Your browser doesn't support javascript.
loading
Show: 20 | 50 | 100
Results 1 - 9 de 9
Filter
Add more filters










Database
Language
Publication year range
1.
Heliyon ; 10(5): e26887, 2024 Mar 15.
Article in English | MEDLINE | ID: mdl-38455541

ABSTRACT

Poly(I:C) and R848, synthetic ligands that activate Toll-like receptor 3 (TLR3) and TLR7/8 respectively, have been well-established for their ability to stimulate the immune system and induce antigen-specific immune responses. These ligands are capable of inducing the production of cytokines and chemokines, and hence support the activation and differentiation of B and T cells. We saw the long-lasting and perdurable immune responses by these adjuvants essentially required for an efficacious subunit vaccine. In this study, we investigated the potential of poly(I:C) and R848 to elicit B and T cell responses to the OVA antigen. We assessed the stimulatory effects of these ligands on the immune system, their impact on B and T cell activation, and their ability to enhanced generation of B and T cells. Collectively, our findings contribute to the understanding how poly(I:C) and R848 can be utilized as an adjuvant system to enhance immune responses to protein-based subunit vaccines. In the end, this work provides insights for the development of novel vaccination strategies and improving the vaccine efficacy. Present work shall help formulate newer strategies for subunit vaccines to address the infectious diseases.

2.
Chem ; 10(2): 686-697, 2024 Feb 08.
Article in English | MEDLINE | ID: mdl-38405332

ABSTRACT

Nitro(hetero)arene derivatives are essential commodity chemicals used in various products, such as drugs, polymers, and agrochemicals. In this study, we leverage the excited-state reactivities of copper catalysts and nitro(hetero)arenes, and the Umpolung reactivity of acyl radicals to convert readily available nitro(hetero)arenes directly to valuable 2-aminophenol derivatives, which are important scaffolds in many top-selling pharmaceuticals. This reaction is applicable to a variety of nitro(hetero)arenes, acyl chlorides, and late-stage modifications of complex molecules, making it a useful tool for the discovery of new functional molecules. Mechanistic studies, including radical trapping experiments, Stern Volmer quenching studies, light ON/OFF experiments, and 18O-labeling studies, suggest a reaction mechanism involving photoexcitation of a copper complex, diradical couplings, and an in-cage contact ion pair (CIP) migration. Our findings offer a streamlined protocol for synthesizing essential pharmacophores from nitro(hetero)arenes while simultaneously advancing knowledge in excited-state and radical chemistry and stimulating new reaction design and development.

3.
J Am Chem Soc ; 144(45): 20884-20894, 2022 11 16.
Article in English | MEDLINE | ID: mdl-36326178

ABSTRACT

Synthesis of α,ß-unsaturated-γ-lactams continue to attract attention due to the importance of this structural motif in organic chemistry. Herein, we report the development of a visible-light-induced excited-state copper-catalyzed [4 + 1] annulation reaction for the preparation of a wide range of γ-H, -OH, and -OR-substituted α,ß-unsaturated-γ-lactams using acrylamides as the 4-atom unit and aroyl chlorides as the 1-atom unit. This modular synthetic protocol features mild reaction conditions, broad substrate scope, and high functional group tolerance. The reaction is amenable to late-stage diversification of complex molecular architectures, including derivatives of marketed drugs. The products of the reaction can serve as versatile building blocks for further derivatization. Preliminary mechanistic studies suggest an inner-sphere catalytic cycle involving photoexcitation of the Cu(BINAP) catalyst, single-electron transfer, and capture of radical intermediates by copper species, followed by reductive elimination or protonation to give the desired γ-functionalized α,ß-unsaturated-γ-lactams.


Subject(s)
Copper , beta-Lactams , Copper/chemistry , Stereoisomerism , Catalysis
4.
Angew Chem Int Ed Engl ; 61(4): e202113841, 2022 01 21.
Article in English | MEDLINE | ID: mdl-34783154

ABSTRACT

Heterocycles are one of the largest groups of organic moieties with significant medicinal, chemical, and industrial applications. Herein, we report the discovery and development of visible-light-induced, synergistic excited-state copper catalysis using a combination of Cu(IPr)I as a catalyst and rac-BINAP as a ligand, which produces more than 10 distinct classes of heterocycles. The reaction tolerates a broad array of functional groups and complex molecular scaffolds, including derivatives of peptides, natural products, and marketed drugs. Preliminary mechanistic investigation suggests in situ generations of [Cu(BINAP)2 ]+ and [Cu(IPr)2 ]+ catalysts that work cooperatively under visible-light irradiation to facilitate catalytic carbo-aroylation of unactivated alkenes, affording a wide range of useful heterocycles.


