Browsing by Author "Priyanka Bose"

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1-(Hydroxymethyl)-1H-benzotriazole: An Efficient Ligand for Copper-Catalyzed Ullmann-Type Coupling Reaction Leading to Expeditious Synthesis of Diverse Benzoxazoles and Benzothiazoles
(Wiley-Blackwell, 2019) Mala Singh; Priyanka Bose; Anoop S. Singh; Vinod K. Tiwari
Cu-catalyzed Ullmann coupling was performed for the facile synthesis of diverse benzoxazoles and benzothiazoles in the presence of 1-(hydroxymethyl)-1H-benzotriazole as ligand and K2CO3 as base in anhydrous DMF at 120 0C. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Click Inspired Synthesis of Novel Cinchonidine Glycoconjugates as Promising Plasmepsin Inhibitors
(Nature Research, 2020) Nidhi Mishra; Anand K. Agrahari; Priyanka Bose; Sumit K. Singh; Anoop S. Singh; Vinod K. Tiwari
Among all the malaria parasites, P. falciparum is the most predominant species which has developed drug resistance against most of the commercial anti-malarial drugs. Thus, finding a new molecule for the inhibition of enzymes of P. falciparum is the pharmacological challenge in present era. Herein, ten novel molecules have been designed with an amalgamation of cinchonidine, carbohydrate moiety and triazole ring by utilizing copper-catalyzed click reaction of cinchonidine-derived azide and clickable glycosyl alkynes. The molecular docking of developed molecules showed promising results for plasmepsin inhibition in the form of effective binding with target proteins. © 2020, The Author(s).
Click inspired synthesis of piperazine-triazolyl sugar-conjugates as potent anti-Hela activity
(Elsevier Ltd, 2023) Priyanka Bose; Anand K. Agrahari; Rajan Singh; Mala Singh; Sunil Kumar; Rakesh K. Singh; Vinod K. Tiwari
To imbibe the aim of synthesizing water-soluble and biocompatible motif, a click-inspired piperazine glycoconjugate has been devised up. In this report, we present a focused approach to design and synthesis of versatile sugar-appended triazoles through ‘Click Chemistry’ along with their pharmacological studies on cyclin-dependent kinases (CDKs) and cell cytotoxicity on cancer cells using in silico and in vitro approaches, respectively. The study has inclusively recognized the galactose- and mannose-derived piperazine conjugates as the promising motifs. The findings suggested that the galactosyl bis-triazolyl piperazine analogue 10b is the most CDK interactive derivative and also possess significant anticancer activity. © 2023 Elsevier Ltd
Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications
(American Chemical Society, 2021) Anand K. Agrahari; Priyanka Bose; Manoj K. Jaiswal; Sanchayita Rajkhowa; Anoop S. Singh; Srinivas Hotha; Nidhi Mishra; Vinod K. Tiwari
Copper(I)-catalyzed 1,3-dipolar cycloaddition between organic azides and terminal alkynes, commonly known as CuAAC or click chemistry, has been identified as one of the most successful, versatile, reliable, and modular strategies for the rapid and regioselective construction of 1,4-disubstituted 1,2,3-triazoles as diversely functionalized molecules. Carbohydrates, an integral part of living cells, have several fascinating features, including their structural diversity, biocompatibility, bioavailability, hydrophilicity, and superior ADME properties with minimal toxicity, which support increased demand to explore them as versatile scaffolds for easy access to diverse glycohybrids and well-defined glycoconjugates for complete chemical, biochemical, and pharmacological investigations. This review highlights the successful development of CuAAC or click chemistry in emerging areas of glycoscience, including the synthesis of triazole appended carbohydrate-containing molecular architectures (mainly glycohybrids, glycoconjugates, glycopolymers, glycopeptides, glycoproteins, glycolipids, glycoclusters, and glycodendrimers through regioselective triazole forming modular and bio-orthogonal coupling protocols). It discusses the widespread applications of these glycoproducts as enzyme inhibitors in drug discovery and development, sensing, gelation, chelation, glycosylation, and catalysis. This review also covers the impact of click chemistry and provides future perspectives on its role in various emerging disciplines of science and technology. ©
Design, Synthesis and Pharmacological Evaluation of Noscapine Glycoconjugates
(Wiley-Blackwell, 2019) Kunj B Mishra; Neeraj Tiwari; Priyanka Bose; Rajan Singh; Arun K Rawat; Sumit K. Singh; Ram C. Mishra; Rakesh K Singh; Vinod K. Tiwari
