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352 Chemistry and Biology of Beta-Lactams
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molecular mechanics was used in conjunction with the Merck molecular force eld (MMFF). All the
structures were made in 2D, and then they were converted into their respective 3D structures by using the
same software. To minimize their energy consumption, they were then analyzed using energy minimization procedures, followed by optimization using the MMFF software.
There is a variational method known as Hartree–Fock (HF) for determining the energy and wave
function of a quantum many-body system. HF is a variational method for nding the energy and wave
function. The Hartree–Fock approximation follows from the Schrödinger equation because it requires
that electrons are independent particles to represent Schrödinger equation. The geometric optimization
was performed using the 6-31G* basis sets after the energy minimization procedure was completed to
calculate the dipole moment.
The correlated models are the models that lessen the effects of the Hartree–Fock approximation on
the analysis. The models can be divided into two broad categories, density functional models and models based on wave functions. The density functional theory (DFT) is a mathematical model based on
quantum mechanics. A lot of work is done with this method to investigate the electronic structure (or
nuclear structure) of many-body systems, such as atoms, molecules, or condensed phases, in particular.
As of right now, the DFT has been viewed as the most effective and promising method for computing
a material’s electronic structure. Different basis sets can be used to make DFT calculations on different levels and at different levels of accuracy. The structures in this study are optimized after the energy
minimization procedure, employing the 6-31G* basis forms at the B3LYP level as a basis for optimizing
the structures. By doing this, a stereochemically stable structure for each compound can be obtained.
As a quantum chemistry post-Hartree–Fock–Fock ab initio method, the Møller–Plesset (MP) perturbation theory method is one of the most widely used quantum chemistry methods in the eld of
computational chemistry.
115
Compared to the Hartree–Fock method, the MP method improves on the
Hartree–Fock method by adding electron correlation effects to the equations using Rayleigh–Schrödinger
perturbation theory (RS-PT). For estimation of basic systems, second (MP2),
fourth (MP4)
118
order calculations are used. As part of the current work, the optimization of the 6-31G
116
th i rd ( M P3),
117
and
basis forms has been done at the MP2 level.
As a result of testing these optically active beta-lactams 1 and 2 against human cancer cell lines, we
found that their anticancer activity differed signicantly. A comparison of their anticancer activities is
given in Table 11.1. A total of seven human cancer cell lines were tested to conrm the results. Human
breast cancer cells are represented by MDA-231; human melanoma cells are represented by BRO; human
ovarian cancer cells are represented by SKOV-3; human colon cancer cells are represented by HT-29;
human prostate cancer cells are represented by PC-3; and human blood cancer cells are represented by
HL-60 and K-562. In Table 11.7, you will nd the values from cisplatin, which is a chemotherapy medicine used as a reference for the study.
In terms of the IC50 values for cell growth inhibition, it seems that the beta-lactams, (−)-1, demonstrate a signicant increase in activity against six human tumor lines when compared to cisplatin and
compound (+)-2. In addition, the results of this study showed that the activity of compound 1 is not uniform across all tumor lines, which suggests that the target of this compound’s action is highly specic.
It was found that compound 1 showed the greatest activity against the colon cancer cell line (HT-29) and
the blood cancer cell line (HL-60). Even though compound 2 showed activity against all seven human
cancer cell lines, the effect was not as strong as cisplatin or compound 1 when compared with each other.
To understand this activity difference between these two isomers, a computational molecular analysis is
the best method.
