Article
Chemistry, Applied
Artur Przydacz, Aleksandra Topolska, Anna Skrzynska, Sebastian Frankowski, Lukasz Albrecht
Summary: This manuscript presents the application of amino isobenzofulvene intermediates as pentaenamines in a 1,6-addition reaction. The alkylation of the indene ring in indene-2-carbaldehydes with para-quinone methides was achieved, with the stereoselectivity controlled by C-2-symmetric 2,5-diphenylpyrrolidine. The developed process utilizes the reactivity of amino isobenzofulvene intermediates derived from indene-2-carbaldehydes in a non-cycloadditive manner.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Xing Zhang, Xiangchuang Tan, Shengfu Duan, Zhiyong Chi, Shaocong Liu, Zhixiang Xie
Summary: (-)-Chamaecydin and (-)-isochamaecydin, two uncommon C-30 terpenoids, were synthesized from β-pinene with (-)-sabinene in 18 and 20 steps, respectively. Key steps include a Claisen-Ireland rearrangement, a Rh catalyzed C-H bond insertion reaction, and a Lewis acid promoted cyclization.
Article
Chemistry, Multidisciplinary
Kai Li, Shengli Huang, Tianyu Liu, Shiqi Jia, Hailong Yan
Summary: We demonstrated an organocatalytic asymmetric dearomatizing hetero-Diels-Alder reaction of benzene derivatives, which allows the synthesis of diverse stereochemically complex compounds and oxahelicenes. The high complexity and three-dimensionality of the products are crucial for their potential applications in materials science and drug discovery.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Shaukat Ali, Muhammad Israr
Summary: This paper highlights the recent studies on the organocatalytic asymmetric dearomatization of nonactivated arenes, obtaining complex stereoisomeric products by harnessing the reactivity of chiral vinylidene ortho-quinone methides (VQMs) generated in situ.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Ganesh Shivayogappa Sorabad, Ding-Yah Yang
Summary: A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4-hydroxycoumarin to afford furano[3,2-c]coumarin and pyrano[3,2-c]coumarin derivatives is reported. The reaction proceeds through the conjugate addition of 4-hydroxycoumarin to the in situ-generated alkynyl o-quinone methide followed by intramolecular 5-exo-dig and 6-endo-dig annulation to form furano[3,2-c]coumarins and pyrano[3,2-c]coumarins, respectively. The prepared o-hydroxyl substituted pyrano[3,2-c]coumarins can be easily transformed into the corresponding coumarin-derived dioxabicycles by acid-mediated cyclization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Lei Dai, Qiuyu Yu, Jinghang Zhang, Fan Wu, Chang Wang, Jinpeng Zhang, Liangce Rong
Summary: An efficient electrochemical radical delta-H sulfonylation reaction of para-quinone methides and sodium sulfinates has been achieved under common laboratory conditions. The reaction allows for the construction of a new C(sp(2))-S bond to synthesize 4-((aryl,arylsulfonyl)methylene)-2,5-cyclohexadiene derivatives with a broad substrate scope and good functional group tolerance. Further studies have shown that the reaction exhibits excellent regional selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Qinfang Yan, Yi Jiang, Xianheng Song, Guoqing Lu, Qianzhong Zhang, Zhibo Du, Albert S. C. Chan, Yong Zou
Summary: A facile and practical approach for the synthesis of natural coumestans and derivatives starting from 2',4'-dihydroxyl-3-arylcoumarins has been developed. The process involves a sequential intramolecular dehydrogenation/oxa-Michael reaction efficiently promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene at 40 degrees C under metal- and ligand-free conditions with good functional group compatibility.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Wanfu Wu, Margaret Warner, Li Wang, Wei-Wei He, Ruipeng Zhao, Xiaoxiang Guan, Cindy Botero, Bo Huang, Charlotte Ion, Charles Coombes, Jan-Ake Gustafsson
Summary: Comparing gene expression profiles of malignant parts and normal adjacent parts of TNBC breasts revealed that CYP-mediated pathways may drive TNBC. However, despite being expressed in TNBC, ER13 is unlikely to be a tumor suppressor as its absence of main tethering partners renders it ineffective on genes related to proliferation and inflammation.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2021)
Article
Agriculture, Multidisciplinary
Chunjing Guan, Guode Zhao, Chen Sun, Mingyu Zhang, Siyu Liu, Ziying Jiang, Weiwei Li, Ying Peng, Jiang Zheng
Summary: This study aims to characterize the reactive metabolites of IPC in vitro and in vivo, identify the cytochrome P450 enzymes responsible for metabolic activation, and determine the correlation between metabolic activation and cytotoxicity of IPC. Results showed that GSH and NAC conjugates were detected after IPC exposure in GSH- or NAC-supplemented microsomal incubations. These conjugates were also found in mouse liver homogenates and urine after IPC administration. IPC was found to be metabolized to a quinone intermediate reactive to GSH, and it induced cytotoxicity in cultured mouse primary hepatocytes. The cytotoxicity was attenuated by the selective CYP3A4/5 enzyme inhibitor, ketoconazole.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shiv Shankar Patel, Dileep Kumar, Chandra Bhushan Tripathi
