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112 2 Transformation of Sulfoximines and Cyclic Sulfoximines
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Chapter 3
Application of Sulfoximines and Cyclic
Sulfoximines
3.1 Application of Sulfoximines
Sulfoximines are widely used i n the process of organic synthesis [1], particularly in
the manufacturing of medicinal [2, 3] and agrochemistry [4, 5]. Their one-of-a-kind
structural characteristics make them valuable building blocks that can be used to
create a wide variety of compounds. Sulfoximines have been used as important parts
in the pharmaceutical industry for a long time because they are bioactive and can
change useful properties. Most of the sulfoximine-containing molecules are f ound
with various bioactivities (Fig.
3.1), such as Bayer (BAY1000394 (Fig. 3.1,I)[6],
Atuveciclib (BAY1143572) (Fig. 3.1,II) [7]), AstraZeneca (AZD6738) (Fig. 3.1, III)
[8]. Furthermore, their prospective uses extend to the field of materials science, where
they have the ability to make a contribution to the design of functional materials that
possess certain electrical or optical properties. The adaptable nature of sulfoximines
continues to be a driving force behind research, with ongoing studies being conducted
to discover new and innovative applications in many different kinds of scientific
fields.
3.1.1 In Drugs
In the field of medicine, sulfoximines are gaining increased attention due to the
wide range of applications they have. One use that stands out is their function as
pharmacophores in the process of drug design [9
]. The following are a few particular
uses of sulfoximines in the field of medicine and drugs.
Agrochemicals and Insecticides; Sulfoxaflor (Fig. 3.1, IV), a substance that
contains sulfoximine, is utilized as an insecticide during agricultural production
[10]. Providing an efficient instrument for the management of pests in agricultural
settings, it performs the function of a powerful antagonist of nicotinic acetylcholine
113
114 3 Application of Sulfoximines and Cyclic Sulfoximines
Atuveciclib
(BAY1143572) (
II
)
N
N
N
HN
S
HN
O
O
F
NN
CF
3
O
OH
HN
S
NH
O
BAY 1000394
Pan-CDK inhibitor (
I
)
Et
Et
N
O
S
O
H
N
Cl
O
HN
N
Cl
O
human FXa
inhibitor (
VII
)
N
CF
3
S
N
O
CN
nAChR agonist
insecticide (
IV
)
O
O
S
N
O
CN
selective COX-2
inhibitor (
V
)
S
N
O
N
N
H
OH
EphB
4
Receptor
inhibitors (
VI
)
S
O
N
N
N
O
HN
F
O
O
OH
MNK Kinase inhibitors
derivatives (
VIII
)
AZD6738 (
III
)
N
O
N
N
N
H
N
S
NH
O
Fig. 3.1 Selected examples of bioactive sulfoximines
receptors found in insects. A class of antibiotics known as sulfa medicines, which are
characterized by the presence of sulfonyl groups, is also known as antifungals. Both
of these compounds include sulfur, despite the fact that they are not sulfoximines.
In the treatment of bacterial infections, for example, sulfamethoxazole is frequently
used in conjunction with trimethoprim.
In inhibitors of enzyme activity, certain sulfoximines have the ability to suppress
enzyme activity. For instance, substances that include sulfoximine have been inves-
tigated for their potential to act as enzyme inhibitors in a variety of conditions, such
as cancer and neurological disorders. Asymmetric synthesis catalysts chiral sulfox-
imines have been utilized as ligands in asymmetric synthesis, for which they have
found applications. They are capable of acting as catalysts in asymmetric transfor-
mations, which makes it possible t o produce enantioenriched molecules, which is an
essential characteristic in the process of medication development. Also, sulfoximine-
containing ligands are capable of forming stable coordination complexes with transi-
tion metals. These complexes have uses in the field of medicinal inorganic chemistry,
namely in the process of developing medications that are based on metal substance.
CNS agents: There is evidence that certain sulfoximine derivatives have the potential
to act as agents for the central nervous system (CNS). Neuroprotective properties
may be exhibited by them, and they may have potential applications in the treatment
of neurodegenerative illnesses.
3.1 Application of Sulfoximines 115
3.1.2 Catalysis and Materials Science
Due to the unique chemical properties that they possess, sulfoximines play a key role
in the field of materials science [
11]. Sulfoximines have a number of important uses
in this area, including the following:
In processing of polymer synthesis, sulfoximines can be integrated into polymer
structures, which opens up new opportunities for the creation of polymers with partic-
ular features. The insertion of s ulfoximine moieties into polymers has the potential
to improve both their thermal stability and their mechanical strength, in addition to
other properties. In the synthesis of functional materials, sulfoximines are utilized
as adaptable building blocks. This allows for the creation of functional materials.
The incorporation of these materials into the design of materials that possess certain
electrical, optical, or catalytic capabilities is possible.
Compounds containing sulfoximine have been investigated for the liquid crystal
qualities they possess. Display technologies, sensors, and other electronic devices
are some of the areas that can benefit from the utilization of liquid crystal materials.
