, and CG/MS
bRequired 20 min to cleave the diselenide
cComparative result of entry 12 using conventional column purifcation/extraction step. Extraction with 50 cm3 CH2Cl2 (66.5 g); column using
10 g of silica fash and 150 cm3 of solution 10% ethyl acetate (13.45 g) in n-hexane (88.96 g)
1 3

R. S. da Silva et al.
bond strengthening by the presence of the electron-donating
group.
very selective activity was observed for compound 6 which
was proved active only against K. pneumoniae. This result
increases the interest for clinical application of these chal-
cogenoesters, because either a broad spectrum of action or
a selective activity is highly desirable depending on the type
of infection observed. When some antimicrobial treatment
is performed based on the results of antimicrobial suscepti-
bility testing, the treatment with narrow-spectrum drugs is
advantageous for preventing the activity of the drug against
benefcial microorganisms of the normal microbiota. How-
ever, in most cases, depending on the severity of the infec-
tion, it is not possible to establish the causal agent. In these
cases, the use of narrow-spectrum drugs is not appropriate,
and the availability of broad-spectrum drugs is fundamental.
To verify the scope of the methodology concerning the
chalcogenium source, experiments were carried out using
diferent species of disulfdes and the results are summarized
in Table 1 (compounds 8–12). In general, disulfdes showed
comparable behavior as diselenides in terms of reactivity
with diferent acyl chlorides and without a deep variation
comparing the electronic efects of the substituents attached
to aromatic ring in the disulfde moiety.
The E-factor calculations for laboratorial reactions could
aford an interesting panorama about the greenest way devel-
oped in the synthetical protocols. Based on the experimental
procedure, it was possible to calculate the E factor of the
described methodology. In this context, an arithmetic aver-
age was calculated to the methodology using Fig. 1. As a
result, it was obtained a medium E-factor total correspond-
ing to the synthesis, extraction and purifcation. For a com-
parative analysis, an extraction and purifcation steps were
introduced in the methodology (Table 1, entry 13) for the
highest E factor obtained, related to entry 12. Using a con-
ventional extraction with 50 cm3 of CH2Cl2 and a traditional
purifcation employing 10 g of silica fash and 150 cm3 of a
mixture of ethyl acetate and n-hexane (10%), the E factor of
this example increased from 15.38 to 817.67, showing how
greenest this methodology is in the synthesis of chalcog-
enoesters (see supplementary data).
Minimal inhibitory concentration (MIC) and minimal
bactericidal concentration (MBC) of compounds 1 and 2
against fsh pathogenic bacteria
Based on the results shown above, compounds 1 and 2 were
tested against fsh pathogenic bacteria (Table 3). The bac-
teria tested and their ascension numbers in GenBank were:
A. hydrophila (MF372509), A. hydrophila (MF372510), A.
veronii (MF372508), C. freundii (MF565839) and R. orni-
thinolytica (MF372511).
Compound 1 showed good bacteriostatic and bactericidal
activity against strains of the genus Aeromonas and moder-
ate activity against the other strains. Compound 2 showed
moderate bacteriostatic activity and weak bactericidal activ-
ity against bacteria isolated from fsh.
Biological activity
Minimal inhibitory concentration (MIC) of compounds
1, 2, 6, 9, and 10 against Gram‑positive (Staphylococcus
aureus and Listeria monocytogenes) and Gram‑negative (K.
pneumoniae and P. aeruginosa) bacterial strains
Florfenicol and oxytetracycline are approved by the
Food and Drug Administration (FDA) for use in aquacul-
ture [45]. These two conventional antimicrobials were tested
against the strains A. hydrophila (MF372510), C. freundii
(MF565839), and R. ornithinolytica (MF372511) in a pre-
vious study under the same experimental conditions. In
this study, the forfenicol MIC values were 1.01 μg/cm3 for
A. hydrophila strain and 8.13 μg/cm3 for C. freundii and
R. ornithinolytica strains. In addition, the oxytetracycline
MIC values were 0.51 μg/cm3 for A. hydrophila strain and
4.06 μg/cm3 for C. freundii and R. ornithinolytica strains
[46].