Summary: This research addresses the generation of alkyl radicals under mild conditions through photoinduced Brönsted acid catalysis. The optimized protocol does not require organic dyes or transition metal photocatalysts. Functionalized arylmethane derivatives are obtained in high yield under blue light irradiation with diphenyl phosphate as a catalyst and dihydropyridine derivatives as a radical source.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Yi-Hang Deng, Wen-Li Xu, Lei Wang, Cheng-Yang Tang, Ji-Ya Fu, Chuan-Bao Zhang
Summary: A base-promoted cyclization using indene-dienes as building blocks has been reported, leading to the synthesis of diverse spirocyclic indene scaffolds. The reaction shows high yields and excellent diastereoselectivities, resulting in hexacyclic spiroindenes with benzo pyran motifs and pentacyclic spiroindenes containing oxindole units.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Fangzhi Hu, Liang Wang, Peng Wang, Zhanshuai Ding, Yuzhuo Chen, Lubin Xu, Xiong-Li Liu, Shuai-Shuai Li
Summary: The controllable synthesis of spirooxindole-fused dibenzo[b,f]oxocines and chromans from oxindole-embedded four-atom synthons and dibrominated compounds has been achieved through [4 + 4] and [4 + 2] cyclization reactions respectively. Additionally, the indole-fused nine-membered oxa-heterocycles can be selectively accessed by the ring expansion of spirooxindole-fused dibenzo[b,f]oxocines through carbocation rearrangement.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Katarina Zlatic, Matej Cindric, Ivana Antol, Lidija Uzelac, Branka Mihaljevic, Marijeta Kralj, Nikola Basaric
Summary: A series of BODIPY dyes were synthesized with photochemically reactive quinone methide (QM) precursor moieties, demonstrating wavelength-dependent photochemistry. Laser flash photolysis experiments confirmed the presence of phenoxyl radicals, while the formation of QMs was not detected due to low efficiency.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Kavyashree Kuppayya Gond, Mahagundappa Rachappa Maddani
Summary: In this study, isochroman-1,4-diones and addition products were selectively synthesized through KOBu-Catalyzed addition of sulfonylphthalides to p-quinone methides. It is noteworthy that isochroman-1,4-diones were obtained via an unprecedented oxidative annulation pathway. The research highlights the broad substrate scope, high yields, shorter reaction time, and mild reaction conditions. Furthermore, some addition products can be transformed into functionalized heterocyclic molecules. Additionally, the scalability experiment demonstrates the practical feasibility of preparing isochroman-1,4-diones in larger scale reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ozge Turbedaroglu, Ferruh Lafzi, Haydar Kilic
Summary: In this work, a mild and selective alkylation method for 8-aminoquinolines using para-quinone methides has been developed. The method allows for C5-H and N-H alkylation and is applicable to unprotected 8-aminoquinolines under metal-free conditions, resulting in high yields.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Medicinal
Lilian Dubois, Nicolas Pietrancosta, Alexandre Cabaye, Isabelle Fanget, Cecile Debacker, Pierre-Andre Gilormini, Patrick M. Dansette, Julien Dairou, Christophe Biot, Roseline Froissart, Anne Goupil-Lamy, Hugues-Olivier Bertrand, Francine C. Acher, Isabelle McCort-Tranchepain, Bruno Gasnier, Christine Anne
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Inorganic & Nuclear
Juan Sanz Garcia, Marie Gaschard, Isabelle Navizet, Mehdi Sahihi, Siden Top, Yong Wang, Pascal Pigeon, Anne Vessieres, Michele Salmain, Gerard Jaouen
Summary: The family of ferrocifens, derived from the anti-oestrogen tamoxifen, exhibit a broad antitumor activity by generating reactive oxygen species and electrophilic quinone methides. In addition to their known targets, cathepsin B was unexpectedly identified as a new target for ferrocifens.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Derek R. Boyd, Narain D. Sharma, Paul J. Stevenson, Patrick Hoering, Christopher C. R. Allen, Patrick M. Dansette
Summary: Enzymatic oxidations of thiophenes play a crucial role in biodesulfurization of crude oil and drug metabolism. The structure and configuration of the metabolites obtained from thiophene enzymatic oxidation depend on the substrate and selected oxygenase, and have significant implications in the pharmaceutical industry and medicine.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Medicinal
Yong Wang, Pascal Pigeon, Wei Li, Jiangkun Yan, Patrick M. Dansette, Mohamed Othman, Michael J. McGlinchey, Gerard Jaouen
Summary: Ferrociphenols, compounds characterized by a biologically active redox motif, have anticancer properties. This study synthesized a variety of ferrociphenols with nitrogen-containing substituents and investigated their structure-activity relationships. Oxidative metabolism experiments and ROS-related bioactivity measurements were conducted to explore the cytotoxicity of imidoferrociphenols. Additionally, dimerization phenomenon observed in the crystal structure of a ferrociphenol may affect its antitumor activity.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Pascal Pigeon, Marie Gaschard, Mohamed Othman, Michele Salmain, Gerard Jaouen
Summary: The addition of imide entities to the ferrociphenol scaffold enhanced cytotoxic activity. By converting alpha-hydroxylactams to N-acyliminium ions, various substituents were grafted to the imide motif, resulting in diverse cytotoxic activities on breast cancer cell lines.
