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332 Chemistry and Biology of Beta-Lactams
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41. Das A, Banik BK. 26 – Dipole moment in medicinal research: Green and sustainable approach. In:
Banik BK, ed. Green Approaches in Medicinal Chemistry for Sustainable Drug Design. Advances in
Green and Sustainable Chemistry. Elsevier; 2020:921–964. doi:10.1016/B978-0-12-817592-7.00021-6
42. Das A, Banik BK. Dipole moment of medicinally active compounds: A sustainable approach. In: Banik
BK, ed. Green Approaches in Medicinal Chemistry for Sustainable Drug Design. Elsevier; 2023.
43. Das A, Das A, Banik BK. Inuence of dipole moments on the medicinal activities of diverse organic
compounds. J Indian Chem Soc. 2021;98(2):100005. doi:10.1016/j.jics.20 21.100005
44. Das A. Quantitative structure-property relationships of Taxol, Taxotere and their epi-isomers. J Indian
Chem Soc. 2020;97(11):9.
45. Das A, Yadav R, Banik BK. Dipole Moment Studies on Anticancer Polyaromatic Compounds. Asian J
Org and Med Chem. Published online 2023.
46. Sondi I, Salopek-Sondi B. Silver nanoparticles as antimicrobial agent: A case study on E. coli as a model
for gram-negative bacteria. J Colloid Interface Sci. 2004;275(1):177–182. doi:10.1016/j.jcis.20 04.02 .012
47. Shi Z, Neoh KG, Kang ET. Surface-grafted viologen for precipitation of silver nanoparticles and their
combined bactericidal activities. Langmuir. 2004;20(16):6847–6852. doi:10.1021/la049132m
48. Choi HJ, Han SW, Lee SJ, Kim K. Structure and thermal behavior of a layered silver hydroxyalkanecar-
boxylate. J Colloid Interface Sci. 2003;264(2):458–466. doi:10.1016/S0021-9797(03)00413-2
49. Li P, Li J, Wu C, Wu Q, Li J. Synergistic antibacterial effects of β-lactam antibiotic combined with silver
nanoparticles. Nanotechnology. 2005;16(9):1912. doi:10.1088/0 957-4484/16/9/082
50. Habash MB, Park AJ, Vis EC, Harris RJ, Khursigara CM. Synergy of silver nanoparticles and aztreo-
nam against pseudomonas aeruginosa PAO1 biolms. Antimicrob Agents Chemother. 2014;58(10):5818 –
5830. doi:10.1128/a a c.0 3170 -14
51. Hwang I sok, Hwang JH, Choi H, Kim KJ, Lee DG. Synergistic effects between silver nanoparticles
and antibiotics and the mechanisms involved. J Med Microbiol. 2012;61(12):1719 –172 6. do i:10.1099/
jmm.0.047100-0
52. Yadav RN, Hossain F, Das A, Srivastava AK, Banik BK. Organocatalysis: A recent development on stereose-
lective synthesis of o-glycosides. Catalysis Reviews. 2022;0(0):1–118. doi:10.108 0/01614940.2022.2041303
53. Das A, Banik BK. Versatile synthesis of organic compounds derived from ascorbic acid. Curr
Organocatal. 20 2 2;9 (1):14 –33.
54. Das A, Banik BK. Microwaves in Chemistry Applications: Fundamentals, Methods and Future Trends.
Elsevier Science; 2021.
55. Das A, Banik BK. Chapter 1 – Foundational principles of microwave chemistry. In: Das A, Banik B,
eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:3–26. doi:10.1016/B978-0-12-822895-1.00005-9
56. Das A, Banik BK. Chapter 2 – Microwave equipment for chemistry. In: Das A, Banik B, eds. Microwaves
in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier; 2021:27–59.