A growing amount of research is showing that organic molecules, particularly anticancer medicines
and candidates for drugs, have an important effect on the proteins in cells and their constituent components. There is a strong correlation between the electronic charges present in the drug molecules and the
tumor cells that accounts for the presence of these interactions. Using this well-known concept as a base,
it was a simple matter to calculate the dipole moment of the beta-lactams. As can be seen from Ta ble
11.8, the ground-state dipole moment values have been calculated for compounds 1 and 2. Five semiempirical methods (AM1, RM1, PM3, PM6, and MNDO) were used to calculate these values. According
to the results obtained, trans-beta-lactam 1 was observed to have a high value of dipole moment ranging
from 7. 13 D to 6.63 D. It was found that the value of the dipole moment for trans-beta-lactam 2 ranged
TABLE 11.6
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Calculated Dipole Moment Values in Debye (D)
β-Lactams MNDO PM6 PM3 RM1 AM1
1 2.30 2.71 3.01 2.67 3.08
2 3.49 3.16 3.34 2.81 2.93
3 2.43 3 3.16 2.65 2.92
4 4.31 4.54 4.90 5.11 5.14
5 4.32 4.53 4.87 5.06 5.13
6 2.65 3.83 2.25 3.08 3.55
TABLE 11.7
β-Lactam’s In Vitro Cytotoxicity on Seven Human
Cancer Cell Lines (µM)
1 2 Cisplatin
PC-3 1.4 15.5 4.66
HT-29 0.7 8.3 16.99
SKOV-3 6.8 8.5 5.99
K-562 1.1 6 2.33
BRO 6.1 22 7.66
HL-60 0.7 5.4 1.66
MDA-231 1.8 8.5 12.33
353The Effects of Dipole Moments on the Biological Activities of Diverse Beta-Lactams
TABLE 11.8
Calculated Values of Dipole Moment Employing
Semiempirical Methods
Dipole moment values
Semiempirical methods
MNDO 6.01 D 4.33 D
PM6 7.13 D 4.65 D
PM3 6.63 D 4.81 D
RM1 6.96 D 5.06 D
AM1 7.12 D 5.11 D
Compound 1 Compound 2
from 4.33 D to 5.11 D. Based on the comparison of other selected calculation methods, the MNDO analysis produced the smallest value for the dipole moment for the molecule. Nevertheless, a similar trend was
observed with compounds 1 and 2 as well.
Several quantum mechanical methods were used to conrm the dipole moment calculations, including
Hartree–Fock (HF), DFT, Møller–Plesset (MP), classical mechanics, and molecular mechanics (MM)
methods. Table 11.9 shows the results obtained. For purposes of comparison, the values obtained from
the AM1/semiempirical method were also included. There is no doubt that compound 1 has a higher
dipole moment than its chiral isomer 2 based on the results of the experiment. Based on a comparison
of MM with other selected methods for calculating the dipole moment, it was found that MM gave the
highest value. When compared to other methods, the MP method took more CPU time to complete the
calculation successfully compared to other methods.
There is no reason why optical isomers should differ in their dipole moment values, regardless of their
values. As it turns out, there are some differences in the values of dipole moments in the ve different
methods that have been used to calculate them.
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TABLE 11.9
Calculated Values of Dipole Moment
Employing Different Methods
Dipole moment values
Methods
MP 7.11 D 6.03 D
HF 7.16 D 6.05 D
MM 6.91 D 5.97 D
DFT 6.74 D 5.93 D
AM1 7.10 D 5.11 D
Compound 1 Compound 2
FIGURE 11.12 The optimized geometry of β-lactam 1 and β-lactam 2 created using the DFT calculation.
There was a signicant difference between compound 1 and compound 2 in terms of its anticancer
activ it y. Figure 11.12 shows the optimized geometry of beta-lactam 1 and beta-lactam 2 that was created from the DFT calculations of the two beta-lactams. A dipole vector is presented by the arrows in
the gure. In the case of isomers, the direction of the dipole vector is distinct. It is important to point
out that the vector arrow on compound 2 does not exactly point at the oxygen atom in the beta-lactam
carbonyl group. Compound 1 on the other hand has its vector arrow pointing directly at a carbonyl group
on the beta-lactam ring in full, as opposed to compound 2. Based on the optimized structures of the two
compounds, we can see that there is a smaller distance between the phenyl group at C4 and the acetoxy
group at C3 in compound 1 than in compound 2.
