Article
Chemistry, Multidisciplinary
Daniel Moser, Kalipada Jana, Christof Sparr
Summary: In this study, the feasibility of atroposelective P-III/P-V=O redox organocatalysis by the Staudinger-aza-Wittig reaction is described. The formation of isoquinoline heterocycles allows for the synthesis of a wide range of valuable atropisomers with high enantioselectivities. The reaction is catalyzed by a chiral phosphine catalyst, with stereocontrol achieved through a silane reductant and Bronsted acid co-catalysis. The products can be easily transformed into N-oxides, naphthol, and triaryl phosphine variants, providing access to diverse aromatic heterocycles with precise control over their configuration.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Keyvan Pedrood, Mohammad Nazari Montazer, Bagher Larijani, Mohammad Mahdavi
Summary: This review summarizes recent studies on heterocyclic compounds focusing on the formation of the C=N bond via the aza-Wittig reaction. It also discusses two different strategies for forming heterocyclic compounds and provides up-to-date information on the synthesis of various N-containing heterocyclic compounds using the aza-Wittig reaction in chemical literature since 2010.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Mingxian Xu, An Chen, Zhilin Ren, Jiying Qiu, Mingming Zu, Yi Zhang, Jiayi Wang, Ping He
Summary: The one-pot synthesis of azide-substituted dihydropyrazoles in isopropanol was successfully achieved, followed by investigation of Staudinger-aza-Wittig-dehydroaromatization reactions with methyl(diphenyl)phosphine for further application in the construction of pyrazolo[1,5- c ]quinazolines.
Article
Chemistry, Organic
Long Zhao, Mao-Lin Yang, Min Liu, Ming-Wu Ding
Summary: A new efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines via sequential Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reaction has been developed.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Rodion Lebedev, Dmitry Dar'in, Grigory Kantin, Olga Bakulina, Mikhail Krasavin
Summary: This study describes the realization of a one-pot Staudinger/aza-Wittig/Castagnoli-Cushman reaction sequence for a series of azido aldehydes and homophthalic anhydrides. The reaction proceeds at room temperature and delivers novel polyheterocycles related to the natural product realm in high yields and high diastereoselectivity. The methodology has been extended to three other cyclic anhydrides, further unraveling the potential of the Castagnoli-Cushman reaction in generating polyheterocyclic molecular scaffolds.
Article
Biochemistry & Molecular Biology
Ana Donaire-Arias, Martin L. Poulsen, Jaime Ramon-Costa, Ana Maria Montagut, Roger Estrada-Tejedor, Jose I. Borrell
Summary: Chalcones, a type of molecule that can be easily synthesized through aldol condensation, lacks standard procedures and often yields low purity and low yields. By comparing aldol condensation and Wittig reaction, the improved procedure of Wittig reaction shows high yield and excellent purity, providing a novel method for the synthesis of chalcones.
Article
Chemistry, Applied
Branko Mitasev, Jiong Yang, Fabian Gusovsky, Dixit Girish, Anil Shahaji Khile, Venkata Sasidhar Balla, Venugopalarao Vikram, Anand Vaddi, Srikanth Bathula, Srinivasa Rao Sugandham, Chiranjeevi Terli, Vijay Kalla, Pavan Kumar Rayaprolu, Ravi Kumar Talabhakthula, Masaharu Gotoda, Bruno Melillo, Stuart L. Schreiber, Francis G. Fang
Summary: This paper describes a crystallization-based synthetic route to the antimalarial BRD5018, which allows for the assembly of a structurally complex bicyclic azetidine scaffold adorned with five stereogenic centers without the need for chromatographic separations.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Organic
Mao-Lin Yang, Hao-Ran Chen, Long Zhao, Ming-Wu Ding
Summary: A new efficient synthesis method for the preparation of 6,12-dihydro-5H-quinazolino[3,2-a]quinazolin-5-ones has been developed. This method involves sequential Ugi/Staudinger/aza-Wittig/addition/nucleophilic acyl substitution reactions and provides a domino and effective strategy for the preparation of various substituted quinazolino[3,2-a]quinazolin-5-ones under mild reaction conditions.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Mei Sun, Yan-Ling Yu, Long Zhao, Ming-Wu Ding
Summary: A new one-pot and divergent synthesis of multisubstituted furo[3,2-cl]quinolines and quinazolin-4(3H)-ones was developed via sequential isocyanide-based three-component/Staudinger/aza-Wittig reactions, yielding good overall yields of the desired products.