The present work is directed to design a series of molecules which are hybrids of two non-toxic biocompatible chemical architectures, noscapine and carbohydrates. Fourteen, 7-O-noscapine analogues have been synthesized out of which one of the analogue is 7-O-propargylated derivative and others are in its glycoconjugate form with triazole bridging achieved via Click reaction, where dinuclear copper(I) thiodiacetate complex [(PPh 3 ) 2 Cu(μ-tda)Cu(PPh 3 ) 2 ].6H 2 O has been emerged as an excellent catalyst for the noscapine-glyco Click-coupling. All the developed noscapine glycoconjugates have been investigated for anticancer activity using HeLa cell line and anti-leishmanial activity against Leishmania donovani. Result indicates that five of the developed noscapine glycoconjugates (5 a, 5 b, 5 c, 5 e and 5 l) showed significant anti-proliferative activity. On the other hand, four of them (5 b, 5 c, 5 e, and 5 l) showed significant anti-leishmanial activity. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Design, Synthesis, and Docking Study of Quinine-9-Triazolyl Conjugates
(John Wiley and Sons Inc, 2023) Priyanka Bose; Mala Singh; Anoop S. Singh; Manoj K. Jaiswal; Vinod K. Tiwari
To develop a better chemotherapeutically potential candidate for lung cancer treatment and cure with repurposed motifs, quinine has been linked with biocompatible CuAAC-inspired regioselective 1,2,3-triazole linker and a series of ten novel 1,2,3-triazolyl-9-quinine conjugates have been developed by utilizing click conjugation of glycosyl ether alkynes with 9-epi-9-azido-9-deoxy-quinine under standard click conditions. In parallel, the docking study indicated that the resulting conjugates have an overall appreciable interaction with ALK-5 macromolecules. Moreover, the mannose-triazolyl conjugate exhibited the highest binding interactions of −7.6 kcal/mol with H-bond interaction with the targeted macromolecular system and indicate the hope for future trials for anti-lung cancer candidates. © 2023 Wiley-VHCA AG, Zurich, Switzerland.
Design, synthesis, and docking study of saccharin N-triazolyl glycoconjugates
(Elsevier Ltd, 2024) Priyanka Bose; Mala Singh; Abhishek Gupta; Sunil Kumar; Faisal Jaah Ansari; Vinay K. Pandey; Anoop S. Singh; Vinod K. Tiwari
To achieve better-repurposed motifs, saccharin has been merged with biocompatible sugar molecules via a 1,2,3-triazole linker, and ten novel 1,2,3-triazole-appended saccharin glycoconjugates were developed in good yield by utilizing modular CuAAC click as regioselective triazole forming tool. The docking study indicated that the resulting hybrid molecules have an overall substantial interaction with the CAXII macromolecule. Moreover, the galactose triazolyl saccharin analogue 3h has a binding energy of −8.5 kcal/mol with 5 H-bonds, and xylosyl 1,2,3-triazolyl saccharin analogue 3d has a binding energy of −8.2 kcal/mol with 6 H-bond interactions and have exhibited the highest binding interaction with the macromolecule system. © 2024 Elsevier Ltd
Docking study of Noscapine Glycoconjugate as Possible Therapeutic Applications to anti-proliferative activity
(Association of Carbohydrate Chemists and Technologists, 2019) Priyanka Bose; Vinod K. Tiwari
The present work concerns about the docking study of noscapine triazolyl glycoconjugate synthesized 'via Click Chemistry. The resulted triazole-linked noscapine glycoconjugates showed significant anti-proliferative activity using HeLa cell line and thus to estimate the interaction pattern, molecular docking study has been carried out on colorectal cancer target protein with the potent compound via AutoDock and Vina software. The docking study shows that the most active moiety has binding affinity of - 6.65 Kcal/mol with two H-bond using AuoDock software and -9.0 Kcal/mol of energy with two H-bond formation using Vina. The glycosylated noscapine has been further docked as fragments and the noscapine and glycosylated fragment found to have binding energies of -7.83 Kcal/mol with one H-bond and -6.43 Kcal/mol with one one H- bond, respectively using AutoDock software. Besides using Vina the noscapine and glycosylated part was found to have binding energies of-8.1 Kcal/mol with one H-bond and -7.1 Kcal/mol with one H-bond, respectively. Conclusively, the value indicates that the moiety is interactive to the macromolecular system. © 2019 Association of Carbohydrate Chemists and Technologists.