Several other physicochemical parameters that are important for the calculation of structure–activity relationships (SARs), structure–property–activity relationships (SPARs), and quantitative structure–
activity relationships (QSARs) have also been calculated. It was necessary to perform three different
calculation methods to check the validity of the data, such as the DFT method, Hartree–Fock (HF)
method, and Möller–Plesset (MP) method. The physicochemical and molecular properties of the mol-
ecules such as molecular weight, total energy, solvation energy, energy of the highest occupied molecular orbital (E HOMO), energy of the lowest unoccupied molecular orbital (E LUMO), polarizability,
octanol–water partition coefcient (Log P), polar surface area (PSA), number of hydrogen bond donors
(HBDs), number of hydrogen bond acceptors (HBAs), surface area, volume of the molecule, and ovality
were all measured. Table 11.10 shows the results obtained.
TABLE 11.10
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Calculated Structural and Physicochemical Properties of β-Lactams 1 and 2
HF MP DFT
Properties
Log P 5.32 5.32 5.32 5.32 5.32 5.32
E HOMO (eV) −7.57 −7.60 −7.14 −7.17 −5.53 −5.57
E LUMO (eV) 2.06 2.03 1.79 1.76 −1.58 −1.63
Energy (au) −1389.2 −1389.2 −1393.2 −1393.2 −1398.2 −1398.2
HBA count 3 3 3 3 3 3
HBD count 0 0 0 0 0 0
Weight (amu) 431.5 431.5 431.5 431.5 431.5 431.5
Polarizability 75.06 75.05 75.33 75.34 76.66 76.63
Ovality 1.58 1.58 1.54 1.55 1.58 1.57
PSA (Å2)
Volume (Å3)
Area (Å2)
1 2 1 2 1 2
36 35.61 37.28 36.44 36.83 36.16
443.23 443.05 444.54 444.68 446.49 446.11
444.74 443.05 435.02 436.58 445.34 442.51
TABLE 11.11
Calculated Quantum Parameters of β-Lactams 1 and
2
Properties β-Lactam 1 β-Lactam 2
ω
η
μ
A 1.58 eV 1.63 eV
I 5.53 eV 5.57 eV
σ
χ
ΔE
3.96 3.94
1.97 eV 1.97 eV
−3.95 −3.94
0.25 0.25
3.55 eV 3.6 eV
3.95 eV 3.94 eV
355The Effects of Dipole Moments on the Biological Activities of Diverse Beta-Lactams
It can be observed from Ta ble 11.10 that most of the considered physicochemical and structural parameters for compound 1 and compound 2 are the same. There is very little variation observed in the E
LUMO, E HOMO, area, volume, and PSA parameters. It is interesting to note that all of the calculation
methods show the same trend. Compared to the dipole moment, these parameters have a much smaller
effect on controlling the bioactivity of the compound.
The reactivity descriptors such as energy gap (ΔE) ionization potential (I), electron afnity (A), electronegativity (χ), global hardness (η), softness (σ), chemical potential (μ), and global electrophilicity
index (ω) were also calculated at the B3LYP/6-31G* level of theory. Table 11.11 lists the obtained values.
It was found that the values of both compounds were comparable.
A number of useful graphical models were also analyzed, such as local ionization potentials, LUMO
maps, and electrostatic potentials, that provided insights into the electron density, nucleophile regions,
and electrophile regions of the molecules.
As far as domain maps of properties are concerned, the electrostatic potential map is the most commonly used and the most important. The charge distribution in a molecule can be determined by using
this indicator. A molecule’s electrostatic potential map is employed as a tool to determine its chemical
reactivity according to its reactivity map. The importance of this graphical analysis is that it allows the
identication of the reactive sites of nucleophilic or electrophilic attack in hydrogen bonding interactions, as well as the understanding of how biological recognition occurs. Figure 11.13 presents a map of
356 Chemistry and Biology of Beta-Lactams
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FIGURE 11.13 Electrostatic potential map of compounds 1 and 2.