Subject(s)
Copper/chemistry , Heterocyclic Compounds/chemical synthesis , Organometallic Compounds/chemistry , Catalysis , Heterocyclic Compounds/chemistry , Molecular Structure
5.
Chem Asian J ; 15(24): 4302-4306, 2020 Dec 14.
Article in English | MEDLINE | ID: mdl-33052020

ABSTRACT

This work reports a sustainable protocol for α-arylation of tetrahydroisoquinolines (THIQs) with aryl diazonium salts using a combination of a cheap and stable oxidant, N-hydroxyphthalimide (NHPI), and an inexpensive dye photosensitizer, Rose Bengal (RB), for the first time. The reaction was performed at ambient temperature using green LED light irradiation under an oxygen atmosphere. The developed α-arylation protocol shows a diverse substrate scope for various THIQs and aryl diazonium salts. The work also explores nitroalkylation and cyanation under the developed reaction conditions. A possible SET mechanism is involved which was confirmed by ESI-MS analysis of the reaction mixture.

6.
Org Biomol Chem ; 17(33): 7596-7631, 2019 09 07.
Article in English | MEDLINE | ID: mdl-31241119

ABSTRACT

Multi-metallic cooperative catalysis has gained a lot of interest in organic synthesis over the past few years exploring various organic transformations. Of all the myriad chemical transformations, multi-metallic cooperative catalysis offers exceptional chemo-, stereo- and regio-selectivities. In recent years, hetero-multi-metallic catalysis has not only been used to synthesise only simpler organic molecules but rather more complex molecules like heteroarenes which include a variety of commercially important molecules. The current review, in this context, emphasises the synthesis of 5- and 6-membered as well as condensed heteroarenes, covering the literature over the last decade. The discussion focusses on the combinations in cooperative catalytic systems in strategies used to achieve selectivity and also highlights the mode of action for the cooperative catalysis leading to the synthesis of a few commercially and biologically relevant heteroarenes. Finally, the review concludes with a brief outlook on the future scope and opportunities in the field of cooperative catalyses and their prospects for providing state-of-the-art solutions for synthetically challenging organic transformations.

7.
Chem Asian J ; 14(15): 2639-2647, 2019 Aug 01.
Article in English | MEDLINE | ID: mdl-31107588

ABSTRACT

Palladium colloids obtained from the degradation of Hermann-Beller palladacycle proved to be an efficient catalytic system in combination with silver oxide as a selective oxidant for the oxidative esterification of differently substituted benzyl alcohols in MeOH as solvent. Excellent reactivity exhibited by the catalytic system also allowed the alcoholic coupling partner to be changed from MeOH to a wide range of alcohols having diverse functionalities. The mildness of the developed protocol also made it possible to employ propargyl alcohol as the coupling partner without any observation of any interference of the terminal alkyne. Selective oxidative coupling of a primary alcoholic functional group over secondary in the case of glycols and glycerols was also made possible using the developed catalyst system. To test the relevancy of Pd/Ag combined catalysis mixed Pd/Ag colloids were synthesized, characterized by TEM, XRD and XPS and applied to oxidative-esterification successfully.

8.
J Org Chem ; 83(21): 13088-13102, 2018 11 02.
Article in English | MEDLINE | ID: mdl-30296085

ABSTRACT

A mild, general, and highly efficient catalytic etherification protocol for chloroheteroarenes was developed using the Pd/PTABS catalytic system. The protocol is selective for the etherification of chloroheteroarenes using a large variety of electron-rich and electron-deficient phenol bearing synthons which include inter alia biologically and commercially important estrone, estradiol, tyrosine, and several other molecules. The mildness of the new protocol is expected to be beneficial for the synthesis of complex drugs and drug intermediates offering late-stage modification of bioactive compounds.

9.
Angew Chem Int Ed Engl ; 57(45): 14700-14717, 2018 11 05.
Article in English | MEDLINE | ID: mdl-29969532

ABSTRACT

The late-stage modification of structurally complex peptides bears great potential for drug discovery, crop protection, and the pharmaceutical industry, among others. Whereas traditional approaches largely rely on prefunctionalizations, C-H activation catalysis has in recent years emerged as an increasingly powerful tool for post-translational peptide modifications in a step-economic manner. Herein, we summarize recent progress in organometallic C-H activation on peptides until June 2018, including position- and chemoselective palladium-, ruthenium-, and manganese-catalyzed processes.


Subject(s)
Amino Acids/chemistry , Peptides/chemistry , Amino Acids/chemical synthesis , Carbon/chemistry , Catalysis , Gold/chemistry , Hydrogen/chemistry , Manganese/chemistry , Palladium/chemistry , Peptides/chemical synthesis , Ruthenium/chemistry
SELECTION OF CITATIONS
SEARCH DETAIL
...