Synthesis of macrocycles containing 1,3,4-oxadiazole and pyridine moieties

Poojari, Subba; Naik, P. Parameshwara; Krishnamurthy, G.

doi:10.1016/j.tetlet.2013.08.099

Cited by 11 publications

(4 citation statements)

References 17 publications

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“…51 Hydrazinolysis of 12 led to the Fmocprotected hydrazide 13 (Scheme 2). 52 Next, N-benzylnortropinone 15 was obtained from acetonedicarboxylic acid 14, tetrahydro-2,5-dimethoxyfuran, and benzylamine following the literature procedures 53 and was then transformed to oxime 16 using hydroxylamine hydrochloride. The oxime 16 was reduced by sodium in n-pentanol to give amine 17.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Structure-Based Design and Development of Chemical Probes Targeting Putative MOR-CCR5 Heterodimers to Inhibit Opioid Exacerbated HIV-1 Infectivity

et al. 2021

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Crystal structures of ligand-bound G-protein-coupled receptors provide tangible templates for rationally designing molecular probes. Herein, we report the structure-based design, chemical synthesis, and biological investigations of bivalent ligands targeting putative mu opioid receptor C−C motif chemokine ligand 5 (MOR-CCR5) heterodimers. The bivalent ligand VZMC013 possessed nanomolar level binding affinities for both the MOR and CCR5, inhibited CCL5-stimulated calcium mobilization, and remarkably improved anti-HIV-1 BaL activity over previously reported bivalent ligands. VZMC013 inhibited viral infection in TZM-bl cells coexpressing CCR5 and MOR to a greater degree than cells expressing CCR5 alone. Furthermore, VZMC013 blocked human immunodeficiency virus (HIV)-1 entry in peripheral blood mononuclear cells (PBMC) cells in a concentrationdependent manner and inhibited opioid-accelerated HIV-1 entry more effectively in phytohemagglutinin-stimulated PBMC cells than in the absence of opioids. A three-dimensional molecular model of VZMC013 binding to the MOR-CCR5 heterodimer complex is constructed to elucidate its mechanism of action. VZMC013 is a potent chemical probe targeting MOR-CCR5 heterodimers and may serve as a pharmacological agent to inhibit opioid-exacerbated HIV-1 entry.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Structure-Based Design and Development of Chemical Probes Targeting Putative MOR-CCR5 Heterodimers to Inhibit Opioid Exacerbated HIV-1 Infectivity

et al. 2021

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“…In this respect, we have reported the synthesis of macrocycles containing 1,3,4-oxadiazole and pyridine moieties as well as a number of pyrimidin-4-ol derivatives [24,25]. In the present work, extensive efforts have been made to design and synthesize novel quinazolinone hybrids via introducing amide, urea, and sulfonamide systems with different possible functionalities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Studies of New Spiropyran Quinazolinone Derivatives with Amide, Urea, and Sulfonamide Moieties

Poojari

Krishnamurthy

et al. 2017

Journal of Heterocyclic Chem

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Three new series of quinazolinone derivatives containing amide, urea, and sulfonamide were synthesized through multistep synthesis. The required intermediates 4‐[(4′‐oxo‐2,3,3′,4′,5,6‐hexahydro‐1′H‐spiro[pyran‐4,2′‐quinazolin]‐1′‐yl)methyl]benzoic acid 4 and 1′‐(3‐aminobenzyl)‐2,3,5,6‐tetrahydro‐1′H‐spiro[pyran‐4,2′‐quinazolin]‐4′(3′H)‐one 8 were prepared by hydrolysis of ester and reduction of nitro intermediates. Three different series of compounds were synthesized from these two scaffolds. The key scaffolds 4 and 8 were successfully converted to target molecules via amides 5a–k, urea 9a–f, and substituted sulfonamides 10a–e. The chemical structures of newly synthesized compounds were characterized by spectral analysis. The structure of 5d was confirmed by X‐ray crystallography study. These newly synthesized compounds were screened for antibacterial studies against Staphylococcus epidermidis, Salmonella typhi, Proteus mirabilis, and Shigella sonnei and for the antifungal activity against Aspergillus niger and Candida albicans. Among all the compounds, 9b–d showed excellent activities against S. typhi. Compound 9a showed moderate activity against all fungi stains, and 5I showed moderate activity against P. mirabilis, while the other derivatives showed fairly good activities.

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“…The method of cyclization since then developed into a general paradigm in peptidomimetic drug design that has been widely used in the discovery of biologically active compounds for studying the cell. These macrocycles represent a new class of structures for further development and for future application in high-throughput screening against a variety of biological targets [11]. Recognition of the importance of complexes containing macrocyclic ligands has led to a considerable effort being invested in developing reliable inexpensive synthetic routes for these compounds.…”

Section: Introduction and Scopementioning

confidence: 99%

Macrocyclic Assembly: A Dive into the Pecking Order and Applied Aspects of Multitalented Metallomacrocycles

Chaudhary

Rawat

2014

International Journal of Inorganic Chemistry

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To aid in knowledge of macrocyclic complexes and biomedical scientists, we are presenting here a review article with compilation of work done so far along in relation to macrocyclic ligands and their metal complexes. The metal ion chemistry of macrocyclic ligands has now become a major subdivision of coordination chemistry. This overview focuses on developments in design, synthesis, and self-assembly of metal-based architectures and ligands related to macrocyclic chemistry.

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Synthesis of macrocycles containing 1,3,4-oxadiazole and pyridine moieties

Cited by 11 publications

References 17 publications

Structure-Based Design and Development of Chemical Probes Targeting Putative MOR-CCR5 Heterodimers to Inhibit Opioid Exacerbated HIV-1 Infectivity

Structure-Based Design and Development of Chemical Probes Targeting Putative MOR-CCR5 Heterodimers to Inhibit Opioid Exacerbated HIV-1 Infectivity

Synthesis and Antimicrobial Studies of New Spiropyran Quinazolinone Derivatives with Amide, Urea, and Sulfonamide Moieties

Macrocyclic Assembly: A Dive into the Pecking Order and Applied Aspects of Multitalented Metallomacrocycles

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