FIGURE 11.14 Local ionization potential map of compounds 1 and 2.
the electrostatic potentials of beta-lactam isomers. The blue region of the diagram presents the highest
positive potential, the red region presents the highest electron density and the negative potential, and the
green region presents the neutral electrostatic potential. Figure 11.13 shows that both compounds have
hydrophobic (neutral) regions and hydrophilic (positive and negative potentials) regions and are comparable in their electrostatic potential maps.
A maximum value of −273.80 kJ/mol can be found for the negative electrostatic potential of compound
1, and a maximum value of 136.72 kJ/mol can be found for the positive electrostatic potential of compound 1. Compound 2 presents a maximum negative electrostatic potential of −284.61 kJ/mol, whereas
its positive electrostatic potential is 134.52 kJ/mol.
It is necessary to map the local ionization potential onto a size surface, to determine the region from
which electrons are most easily ionized. Fig u re 11.14 shows the maps of the local ionization potentials of
the compounds. Also, in terms of electrophilic reactions, the ionization potential can be used as a tool to
assess chemical reactivity and selectivity. It can be seen that this overlay represents the energy required
to remove electrons (ionization) on the density of electrons. In the case of molecule 1, the energy ranges
357The Effects of Dipole Moments on the Biological Activities of Diverse Beta-Lactams
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FIGURE 11.15 LUMO map of compounds 1 and 2.
from 13.74 eV to 42.94 eV; in the case of molecule 2, the energy ranges from 12.99 eV to 43.39 eV. As far
as the map and energy range values are concerned, there have been no variations observed.
In Fig u r e 11.15, a schematic diagram illustrating the LUMO maps of beta-lactam isomers is shown.
In its simplest form, a LUMO map is a way of identifying the sites on a molecule that are most electron
decient, that is, the sites that are most likely to be attacked by nucleophiles. As such, it can be used to
indicate nucleophilic addition, since it is derived from an overlay of the absolute value of the LUMO on
the density of electron of the molecule. According to the map, it appears that both of the LUMO maps
for the two compounds are identical. There is once again conrmation that all of the compounds have
the same LUMO energy. Colors toward red show low (close zero) LUMO values.
The physicochemical and geometrical parameters such as total energy, weight, dipole moment, solvation energy, energy gap (ΔE), E LUMO, E HOMO, polarizability, Log P, HBD, PSA, HBA, volume of
the molecule, surface area, ovality, electron afnity (A), ionization potential (I), global hardness (η),
electronegativity (χ), softness (σ), global electrophilicity index (ω), and chemical potential (μ) of opti-
cally active beta-lactams were calculated in this work. Likely, such an exploratory study of optically
active trans-enantiomeric beta-lactams and their anticancer activity has never been conducted before.
This makes this study unique. To verify the data, several graphical quantities have also been analyzed,
including local ionization potential, LUMO maps, and electrostatic potential.
11.6 Conclusion
The importance of dipole moment in determining the biological activity of diverse beta-lactams is discussed in this chapter. It was found that in many of the compounds, the dipole moment correlated directly
with the biological activity.
Acknowledgments
AD is grateful to CEA-Grenoble, Joseph Fourier University, University of Göttingen, and University of
California, Los Angeles, for their support. BKB is grateful to the US NIH, the US NCI, Texas Kleberg
Foundation, Stevens Institute of Technology, University of Texas MD Anderson Cancer Center, University
of Texas-Pan American, and Community Health Systems of Texas for their nancial and moral support
to his research. AD and BKB are also grateful to their current employer, Prince Mohammad Bin Fahd
Un iversit y.
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REFERENCES
1. Brau CA. Modern Problems in Classical Electrodynamics. OUP USA; 2003.
2. 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
3. Das A, Banik BK. Dipole moment studies on beta lactams. In: Banik BK, ed. Green Approaches in
Medicinal Chemistry for Sustainable Drug Design. Elsevier; 2023.