Article
Biochemistry & Molecular Biology
Feten Najlaoui, Benoit Busser, Germain Sotoing Taiwe, Pascal Pigeon, Nathalie Sturm, Diane Giovannini, Naziha Marrakchi, Ali Rhouma, Gerard Jaouen, Stephane Gibaud, Michel De Waard
Summary: SuccFerr has remarkable antiproliferative effects and shows potential for clinical research. The water insolubility of SuccFerr is solved by complexation with RAMEssCDs, enabling in vivo experiments. The compound does not exhibit toxic effects on organs in vivo, and it can halt tumor progression in rats with xenografted tumors, possibly through an immunological defense response.
Article
Pharmacology & Pharmacy
Pierre Idlas, Abdallah Ladaycia, Fariba Nemati, Elise Lepeltier, Pascal Pigeon, Gerard Jaouen, Didier Decaudin, Catherine Passirani
Summary: Ovarian cancer is a deadly malignancy in women due to multidrug resistance. This study evaluated the efficacy of ferrocifen stealth lipid nanocapsules in treating ovarian cancer, and found that combination therapy with ferrocifen and standard chemotherapy can effectively treat resistant ovarian cancer.
INTERNATIONAL JOURNAL OF PHARMACEUTICS
(2022)
Article
Biochemistry & Molecular Biology
Charles Fayolle, Pascal Pigeon, Nathalie Fischer-Durand, Michele Salmain, Olivier Buriez, Anne Vessieres, Eric Labbe
Summary: The first fluorescent ferrociphenol derivative has been synthesized, and its fluorescence properties were found to be dependent on the redox state of the ferrocene group. This compound could serve as a useful tool to study the biodistribution and redox state of ferrociphenols in cancer cells.
Article
Chemistry, Multidisciplinary
Pierre Idlas, Guillaume Bastiat, Pascal Pigeon, Michael J. McGlinchey, Nolwenn Lautram, Anne Vessie, Gerard Jaouen, Catherine Passirani, Elise Lepeltier
Summary: By modifying the structure of ferrocifens, the drug loading in lipid nanocapsules can be improved, and the formation of a gel can be achieved. This has potential implications for the treatment of multidrug-resistant cancers and glioblastoma.
Article
Biochemistry & Molecular Biology
Pascal Pigeon, Feten Najlaoui, Michael James McGlinchey, Juan Sanz Garcia, Gerard Jaouen, Stephane Gibaud
Summary: This study aimed to determine the most suitable cyclodextrins (CDs) for solubilizing a patented succinimido-ferrociphenol compound (SuccFerr) with powerful anticancer activity but low water solubility. Phase solubility experiments and computational modeling were conducted on various CDs. The modeling and experiments suggest that supramolecular assemblies of SuccFerr with two CDs, particularly randomly methylated β-cyclodextrins (RAME-β-CDs), are predominant and superior. Additionally, the modeling reveals competing combinations of inserted moieties of SuccFerr and the contribution of ferrocene to high stabilization through atypical hydrogen bonding with CD hydroxyl groups.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Anne Vessieres, Emie Quissac, Nolwenn Lemaire, Agusti Alentorn, Patrycja Domeracka, Pascal Pigeon, Marc Sanson, Ahmed Idbaih, Maite Verreault
Summary: Members of the iron-based ferrocifen family exhibit varying cytotoxic effects on GBM, with differences in response patterns and higher efficacy in certain compounds. The study reveals insights into the mechanisms of action of certain ferrocifens and advocates for a molecular-based personalized approach in the future treatment of GBM.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
