Article
Chemistry, Organic
Zhen Fu, Chengming Wang, Cong-Ying Zhou
Summary: In this study, an alkylcarbene-mediated intramolecular alkene cyclopropanation was developed for the synthesis of azabicyclo[3.1.0]hexanes. With the catalyst Rh2(esp)2, alkyl diazomethanes generated in situ from 2,4,6-triisopropylbenzenesulfonylhydrazones underwent intramolecular cyclopropanation with alkenes, leading to the formation of azabicyclo[3.1.0]hexanes in good to high yields under mild reaction conditions. This method has important synthetic applications.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Tao Liu, Tuanli Yao, Ruihua Guo, Xiangyang Qin
Summary: A palladium-catalyzed cascade reaction was developed for the synthesis of tetrahydro-beta-carbolines and other polycyclic indoles from 2-(hydroxyenyl)sulfonanilides by combining Pd(ii)-catalyzed cyclization of alkynes and intramolecular redox-relay Heck arylation of alkenols. This method allows the construction of two rings and installation of a remote carbonyl group in a single operation, offering broad synthetic utility for further elaborations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Sen Ke, Huanqing Liao, Hao Qin, Yan Wang, Yi Li
Summary: In this study, a facile access to benzocyclic boronates was reported through photopromoted intramolecular arylborylation of allyl aryldiazonium salts. This simple protocol exhibited a broad scope and allowed the formation of variously functionalized borates with dihydrobenzofuran, dihydroindene, benzothiophene, and indoline skeletons under mild and sustainable conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yulong Wang, Shenyu Shen, Chonglong He, Youkang Zhou, Keyuan Zhang, Bin Rao, Tian Han, Yaqiong Su, Xin-Hua Duan, Le Liu
Summary: Here, we report a practical copper-mediated direct intramolecular cyclopropanation of distal olefinic acetate to synthesize cyclopropane-fused gamma-lactones and lactams. This cascade reaction proceeds through a hydrogen atom transfer-induced radical cyclization and copper-mediated cyclopropanation sequence. The protocol features high atom- and step-economy, excellent diastereoselectivity, broad tolerance of functional groups, and operational simplicity.
Article
Chemistry, Applied
Bita Manavi, Hossein Zahedian Tejeneki, Frank Rominger, Mahsa Armaghan, Walter Frank, Hamid Reza Bijanzadeh, Saeed Balalaie
Summary: This report discusses two distinctive intramolecular cyclizations of o-propargyloxy diketopiperazines achieved via a copper(I)-catalyzed reaction, offering an opportunity for the synthesis of challenging Diazabicyclics and Spiro-Diketopiperazinochromanes with high yields and exclusive diastereoselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Ramesh Samikannu, Sankaranarayanan Sethuraman, Nagaraja Akula, Vignesh Radhakrishnan, Srinivasarao Kamisetti, Shabana Banu, Muthalagu Vetrichelvan, Anuradha Gupta, Jianqing Li, Richard Rampulla, Arvind Mathur
Summary: A facile intramolecular cyclization of 3-hydroxy-3-(2-((3-methoxybenzyl)oxy)phenyl)indolin-2-one derivatives for the synthesis of spirooxindoles fused with dibenzoxepine moieties is described. The success of this reaction is highly dependent on solvent choice and the electronic nature of the aromatic ring. Various dibenzoxepine-fused spirooxindoles were successfully synthesized in up to 98% yield, providing libraries of structurally diverse and medicinally important small molecules for the search for new bioactive compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Qi-Liang Yang, Rui-Cong Ma, Zhi-Hao Li, Wan-Wan Li, Gui-Rong Qu, Hai-Ming Guo
Summary: Here, we developed an environmentally friendly electrooxidative method for the synthesis of indolizines substituted with various formyl and acyl groups. This method allows for the sequential formation of C-N and C-O bonds, and has good yields. It utilizes sub-equivalent amounts of iodide salts as the redox mediator, and shows broad substrate scope, excellent functional group tolerance, and eliminates the need for oxidizing reagents.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Multidisciplinary Sciences
