Enantioselective Synthesis and Biological Evaluation of Pyrrolidines Bearing Quaternary Stereogenic Centers DOI

Han‐Yue Qiu,

Zhuanzhuan Du,

Yankun Zhao

и другие.

Journal of Medicinal Chemistry, Год журнала: 2023, Номер 66(14), С. 9866 - 9880

Опубликована: Июль 10, 2023

Molecular complexity plays an increasingly important role in the modern pharmaceutical industry. Setting up multiple stereogenic centers privileged substructures may give rise to improved or even unprecedented bioactivities; however, this area remains largely unexplored due tremendous synthetic challenges. Herein, we report a series of multisubstituted pyrrolidines with four continuous centers, including two aza-QSCs (quaternary centers). Systematic evaluations, phenotypic screening, molecular docking, dynamics, bioinformatics, and bioactivity analysis, have been performed screen entities pharmacological properties interest. Among them, compound 4m QSCs was identified be potent antiproliferation agent through disturbing mitosis exit, presence found crucial for anticancer efficacy. This work illustrates that introduction scaffolds not only helps expand unpatented chemical space but also provides new opportunities discovery novel therapeutic agents.

Язык: Английский

Design, synthesis, biological evaluation and docking analysis of pyrrolidine-benzenesulfonamides as carbonic anhydrase or acetylcholinesterase inhibitors and antimicrobial agents DOI
Samet Poyraz, H. Ali Döndaş, Cem Yamalı

и другие.

Journal of Biomolecular Structure and Dynamics, Год журнала: 2023, Номер 42(7), С. 3441 - 3458

Опубликована: Май 26, 2023

AbstractAbstractThe synthesis and biological assessment of novel multi-functionalized pyrrolidine-containing benzenesulfonamides were reported along with their antimicrobial, antifungal, CAs inhibition, AChE inhibition as well DNA-binding effects. The chemical structure the compounds was elucidated by using FTIR, NMR, HRMS. Compound 3b, which had Ki values 17.61 ± 3.58 nM (hCA I) 5.14 0.61 II), found be most potent inhibitor. Compounds 6a 6b showed remarkable effects 22.34 4.53 27.21 3.96 in comparison to tacrine. 6a–6c moderate antituberculosis effect on M. tuberculosis a MIC value 15.62 μg/ml. weaker antifungal antibacterial activity range 500–62.5 μg/ml against standard bacterial fungal strains. Besides these above, molecular docking studies performed examine evaluate interaction (3b, 6b) current enzymes (CAs AChE). Novel gained interest terms enzyme inhibitory potencies. Therefore, inhibitors may considered lead modified for further research.Communicated Ramaswamy H. SarmaKeywords: Acetylcholinesteraseantimicrobialbenzenesulfonamidecarbonic anhydrasemolecular dockingpyrazolepyrrolidines Disclosure statementNo potential conflict author(s).Additional informationFundingWe gratefully acknowledge financial support from Çukurova University (Projects No: TSA-2021-13814 TSA-2021-13443).Correction StatementThis article has been corrected minor changes. These changes do not impact academic content article.

Язык: Английский

Процитировано

11
Nickel Pincer Complexes Catalyzed Sustainable Synthesis of 3,4-Dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides via Acceptorless Dehydrogenative Coupling of Primary Alcohols DOI
Pennamuthiriyan Anandaraj, Rengan Ramesh

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2494 - 2504

Опубликована: Фев. 7, 2024

We report the atom-economic and sustainable synthesis of biologically important 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxide (DHBD) derivatives from readily available aromatic primary alcohols 2-aminobenzenesulfonamide catalyzed by nickel(II)-N∧N∧S pincer-type complexes. The synthesized nickel complexes have been well-studied elemental spectroscopic (FT-IR, NMR, HRMS) analyses. solid-state molecular structure complex 2 has authenticated a single-crystal X-ray diffraction study. Furthermore, series (24 examples) utilizing 3 mol % Ni(II) catalyst through acceptorless dehydrogenative coupling benzyl with benzenesulfonamide. Gratifyingly, catalytic protocol is highly selective yield up to 93% produces eco-friendly water/hydrogen gas as byproducts. control experiments plausible mechanistic investigations indicate that in situ generated aldehyde benzenesulfonamide leads desired product. In addition, large-scale one thiadiazine unveils synthetic usefulness current methodology.

Язык: Английский

Процитировано

3
Synthesis and Evaluation of Biologically Active Compounds from Heterocycles Class DOI Creative Commons
Ștefania‐Felicia Bărbuceanu, Octavian Tudorel Olaru

Molecules, Год журнала: 2025, Номер 30(2), С. 394 - 394

Опубликована: Янв. 18, 2025

Heterocyclic compounds represent one of the most important classes natural and synthetic compounds, playing essential roles in various fields, including medicinal chemistry [...]