doi:10.1016/B978-0-12-822895-1.00002-3
57. Das A, Banik BK. Chapter 3 – Modeling and interpreting microwave effects. In: Das A, Banik B,
eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:61–104. doi:10.1016/B978-0-12-822895-1.00007-2
58. Das A, Banik BK. Chapter 4 – Microwave-assisted synthesis of oxygen- and sulfur-containing organic
compounds. In: Das A, Banik B, eds. Microwaves in Chemistry Applications. Advances in Green and
Sustainable Chemistry. Elsevier; 2021:107–142. doi:10.1016/ B978-0-12-822895 -1.0 0 010 -2
59. Das A, Banik BK. Chapter 5 – Microwave-assisted synthesis of N-heterocycles. In: Das A, Banik B,
eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:143 –198. doi:10.1016/B978-0-12-822895-1.00006-0
60. Das A, Banik BK. Chapter 6 – Microwave-assisted oxidation and reduction reactions. In: Das A, Banik
B, eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:199–244. doi:10.1016/B978-0-12-822895-1.00001-1
61. Das A, Banik BK. Chapter 7 – Microwave-assisted enzymatic reactions. In: Das A, Banik B, eds.
Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:245–281. doi:10.1016/B978-0-12-822895-1.00009-6
62. Das A, Banik BK. Chapter 8 – Microwave-assisted sterilization. In: Das A, Banik B, eds. Microwaves
in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier; 2021:285–328.
doi:10.1016/B978-0-12- 822895 -1.0 0 011-4
333Antibacterial Effects of Beta-Lactam Antibiotics with Nanoparticles
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63. Das A, Banik BK. Chapter 9 – Microwave-assisted CVD processes for diamond synthesis. In: Das A,
Banik B, eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry.
Elsevier; 2021:329–374. doi:10.1016/B978-0-12-822895-1.00004-7
64. Das A, Banik BK. Chapter 10 – Future trends in microwave chemistry and biology. In: Das A, Banik B,
eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:375–384. doi:10.1016/B978-0-12-822895-1.00003-5
65. Das A, Banik BK. Microwave-induced biocatalytic reactions toward medicinally important compounds.
Phys Sci Rev. 2022;7(4–5):507–538. doi:10.1515/psr-2021-0064
66. Das A, Banik BK. 3 Microwave-induced biocatalytic reactions toward medicinally important com-
pounds. In: 3 Microwave-Induced Biocatalytic Reactions toward Medicinally Important Compounds.
De Gruyter; 2022:57–88. doi:10.1515/9783110732542 -003
67. Das A, Yadav R, Banik B. Microwave-induced surface-mediated highly efcient regioselective nitration
of aromatic compounds: Effects of penetration depth. Asian J Chem. 2021;33:2203–2206. doi:10.14233/
ajchem.20 21.2 3131
68. Das A, Banik BK. Microwave in research-more miracles. Asian J Microw Ind Chem. Published online
2023.
69. Das A, Banik BK. Expeditious synthesis of oxygen and sulfur heterocycles by microwave. Asian J
Microw Ind Chem. Published online 2023.
70. Das A, Banik BK. Advances in heterocycles as DNA intercalating cancer drugs. Phys Sci Rev. Published
online January 5, 2022. doi:10.1515/psr-2021-0065
71. Das A, Banik BK. 4 Advances in heterocycles as DNA intercalating cancer drugs. In: Heterocyclic
Anticancer Agents. De Gruyter; 2022:111–160. doi:10.1515/9783110735772-0 04
72. Da s A, Ashraf MW, Banik BK. Th ione derivatives as medicinally imp ortant compou nds. ChemistrySelect.
2021;6 (34):90 69–9100. doi:10.10 02/slct.202102398
73. Banik BK, Das A. Natural Products as Anticancer Agents. Elsevier Science; 2023.
74. Banik BK, Das A. Anticancer activity of natural compounds from marine plants. In: Banik BK, Das A,
eds. Natural Products as Anticancer Agents. Elsevier; 2023:237–284.
75. Banik BK, Das A. Anticancer activity of natural compounds from bacteria. In: Banik BK, Das A, eds.
Natural Products as Anticancer Agents. Elsevier; 2023:287–328.