Metal–organic frameworks (MOFs); Sulfoximines have been utilized in the process
of designing and constructing metal–organic frameworks. In addition to their use in
gas storage and separation, these porous materials also have uses in catalysis.
Materials capable of self-healing sulfoximines have the potential to make a contri-
bution to the creation of self-healing materials. Because of the reversible nature of
some sulfoximine reactions, it is possible to create materials that are capable of
repairing themselves after being damaged, which in turn extends the lifespan of the
material. Materials with optical qualities sulfoximine-containing compounds possess
optical qualities that make them appropriate for usage in materials that have partic-
ular light-absorbing or light-emitting features. Specifically, this has the potential to
be utilized in optoelectronic devices and sensors.
In addition, sulfoximines can be used into adhesives and coatings, which then
results in improved adherence and durability. Construction, aerospace, and the auto-
mobile industry are just some of the industries that can benefit from these materials.
Sulfoximine-based materials have been investigated for use in sensor technologies
based on their potential applications. In order to detect gasses, chemicals, or biolog-
ical molecules, they can be constructed to preferentially bond with particular analytes.
This makes them helpful for the detection of these substances.
3.1.3 In Biology Studies
Through their contributions to a wide range of chemical reactions, sulfoximines have
found numerous applications in the field of biological catalysis [
12
]. In the field of
catalysis, the following are some important examples of sulfoximines:
Asymmetric synthesis, chiral sulfoximines have the potential to function in asym-
metric synthesis either as ligands or as organocatalysts respectively. The synthesis of
116 3 Application of Sulfoximines and Cyclic Sulfoximines
chiral compounds that have a high optical purity is made possible as a result of their
ability to allow enantioselective reactions. When it comes to the production of phar-
maceuticals and agrochemicals, this is an especially valuable characteristic. In cata-
lysts for metal coordination, sulfoximines have the ability to coordinate with transi-
tion metal catalysts, which allows them to act as ligands in processes that are catalyzed
by metals. These metal-sulfoximine complexes have been utilized in a variety of
catalytic activities, such as cross-coupling reactions and C-H functionalization,
among others.
Also, sulfoximines play role in oxidation reactions, sulfoximines have the poten-
tial to act as catalysts in oxidation reactions. As a result of their involvement in the
activation of oxygen or other oxidants, they make the oxidation of substrates easier
to accomplish. There are uses for this in the production of medicinal intermediates
as well as highly refined compounds. Transformations of functional groups sulfox-
imines play the role of catalysts in transformations that include the activation of
functional groups. Since for example, they are able to catalyze the transformation
of aldehydes into esters, they are an extremely useful instrument in the reactions of
organic synthesis.
Moreover, in catalytic asymmetric hydrogenation; chiral sulfoximine-containing
catalysts have been used in asymmetric hydrogenation reactions since their introduc-
tion. High degrees of enantioselectivity are achieved through the utilization of these
catalysts, which allow for the reduction of unsaturated molecules. Also, as Lewis acid
catalysis, certain sulfoximine derivatives have the ability to operate as Lewis Acids,
which allows them to catalyze a wide range of processes, such as aldol reactions and
Diels–Alder reactions. The Lewis acid catalysis using sulfoximines technique offers
an alternative to the conventional catalysts that are typically used.
Additionally, sulfoximine-containing catalysts have been exploited in enantios-
elective fluorination processes. This process is known as catalytic selective fluori-
nation. When it comes to the synthesis of fluorinated compounds, which frequently
find applications in medicinal chemistry, this is an extremely useful tool. Catalysis
in cross-coupling reactions sulfoximines have the ability to take part in catalytic
cross-coupling reactions, which makes it easier for C–C bonds to be formed. When
it comes to the synthesis of complex organic compounds, this is a crucial factor.
As a result of their variable chemical structure, sulfoximines are valuable building
blocks in the process of drug discovery and development. Research is currently being
conducted to investigate new possibilities for sulfoximines in the medical field. The
significance of sulfoximines in medicinal chemistry can be attributed, in part, to the
fact that they possess a number of distinctive characteristics, such as the capacity to
take part in a variety of reactions and to function as chiral scaffolds.
3.2 Application of Cyclic Sulfoximines 117
3.2 Application of Cyclic Sulfoximines
3.2.1 Pharmacological Medicines
With their distinctive structural characteristics and adaptable reactivity, cyclic sulfox-
imines have applications in a wide variety of sectors [
13]. The following is a list of
common applications for cyclic sulfoximines; r esearchers utilize cyclic sulfoximines
in the process of drug discovery and development in the field of medicinal chemistry
because they have the potential to be bioactive molecules [
14]. Additionally, they have
the potential to function as essential structural motifs in pharmacological medicines
that target a variety of biological actions. The production of agrochemicals, such as
insecticides and fungicides, requires the utilization of cyclic sulfoximines as a key
component. Because of the structural qualities they possess, they are useful in the
process of creating chemicals that have pesticidal effects.
3.2.2 Catalysts
In the field of catalysis, cyclic sulfoximines can act as ligands in transition metal
catalysis, which helps make breakthrough processes possible in organic synthesis.
