68070-35-9Relevant articles and documents
Isotretinoin condensation compound as well as preparation method and application thereof
-
Paragraph 0029-0043; 0046-0060; 0062-0076; 0078-0084, (2020/08/06)
The invention provides an isotretinoin condensation compound and a preparation method and application thereof. The preparation method of the isotretinoin condensation compound comprises the steps: heating and stirring isopropyl alcohol, C15-triphenylphosphine chloride and C5-lactone and then stepwisely cooling the mixture, thus preparing a feed liquid I; heating and stirring isopropanol and potassium hydroxide to obtain a feed liquid II; dropwise adding the feed liquid II into the feed liquid I, and carrying out heat preservation and stirring to obtain a condensation reaction liquid; adding the condensation reaction liquid into deionized water with the temperature of 0-10 DEG C with stirring and mixing to obtain a feed liquid mixture; mixing the feed liquid; repeatedly layering through petroleum ether and other components, and extracting an organic layer to obtain the isotretinoin condensate. The isotretinoin condensate obtained by the preparation method disclosed by the invention hasthe advantages of higher purity, no solvent residue and mild reaction conditions, and is easy for industrial production.
Z -isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis
Kahremany, Shirin,Sander, Christopher Lane,Tochtrop, Gregory P.,Kubas, Adam,Palczewski, Krzysztof
supporting information, p. 8125 - 8139 (2019/09/19)
Catalytic Z-isomerization of retinoids to their thermodynamically less stable Z-isomer remains a challenge. In this report, we present a photochemical approach for the catalytic Z-isomerization of retinoids using monochromatic wavelength UV irradiation treatment. We have developed a straightforward approach for the synthesis of Z-retinoids in high yield, overcoming common obstacles normally associated with their synthesis. Calculations based on density functional theory (DFT) have allowed us to correlate the experimentally observed Z-isomer distribution of retinoids with the energies of chemically important intermediates, which include ground- and excited-state potential energy surfaces. We also demonstrate the application of the current method by synthesizing gram-scale quantities of 9-cis-retinyl acetate 9Z-a. Operational simplicity and gram-scale ability make this chemistry a very practical solution to the problem of Z-isomer retinoid synthesis.
Synthesis of 11C-labeled retinoic acid, [11C]ATRA, via an alkenylboron precursor by Pd(0)-mediated rapid C-[11C] methylation
Suzuki, Masaaki,Takashima-Hirano, Misato,Ishii, Hideki,Watanabe, Chika,Sumi, Kengo,Koyama, Hiroko,Doi, Hisashi
supporting information, p. 3622 - 3625 (2014/07/22)
Retinoids are a class of chemical compounds which include both natural dietary vitamin A (retinol) metabolites and active synthetic analogs. Both experimental and clinical studies have revealed that retinoids regulate a wide variety of essential biological processes. In this study, we synthesized 11C-labeled all-trans-retinoic acid (ATRA), the most potent biologically active metabolite of retinol and used in the treatment of acute promyelocytic leukemia. The synthesis of 11C-labeled ATRA was accomplished by a combination of rapid Pd(0)-mediated C-[11C] methylation of the corresponding pinacol borate precursor prepared by 8 steps and hydrolysis. [11C]ATRA will prove useful as a PET imaging agent, particularly for elucidating the improved therapeutic activity of ATRA (natural retinoid) for acute promyelocytic leukemia by comparing with the corresponding PET probe [11C]Tamibarotene (artificial retinoid).