76. Banik BK, Das A. Anticancer activity of natural compounds from fungi. In: Banik BK, Das A, eds.
Natural Products as Anticancer Agents. Elsevier; 2023:329–366.
77. Banik BK, Das A. Anticancer drugs from hormones and vitamins. In: Banik BK, Das A, eds. Natural
Products as Anticancer Agents. Elsevier; 2023:369–413.
78. Banik BK, Das A. Future prospect in anticancer natural products. In: Banik BK, Das A, eds. Natural
Products as Anticancer Agents. Elsevier; 2023:415–425.
79. Das A, Banik BK. Anticancer activity of natural compounds from leaves of the plants. In: Banik BK,
Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2023:3–48.
80. Das A, Banik BK. Anticancer activity of natural compounds from stems/barks of the plants. In: Banik
BK, Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2023:49–86.
81. Das A, Banik BK. Anticancer activity of natural compounds from roots of the plants. In: Banik BK, Das
A, eds. Natural Products as Anticancer Agents. Elsevier; 2023:87–131.
82. Das A, Banik BK. Anticancer activity of natural compounds from fruits and vegetables. In: Banik BK,
Das A, eds. Natural Products as Anticancer Agents. Elsevier; 2023:133–177.
83. Das A, Banik BK. Anticancer activity of natural compounds from marine animals. In: Banik BK, Das
A, eds. Natural Products as Anticancer Agents. Elsevier; 2023:181–235.
84. Das A, Banik BK. Combatting the coronavirus utilizing natural cinnamon and its derived products.
Asian J Synth Nat Prod Chem. 2023;1(1). doi:10.1016/ b978- 0 -323-91296 -9.21002 -2
85. Das A, Banik BK. 15 – Versatile thiosugars in medicinal chemistry. In: Banik BK, ed. Green Approaches
in Medicinal Chemistr y for Sustainable Drug Design. Advances in Green and Sustainable Chemistry.
Elsevier; 2020:549–574. doi:10.1016/B978-0-12-817592-7.00015-0
86. Das A, Banik BK. Versatile thiosugars in medicinal chemistry. In: Banik BK, ed. Green Approaches in
Medicinal Chemistry for Sustainable Drug Design. Elsevier; 2023.
87. Das A, Yadav RN, Banik BK. Ascorbic acid-mediated reactions in organic synthesis. Curr Organocatal.
2020;7(3):212–241.
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88. Das A, Banik BK. Graphene oxide and modied graphene oxide-mediated synthesis of medicinally
active compounds. In: Banik BK, ed. Green Approaches in Medicinal Chemistry for Sustainable Drug
Design. Elsevier; 2023.
89. Das A, Banik BK. Synthesis of natural products by photochemistry. In: Banik BK, ed. Green Approaches
in Medicinal Chemistr y for Sustainable Drug Design. Elsevier; 2023.
90. Das A, Banik BK. Green synthesis of biologically active N-heterocyclic compounds via C-H function-
alization. In: Banik BK, ed. Green Approaches in Medicinal Chemistr y for Sustainable Drug Design.
Elsevier; 2023.
91. Das A, Banik BK. Sustainable reactions in the synthesis of heterocycles. Curr Organocatal. 20 22; 9(1):3 –
3. doi:10.2174/221333720901220328164523
92. Fayaz AM, Balaji K, Girilal M, Yadav R, Kalaichelvan PT, Venketesan R. Biogenic synthesis of silver
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nation with antibiotics, on model gram-negative and gram-positive bacteria. Bioinorg Chem Appl.
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M, Peralta-Rodríguez RD, et al. Synthesis of CuO and ZnO nanoparticles by a novel green route:
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The Effects of Dipole Moments on the Biological
Activities of Diverse Beta-Lactams
Aparna Das1 and Bimal Krishna Banik
1
Department of Mathematics and Natural Sciences, College of Sciences and Human Studies,
Prince Mohammad Bin Fahd University, Al Khobar 31952, Kingdom of Saudi Arabia.