4. 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.
5. 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
6. Das A, Banik BK. β-Lactams: Geometry, dipole moment and anticancer activity. J Indian Chem Soc.
2020;97(11b):2461–2 467. d oi:10.5281/zenodo.5656689
7. Das A. Quantitative structure-property relationships of Taxol, Taxotere and their epi-isomers. J Indian
Chem Soc. 2020;97(11):9.
8. Das A, Alqashqari AA, Banik BK. Quantum mechanical calculations of dipole moment of diverse
imines. J Indian Chem Soc. 2021;97(9b):1563–1566.
9. Das A, Banik BK. Dipole moment studies on α-hydroxy-β-lactam derivatives. J Indian Chem Soc.
2021;97(9b):1567–1571.
10. Das A, Banik BK. Studies on dipole moment of penicillin isomers and related antibiotics. J Indian
Chem Soc. 2020;97:6.
11. Das A, Banik BK. Dipole moment and anticancer activity of beta lactams. Indian J Pharm Sci.
2021;83(5):1071–1074. doi:10.36468/pharmaceutical-sciences.862
12. Das A, Banik BK. Computational studies of physicochemical parameters on optically active anticancer
β-lactams. Heterocycl Lett. 2023;13(1). doi:10.36468/pharmaceutical-sciences.862
13. Das A, Yadav R, Banik BK. Dipole Moment Studies on Anticancer Polyaromatic Compounds. Asian J
Org and Med Chem. Published online 2023.
14. Holten KB, Onusko EM. Appropriate prescribing of oral beta-lactam antibiotics. Am Fam Physician.
2000;62(3):611–620.
15. Page MI. The Chemistry of β-Lactams. Springer Science & Business Media; 2012.
16. O’Driscoll M, Greenhalgh K, Young A, Turos E, Dickey S, Lim DV. Studies on the antifungal properties
of N-Thiolated β-lactams. Bioorg Med Chem. 2008;16(16):7832–7837. doi:10.1016/j.bmc.2008.06.035
17. Lall MS, Ramtohul YK, James MNG, Vederas JC. Serine and threonine β-lactones: A new class of
hepatitis A virus 3C cysteine proteinase inhibitors. J Org Chem. 2002;67(5):1536–1547. doi:10.1021/
jo0109 016
18. Saturnino C, Fusco B, Saturnino P, De Martino G, Rocco F, Lancelot JC. Evaluation of analge-
sic and anti-inammatory activity of novel beta-lactam monocyclic compounds. Biol Pharm Bull.
2000;23(5):654–656. doi:10.1248/bpb.23.654
19. Goel RK, Mahajan MP, Kulkarni SK. Evaluation of anti-hyperglycemic activity of some novel monocy-
clic beta lactams. J Pharm Pharm Sci. 20 0 4;7(1):8 0 –83.
20. Guillon CD, Koppel GA, Brownstein MJ, Chaney MO, Ferris CF, Lu S fang, et al. Azetidinones as
vasopressin V1a antagonists. Bioorg Med Chem. 2007;15(5):2054–2080. doi:10.1016/j.bmc.2006 .12 .031
21. Burnett DA, Caplen MA, Davis HRJr, Burrier RE, Clader JW. 2-Azetidinones as inhibitors of choles-
terol absorption. J Med Chem. 1994;37(12):1733–1736. doi:10.1021/jm00038a001
22. Banik I, Becker FF, Banik BK. Stereoselective synthesis of β-lactams with polyaromatic imines: Entry
to new and novel anticancer agents. J Med Chem. 2003;46(1):12–15. doi:10.1021/jm 0255825
23. Ojima I. Recent advances in the α-lactam synthon method. Acc Chem Res. 1995;28(9):383–389.
doi:10.1021/ar00057a004
24. Alcaide B, Almendros P. Beta-lactams as versatile synthetic intermediates for the preparation of hetero-
cycles of biological interest. Curr Med Chem. 2004;11(14):1921–1949. do i:10.2174/0929867043364856
25. Shaikh AL, Das A, Banik BK. Indium-mediated reduction of aromatic nitro groups in β-lactams to
oxazines. Asian J Met Salt. Published online 2023.