Min Jin, Congyun Tang, Yingying Li, Shuai Yang, Ying-Tao Yang, Lin Peng, Xiao-Nian Li, Wenjing Zhang, Zhili Zuo, Fabien Gagosz, Liang-Liang Wang
Summary: In this study, the authors present a catalytic asymmetric inverse-electron-demand-hetero-Diels-Alder reaction between neutral alkenes and alpha, beta-unsaturated ketones or aldehydes using a chiral phosphoric acid catalyst. This complex transformation allows for the formation of chiral fused heterocycles containing a central tetrahydropyran ring with high regio-, diastereo- and enantioselectivity. The stereocontrol achieved in this process is attributed to a key remote double hydrogen atom bonding interaction between the linear substrate and the catalyst.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Min Li, Yin Wei, Min Shi
Summary: This paper describes the development of a thermally-induced intramolecular [2 + 2] cycloaddition reaction for the rapid construction of polycyclic heterocycles. The reaction proceeds under relatively mild conditions, offering excellent total yields and good functional group compatibility. The mechanism of the reaction has been clarified through control experiments and DFT calculations, revealing a stepwise process involving a key intermediate with a seven-membered ring rather than a concerted pathway.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Lin Lu, Zuoliang Zheng, Yongjie Yang, Bo Liu, Biaolin Yin
Summary: Polycyclic indolines and indolenines were synthesized via base-catalyzed intramolecular dearomatizing 3-alkenylation reactions of alkynyl indoles at room temperature. The base enhanced the nucleophilicity of the carbon at the 3-position of the indole moiety, facilitating an exclusive 5-exo-dig cyclization reaction with the alkyne to form spiroindolenines. The imine functionality of the spiroindolenines could undergo in situ nucleophilic addition to form spiroindolines when R was a carbamoyl group or reduction to form spiroindolines when R was H.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Quan-Bing Wang, Shi Tang, Ying-Jie Wang, Yue Yuan, Tieqiao Chen, Ai-Qun Jia
Summary: The PIDA mediated intramolecular oxidative C-N coupling and subsequent detosylative aromatization allowed for the synthesis of valuable indolo[2,3-b]quinoline derivatives, providing an efficient method for their preparation.
Article
Chemistry, Organic
Jian Xiao, Ya-Wen Wang, Zhong-Ping Qiu, Yu Peng
Summary: The facile access to the tetracyclic skeleton of podophyllotoxin, a medicinally important lignan natural product, was efficiently achieved via a unique intramolecular alkylarylation of the tethered alkene in a dihalide under mild conditions using reductive nickel catalysis.
Article
Chemistry, Organic
Mina Hariri, Fatemeh Darvish, Karen-Pacelye Mengue Me Ndong, Nora Sechet, Geraud Chacktas, Hooriye Boosaliki, Minh Loan Tran Do, Gabin Mwande-Maguene, Jacques Lebibi, Alexander R. Burilov, Tahar Ayad, David Virieux, Jean-Luc Pirat
Summary: This study presents a straightforward synthesis of phosphorus-based heterocycles, 2-phenyl 1H-isophosphinoline 2-oxides 1, using a gold(I) catalyzed reaction with electron-poor alkynes. The reaction, conducted under microwave activation with PPh3AuCl precatalyst and triflic acid, resulted in moderate to quantitative yields of isophosphinoline 2-oxides 1 through a regioselective 6-endo-dig hydroarylation cyclization, demonstrating a promising approach for the synthesis of phosphorus heterocycles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Subhasish Ray, Vipin Kumar, Saurabh Singh, Krishanu Bandyopadhyay, Satyen Saha, Maya Shankar Singh
Summary: A cascade one-pot strategy has been developed for the construction of 31 examples of furo-fused quinoxalines in high yields. The reaction utilizes readily accessible beta-ketothioamides and quinoxalin-2-ones under TBHP mediated conditions at room temperature. Mechanistic studies have revealed the seamless integration of intermolecular radical coupling and intramolecular cyclization through desulfhydration of C=S bond cleavage. The process is highly attractive due to the generation of H2S as the only by-product. Furthermore, the photophysical behavior of the furo-fused quinoxalines has been investigated.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Nicholas R. Lauta, Ryan E. Williams, David T. Smith, Vlad K. Kumirov, Jon T. Njardarson