2
Department of Mathematics and Natural Sciences, College of Sciences and
Human Studies, Deanship of Research Development, Prince Mohammad
Bin Fahd University, Al Khobar 31952, Kingdom of Saudi Arabia.
*Corresponding authors: Aparna Das, email: aparnadasam @gmail .c om;
BimalKrishna Banik, email: bimalbanik10 @gmail .c om; bbanik @pmu .edu .sa
2
11.1 Introduction and Background
A dipole is basically a system containing two poles, which happen to be opposite to each other in nature.
A dipole is characterized by its dipole moment (µ), a measurement of the overall polarity of the system,
which can be regarded as a vector quantity. In electromagnetism, two types of dipole moments are recognized. Among these are the electric dipole moment, a measurement of the polarity of electric charges
in a system of charges, as well as the magnetic dipole moment,1 which measures the magnetic polarity
of a system of charges. An electric dipole is established when positive (q+) and negative (q−) electrical charges with equal magnitude are separated by a distance (d). There are different types of electric
dipoles that can be found. When a transition occurs between two states, the electric dipole moment that
is associated with the transition is known as the transition dipole moment, the electrical dipole moment
in quantum mechanics. A molecular dipole moment is the electric dipole moment that occurs when the
distribution of positive and negative charges on the various atoms within a molecule is not uniform.
The bond dipole moment is a measurement of the polarity of a chemical bond within a molecule that is
used to determine the degree of polarity. Typically, electron electric dipole moments are dened as the
measure of the charge distribution within an electron and are one of the intrinsic properties of electrons.
We will mostly be discussing the molecular dipole moment in this chapter. The dipole moment associated with a molecule is a result of differences in electronegativity between atoms, which is the measure
of the polarity of the molecule. The three types of dipoles that can be observed in molecules are permanent dipoles, instantaneous dipoles, and induced dipoles. Molecules with permanent dipole moments
are called polar molecules. The components of the cell can be inuenced by organic compounds. This
interaction is possible due to the electronic charges in molecules and within cancer cells. As a result,
performing dipole moment calculations on biologically active compounds may be of utmost importance.
In several studies, dipole moment values of numerous compounds are discussed in relation to their biolog ica l act ivity.
dipole moments and their biological activity.
In the eld of medicine, lactams are extremely important molecules that play a crucial role. Some
of the most important antibiotics that contain these molecules include penicillins, cephalosporins, carbapenems, thienamycins, cephalosporins, monobactams, and carbacephems.
beta-lactams possess a wide range of medicinal properties, including antifungal, anti-inammatory,
analgesic, antihepatitis, LHRH antagonist, antihyperglycemic, anticancer, and cholesterol absorption
inhibitors.
2–13
Numerous compounds have been shown to have a direct relationship between their
14, 15
It has been shown that
16–22
To add to this, it must also be said that these beta-lactams are used in organic chemistry
DOI: 10.1201/9780367816339-11
337
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as intermediates in forms such as chiral or achiral that might be of interest to organic chemists.
now, there have been numerous reports regarding the synthesis of beta-lactams.
25–34
One might consider
23, 24
Until
the indolizidine alkaloids, taxoids, docetaxel, paclitaxel, cryptophycins, lankacidins, nonprotein amino
acids, oligopeptides, peptidomimetics, and heterocycles as beta-lactam-based compounds. Beta-lactams
have gained popularity for their use in the synthesis of Taxol (paclitaxel) and Taxotere (docetaxel).35 Our
research group has been investigating beta-lactams’ biological properties for the last three decades. As a
result of these increasingly intensive investigations, more than 150 publications have been published.
36–39
In this chapter, dipole moment calculations for a number of beta-lactams are presented, and their effects
on biological activity are discussed.
11.2 Dipole Moment of Schiff Bases: Precursors for β-Lactams
It is worth mentioning that Schiff bases are an extensive group of compounds that are characterized
by the presence of a double bond connecting carbon and nitrogen atoms, the versatility of which can
be generated by the way in which they can be combined with a variety of alkyl or aryl substituents. In
nature, compounds of this type are found in abundance. In the laboratory, they can also be synthesized.
