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122 Chemistry and Biology of Beta-Lactams
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131. Shaikh AL, Kale AS, Shaikh MdA, Puranik VG, Deshmukh ARAS. Asymmetric synthesis of β-lactams
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132. Das A, Banik BK. Advances in heterocycles as DNA intercalating cancer drugs. Phys Sci Rev. Published
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133. Das A, Ashraf M W, Ban ik BK. Thione derivatives as med icinally impor tant compounds. ChemistrySelect.
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134. Das A, Banik BK. 4 Advances in heterocycles as DNA intercalating cancer drugs. In: Heterocyclic
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135. Das A. LED light sources in organic synthesis: An entry to a novel approach. Lett Org Chem.
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136. Banik BK, Das A. Natural Products as Anticancer Agents. Elsevier Science; 2023.
137. 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.
138. Banik BK, Das A. Anticancer activity of natural compounds from bacteria. In: Banik BK, Das A, eds.
Natural Products as Anticancer Agents. Elsevier; 2023.
139. Banik BK, Das A. Anticancer activity of natural compounds from fungi. In: Banik BK, Das A, eds.
Natural Products as Anticancer Agents. Elsevier; 2023.
140. Banik BK, Das A. Anticancer drugs from hormones and vitamins. In: Banik BK, Das A, eds. Natural
Products as Anticancer Agents. Elsevier; 2023.
141. Banik BK, Das A. Future prospect in anticancer natural products. In: Banik BK, Das A, eds. Natural
Products as Anticancer Agents. Elsevier; 2023.
142. 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.
143. 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.
144. 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.
145. 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.
146. 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.
147. Das A, Banik BK. Combatting the coronavirus utilizing natural cinnamon and its derived products.
Asian J Synth Nat Prod Chem. 2 023;1(1):11–15.
148. Das A, Yadav R, Banik BK. Dipole moment studies on anticancer polyaromatic compounds. Asian J
Org Med Chemi. Published online 2023.
149. 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
128 Chemistry and Biology of Beta-Lactams
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150. Das A, Das A, Banik BK. Inuence of dipole moments on the medicinal activities of diverse organic
compounds. J Indian Chem Soci. 2021;98(2):100005. doi:10.1016/j.jics.2021.10 0005
151. Das A, Banik BK. β-lactams: Geometry, dipole moment and anticancer activity. J Indian Chem Soc.
2020;Vol. 97, No. 11b(Nov 2020):2461–2467. doi:10.5281/zenodo.5656689
152. Das A. Quantitative structure-property relationships of taxol, taxotere and their epi-isomers. J Indian
Chem Soc. 2020;97(11):9.
153. Das A, Alqashqari AA, Banik BK. Quantum mechanical calculations of dipole moment of diverse
imines. J Indian Chem Soc. 2021;97(9b):1563–1566.
154. Das A, Banik BK. Dipole moment studies on α-hydroxy-β-lactam derivatives. J Indian Chem Soc.
2021;97(9b):1567–1571.
155. Das A, Banik BK. Studies on dipole moment of penicillin isomers and related antibiotics. J Indian
Chem Soc. 2020;97:6.
156. 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.
157. Das A, Banik BK. Computational studies of physicochemical parameters on optically active anticancer
β-lactams. Heterocycl Lett. 202 3;13 (1).
158. 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
159. 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.
160. Shaikh AL, Yadav RN, Banik BK. Microwave-induced enantiospecic synthesis of trans -(3R, 4R)-3
-acet oxy-4 -aryl -1-(c hryse n-6-y l)aze tidin -2-on es via the Staudinger cycloaddition reaction of (+)-car-3ene with polyaromatic imines. Russ J Org Chem. 2 020;56(5):910 –915. doi:10.1134/S1070428020050 267
161. 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.
162. 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.
163. 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.
164. Das A, Yadav RN, Banik BK. Ascorbic acid-mediated reactions in organic synthesis. Curr Organocatal.
2020;7(3):212–241.
165. Das A, Banik BK. Sustainable reactions in the synthesis of heterocycles. Curr Organocatal. 2022 ;9(1):3–
3. doi:10.2174/221333720901220328164523
166. Das A, Banik BK. 15 – Versatile thiosugars in medicinal chemistry. In: Banik BK, ed. Banik BK,
ed. Green Approaches in Medicinal Chemistry for Sustainable Drug Design. Advances in Green and
Sustainable Chemistry. Elsevier; 2020:549–574. doi:10.1016/B978-0-12-817592-7.00015-0
167. Shaikh AL, Banik BK. A novel asymmetric synthesis of 3-(1H-Pyrrol-1-yl)-substituted β-lactams
via a bismuth nitrate-catalyzed reaction. Helv Chim Acta. 2012;95(5):839–844. doi:10.1002/
hlca.201100202
168. Yadav RN, Hossain F, Das A, Srivastava AK, Banik BK. Organocatalysis: A recent development on
stereoselective synthesis of o-glycosides. Catal Rev. 2022;0(0):1–118. doi:10.1080/01614940.2022.20413
03
169. Das A, Banik BK. Versatile synthesis of organic compounds derived from ascorbic acid. Curr
Organocatal. 9(1):14 –33.
170. Das A, Banik BK. Versatile thiosugars in medicinal chemistry. In: Banik BK, ed. Green Approaches in
Medicinal Chemistry for Sustainable Drug Design. Elsevier; 2023.