Because of their chiral nature, they are especially beneficial in asymmetric catalysis
conditions. Material Science: Because of their one-of-a-kind characteristics, cyclic
sulfoximines are intriguing possibilities for use in the field of materials science
studies. They are able to be included in polymers or materials that have qualities
that can be customized to be used for particular reasons. Fluorine chemistry; fluori-
nated cyclic sulfoximines are of importance in the field of fluorine chemistry. These
substances have the potential to act as precursors in the process of incorporating
fluorine-containing groups into organic compounds.
In asymmetric synthesis, cyclic sulfoximines are very helpful in asymmetric
synthesis [
15], because they allow for very selective stereochemistry when creating
chiral centers. The production of molecules that are enantiomerically enhanced is one
of their applications. Cyclic sulfoximines are used in the design of peptidomimetics
to imitate specific structural characteristics displayed by peptides. When compared
to natural peptides, these molecules might have lower levels of bioavailability and
higher levels of stability. Cyclic sulfoximines in biochemical probes can be used to
investigate specific cellular processes or interactions. Their one-of-a-kind structure
makes it possible to develop probes that have features that allow for selective binding.
Some cyclic sulfoximines are excellent candidates for photopharmacology because
of their photochemical reactivity. In photopharmacology, light is used to modify the
activity of a medicine or chemical substance. It is possible for cyclic sulfoximines
to work as organocatalysts in a number of different transformations. This makes it
easier to make complex compounds very efficiently.
118 3 Application of Sulfoximines and Cyclic Sulfoximines
S
N
O
I
S
O
N
O
II
N
S
O
O
Me
OH
H
N
O
N
S
Me
III
Meloxicam
N
S
O
O
Me
OH
N
H
O N
IV
Piroxicam
Fig. 3.2 Structures of bioactive molecules
3.2.3 Treatments and Scientific Researches
In the area of cancer treatment, sulfoximine, which was discovered as a hazardous
molecule in nineteenth century, is today referred to as rising star due to the particular
significance. It has played in the creation of new drugs in recent years. As a result
of the fact that sulfoximines are the isosteres of sulfones equipped with a mono-aza
nitrogen atom, they possess unique characteristics. These characteristics include the
sulfur atom possessing an optical rotation property the S=N bond possessing the
double bond property, and nitrogen possessing a weak nucleophilicity. The synthesis
of bioactive compounds, asymmetric catalysis, and the current pharmaceutical and
agrichemical industries are all examples of areas in which sulfoximines have found
widespread application. Researchers have focused a significant amount of their atten-
tion on cyclic sulfoximines over the course of the last few decades since they are an
essential type of sulfoximine derivatives. The exceptional biological properties of
these molecules led to the appearance of a number of molecules that have the poten-
tial to be used in medical applications. These molecules include, for instance, the
five-membered cycle I, which performed exceptionally well in in vitro pharmacoki-
netic studies, and motif II, which has the potential to be transformed into potential
scaffolds for peptide mimetics. In addition, it was discovered that anti-inflammatory
medications can be acquired from analogues that also possess the S=O bond and
the S–N link. These analogues include 1,2-benzothiazine 1,1-dioxides III and IV
(Fig.
3.2).
There are a variety of scientific and industrial applications for cyclic sulfoximines,
and these applications illustrate the diversity of these compounds. Researchers are
using cyclic sulfoximines in a wide variety of synthetic and biological settings [
16],
and their ongoing research in this area continues to reveal new applications and
enhance their value.
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Chapter 4
Conclusions and Outlook
Sulfoximines-related study has become more interesting to organic chemists over
the last few decades. It includes both the steps for making NH-sulfoximine and the
changes that can be made to it. NH-sulfoximines can be synthesized by a number
of different successful synthetic methods. Aside from the N atom of sulfoximines,
however, not many studies have done on the reactions that occurs at other loca-
tions. There are a lot of studies on N-acylation and N-arylation, but not many on
N-alkylation and N-vinylation. These are the reactions which occur when nitrogen
in NH-sulfoximines is substituted . New methods like electrochemistry, photochem-
istry, C–H bond functionalization, C–C bond cleavage, and free radical chemistry are
likely to be used in the near future to do more study on the alkyl and/or aryl groups
of sulfoximines. It is expected that even S=O and S=N groups can change into other
types of functional groups. As a result of the growing number of uses, particularly
in the field of medicine, sulfoximines may eventually see a rapid development in the
nearly future.
More importantly, sulfoximines are useful building blocks in drug discovery and
development due to their varied chemical structure. Exploring novel applications of
sulfoximines in medicine is an active area of research at the moment. The unique
properties of sulfoximines, such as their ability to participate in different reactions and
to serve as chiral scaffolds, contribute to their importance in medicinal chemistry. An
important component in the development of innovative materials with customized
properties, sulfoximines are versatile in terms of reactivity and functional group
modifications. Novel synthetic approaches and materials science uses for sulfox-
imines are still the subject of active i nvestigation. Sulfoximines have the potential to
revolutionize catalysis with their exceptional electrical and steric properties, opening
up new avenues for the creation of selective and efficient catalytic processes. New
uses and principles for sulfoximines in catalysis are being investigated in ongoing
research.
121