Article
Chemistry, Organic
Hai Xie, Qingqing Hu, Lu Li, Xiuting Qin, Yali Zhang, Haiqing Wang
Summary: This paper presents a convenient route for the synthesis of bis-1,2,4-oxadiazoles. By one-pot reaction of diazidoglyoxime esters and triphenylphosphine, followed by Staudinger/aza-Wittig reaction, bis-1,2,4-oxadiazole derivatives were obtained in good overall yields.
Article
Chemistry, Organic
Vitalii V. Izhyk, Anton O. Poliudov, Alexey V. Dobrydnev, Taras V. Omelian, Maria V. Popova, Yulian M. Volovenko
Summary: In this study, we present a short and cost-effective synthesis approach for alkyl isothiazolidine-1,1-dioxide 3-carboxylates starting from commercially available α-amino acid ester hydrochlorides. These compounds were designed as sulfonamide-containing bioisosteres of the known pharmacological template - pyroglutamic acid (pGlu).
Article
Chemistry, Multidisciplinary
Xinxin Tang, Raj K. Tak, Hidetoshi Noda, Masakatsu Shibasaki
Summary: We report the stereoselective synthesis of remotely decorated, trisubstituted beta-prolines via Rh-catalyzed C-H amination. The method works well in the presence of various functionalities, with carboxylic acids in the products serving as gateways for diverse downstream transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Karolina Koselak, Stanislaw Porwanski
Summary: This publication discusses the assumption of using carbon dioxide to obtain urea derivatives of saccharides as organocatalysts or cryptands in modern organic synthesis. It explores the advantages of sugars as compounds of natural origin with high optical purity, easy availability, and low cost as substrates, while also being able to perform reactions in water. The main focus is on combining the advantages of saccharides with the elimination of carbon dioxide from the environment.
JOURNAL OF CO2 UTILIZATION
(2022)
Article
Chemistry, Organic
Jinni Liu, Yibi Xie, Qingqing Yang, Nianyu Huang, Long Wang
Summary: This study reports a novel tandem reaction strategy for the synthesis of nitrogen-heterocycles by utilizing the Ugi four-component reaction and subsequent modification reaction based on the in situ capture of amines. The strategy has expanded the scope of substrates, solved the problems associated with easily oxidized, unstable, and less versatile amines. A plausible mechanism for the reaction has been proposed based on a series of conditional control experiments.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Hai Xie, Qing-Qing Hu, Ya-Li Zhang, Xiu-Ting Qin, Lu Li
Summary: Two efficient and scalable routes for the synthesis of bis-1,2,4-oxadiazole were developed by tandem Staudinger/aza-Wittig reaction using the same starting material diaziglyoxime, isocyanates, and triphenylphosphonium, resulting in good yields.
CURRENT ORGANIC SYNTHESIS
(2023)
Review
Chemistry, Medicinal
Feryel Soualmia, Chahrazade El Amri
EXPERT OPINION ON THERAPEUTIC PATENTS
(2018)
Article
Biochemistry & Molecular Biology
Feryel Soualmia, Elodie Bosc, Sabrina Ait Amiri, Dirk Stratmann, Viktor Magdolen, Dalila Darmoul, Michele Reboud-Ravaux, Chahrazade El Amri
BIOLOGICAL CHEMISTRY
(2018)
Article
Chemistry, Organic
G. Cutolo, F. Reise, M. Schuler, R. Nehme, G. Despras, J. Brekalo, P. Morin, P. -Y. Renard, T. K. Lindhorst, A. Tatibouet
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Article
Thermodynamics
Irina Zarafu, Rodica Olar, Mariana Carmen Chifiriuc, Coralia Bleotu, Petre Ionita, Mihaela Multescu, Gabriela Ionita, Gratiela Gradisteanu, Arnaud Tatibouet, Mihaela Badea
JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY
(2018)
Article
Thermodynamics
Irina Zarafu, Mihaela Badea, Gabriela Ionita, Mariana Carmen Chifiriuc, Coralia Bleotu, Marcela Popa, Petre Ionita, Arnaud Tatibouet, Rodica Olar
JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY
(2019)
Article
Biochemical Research Methods
Jean Wilfried Fredy, Giuliano Cutolo, Benjamin Poret, Reine Nehme, Marie Hubert-Roux, Pierrick Gandolfo, Helene Castel, Marie Schuler, Arnaud Tatibouet, Cyrille Sabot, Pierre-Yves Renard