Язык: Английский

Процитировано

0
Efficient, One‐Pot, Green Syntheses of Analogues of 3,4‐Dihydro‐2H Pyrroles as Potential New Antifungal and Antibacterial Agents. DOI

Pooja Sivaganesan,

Lakshmi Ganesan,

Subiksha VL

и другие.

ChemistrySelect, Год журнала: 2025, Номер 10(3)

Опубликована: Янв. 1, 2025

Abstract An efficient method offering high convenience and sustainability, showcasing the potential for green synthesis strategies has been developed. The protocol presents a straightforward, environmentally friendly approach construction of substituted 3,4‐dihydro‐2 H pyrroles in an aqueous ethanol that describes one‐pot multistep reaction sequence, initiated with Claisen–Schmidt Condensation, followed by Michael addition nitro methane to chalcone, next line being reduction intramolecular cyclization steps yield desired product moderate higher yields. Underscoring effectiveness biological activities also evaluated compounds. Preliminary studies indicating promising antibacterial antifungal properties, make these compounds significant further pharmaceutical development. use as solvent pyrroline process underscores importance solvents, significantly reducing environmental impact aligning principles sustainable chemistry. synthetic strategy combined notable demonstrates dual benefit this research, contributing both field chemistry therapeutic drug discovery.

Язык: Английский

Процитировано

0
The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

и другие.

Advances in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0
Skeletal Reorganization of Saturated Six-Membered Aza-cycles to Sulfonated Pyrrolidines under Redox-Neutral Conditions DOI
Shi‐Hui Shi,

Qing-Gen Wang,

Yihan Yang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 21, 2025

Ring contraction in skeletal reorganization strategies is one of the most intriguing yet surprisingly challenging transformations. Herein, we report for first time a ring tandem sulfonation between saturated six-membered N-heterocyclic nitroxides and sulfonyl hydrazides to access sulfonated pyrrolidine derivatives by an electrochemical redox cascade under redox-neutral metal-free conditions, which unavailable via conventional synthetic approaches. This benign approach has been further demonstrated gram-scale preparation pharmaceutical molecule synthesis mild conditions.

Язык: Английский

Процитировано

0
Theoretical Study of Azetidine Derivative by Quantum Chemical Methods, Molecular Docking and Molecular Dynamic Simulations DOI
Prashasti Sinha, Anil Kumar Yadav

ChemistrySelect, Год журнала: 2023, Номер 8(16)

Опубликована: Апрель 24, 2023

Abstract Azetidine substituent group has a wide range of application in organic chemistry and medical field. In this study, novel azetidine derivative its reaction mechanism been reported. Using quantum chemical method spectroscopic analysis other parameters such as electronic thermodynamic properties were studied to understand the physical well behavior reported compound. Additionally, study antiviral activity, molecular docking studies carried out against Hepatitis virus C (HCV) NS5B genotype Norovirus target protein. order validate results dynamic (MD) simulation Molecular Mechanics‐Poisson‐Boltzmann Surface Area (MM‐PBSA) calculated at 90 ns. The RMSD was obtained within 0.75 Å 1.5 binding energies (ΔG bind ) for two complexes found be −18.34 kJ/mol −16.10 each respective targets.It that compound can act potential inhibitor HCVand Norovirus.

Язык: Английский

Процитировано

8
Design, synthesis, biological evaluation and molecular docking study of new pyrazolo[1,5-a]pyrimidines as PIM kinase inhibitors and apoptosis inducers DOI
Fatma G. Abdulrahman, Rehab Sabour, Shimaa M. Abd El‐Gilil

и другие.

Journal of Molecular Structure, Год журнала: 2023, Номер 1295, С. 136811 - 136811

Опубликована: Окт. 9, 2023

Язык: Английский

Процитировано

8
Development of diphenylmethylpiperazine hybrids of chloroquinoline and triazolopyrimidine using Petasis reaction as new cysteine proteases inhibitors for malaria therapeutics DOI
Hari Madhav, Tarosh S. Patel, Zeba Rizvi

и другие.

European Journal of Medicinal Chemistry, Год журнала: 2023, Номер 258, С. 115564 - 115564

Опубликована: Июнь 12, 2023

Язык: Английский

Процитировано

7
Visible‐Light‐Catalyzed Formal [3+2] Annulation‐Aromatization of Amidines with Isoquinolinium N‐Ylides: Access to Imidazo[2,1‐a]isoquinolines DOI Open Access
Lvyin Zheng,

Xiaoying Zou,

Xiaojuan Yang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(21), С. 3629 - 3636

Опубликована: Сен. 21, 2023

Abstract A visible‐light‐catalyzed formal [3+2] annulation‐aromatization reaction for the synthesis of various substituted imidazo[2,1‐ a ]isoquinolines from amidines with stabilized isoquinolinium N ‐ylides in presence bases is developed. The procedure reported here involves direct C−H activation and formation C−C/C−N bonds one‐pot. mechanism probed by radical‐trapping experiment, fluorescence quenching, light on/off experiments. late‐stage modification experiments provide potential applications field organic medicinal chemistry chemists.

Язык: Английский

Процитировано

7