26. Das A, Yadav RN, Banik BK. Microwave-induced conversion of electromagnetic energy into heat
energy in different solvents: Synthesis of β-lactams. Chem J Mold. 2022;17(1):62–66. doi:10.19261/
cjm.2021.864
359The Effects of Dipole Moments on the Biological Activities of Diverse Beta-Lactams
https://t.me/med1917
27. Das A, Banik BK. Microwave-induced catalytic transfer hydrogenation in different solvents toward
optically active hydroxy beta lactams: Effects of penetration depth. Asian J Org Med Chem. Published
online 2023.
28. Das A, Yadav R, Banik BK. Microwave-induced ferrier rearrangement of hyroxy beta-lactams with
glycals. Appl Chem Eng. Published online 2023.
29. Das A. LED light sources in organic synthesis: An entry to a novel approach. Lett Org Chem.
2022;19(4):283–292.
30. Das A, Yadav RN, Banik BK. A novel baker’s yeast-mediated microwave-induced reduction of racemic
3-keto-2-azetidinones: Facile entry to optically active hydroxy β-lactam derivatives. Curr Organocatal.
2022;9:195 –198.
31. Das A, Yadav RN, Banik BK. Conceptual design and cost-efcient environmentally Benign synthesis
of beta-lactams. Phys Sci Rev. Published online May 4, 2022. doi:10.1515/psr-2021-0088
32. Das A, Yadav R, Banik BK. 10 conceptual design and cost-efcient environmentally benign synthe-
sis of betalactams. In: 10 Conceptual Design and Cost-Efcient Environmentally Benign Synthesis of
Betalactams. De Gruyter; 2022:357–388. doi:10.1515/978311079 7428-010
33. Das A, Bose AK, Banik BK. Stereoselective synthesis of β-lactams under diverse conditions:
Unprecedented observations. J Indian Chem Soc. 2020;97:10.
34. Yadav RN, Shaikh AL, Das A, Ray D, Banik BK. Asymmetric synthesis of 3-pyrrole substituted
β-lactams through p-toluene sulphonic acid-catalyzed reaction of azetidine-2,3-diones with hydroxyprolines. Curr Organocatal. 2022;9(4):337–345.
35. Hattori K, Yamamoto H. Practical preparation of α-hydroxy-β-amino ester units; Stereoselective
synthesis of taxol side chain and norstatine. Tetrahedron. 1994;50(9):2785–2792. doi:10.1016/
S0040-4020(01)86992-1
36. Banik BK, Becker FF. Selective anticancer activity of β-lactams derived from polyaromatic compound.
Mol Med Rep. 2010;3(2):315–316. doi:10.3892/mmr_00000257
37. Banik BK, Becker FF. Unprecedented stereoselectivity in the Staudinger reaction with polycyclic aro-
matic imines. Tetrahedron Lett. 2000;41(34):6551–6554. doi:10.1016/S0040-4039(00)01126-6
38. Bose AK, Banik BK, Manhas MS. Stereocontrol of β-lactam formation using microwave irradiation.
Tetrahedron Lett. 1995;36(2):213–216. doi:10.1016/0 040-4039(94)02225-Z
39. Bandyopadhyay D, Yanez M, Banik B. Microwave-induced stereoselectivity of β-lactam formation:
Effects of solvents. Heterocycl Lett. 2011;1: 6 5 – 67.
40. Bajema EA, Roberts KF, Meade TJ. Cobalt-schiff base complexes: Preclinical research and potential
therapeutic uses. Met Ions Life Sci. 2019;19. doi:10.1515/9783110527872-017
41. Schiff H. Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen.
Justus Liebigs Ann Chem. 1864;131(1):118 –119. doi :10.1002/jlac.18641310113
42. Cao J, Yang X, Hua X, Deng Y, Lai G. Synthesis of 2-Azaanthracenes via a sequential sonogashira cou-
pling/alkynyl imine−allenyl imine isome rizat ion/a za-di els−a lder/ elimi natio n−aro matiz ation reaction.