BIOCONJUGATE CHEMISTRY
(2019)
Article
Chemistry, Analytical
Berengere Claude, Giuliano Cutolo, Amal Farhat, Irina Zarafu, Petre Ionita, Marie Schuler, Arnaud Tatibouet, Philippe Morin, Reine Nehme
ANALYTICA CHIMICA ACTA
(2019)
Article
Pharmacology & Pharmacy
Irina Zarafu, Bianca Patrascu, Luminita Marutescu, Coralia Bleotu, Carmen Limban, Arnaud Tatibouet, Mariana Carmen Chifiriuc, Diana Camelia Nuta, Petre Ionita
Article
Biochemistry & Molecular Biology
Irina Zarafu, Lilia Matei, Coralia Bleotu, Petre Ionita, Arnaud Tatibouet, Anca Paun, Ioana Nicolau, Anamaria Hanganu, Carmen Limban, Diana Camelia Nuta, Roxana Maria Nemes, Carmen Cristina Diaconu, Cristiana Radulescu
Article
Chemistry, Organic
Maria Domingues, Justyna Jaszczyk, Maria Isabel Ismael, Jose Albertino Figueiredo, Richard Daniellou, Pierre Lafite, Marie Schuler, Arnaud Tatibouet
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Polymer Science
Guillaume Taing, Vanessa Legros, Francoise Ta, David Da Silva, Cyril Colas, Marylene Vayer, Marie Schuler, Kamel Chougrani, Christophe Sinturel, Arnaud Tatibouet
Summary: The study focuses on the polymerization of glycidyl carbamates, a new class of monomers obtained from glycerol carbonate. It suggests that low basicity and high nucleophilicity are the most suitable conditions for polymerizing glycidyl carbamates due to the sensitivity of the urethane moiety. Furthermore, the obtained poly(glycidyl carbamates) affinity toward the solvent has been studied to further characterize the properties of these novel polyethers.
Article
Chemistry, Medicinal
Sabrina Ait Amiri, Cyrille Deboux, Feryel Soualmia, Nancy Chaaya, Maxime Louet, Eric Duplus, Sandrine Betuing, Brahim Nait Oumesmar, Nicolas Masurier, Chahrazade El Amri
Summary: In this study, low-molecular-weight inhibitors targeting KLK6 were designed and evaluated, with selected hit compounds showing selectivity within the KLK6 proteolytic network involved in MS pathology. These hit compounds were found to be noncytotoxic on primary cultures of neurons and OPCs, and two compounds were shown to promote OPC differentiation into mature oligodendrocytes, suggesting their potential as leads for regenerative therapies.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Khadija El Hadri, Remy Smith, Eric Duplus, Chahrazade El Amri
Summary: Atherosclerosis is a major cause of cardiovascular diseases worldwide, characterized by chronic inflammation, oxidative stress, and cellular senescence. Current therapeutic options include lipid-lowering drugs, anti-inflammatory interventions, and lifestyle changes. Targeting oxidative stress and senescent cells has emerged as promising strategies for atherosclerosis treatment.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Hayet Bouzid, Feryel Soualmia, Katerina Oikonomopoulou, Antoninus Soosaipillai, Francine Walker, Khaoula Louati, Rea Lo Dico, Marc Pocard, Chahrazade El Amri, Natalia A. Ignatenko, Dalila Darmoul
Summary: KLK6 overexpression in colon cancer is associated with poor prognosis and aggressive behavior. KLK6 activates PAR2, leading to calcium flux and ERK1/2 phosphorylation, promoting tumor formation and invasion. Furthermore, KLK6 abnormal expression can be used to differentiate between malignant and benign ascites.
Article
Cell Biology
Elodie Bosc, Julie Anastasie, Feryel Soualmia, Pascale Coric, Ju Youn Kim, Lily Q. Wang, Gullen Lacin, Kaitao Zhao, Ronak Patel, Eric Duplus, Philippe Tixador, Andrew A. Sproul, Bernard Brugg, Michelle Reboud-Ravaux, Carol M. Troy, Michael L. Shelanski, Serge Bouaziz, Michael Karin, Chahrazade El Amri, Etienne D. Jacotot
Summary: This study presents new peptidomimetics that selectively and strongly inhibit Caspase-2, a therapeutic target for nonalcoholic steatohepatitis (NASH) and Alzheimer's disease (AD). The compounds showed high selectivity and potency in inhibiting Caspase-2, and demonstrated potential in preventing disease development.
CELL DEATH & DISEASE
(2022)
