16760-45-5Relevant articles and documents
Assignment of 1H and 13C NMR Spectra of Retinoic Acid Ester Isomers Observed in the Long-Wavelength UV-Induced Photostationary State
Curley, Robert W.,Fowble, John W.
, p. 707 - 709 (1989)
1H and 13C chemical shift assignments, obtained with the aid of two-dimensional hetenuclear shift correlation and double-quantum coherence 13C-INADEQUATE experiments, are reported for four retinoic acid ester isomers observed at the photostationary state.Also detailed are 1H assignments for three additional isomers obtained in insufficient amounts for 13C measurements.KEY WORDS - Retionic acid esters Isomer identification 1H-13C correlation spectra 13C-INADEQUATE experiment
AN IMPROVED PROCESS FOR THE PREPARATION OF 4-OXOISOTRETINOIN
-
Page/Page column 12, (2022/02/28)
The present invention relates to an improved process for the preparation of 4-Oxoisotretinoin and purification process of 4-Oxoisotretinoin (I) and crystalline 5 form of 4-Oxoisotretinoin (I).
13-CIS-RAMBA RETINAMIDES THAT DEGRADE MNKS FOR TREATING CANCER
-
Page/Page column 52, (2016/06/20)
The synthesis and in vitro and in vivo anti-breast and anti-prostate cancers activities of novel C-4 heteroaryl 13-cis retinamides that modulate Mnk-eIF4E and AR signaling are discussed. In both breast and prostate cancer cell lines, these compounds induc
Novel C-4 heteroaryl 13- cis -retinamide Mnk/AR degrading agents inhibit cell proliferation and migration and induce apoptosis in human breast and prostate cancer cells and suppress growth of MDA-MB-231 human breast and CWR22Rv1 human prostate tumor xenografts in mice
Mbatia, Hannah W.,Ramalingam, Senthilmurugan,Ramamurthy, Vidya P.,Martin, Marlena S.,Kwegyir-Afful, Andrew K.,Njar, Vincent C. O.
, p. 1900 - 1914 (2015/04/27)
The synthesis and in vitro and in vivo antibreast and antiprostate cancers activities of novel C-4 heteroaryl 13-cis-retinamides that modulate Mnk-eIF4E and AR signaling are discussed. Modifications of the C-4 heteroaryl substituents reveal that the 1H-imidazole is essential for high anticancer activity. The most potent compounds against a variety of human breast and prostate cancer (BC/PC) cell lines were compounds 16 (VNHM-1-66), 20 (VNHM-1-81), and 22 (VNHM-1-73). In these cell lines, the compounds induce Mnk1/2 degradation to substantially suppress eIF4E phosphorylation. In PC cells, the compounds induce degradation of both full-length androgen receptor (fAR) and splice variant AR (AR-V7) to inhibit AR transcriptional activity. More importantly, VNHM-1-81 has strong in vivo antibreast and antiprostate cancer activities, while VNHM-1-73 exhibited strong in vivo antibreast cancer activity, with no apparent host toxicity. Clearly, these lead compounds are strong candidates for development for the treatments of human breast and prostate cancers.
Novel retinoic acid metabolism blocking agents endowed with multiple biological activities are efficient growth inhibitors of human breast and prostate cancer cells in vitro and a human breast tumor xenograft in nude mice
Patel, Jyoti B.,Huynh, Carlic K.,Handratta, Venkatesh D.,Gediya, Lalji K.,Brodie, Angela M. H.,Goloubeva, Olga G.,Clement, Omoshile O.,Nanne, Ivo P.,Soprano, Dianne Robert,Njar, Vincent C. O.
, p. 6716 - 6729 (2007/10/03)
Novel retinoic acid metabolism blocking agents (RAMBAs) have been synthesized and characterized. The synthetic features include introduction of nucleophilic ligands at C-4 of all-trans-retinoic acid (ATRA) and 13-cis-retinoic acid, and modification of ter
Reactivity of retinoids and carotenoids in autoxidation
Finkelshtein,Krasnokutskaya
, p. 411 - 418 (2007/10/03)
The autoxidation of various retinyl polyenes and carotenoids in chlorobenzene at 45 °C and in thin solid films on a support at room temperature was investigated. The compounds used were β-carotene, canthaxanthin, retinyl acetate, methyl (all-E)-retinoate, methyl (13Z)-retinoate, retinal, C18 ketone, β-ionylidene acetaldehyde, ψionone, β-ionone and ethyl sorbate as a model compound. It was shown that the isomerization of polyenyl peroxy radicals occurs during autoxidation of all the compounds studied, excepting β-ionone. A kinetic scheme for the polyene autoxidation process was considered and analysed. The conditions under which the rate constants of elementary reactions may be determined were defined and the rate constants of propagation and termination reactions for different polyenes were evaluated. The disappearance and formation of different functional groups were monitored by the spectroscopic investigation of autoxidation of polyene solid films. Mechanisms of the initial stages of the process are proposed for different polyenes.
Low-valent titanium reductive elimination: a direct and highly stereoselective synthesis of vitamin A aldehyde and all-trans retinoic acid orthothioester
Solladie, G.,Berl, V.
, p. 568 - 574 (2007/10/02)
It is shown that low-valent titanium reductive elimination can be carried out in the presence of a thioacetal or an orthothioester group.The application to the synthesis of vitamin A aldehyde and all-trans retinoic acid orthothioester is described.Keywords - Ti(0) reductive elimination / vitamin A aldehyde / all-trans retinoic acid
SYNTHETIC INVESTIGATIONS IN THE CHEMISTRY OF POLYENE COMPOUNDS LII. SYNTHESIS OF RETINOIC AND DIHYDRORETINOIC ESTERS BY THE REFORMATSKII REACTION
Tutorskaya, O. O.,Miropol'skaya, M. A.,Samokhvalov, G. I.
, p. 1237 - 1240 (2007/10/02)
The esters of 7,8- and 7,14-dihydroretinoic acids were obtained by the reaction of 6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5-octadien-2-one with bromoacetic ester in the Reformatskii reaction followed by dehydration.The 7,8- and 7,14-dihydroretinoic
NEW MASKED BUILDING BLOCK FOR ISOPRENOID POLYENE CHAIN SYNTHESIS
Mandai, T.,Iuchi, Y.,Suzuki, K.,Kawada, M.,Otera, J.
, p. 4721 - 4724 (2007/10/02)
The new building blocks 2, 3, and 4 have been effectively synthesized starting from 2-hydroxymethyl-4-phenylthio-1-butene (1a).A convenient synthesis of retinoic acid methyl ester (9) using 2 is also described.