Summary: A new intramolecular oxidative amino-hydroxylation of o-allenyl anilines is reported, where lead(IV) carboxylates are used to achieve tandem C-N and C-O bond formation at room temperature. Mechanistic and kinetic studies suggest a process involving Wessely dearomatization, cyclization, and rearomatization.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Amalia Garcia-Garcia, Sara Rojas, Lorenzo Rivas-Garcia, Maria D. Navarro-Hortal, Jose M. Romero-Marquez, Jose G. Fernandez-Bolanos, Duane Choquesillo-Lazarte, Alfonso Salinas-Castillo, Oscar Lopez, Jose L. Quiles, Antonio Rodriguez-Dieguez
Summary: A new palladium coordination compound based on gliclazide has been synthesized and characterized, showing promising inhibitory activity against an enzyme related to Alzheimer's disease and protective activity in a Caenorhabditis elegans model.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Medicinal
Francisco J. Hicke, Adrian Puerta, Jelena Dinic, Milica Pesic, Jose M. Padron, Oscar Lopez, Jose G. Fernandez-Bolanos
Summary: Novel mitochondria-targeted compounds, combining a phenethyl alcohol motif with a triphenyl phosphonium scaffold, exhibited strong antiproliferative activities against tumor cells, showing up to 350-fold improvement compared to classical chemotherapeutic agents. These compounds also demonstrated promising selectivity and potency, including towards multidrug resistant cells when co-administered with a pump-efflux inhibitor.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Alma Fuentes-Aguilar, Penelope Merino-Montiel, Sara Montiel-Smith, Socorro Meza-Reyes, Jose Luis Vega-Baez, Adrian Puerta, Miguel X. Fernandes, Jose M. Padron, Andrea Petreni, Alessio Nocentini, Claudiu T. Supuran, Oscar Lopez, Jose G. Fernandez-Bolanos
Summary: In this study, a small library of 2-aminobenzoxazole-appended coumarins was designed, synthesized, and evaluated as novel inhibitors of tumour-related CA IX and XII. The structure-activity relationships were established through modifications on substituents and linker length. The compounds exhibited good selectivity towards CA IX and XII and the introduction of a chlorine atom on the coumarin moiety showed the strongest antiproliferative activity.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Physical
Oscar Lopez, Jose M. Padron
Summary: Transition metal catalysts are crucial in industrial organic processes, enabling sustainable chemical production. The development of metal-supported catalysts, nanosystems, and electrochemical and photochemical catalysts has provided more sustainable strategies for the production of biologically active compounds or precursors in the pharmaceutical industry.
Article
Chemistry, Medicinal
Vasco Cachatra, Maria Conceicao Oliveira, Oscar Lopez, Jose G. Fernandez-Bolanos, Amelia Pilar Rauter
Summary: We disclosed a new family of purine nucleoside cholinesterase inhibitors by tuning the structural and stereochemical features of nucleosides with perbenzylated glycosyl moieties. The design, synthesis, and biological evaluation of new purine nucleosides were conducted to investigate the required glycon protecting group pattern for anticholinesterase activity and selectivity. Regioselective chemistry and N-glycosylation were used to obtain the target nucleosides, which showed cholinesterase inhibition and selectivity for butyrylcholinesterase.
MEDICINAL CHEMISTRY
(2023)
Article
Pharmacology & Pharmacy
Adrian Sanchez, Carlos J. Carrasco, Francisco Montilla, Eleuterio Alvarez, Agustin Galindo, Maria Perez-Aranda, Eloisa Pajuelo, Ana Alcudia
Summary: In this study, a series of imidazole silver complexes with different alkyl groups were prepared and their antimicrobial properties were evaluated. The results showed that the antimicrobial activity of the complexes was related to their structure and the steric properties of the alkyl groups.