Org Lett. 2011;13(3):478– 481. doi:10.1021/ol1028207
43. Unsworth WP, Gallagher KA, Jean M, Schmidt JP, Diorazio LJ, Taylor RJK. Direct imine acyla-
tion: Synthesis of the proposed structures of ‘Upenamide. Org Lett. 2013;15(2):262–265. doi:10.1021/
ol3030764
44. Banik BK. Beta-Lactams: Novel Synthetic Pathways and Applications. Springer; 2017.
45. Martinez JL. Environmental pollution by antibiotics and by antibiotic resistance determinants. Environ
Pollut. 2009;157(11):2893–2902. doi:10.1016/j.envpol.2009.05.051
46. Fleming A. The discovery of penicillin. Br Med Bull. 1944;2(1):4–5. doi:10.1093/oxfordjournals.bmb.
a071032
47. Farrar WE, O’dell NM. β-lactamases and resistance to penicillins and cephalosporins in Serratia marc-
escens. J Infect Dis. 1976;134(3):2 45 –251. doi:10.1093/infdis/134.3.245
48. Waley SG. A spectrophotometric assay of β-lactamase action on penicillins (Short communication).
Biochem J. 1974;139(3):789–790.
49. Andersen SJ, Frisvad JC. Penicillin production by Penicillium nalgiovense. Lett Appl Microbiol.
1994;19(6):486–488. doi:10.1111/j.1472 -765X .1994.tb00988 .x
50. Coenen S, Ferech M, Haaijer‐Ruskamp FM, Butler CC, Stichele RHV, Verheij TJM, et al. European
surveillance of antimicrobial consumption (ESAC): Quality indicators for outpatient antibiotic use in
Europe. Qual Saf Health Care. 2007;16(6):440–445. doi:10.1136/q shc. 20 0 6.021121
360 Chemistry and Biology of Beta-Lactams
https://t.me/med1917
51. Quinn R. Rethinking antibiotic research and development: World War II and the penicillin collabora-
tive. Am J Public Health. 2013;103(3):426 – 434. doi:10.2105/AJPH.2012.300693
52. Fusté E, Galisteo GJ, Jover L, Vinuesa T, Villa TG, Viñas M. Comparison of antibiotic susceptibility of
old and current Serratia. Future Microbiol. 2012;7(6):781–786. doi:10.2217/f mb.12.40
53. Li D, Yang M, Hu J, Zhang Y, Chang H, Jin F. Determination of penicillin G and its degradation prod-
ucts in a penicillin production wastewater treatment plant and the receiving river. Water Res. 20 08;42(1–
2):3 0 7 –317. doi:10 .1016/j.w a t r e s . 2 0 07.0 7. 016
54. Díaz N, Suárez D, Sordo TL. Conformational properties of penicillins: Quantum chemical calculations
and molecular dynamics simulations of benzylpenicillin. J Comput Chem. 2003;24(15):1864–1873.