Growing impact of sialic acid-containing glycans in future drug discovery
(Elsevier Ltd, 2023) Priyanka Bose; Manoj K. Jaiswal; Sumit K. Singh; Rakesh K. Singh; Vinod K. Tiwari
In nature, almost all cells are covered with a complex array of glycan chain namely sialic acids or nuraminic acids, a negatively charged nine carbon sugars which is considered for their great therapeutic importance since long back. Owing to its presence at the terminal end of lipid bilayer (commonly known as terminal sugars), the well-defined sialosides or sialoconjugates have served pivotal role on the cell surfaces and thus, the sialic acid-containing glycans can modulate and mediate a number of imperative cellular interactions. Understanding of the sialo-protein interaction and their roles in vertebrates in regard of normal physiology, pathological variance, and evolution has indeed a noteworthy journey in medicine. In this tutorial review, we present a concise overview about the structure, linkages in chemical diversity, biological significance followed by chemical and enzymatic modification/synthesis of sialic acid containing glycans. A more focus is attempted about the recent advances, opportunity, and more over growing impact of sialosides and sialoconjugates in future drug discovery and development. © 2023 Elsevier Ltd
MoS2-Modified Curcumin Nanostructures: The Novel Theranostic Hybrid Having Potent Antibacterial and Antibiofilm Activities against Multidrug-Resistant Hypervirulent Klebsiella pneumoniae
(American Chemical Society, 2019) Ashish Kumar Singh; Himanshu Mishra; Zeba Firdaus; Shivangi Yadav; Prerana Aditi; Nabarun Nandy; Kavyanjali Sharma; Priyanka Bose; Akhilesh Kumar Pandey; Brijesh Singh Chauhan; Kaushik Neogi; Kunwar Vikram; Anchal Srivastava; Amrita Ghosh Kar; Pradyot Prakash
The recent emergence of hypervirulent clinical variants of Klebsiella pneumoniae (hvKP) causing community-acquired, invasive, metastatic, life-threatening infections of lungs, pleura, prostate, bones, joints, kidneys, spleen, muscles, soft-tissues, skin, eyes, central nervous system (CNS) including extrahepatic abscesses, and primary bacteremia even in healthy individuals has posed stern challenges before the existing treatment modalities. There is therefore an urgent need to look for specific and effective therapeutic alternatives against the said bacterial infection or recurrence. A new type of MoS2-modified curcumin nanostructure has been developed and evaluated as a potential alternative for the treatment of multidrug-resistant isolates. The curcumin quantum particles have been fabricated with MoS2 via a seed-mediated hydrothermal method, and the resulting MoS2-modified curcumin nanostructures (MQCs) have been subsequently tested for their antibacterial and antibiofilm properties against hypervirulent multidrug-resistant Klebsiella pneumoniae isolates. In the present study, we found MQCs inhibiting the bacterial growth at a minimal concentration of 0.0156 μg/mL, while complete inhibition of bacterial growth was evinced at concentration 0.125 μg/mL. Besides, we also investigated their biocompatibility both in vitro and in vivo. MQCs were found to be nontoxic to the SiHa cells at a dose as high as 1024 μg/mL on the basis of the tested adhesion, spreading of the cells, and also on the various serological, biochemical, and histological investigations of the vital organs and blood of the Charles Foster Rat. These results suggest that MQCs have potent antimicrobial activities against hvKP and other drug resistant isolates and therefore may be used as broad spectrum antibacterial and antibiofilm agents. Copyright © 2019 American Chemical Society.
Recent developments on ionic liquids-mediated synthetic protocols for biologically relevant five- and six-membered heterocyclic skeletons
(Elsevier, 2021) Priyanka Bose; Anand K. Agrahari; Sumit K. Singh; Anoop S. Singh; Mangal S. Yadav; Sanchayita Rajkhowa; Vinod K. Tiwari
More than two decades have passed with the glorified research works in the field of ionic liquids (ILs), and the explorartion is still counting by varying research groups across the world. ILs find versatile applications in organic synthesis as solvents, reaction media, and catalysts. The eye-catching advantages of ILs include easy handling, green approach, adjustable-desired physico-chemical properties, and versatile applications in preestablished reactions with much more cost-effective manner. Applications of ILs in developing suitable protocols for the syntheses of different heterocyclic skeletons have been explored with much positivity in the recent past. Among heterocycles, particularly five- and six-membered heterocycles are in the lime-light of medicinal chemistry for pharmacological activities and investigations. This chapter focuses on the properties and wide-spread applications of versatile ILs in the syntheses of heterocyclic scaffolds of promising pharmacological potential. © 2021 Elsevier Inc. All rights reserved.