Article
Biochemistry & Molecular Biology
Dolores Linde, Elena Santillana, Elena Fernandez-Fueyo, Alejandro Gonzalez-Benjumea, Juan Carro, Ana Gutierrez, Angel T. Martinez, Antonio Romero
Summary: This study successfully crystallized two UPO enzymes, rMroUPO and rCviUPO, from different fungal groups through sequence optimization and Escherichia coli expression, revealing their crystal structures and dimeric protein characteristics.
Article
Biochemistry & Molecular Biology
Dolores Linde, Alejandro Gonzalez-Benjumea, Carmen Aranda, Juan Carro, Ana Gutierrez, Angel T. Martinez
Summary: Vegetable oils are valuable renewable resources for the production of bio-based chemicals and intermediates. Enzymes can be used as environmentally friendly alternatives to chemical catalysis in the epoxidation reactions of vegetable oils. By engineering the active site of the enzyme and optimizing the process, the epoxidation yield can be significantly enhanced.
Article
Green & Sustainable Science & Technology
A. Anouar, A. Grirrane, E. Alvarez, N. Katir, A. Primo, H. Garcia, A. El Kadib
Summary: Heteroatom-doped porous carbon materials with tunable structures can be obtained by modifying and graphitizing chitosan, a marine waste. These materials exhibit good catalytic activity and the approach combining active metals and discarded biowaste provides a versatile method for the preparation of heterogeneous carbon-based catalysts.
MATERIALS TODAY SUSTAINABILITY
(2022)
Article
Biochemistry & Molecular Biology
I. Caroline Vaaland, Oscar Lopez, Adrian Puerta, Miguel X. Fernandes, Jose M. Padron, Jose G. Fernandez-Bolanos, Magne O. Sydnes, Emil Lindback
Summary: The copper-catalysed azide-alkyne cycloaddition was successfully utilized to synthesize a series of heterodimers containing a tacrine residue and a 1,4-dideoxy-1,4-imino-D-arabinitol or 1,4-dideoxy-1,4-imino-L-arabinitol moiety, which showed potential as enzyme inhibitors.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Paloma Begines, Alessandro Bonardi, Alessio Nocentini, Paola Gratteri, Simone Giovannuzzi, Roberto Ronca, Camilla Tavani, Maria Luisa Massardi, Oscar Lopez, Claudiu T. Supuran
Summary: This study successfully synthesized a variety of compounds that conjugate biotin with sulfonamide motifs and tested their efficacy as carbonic anhydrase inhibitors in vitro. Most of the synthesized compounds showed interesting inhibition profiles in the nanomolar range, and some compounds exhibited good selectivity towards tumor-associated enzymes. One compound demonstrated anti-proliferative activity in multiple tumor cell lines.
BIOORGANIC & MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Maria M. Alcaide, Matteo Pugliesi, Eleuterio Alvarez, Joaquin Lopez-Serrano, Riccardo Peloso
Summary: Two highly sterically demanding phosphonite ligands were synthesized and their structural features and steric descriptors were examined using DFT methods. The ligands were found to have a high tendency for C-H activation and could generate various coordination complexes.
Article
Chemistry, Inorganic & Nuclear
Maria M. Alcaide, Praxedes Sanchez, Eleuterio Alvarez, Celia Maya, Joaquin Lopez-Serrano, Riccardo Peloso
Summary: In this study, Pt(ii) alkylidene 1a was reacted with terminal alkynes to form ylide complexes 3a-d through electrophilic activation and insertion. DFT calculations demonstrated that the observed regioselectivity is determined by the nucleophilic attack of the alkyne to the alkylidene carbon.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Inorganic & Nuclear
Carlos J. Carrasco, Francisco Montilla, Eleuterio Alvarez, Agustin Galindo, Maria Perez-Aranda, Eloisa Pajuelo, Ana Alcudia
Summary: In this study, novel one-dimensional or two-dimensional coordination polymers were synthesized and their antimicrobial properties were evaluated. The results showed that complexes 2a and 2b' exhibited the best antimicrobial activity against the tested pathogens.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
