163955-59-7Relevant articles and documents
AN IMPROVED PROCESS FOR THE PREPARATION OF 4-OXOISOTRETINOIN
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, (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).
Preparation method of olefine acid impurity
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Paragraph 0057-0058, (2021/01/11)
The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of an olefine acid impurity. The impurity is (13E) -3, 7-dimethyl -9 -[(3RS) -3-methoxy -2, 6, 6-trimethyl cyclohexenyl] -2, 4, 6, 8-azela
13-CIS-RAMBA RETINAMIDES THAT DEGRADE MNKS FOR TREATING CANCER
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, (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
A convenient synthesis of retinal derivatives with modified trimethylcyclohexene ring
Mironova,Leont'eva,Shevyakov,Alexeeva,Shvets,Demina,Krasnokutskaya,Finkel'shtein,Khodonov
, p. 487 - 493 (2007/10/03)
A method of simultaneous one-stage synthesis of three retinal derivatives (5,6-dioxo-5,6-seco-, 5,6-dihydro-5,6-epoxy-, and 4-oxoretinal) was proposed, with the yield of the first derivative being ～50%. These compounds are useful tools for studying the an
Potent inhibition of retinoic acid metabolism enzyme(s) by novel azolyl retinoids
Njar, Vincent C.O.,Nnane, Ivo P.,Brodie, Angela M.H.
, p. 1905 - 1908 (2007/10/03)
Novel (±)-4-azolyl retinoic acid analogues 4, 5, 7 and 8 have been designed and synthesized and have been shown to be powerful inhibitors of hamster microsomal all-trans-retinoic acid 4-hydroxylase enzyme(s). (±)-4-(1H-Imidazol-1-yl)retinoic acid (4) is t
Specific oxidation of retinoic acid to 4-oxo-retinoic acid in diluted acid solutions
Tanaka,Kagechika,Shudo
, p. 356 - 358 (2007/10/02)
Treatment of retinoic acid (1a) or its methyl ester (2a) with hydrochloric acid in methanol gave methyl 4-oxo-retinoates (4a - c). Similar oxidation proceeded when 2a was treated with trifluoromethanesulfonic acid in the presence of lithium chloride in methanol.
Cancer Chemopreventive 3-Substituted-4-oxoretinoic Acids
Shealy, Y. Fulmer,Hosmer, Carla A.,Riordan, James M.,Wille, John W.,Rogers, Tina S.,Hill, Donald L.
, p. 3051 - 3056 (2007/10/02)
The introduction of substituents at position 3 of methyl 4-oxoretinoate can be effected in good yields by alkylating the lithium dienolate.A second substituent can be introduced also, but the resulting 3,3-disubstituted-4-oxoretinoates were isolated in lo
Modification of the intact retinoid structure in the cyclohexenyl region: Alkylation of methyl 4-oxoretinoate
Shealy,Hosmer,Riordan
, p. 1095 - 1098 (2007/10/02)
Alkylation of methyl 4-oxoretinoate under kinetic-control conditions gives predominantly 3-alkyl-4-oxoretinoates. 3,3-Disubstituted 4-oxoretinoates are obtained similarly from the 3-monosubstituted derivatives, although introduction of the second substituent is more difficult. Evidence has been obtained for a much slower rate of alkylation α to the ester group.
