Synthesis, Cytotoxic Activity and In Silico Study of Novel Dihydropyridine Carboxylic Acids Derivatives DOI Open Access
Ricardo Ballinas-Indilí, María Inés Nicolás‐Vázquez, Joel Martínez

и другие.

International Journal of Molecular Sciences, Год журнала: 2023, Номер 24(20), С. 15414 - 15414

Опубликована: Окт. 21, 2023

To aid the possible prevention of multidrug resistance in tumors and cause lower toxicity, a set sixteen novel dihydropyridine carboxylic acids derivatives 3a-p were produced; thus, activation various ynones with triflic anhydride was performed, involving nucleophilic addition several bis(trimethylsilyl) ketene acetals, achieving good yields requiring easy workup. The target molecules unequivocally characterized by common spectroscopic methods. In addition, two tested compounds (3a, 3b) selected to perform silico studies due highest cytotoxic activity towards HCT-15 cell line (7.94 ± 1.6 μM 9.24 0.9 μM, respectively). Employing theoretical calculations density functional theory (DFT) using B3LYP/6-311++G(d,p) showed that molecular parameters correlate adequately experimental results. contrast, predictions employing Osiris Property Explorer 3a 3b present physicochemical characteristics would likely make it an orally active drug. Moreover, performance Docking proteins related apoptosis pathway allowed proposal which could interact PARP-1 protein. Pondering obtained results (synthesis, silico, activity) compounds, they can be judged as suitable antineoplastic agent candidates.

Язык: Английский

Phosphine-Catalyzed Stereospecific and Enantioselective Desymmetrizative [3+2] Cycloaddition of MBH Carbonates and N-(2-tert-Butylphenyl)maleimides DOI

Jie Hou,

Hao Wei, Ying Chen

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 9068 - 9077

Опубликована: Июнь 1, 2024

Herein, we report an l-valine-derived amide phosphine-catalyzed [3+2] cyclization of MBH carbonates and N-(2-tert-butylphenyl)maleimides via asymmetric desymmetrization. Bicyclic N-aryl succinimide derivatives bearing three continuous chiral centers with a remote C–N atropisomeric chirality were constructed stereospecifically enantioselectively. A wide variety could be employed in this process to deliver highly optically pure moderate excellent yields.

Язык: Английский

Процитировано

6
Recent Advances in Catalytic Desymmetrization for the Synthesis of Axially Chiral Biaryls DOI Creative Commons

Junsoo Moon,

Sangji Kim,

Su Jin Lee

и другие.

ChemCatChem, Год журнала: 2024, Номер unknown

Опубликована: Июнь 7, 2024

Abstract Atropisomeric compounds have been discovered in pharmaceuticals and materials science, their enantioselective syntheses gained tremendous attention. Among strategies for catalytic atroposelective synthesis, desymmetrization provides robust straightforward approaches to axially chiral biaryls. Due the relative ease of substrate design compared other strategies, has emerged as a pivotal stage converting fascinating chemistry into its counterpart, despite challenges such formation achiral products by subsequent reactions long distance between reaction site stereogenic axis. This review offers comprehensive overview recent advancements using organo‐ metal catalysts, addressing solutions, aims provide insights future developments this field.

Язык: Английский

Процитировано

4
Alkoxy-Directed Dienamine Catalysis in [4 + 2]-Cycloaddition: Enantioselective Synthesis of Benzo-[3]-ladderanol DOI
Sayan Ray, Deepak Behera, Mahesh Singh Harariya

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Янв. 11, 2025

Despite tremendous progress of dienamine catalysis along with its application in enantioselective synthesis over nearly two decades, certain limitations, especially respect to the regioselectivity generation step, continue persist. To overcome these shortcomings classical catalysis, we now introduce concept alkoxy-directed and apply it de novo arene construction by desymmetrizing meso-enediones through [4 + 2]-cycloaddition. Catalyzed a diphenylprolinol silyl ether, this reaction utilizes γ-alkoxy α,β-unsaturated aldehydes as substrate proceeds highly regioselective fashion intermediacy δ-alkoxy dienamine. Besides carrying out mechanistic elucidation density functional theory (DFT) calculation, utility newly developed strategy is demonstrated for concise benzo-analogue natural ladderane phospholipid component (+)-[3]-ladderanol. Designed analogue [3]-ladderanol, unnatural benzo-[3]-ladderanol was found impart lower proton permeability higher stability membrane compared counterpart.

Язык: Английский

Процитировано

0
Organic Catalysts and Ligands Derived from Amino Acids and Peptides DOI

Lipat Kaur,

Karuna Thakare,

Aman Singh Barahdia

и другие.