Sialic acid-containing molecules in drug discovery and development
(Elsevier, 2020) Priyanka Bose; Anand K. Agrahari; Anoop S. Singh; Manoj K. Jaiswal; Vinod Kumar Tiwari
In nature, all cells are covered with a complex array of carbohydrates particularly sialic acids which is chemically a negatively charged nine-carbon α-keto aldonic acids. Because of their significant role on cell surfaces, the sialic acid-containing glycans certainly can mediate and modulate many important cellular interactions. Further, proteins having receptors to bind sialic acids are recognized to be involved in a wide variety of biological processes. Thus evaluation of carbohydrate-protein interaction and further their roles in vertebrates may results in enhanced understanding of normal physiology, pathological variance and human evolution. This chapter summarizes the structures and biological significance of sialic acid, their chemical diversity, biosynthesis followed by chemical modification and enzymatic synthesis of sialic acids, their impact in chemical biology, and also the neurobiology of sialic acid. Conclusively, this chapter highlights the recent advances and challenges at the interface of chemistry and biology of sialic acids in order to find out their scope in drug discovery and development. © 2020 Elsevier Inc. All rights reserved.
Synthesis of 1-(2-bromo-1-arylethyl)-1H-benzotriazoles via NBS promoted addition of 1H-benzotriazole to alkene: Relevance in benzotriazole ring cleavage
(Elsevier Ltd, 2020) Mala Singh; Priyanka Bose; Anoop S. Singh; Vinod K. Tiwari
A cost-effective and expeditious one-pot synthesis of 1-(2-bromo-1-arylethyl)-1H-benzotriazoles has been devised by reacting styrene and their derivatives with 1H-benzotriazole in presence of N-bromosuccinimide in anhydrous CH2Cl2 at room temperature. Further, the resulted compounds undergo E2-ellimination to afford the respective 1-(1-aryl-vinyl)-1H-benzotriazoles. At the end, 1-(1-phenylvinyl)-1H-benzotriazoles underwent benzotriazole ring cleavage (BtRC) under free radical condition to produce phenanthridine as the final product. © 2020 Elsevier Ltd
Synthetic Utility of N -Acylbenzotriazoles
(Georg Thieme Verlag, 2023) Mangal S. Yadav; Abhishek Gupta; Priyanka Bose; Anoop S. Singh; Prabhu P. Mohapatra; Vinod K. Tiwari
N-Acylbenzotriazoles are valuable synthons in organic synthesis. They are particularly used as acylating agents and an alternative to acyl chlorides. They have been widely explored for a diverse range of applications. This review summarizes methods for the preparation of Nacylbenzotriazole derivatives and their diverse applications, in particular demonstrating their ability to serve as alternative acylating agents in organic transformations such as N-, O-, C-, and S-acylating agents for the convenient synthesis of a wide range of biologically important organic compounds. We also emphasize the synthesis of diverse compounds using benzotriazole ring cleavage (BtRC) methodology, including its pharmacophore study and some notable utilities as valuable starting materials, ligands, and intermediates in the field of organic synthesis. 1 Introduction 2 Synthesis of N-Acylbenzotriazoles 3 Applications of N-Acylbenzotriazoles in Organic Synthesis 3.1 N-Acylation Using N-Acylbenzotriazoles 3.2 C-Acylation of Heterocycles Using N-Acylbenzotriazoles 3.3 Preparation of F-Keto Esters and F-Diketones by Acylative Deacetylation 3.4 N-Acylbenzotriazoles Used for the Preparation of Other Valuable Intermediates 3.5 Benzotriazole Ring Cleavage (BtRC) Reactions 4 N-Acylbenzotriazoles as Catalysts and Ligands 5 Pharmacological Applications of N-Acylbenzotriazoles 6 Conclusions and Future Outlook © 2023 The Author(s).