The evaluation of the antibacterial activity of compounds
1, 2, 6, 9, and 10 was performed through the technique of
micro-dilution, in which the MIC of the tested compounds
can be observed against Gram-positive (S. aureus and L.
monocytogenes) and Gram-negative (K. pneumoniae and P.
aeruginosa) bacterial strains (Table 2).
Interestingly, the respective chalcogenoesters showed a
modulation in the antimicrobial activity according to the
groups present in the molecules. For instance, a broad activ-
ity against all strains was observed for compound 1, while a
Table 3 MIC and MBC values
Comp
A. hydrophila
A. hydrophila
A. veronii
C. freundii
R. ornithinolyt-
of compounds 1 and 2, against
fsh-isolated bacterial strains in
mg/cm3
MF372509
MF372510
MF372508
MF565839
ica MF372511
MIC
MBC
MIC
MBC
MIC
MBC
MIC
MBC
MIC
MBC
1
2
0.65
2.3
0.65
2.3
0.65
2.3
0.65
2.3
1.3
2.3
1.3
4.6
2.6
2.3
2.6
>4.6
2.6
4.6
2.6
>4.6
1 3

Green synthesis and antibacterial activity of chalcogenoesters
ppm; 13C NMR (100 MHz, CDCl3): δ=189.9, 161.6, 151.0,
Conclusions
141.8, 136.7, 128.7, 124.2, 117.1, 115.5, 55.7 ppm.
In summary, a new methodology for the ’greener’ synthesis
of chalcogenoesters was developed. Following an easy, clean
and not expensive synthetical protocol, 12 chalcogenoesters
were obtained in good-to-excellent yields, in short reaction
times and employing a low toxicity metal as the reducing
agent. Among them, chromatographic purifcation methods
are not required, eliminating the use of a large amount of
solvents afording low waste generation and leading to an
appreciably low E-factor value. In addition, the synthesized
compounds showed an antimicrobial activity, notably on
clinically important microorganisms and also against fsh
pathogenic bacterial strains. Consequently, these chalcog-
enoesters open up possibilities for the development of new
small molecular architectures for antimicrobial drugs, with
both narrow and broad spectra of antimicrobial activity.
S ‑(4‑ Chlorophenyl) 2‑ chlorobenzothioate (12,
C13H8Cl2OS) Yield: 79%; H NMR (400 MHz, CDCl3):
1
δ=7.75 (dd, J=7.58, 1.22 Hz, 1H), 7.50–7.41 (m, 6H), 7,36
(td, J=7.58, 1.71 Hz) ppm; 13C NMR (100 MHz, CDCl3):
δ=189.5, 136.7, 136.2, 135.9, 132.6, 130.9, 129.6, 129.1,
126.8, 126.6, 125.9 ppm.
Microorganisms
For the evaluation of the biological activity of the chalcog-
enoesters prepared, compounds 1, 2, 6, 9, and 10 were tested
for their efcacy as antibacterial agents against Gram-pos-
itive (Staphylococcus aureus and Listeria monocytogenes)
and Gram-negative (K. pneumoniae and P. aeruginosa) bac-
terial strains, expressed through MIC (minimal inhibitory
concentration). Also, MIC and MBC (minimal bactericidal
concentration) assays were performed against fsh patho-
genic bacteria, their ascension numbers in GenBank were
A. hydrophila (MF372509), A. hydrophila (MF372510), A.
veronii (MF372508), C. freundii (MF565839), and R. orni-
thinolytica (MF372511).