Many chemists and biochemists have been greatly inspired by Schiff bases over the past few decades. As
a subclass of imines, they can be classied either as secondary ketimines or secondary aldimines according to the structure of the molecule. In order to synthesize Schiff bases, aliphatic or aromatic amines are
added nucleophilically to carbonyl compounds, resulting in a hemiaminal molecule, and then the hemiaminal is dehydrated to yield an imine molecule. The activity of Schiff bases has been studied in relation
to a wide range of contexts, including antimicrobial, antiviral, and anticancer properties, among others.
Furthermore, they are also suspected to be effective in inhibiting amyloid beta-aggregation as well.
As a prerequisite to the preparation of beta-lactams, it is essential to have the proper imines (Schiff
bases).41 Carbonyl compounds as well as primary amines can be used as sources of aldimines and ketimines, respectively. In the preparation of heterocycles, imines are a key component of the materials that
are used.
42, 43
A quantum mechanics calculation is used to calculate the dipole moments of aldimines and
ketimines. From the values of the dipole moments, it is possible to gain a great deal of useful information
that can be applied to other situations.
In order to calculate the dipole moments for Schiff bases, two different types of Schiff bases have to
be considered. The process of preparing imines can be seen in Scheme 11.1. As a result of the reaction of
a carbonyl compound 2 with a primary amine 1, it was found that an imine could be synthesized under
reux conditions in the presence of a solvent (toluene or benzene). It was possible to synthesize two
imines, 3 and 4, in terms of their structure.
Fig u r e 11.1 shows a schematic representation of these imines. There are different types of aromatic
groups connected to the nitrogen and carbon atoms, such as phenyl, anthracene, phenanthrene, and chrysene. Ketimines with different functionalities have been investigated as part of the study, and a few of
these have been found to be effective (Fi g u r e 11. 2).
40
SCHEME 11.1 Synthesis of Ketimines and Aldimines.
FIGURE 11.1 Molecular structures of the aldimines.
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339The Effects of Dipole Moments on the Biological Activities of Diverse Beta-Lactams
FIGURE 11.2 Molecular structures of the ketimines.
TABLE 11.1
Dipole Moment Values of Ketimines and Aldimines
Ketimines Aldimines
Z-aldimine E-aldimine Z-ketimine E-ketimine
Compounds
9a 2.08D 10a 1.95D 5a 2.35D 6a 1.67D
9b 2.18D 10b 2.08D 5b 2.17D 6b 1.50D
11b 2.39D 12b 2.09D 7b 2.46D 8b 1.86D
9c 2.18D 10c 1.87D 5c 2.19D 6c 1.39D
11c 2.09D 12c 1.88D 7c 2.29D 8c 1.45D
9d 2.17D 10d 1.85D 5d 2.23D 6d 1.36D
11d 2.18D 12d 1.86D 7d 2.35D 8d 1.48D
Dipole
moment Compounds
Dipole
moment Compounds
Dipole
moment Compounds
Dipole
moment
In order to generate the results for the dipole moment analyses of the imines, SPARTAN 18 was used
as a software tool. The measurements were made at ground state using the Austin Model (AM1) method
and the semiempirical quantum chemistry method. As a result of the energy minimization method that
was applied to the 2D imine structures, the imine structures were converted into their 3D forms. The
dipole moment for imines at the ground state in Debye (D) is presented in Table 11.1.
According to the dipole moment values, there was a signicant similarity between the values of the
dipole moments of the aldimines and the ketimines. As far as the steric interaction between the methyl
group and the hydrogen atom is concerned, there was no difference in the case of imines. It is due to
the inductive effect in which the methyl group has the ability to donate electrons. Dipole moments were
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observed to be high for compounds 7b, 8b, 10b, and 11b. These compounds contain anthracene groups
that are present either on the carbon atoms or on the nitrogen atoms of these compounds. As compared
to the E-imines, the Z-imines exhibited higher dipole moments. It has been found that the number of
aromatic rings in imines has a positive effect on the dipole moment value when it is increased. The gap
in dipole moment value between compound 6b and compound 5b, for example, was 0.67 D, if compound
5b is taken as an example. In contrast, compound 6d and compound 5d have a 0.87 D difference in terms
of the value of the dipole moment.
