807-05-6Relevant academic research and scientific papers
Synthesis of 6-(methoxycarbonyl)prednisolone and its derivatives as new antiinflammatory steroidal antedrugs
Hong,Heiman,Kwon,Lee
, p. 357 - 361 (1994)
The synthesis and pharmacological evaluation of 6- (methoxycarbonyl)prednisolone (11) (a 3:1 mixture of 6α-isomer 11a and 6β- isomer 11b), its 21-ol acetates 13a (6α-isomer) and 13b (6β-isomer), and 17,21-diol acetonide 14 (a 6:1 mixture of 6α-isomer 14a and 6β-isomer 14b) as local antiinflammatory steroidal antedrugs are described. The lead compound 11 was prepared via 12 steps from hydrocortisone (1). In the croton oil-induced ear edema assay, the topical antiinflammatory activity of 13a was higher than that of its epimer 13b. Except for 13a, the compounds (11, 13b, and 14) showed less activity than prednisolone. The systemic activities were assessed after 5 days of consecutive administration of these compounds at equlactive doses. Neither 11 nor 14 depressed plasma corticosteroid levels or significantly altered adrenal weights. Thymic involution was absent for 14, 15% for 11, and 47% for prednisolone at the equiactive doses. Both 13a and 13b showed significant reduction of adverse systemic effects assessed as the increase of body weight and the decreases of adrenal and thymus weights. The putative metabolite, carboxylic acid 12, showed 26 times less topical antiinflammatory activity than prednisolone. These results suggest that introduction of a labile methoxycarbonyl group at the C-6 position of prednisolone results in retention of antiinflammatory activity while reducing systemic effects noted following topical application of the parent compound prednisolone.
Synthesis of the antiproliferative agent hippuristanol and its analogues from hydrocortisone via Hg(II)-catalyzed spiroketalization: Structure-activity relationship
Somaiah, Ragam,Ravindar, Kontham,Cencic, Regina,Pelletier, Jerry,Deslongchamps, Pierre
, p. 2511 - 2523 (2014/04/17)
An efficient synthesis of hippuristanol (1), a marine-derived highly potent antiproliferative steroidal natural product, and nine closely related analogues has been accomplished from the commercially available hydrocortisone utilizing Hg(II)-catalyzed spi
METHODS FOR PREPARING SYNTHETIC BILE ACIDS AND COMPOSITIONS COMPRISING THE SAME
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Page/Page column 80, (2012/04/23)
This invention relates generally to methods for preparing certain bile acids from non-mammalian sourced starting materials as well as to synthetic bile acids and compositions comprising such acids wherein the acids are characterized by a different C14 population than naturally occurring bile acids as well as being free from any mammalian pathogens. This invention is also directed to the synthesis of intermediates useful in the synthesis of such bile acids. Accordingly, the C ring of the steroidal scaffold is oxidized to provide a synthetic route and intermediates to DCA. This invention also provides synthetic methods for preparing deoxycholic acid or a salt thereof starting from aromatic steroids such as estrogen, equilenin, and derivatives thereof. This invention is also directed to intermediates such as 12-oxo or delta-9,11-ene steroids as well as novel processes for their preparation. In preferred embodiments, bile acids are provided herein which have substituents on the B-ring and/or D-ring side chain and optionally on the hydroxy group of the A-ring.
Synthesis of 3- and 21-monosulfates of [2,2,3β,4,4-2H 5]-tetrahydrocorticosteroids in the 5β-series as internal standards for mass spectrometry
Ikegawa, Shigeo,Nagae, Kaori,Mabuchi, Takayuki,Okihara, Rika,Hasegawa, Maki,Minematsu, Toshie,Iida, Takashi,Mitamura, Kuniko
experimental part, p. 1232 - 1240 (2011/11/06)
The 3- and 21-monosulfates of pentadeuterated 5β- tetrahydrocorticosteroides were synthesized, starting from cortisol and 11-deoxycotisol. The principal reactions used were (1) perdeuteration of the methylene groups adjacent to the 3-oxo group of 17,20:20,21-bismethylendioxy- 5β-3-ketosteroids with NaOD in CH3OD followed by stereoselective reduction with NaBD4, (2) sulfation of hydroxy groups with sulfur trioxide-trimethylamine complex, and (3) removal of the 17,20:20,21- bismethylendioxy group with hydrogen fluoride. The labeled compounds can be used as internal standards in liquid chromatography/mass spectrometry assays for clinical and biochemical studies.
NOVEL [3,2-c] HETEROARYL STEROIDS AS GLUCOCORTICOID RECEPTOR AGONISTS, COMPOSITIONS AND USES THEREOF
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Page/Page column 99, (2010/12/31)
The present invention provides compounds of Formula (I), and pharmaceutically acceptable salts, solvates, esters, prodrugs, tautomers, or isomers of said compounds), having the general structure: Formula (I) wherein L, R1, R2, R
Synthesis of novel arylpyrazolo corticosteroids as potential ligands for imaging brain glucocorticoid receptors
Wuest, Frank,Carlson, Kathryn E.,Katzenellenbogen, John A.
, p. 177 - 191 (2007/10/03)
Corticosteroids regulate a variety of essential physiological functions, such as mineral balance and stress. The great interest in these steroids, especially the glucocorticoids, stems from roles they are thought to play in neuropsychiatric disorders, suc
Total Synthesis of Cortisol: Application to Selective Deuteriation at C-1 and C-19
Minagawa, Kazuo,Furuta, Takashi,Kasuya, Yasuji,Fujino, Akiharu,Avery, Mitchell A.,Tanabe, Masato
, p. 587 - 592 (2007/10/02)
An 11-step total synthesis of cortisol and its application to selective deuteriation at the 19-methyl and the C-1 positions is described.The dihydroxy acetone group at C-17 of prednisone (3) was protected as the bismethylenedioxy derivative (4) and degraded to the ring C/D fragment, oxoindanylpropionic acid (2), by Birch reduction followed by ozonolysis.The reaction of deuterioisopropenyl anion with compound (2) followed by dehydration, cyclisation, and osonolysis produced -4,5-seco-17α,20;20,21-bismethylenedioxypregnane-3,5,11-trione .Cyclisation of (16a) in KOH-MeOH affordedthe bismethylenedioxy cortisone (17), wich upon reduction with KBH4 gave the desired (2)H5 cortisol (19).