doi:10.1002/jcc.10350
55. Nangia A, Desiraju GR. Axial and equatorial conformations of penicillins, their sulphoxides and sul-
phones: the role of N-H⋯S and C-H⋯O hydrogen bonds. J Mol Struct. 1999;474(1):65–79. doi:10.1016/
S0022-2860(98)00561-4
56. de Paula MC, Valle MS, Pliego JR. Electron afnity and dipole moment of 1,2,4,5-tetraoxanes antima-
larials and correlation with activity against Plasmodium falciparum. Med Chem Res. 2014;23(12):5197–
5203. doi:10.1007/s00 0 44-014-1088-8
57. Al-Sehemi AG, Irfan A, Alrumman SA, Hesham AE. Antibacterial activities, DFT and QSAR studies
of quinazolinone compounds. Bull Chem Soc Ethiop. 2016;30(2):307–316. doi:10.4314/bcse.v30i2.15
58. De Paiva R, Da Silva J, Moreira H, Pinto O, Camargo L, Naves P, et al. Synthesis, antimicrobial activity
and structure-activity relationship of some 5-arylidene-thiazolidine-2,4-dione derivatives. J Braz Chem
Soc. Published online 2018. doi:10.21577/0103-5053.20180167
59. Murcia RA, Leal SM, Roa MV, Nagles E, Muñoz-Castro A, Hurtado JJ. Development of antibacte-
rial and antifungal triazole chromium(III) and cobalt(II) complexes: Synthesis and Biological activity
evaluations. Molecules. 2018;23(8):2013. doi:10.3390/molecules23082013
60. Datar PA. 2D-QSAR Study of indolylpyrimidines derivative as antibacterial against Pseudomonas
aeruginosa and Staphylococcus aureus: A comparative approach. J Comput Med. 2014;2014:e765457.
doi:10.1155/2014/765457
61. Motohashi N, Kurihara T, Yamanaka W, Satoh K, Sakagami H, Molnár J. Relationship between biologi-
cal activity and dipole moment in benzo[a]phenothiazines. Anticancer Res. 1997;17(5A):3431–3435.
62. Chavva K, Pillalamarri S, Banda V, Gautham S, Gaddamedi J, Yedla P, et al. Synthesis and biologi-
cal evaluation of novel alkyl amide functionalized triuoromethyl substituted pyrazolo[3,4-b]pyridine
derivatives as potential anticancer agents. Bioorg Med Chem Lett. 2013;23(21):5893–5895. doi:10.1016/j.
bmcl.2013.08.089
63. 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
64. 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
65. 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
66. Das A, Banik BK. Versatile thiosugars in medicinal chemistry. In: Banik BK, ed. Green Approaches in
Medicinal Chemistry for Sustainable Drug Design. Elsevier; 2023.
67. Banik BK, Das A. Natural Products as Anticancer Agents. Elsevier Science; 2023.
68. 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.
69. Banik BK, Das A. Anticancer activity of natural compounds from bacteria. In: Banik BK, Das A, eds.
Natural Products as Anticancer Agents. Elsevier; 2023.
70. 12. Banik BK, Das A. Anticancer activity of natural compounds from fungi. In: Banik BK, Das A, eds.
Natural Products as Anticancer Agents. Elsevier; 2023.
71. Banik BK, Das A. Anticancer drugs from hormones and vitamins. In: Banik BK, Das A, eds. Natural
Products as Anticancer Agents. Elsevier; 2023.
72. Banik BK, Das A. Future prospect in anticancer natural products. In: Banik BK, Das A, eds. Natural
Products as Anticancer Agents. Elsevier; 2023.
73. 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.
361The Effects of Dipole Moments on the Biological Activities of Diverse Beta-Lactams
https://t.me/med1917
74. 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.
75. 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.
76. 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.
77. 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.
78. Das A, Banik BK. Versatile synthesis of organic compounds derived from ascorbic acid. Curr
Organocatal. 20 2 2;9 (1):14 –33.
79. 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
80. Das A, Yadav RN, Banik BK. Ascorbic acid-mediated reactions in organic synthesis. Curr Organocatal.
2020;7(3):212–241.
81. 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.
82. 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.
83. 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.
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. 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
86. Das A, Banik BK. Sustainable reactions in the synthesis of heterocycles. Curr Organocatal. 20 22; 9(1):3 –
3. doi:10.2174/221333720901220328164523
87. Das A, Banik BK. Microwaves in Chemistry Applications: Fundamentals, Methods and Future Trends.
Elsevier Science; 2021.
88. 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
89. 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
90. 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
91. 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
92. 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
93. 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
94. 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
95. 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
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