Z-aldimine 5 is shown in Fig ure 11.3 as a geometric model (with energy minimization) of the structure. An arrow was used as a symbol to represent the direction in which the dipole was pointing. The
resultant dipole vector was observed to point toward the nitrogen atom in all four compounds, 5a–5d.
According to the ndings of the researchers, nitrogen possesses a stronger lone pair power than aromatic
groups attached to carbon, which are able to withdraw electrons more efciently. It should be noted that
the groups of aromatic were not directly linked to the nitrogen atoms in these molecules.
The geometry (energy minimized) of Z-aldimine 7 is shown in Figure 11.4. Each of these molecules,
7b–7d, had a dipole vector that pointed toward the aromatic ring. There is a direct connection between
the aromatic groups and the nitrogen atoms in these molecules. In contrast to nitrogen’s lone pair effect,
aromatic systems were more effective at withdrawing electrons.
Despite the group uniting carbon and nitrogen atoms in Z-imines, dipole moment values were high.
The dipole moments of aldimines and ketimines, however, were similar. Despite a small difference in
dipole moments, it was apparent that the imines preferred different reactions.
FIGURE 11.3 The structure (energy minimized) of the Z-aldimine 5 derivatives.
FIGURE 11.4 The structure (energy minimized) of the Z-aldimine 7 derivatives.
341The Effects of Dipole Moments on the Biological Activities of Diverse Beta-Lactams
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11.3 Dipole Moment of α-Hydroxy and α-Acetoxy-β-Lactam Derivatives
Fig u r e 11. 5 shows the energy-minimized structures of the α-acetoxy-beta-lactams. There is an important
point to note here that compound 1 and compound 2 are stereoisomers. With regard to the stereoisomers,
there had been differences in their properties which had to do with their different structures. For this
reason, both the cis and the trans-isomers had to be investigated in order to be able to examine the effects
of the dipole moments. In compound 1, a cis-geometry was observed, whereas a trans-geometry was
observed in compound 2. In both cases, the N1 position is connected with a phenyl group, the oxygen
is connected with the C2 position, the acetoxy functionality is connected with the C3 position, and the
phenyl group is connected with the C4 position. Using compounds 3 and 4 as examples, the substitutional
group’s effect at the N1 position has been studied. Compounds 4 and 5 contain a group of CO-phenyl
groups connected to the N1 position of the ring. Additionally, it should also be noted that the transcompound 4 as well as the cis-compound 3 are stereoisomers of each other.
Fig u r e 11.6 shows the energy-minimized geometries of the α-hydroxy-beta-lactams. There are two
compounds that are stereoisomers of each other, 5 and 6. On both of them, there is a group of phenyls
attached to the N1 location of the ring, and there is also an oxygen atom attached to the C2 center, as well
as a phenyl group attached to the C4 center. It should be noted that the other two compounds, 8 and 7,
do not have phenyl groups attached to the N1 of the ring, but rather have a group of CO-phenyls attached
to it instead.
In the past decades, a variety of procedures have been described for the preparation of α-hydroxybeta-lactams.44 Scheme 11.2 displays a schematic diagram showing the steps involved in the synthesis of
compound 3 and compound 4, respectively.
SPARTAN 18 software package was used as part of the calculation of the dipole moment. In order to
carry out the calculations, semiempirical quantum chemistry procedures were used with an equilibrium
geometry at the ground-state conguration. Specically, Recife Model 1 (RM1), Parametric Model 3
(PM3), Parametric Model 6 (PM6), and Austin Model 1 (AM1) were used in the analysis. In order to
make them more usable, the original structures were created in 2D, and using the same software, they
were converted into their 3D forms.
FIGURE 11.5 The optimized and chemical geometries of the α-acetoxy-β-lactams.
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