Experimental
General procedure for the synthesis
of chalcogenoesters 1–12
In a Schlenck tube under argon atmosphere was added
2 mmol of zinc dust, (ArY)2 (0.5 mmol), 1 cm3 acetone,
and 0.75 cm3 of HCl (1 M) in this sequence. The mixture
was stirred until complete disappearance of coloration and
then acyl chloride (1.0 mmol) was added. The reaction was
stirred during 30 min at room temperature. Then, 5 cm3 HCl
(0.1 M) was added and the reaction mixture was quickly fl-
trated under vacuum. The mixture between Zn0 and chalcog-
enoester was transferred to an Erlenmeyer fask and 3 cm3
acetone was added. After solubilizing the entire product, a
new fltration was performed to separate the product and
zinc dust. The solution was evaporated under reduced pres-
sure and the desired product dried in vacuum pump. The
NMR data and spectra of all compounds are available in the
Supplementary Material.
Antibacterial activity
The antibacterial activity of chalcogenoesters 1, 2, 6, 9, and
10 was determined by the minimal inhibitory concentration
(MIC) according to the Clinical and Laboratory Standards
Institute (CLSI) (Wayne, 2009). The MIC was determined by
micro-dilution technique in Mueller–Hinton broth (Difco).
The assay was carried out in 96-well microtitre plates. In
each well with Müller–Hinton broth was placed an inoculum
prepared in the same medium at a density adjusted per tube
to 0.5 of the McFarland scale (1.5×108 CFU/cm3) with ster-
ile saline and lastly placed diferent concentrations of chal-
cogenoesters performed in triplicate. Microtiter trays were
incubated at 37 °C and the MICs were recorded after 24 h of
incubation. There was bacterial growth in the wells selected
as positive growth and no bacterial growth was observed
in the wells that did not receive the inoculums (negative
controls—DMSO). The MIC was defned as the lowest con-
centration of compound that inhibits microbial growth. The
tests to evaluate the antibacterial activity (MIC) and minimal
bactericidal concentration (MBC) of compounds 1 and 2
against fsh pathogenic bacteria were performed according to
CLSI specifc for these microorganisms (Wayne 2014) and
at 28 °C. Values of MBC were confrmed by re-inoculation
of 10 mm3 of each bacterial culture on Mueller–Hinton Agar
(28 °C/24 h), and the lowest concentration of the substances
showing no growth was defned as the MBC.
Se‑(2‑Methoxyphenyl) 4‑methylbenzoselenoate (5,
1
C15H14O2Se) Yield: 89%; H NMR (400 MHz, CDCl3):
δ=7.58 (d, J=8.07 Hz, 2H), 7.60 (m, 1H), 7.42 (td, J=7.58,
1.51 Hz, 1H), 7.25 (d, J=8.07 Hz, 2H), 7.00 (m, 2H) ppm;
13C NMR (100 MHz, CDCl3): δ = 191.9, 159.2, 144.6,
138.3, 136.0, 131.2, 129.4, 127.4, 121.4, 114.8, 111.2, 56.0,
21.7 ppm.
S‑(4‑Methox yphenyl) 4‑nitrobenzothioate (11,
1
C14H11NO4S) Yield: 85%; H NMR (400 MHz, CDCl3):
δ=8.33 (d, J=8.8 Hz, 2H), 8.16 (d, J=8.80 Hz, 2H), 7.42
(d, J=8.80 Hz, 2H), 7.02 (d, J=8.80 Hz, 2H), 3.85 (s, 3H)
1 3

R. S. da Silva et al.
28. Godoi M, Galetto FZ, Botteselle GV, Ricardo EW, Braga AL
(2012) Green Chem 14:456
Acknowledgements The authors gratefully acknowledge CAPES-
Finance Code 001, CAPES PRINT-NANOMATERIAIS, CAPES-
PROEX, CAPES-PRINT, CNPq (Ed. Universal 400791/2016-1,
Produtividade em Pesquisa 303387/2015-7, 306240/2018-1 Pesquisa-
dor Visitante-401397/2014-9) for fnancial support.
29. Horváth IT, Anastas P (2007) Chem Rev 107:2167
30. Horváth IT, Anastas PT (2007) Chem Rev 107:2169
31. Narayanaperumal S, Alberto EE, Gul K, Kawazoko CY, Dornelles
L, Rodrigues OED, Braga AL (2011) Tetrahedron 67:4723
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