This article reports the synthesis of spiro compounds based on an indanedione-cyclopropane-pyrazolone framework. The reaction relied upon the Michael-initiated ring closure strategy and was carried out under Cu(OAc) catalysis, assisted by an oxygen atmosphere and the base EtN. The final compounds were obtained as an inseparable mixture in most cases with modest to good yields using diverse substrates. Among the two plausible routes, computational studies indicated the feasibility of a route which involves a four-membered Cu containing intermediate. Given the generic nature of the developed method, it may be utilised to synthesise other analogous spiro systems.
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http://dx.doi.org/10.1039/d1ob02351a | DOI Listing |
Zhong Nan Da Xue Xue Bao Yi Xue Ban
July 2024
Department of Endocrinology &Metabolism, West China Hospital, Sichuan University, Chengdu 610041.
Cushing's disease is a rare endocrine disorder characterized by hypercortisolism. Chronic elevated cortisol levels can lead to dysfunction or complications in multiple organs of systems, including cardiovascular, glucose, and bone metabolism, severely impacting patients' quality of life and posing life-threatening risks. Surgery is the first-line treatment for Cushing's disease.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Changchun Institute of Applied Chemistry Chinese Academy of Sciences: Chang Chun Institute of Applied Chemistry Chinese Academy of Sciences, Jilin Province Key Lab of Green Chemistry and Process, CHINA.
A modular approach was developed for the first catalytic asymmetric total syntheses of naturally occurring C30 terpene quinone methides and their non-natural stereoisomers, which feature the presence of an unprecedented spiro[4.4]nonane-containing 6-6-6-5-5-3 hexacyclic skeleton. Resting on a chiral phosphinamide-catalyzed enantioselective reduction of 2,2-disubstituted cyclohexane-1,3-dione, a concise route for the synthesis of enantioenriched 6-6 bicyclic fragment was developed.
View Article and Find Full Text PDFChemistry
January 2025
Zhengzhou University, School of Pharmaceutical Sciences, 100 Science Avenue, 450001, Zhengzhou, CHINA.
An unprecedented formal [1+5] cyclization of indoline-derived azadienes with 1,3,5-triazinanes has been realized, providing a facile access to biologically important indoline-spiro-hexahydropyrimidines with good to excellent yields (up to 99% yield). Different from previous reports, this is the first study that indoline-derived azadienes could participate in cyclizations as one-atom synthons. This methodology is also distinguished by not involving any additive or catalyst, readily available starting materials, wide range of substrate applicability, operational simplicity and simultaneously reassembling two C-N and two C-C bonds in one-step reaction.
View Article and Find Full Text PDFInt J Mol Sci
December 2024
College of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, China.
A synthetic strategy of a three-component spiro-pyrrolidine compound based on benzofuran via an [3+2] azomethine ylide cycloaddition reaction is reported herein. Under mild optimal conditions, this reaction can quickly produce potentially bioactive compounds with a wide range of substrates, high yield, and simple operation. The desired products were obtained with a yield of 74-99% and a diastereomeric ratio (dr) of >20:1.
View Article and Find Full Text PDFMedicina (Kaunas)
November 2024
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia.
Revumenib (SNDX-5613) is a powerful and specific inhibitor of the menin-KMT2A binding interaction. It is a small molecule that is currently being researched to treat KMT2A-rearranged (KMT2Ar) acute leukemias. Revumenib (RVB) has received Orphan Drug Designation from the US FDA for treating patients with AML.
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