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134671 - 134671

Опубликована: Апрель 1, 2025

Язык: Английский

Процитировано

0
N‐Heterocyclic Carbene Control over Multiple Stereogenicities: Atroposelective Synthesis of Axially Chiral Phthalimides DOI Creative Commons
Manuel Barday, Jéssica Ferreira Rodrigues,

Pierre Bouillac

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 365(2), С. 148 - 155

Опубликована: Дек. 22, 2022

Abstract The design of a NHC‐catalyzed methodology for the straightforward access to hitherto unknown axially chiral N ‐aryl phthalimides has provided breakthrough in field multichirality control. Anticipating formal (4+2) oxidative annulation, use NHC‐derived dienolate as ambident partner toward maleimides unexpectedly yields original bis ‐succinimide‐type compounds featuring multichiral architecture with up four stereogenic centers and two remote axes. overall pseudo‐three components reaction between an enal equivalents maleimide proceeds excellent enantioselectivity complete diastereoselectivity. This study illustrates high synthetic potential NHC‐activated dienolates rapid highly diastereo‐ enantioselective preparation underexplored atropisomers pentatomic series, multiple elements including challenging C sp 2 −N practicality this is highlighted by broad substrate scope scaled‐up synthesis. Moreover, easy base‐induced transformation ‐succinimide precursors allows prepare initially planned phthalimide retention enantiopurity. magnified image

Язык: Английский

Процитировано

17
N-heterocyclic carbene-catalyzed atroposelective synthesis of N-Aryl phthalimides and maleimides via activation of carboxylic acids DOI Creative Commons

Soumen Barik,

Sowmya Shree Ranganathappa,

Akkattu T. Biju

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Июль 9, 2024

Abstract Traditionally, N -aryl phthalimides are synthesized by the condensation of phthalic anhydride and aniline derivatives, usually proceeding under harsh conditions. The alternative mild organocatalytic strategies for their synthesis underdeveloped. Herein, we demonstrate atroposelective via traditional N-C C=O disconnection in-situ acid activation phthalamic subsequent N-heterocyclic carbene (NHC)-catalyzed amidation allowed well-decorated in excellent yields enantioselectivities. Mechanistic studies reveal addition NHC to situ generated isoimides, thus introducing a unique mode generating acylazoliums. Interestingly, both enantiomers product can be accessed from same using pre-catalyst. Moreover, this strategy has been extended maleimides.

Язык: Английский

Процитировано

3
Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds DOI Open Access
Wanting Chen, Xiongwei Zhong, Jiale Xing

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(2), С. 349 - 349

Опубликована: Янв. 1, 2024

Enantioenriched C-N axial chiral compounds are ubiquitous in many important field, such as natural products, drugs and ligands.Therefore, efficient construction of axis chirality through asymmetric catalytic synthesis has attracted more attention research interest.In this review, the recent progress been discussed, mainly from three aspects: desymmetrization prochiral molecules or kinetic resolution racemates, atroposelective functionalization axis, coupling reaction.The topic focuses on evolution system key factors control.The existing problems future development direction field also discussed.This paper is a timely systematic review will stimulate extensive interest.

Язык: Английский

Процитировано

2
Enantioselective N-Heterocyclic Carbene-Catalyzed Hauser-Kraus Annulations for the Construction of C–N Axially Chiral Phthalimde Derivatives DOI

Panlong Ren,

Qing Zhao, Ke Xu

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(17)

Опубликована: Авг. 19, 2024

The Hauser-Kraus annulation is one of the most powerful methods to construct polycyclic hydroquinone from 3-cyano phthalides and Michael acceptors. Although these have been developed for more than 46 years, asymmetric catalytic version has remained underdeveloped. Inspired by N-heterocyclic carbene (NHC)-catalyzed Stetter reaction via Breslow intermediate, herein, we an NHC-catalyzed enantioselective a phthalide-type intermediate. With help NHC catalyst ynamide coupling reagent, proceeds under mild conditions at room temperature, giving corresponding chiral in moderate good yields, with high enantioselectivities. key intermediate was successfully isolated confirmed. kinetic thermal dynamic features cascade were also explored density functional theory (DFT) calculation. Learning wide application annulation, this method hopeful bring shortcuts facile synthesis sophisticated compounds. Besides, discovery expand synthetic potentials organocatalysis.

Язык: Английский

Процитировано

2
Catalytic Enantioselective Functionalization of Maleimides: An Update DOI Creative Commons
Muriel Amatore, Damien Bonne,

Thierry Constantieux

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(24), С. 3605 - 3622

Опубликована: Ноя. 13, 2024

Comprehensive Summary Maleimide derivatives are well‐established reactive intermediates also found in natural products, synthetic pharmaceuticals and functional polymers. Their specific reactivity widespread applications the field of bioconjugation allowed for development highly selective functionalizations based on simple additions cycloadditions with possible control central C–N axial chirality. These multisite‐reactive scaffolds have aroused a long‐standing interest throughout scientific community more particularly as powerful electrophilic partners recently nucleophilic some transformations. The persistent these easily accessible platforms over last decade has enabled new enantioselective transformations major advancements this presented review. Key Scientists

Язык: Английский

Процитировано

2
Atropselective Organocatalytic Synthesis of Chiral Compounds Containing Nitrogen along the Axis of Chirality DOI Open Access
Ana Maria Faísca Phillips, Armando J. L. Pombeiro

Symmetry, Год журнала: 2023, Номер 15(6), С. 1261 - 1261

Опубликована: Июнь 15, 2023

Atropisomers, i.e., stereoisomers that are distinct because their free rotation about a single bond is hindered by steric interactions between nearby bulky groups or electrostatics, may interact with surroundings in different ways, and also exhibit properties. They be found as natural products, pharmaceutical agricultural active ingredients, chiral ligands organocatalysts, functional materials. Our ability to synthesize them stereoselectively sustainable way, using achiral materials simply the aid of an organocatalyst mild conditions, has become hot topic research. This review provides overview recent achievements synthesis atropisomers containing C-N N-N axes chirality.

Язык: Английский

Процитировано

5