171. Shaikh AL, Das A, Banik BK. Indium-mediated reduction of aromatic nitro groups in β-lactams to
oxazines. Asian J Met Sal. Published online 2023.
172. 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
173. Das A, Banik BK. Microwaves in Chemistry Applications: Fundamentals, Methods and Future Trends.
Elsevier Science; 2021.
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174. 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
175. 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
176. 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
177. 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
178. 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
179. 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
180. 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
181. 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
182. 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
183. 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
184. 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
185. 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
186. 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
187. 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 Chemi. Published
online 2023.
188. Das A, Banik BK. Microwave in research-more miracles. Asian J Microw Ind Chem. Published online
2023.
189. Das A, Banik BK. Expeditious synthesis of oxygen and sulfur heterocycles by microwave. Asian J
Microw Ind Chem. Published online 2023.
190. Yadav RN, A. L S, Banik BK. Lactam. Heterocycl Lett. 2 023;13:241.
191. Guerrini A, Varchi G, Daniele R, Samorì C, Battaglia A. Synthesis of chiral β2,2,3-3-amino-2-
hydroxyalkanoates and 3-alkyl-3-hydroxy-β-lactams by double asymmetric induction. Tetrahedron.
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192. Li XG, Lähitie M, Päiviö M, Kanerva LT. Enantioselective acylation of alcohols with uori-
nated β-phenyl-β-lactams in the presence of Burkholderia cepacia lipase. Tetrahedron: Asymmetry.
2007;18(13):1567–1573. doi:10.1016/j.tet asy.2 007.06.033
193. Alcaide B, Almendros P, del Campo TM, Rodríguez-Acebes R. Diversity-oriented preparation of enan-
tiopure spirocyclic 2-azetidinones from α-oxo-β-lactams through barbier-type reactions followed by
metal-catalyzed cyclizations. Adv Synth Catal. 2007;349(4–5):749–758. doi:10.1002/adsc.200600502
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195. Berlin JM, Fu GC. Enantioselective nucleophilic catalysis: The synthesis of aza-β-lactams through [2+2]
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approach. Adv Synth Catal. 2008;350(14–15):2279–2285. doi:10.1002/adsc.200800432
197. Sakamoto M, Kawanishi H, Mino T, Fujita T. Asymmetric synthesis of β-lactams using chiral-memory
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4
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Polyaromatic Beta-Lactams:
Synthesisand Anticancer Activities
Bimal Krishna Banik1 and Aparna Das
1
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.
2
Department of Mathematics and Natural Sciences, College of Sciences and Human Studies,
Prince Mohammad Bin Fahd University, Al Khobar 31952, Kingdom of Saudi Arabia.
*Corresponding authors: Bimal Krishna Banik, email: bimalbanik10 @gmail .c om;
bbanik @pmu .edu .sa; Aparna Das, email: aparnadasam @gmail .c om
2
4.1 Introduction
The investigation of novel anticancer agents that are selective for malignant cells with a tolerable toxicity has been a main focus of a drug discovery process in recent years. Despite an enormous success as
clinically active antibiotics, studies of β-lactams as anticancer agents are very limited. In fact, Banik and
his group synthesized the rst anticancer β-lactams and reported their ndings in 2003 for the rst time.
It was believed that novel anticancer β-lactams with greater potency and less toxicity in comparison to
other available drugs can be identied through syntheses, biological assays, and mechanistic studies.
Some unique β-lactams derived from polycyclic aromatic compounds following cycloaddition as the
main reaction were synthesized. In contrast to the literature, this reaction produced trans-β-lactams as
the exclusive products in many examples. Systematic analyses on the anticancer activities of these new
β-lactams in racemic and optically active forms were conducted. It was demonstrated that some of these
β-lactams possess selective antitumor activity in vitro against many cancer cell lines (diverse forms
of ovarian, colon, breast, leukemia, pancreas, prostate, and melanoma) and in animal models. It was
established that these agents have demonstrated an extremely active blockade of the G2/M checkpoint
in cancer cell lines. A few of these β-lactams demonstrated remarkable anticancer activity against a
number of pancreatic cancer cell lines including against Gemcitabine (GEM)-resistant cancer cell lines.
Importantly, many of these compounds had excellent bioavailability and permeability. These results were
extremely exciting since these uncover an opportunity for translational research to develop β-lactams
as useful small molecules against various cancers. Our results on a highly active anticancer β-lactam
diminished the expression of FOXO-1 in PANC-1 after 24-h exposure. The expression of CDC-2, a gene
involved in the G2/M checkpoint, was also decreased at 24 h. These results encouraged us in conducting
innovating research on the very challenging anticancer β-lactam eld.
We prepared optically active and racemic β-lactams in order to identify the structural and mechanistic
correlation of anticancer activity. In particular, several aims were targeted on these novel and new classes
of anticancer β-lactams, and some of these were as follows:
(a) Structurally diverse racemic and optically active analogues of the lead anticancer β-lactams
were prepared. These efforts used numerous synthetic methods including Staudinger cycloaddition reaction between imines and acid chloride (equivalent), metal-mediated reactions, chemoenzymatic reactions, and other related methods.
DOI: 10.1201/9780367816339-4
131
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