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3β-tosyloxyandrost-5-ene-17-one is a chemical compound derived from the androstane steroid family, characterized by the presence of a tosyloxy group (tosylate) at the 3β position and a ketone group at the 17 position. 3β-tosyloxyandrost-5-ene-17-one is structurally similar to testosterone, a naturally occurring hormone, but with a modified side chain and an additional functional group. It is often used in organic synthesis and as an intermediate in the preparation of various steroidal compounds, including pharmaceuticals and other bioactive molecules. The tosyloxy group can be used as a protecting group in chemical reactions, allowing for selective functionalization of the steroidal core.

2719-96-2

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2719-96-2 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 2719-96-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,7,1 and 9 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2719-96:
(6*2)+(5*7)+(4*1)+(3*9)+(2*9)+(1*6)=102
102 % 10 = 2
So 2719-96-2 is a valid CAS Registry Number.

2719-96-2Relevant academic research and scientific papers

Catalytic cyclometallation in steroid chemistry VI: Targeted synthesis of hybrid molecules based on steroids and tetradeca-5Z,9Z-diene-1,14-dicarboxylic acid and study of their antitumor activity

D'yakonov, Vladimir A.,Tuktarova, Regina A.,Dzhemileva, Lilya U.,Ishmukhametova, Svetlana R.,Yunusbaeva, Milyausha M.,Dzhemilev, Usein M.

, p. 6 - 13 (2018)

Hybrid molecules based on a number of steroids (cholesterol, pregnenolone, androsterone) and 1,14-tetradeca-5Z,9Z-dienedicarboxylic acid linked via mono- and diethylene glycol spacers were synthesized for the first time and studied for antitumor activity in vitro. The acid was prepared using catalytic cyclomagnesiation of oxygenated 1,2-dienes with Grignard reagent in the presence of Cp2TiCl2 as the key synthetic step. Using flow cytometry, the new molecules were shown for the first time to be efficient apoptosis inducers in the HeLa, Hek293, U937, Jurkat, and K562 cell cultures and to have dose-dependent effect on the S and G2 phases of the cell cycle.

Experimental evidence for enzyme-enhanced coupled motion/quantum mechanical hydrogen tunneling by ketosteroid isomerase

Wilde, Thomas C.,Blotny, Grzegorz,Pollack, Ralph M.

, p. 6577 - 6585 (2008)

Although there are considerable data demonstrating that quantum mechanical hydrogen tunneling (HT) occurs in both enzymatic and nonenzymatic systems, little data exist that address the question of whether enzymes enhance the amount of HT relative to the c

COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS

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Paragraph 0895, (2021/01/23)

Provided herein is a compound of Formula (1-I): or a pharmaceutically acceptable salt thereof, wherein R2a, R2b, R3, R4a, R4b, R5, R6a, R6b, R11a, R11b

CYP11B, CYP17, AND/OR CYP21 INHIBITORS

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Page/Page column 201, (2012/06/30)

Provided herein are inhibitors of CYP11B, CYP17, and/or CYP21 enzymes of Formula (Z), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), or (XVII). Also described herein are pharmaceutical compositions that include at least one compound described herein and the use of a compound or pharmaceutical composition described herein to treat androgen-dependent diseases, disorders and conditions. Formula (Z)

Synthesis, antiproliferative activity, acute toxicity and assessment of the antiandrogenic activities of new androstane derivatives

Dhingra, Neelima,Bhardwaj,Mehta, Neeraj,Mukhopadhyay, Tapas,Kumar, Ashok,Kumar, Manoj

experimental part, p. 1055 - 1063 (2012/07/28)

A number of 17-oxo-5-androsten-3β-yl esters (9a-9f) and 3β-alkoxy-5-androsten-17-ones (11a-11e) were synthesized from commercially available (25R)-5-spirosten-3β-ol (Diosgenin) (4) as starting material. The synthesized compounds were evaluated for their antiproliferative activity against the prostate-specific cancer cell line DU-145, acute toxicity and effect on serum androgen levels, and compared with finasteride as positive control. Some of the compounds exhibited better cytotoxicity and antiandrogenic activity than the reference control. The detailed synthesis, spectroscopic data and biological activity of the synthesized compounds are reported.

AMINO DERIVATIVES OF ANDROSTANES AND ANDROSTENES AS MEDICAMENTS FOR CARDIOVASCULAR DISORDERS

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Page/Page column 49-50, (2011/04/14)

Compounds of formula (I) wherein: the groups are as defined in the description, are useful for the preparation of medicaments for the treatment of cardiovascular disorders, in particular heart failure and hypertension. The compounds are inhibitors of the enzymatic activity of the Na+, K+-ATPase. Said compounds are used for the preparation of a medicament for the treatment of a disease caused by the hypertensive effects of endogenous ouabain, such as renal failure progression in autosomal dominant polycystic renal disease (ADPKD), preeclamptic hypertension and proteinuria and renal failure progression in patients with adducin polymorphisms.

Total synthesis of candicanoside A, a rearranged cholestane disaccharide, and its 4″-O-(p-methoxybenzoate) congener

Tang, Pingping,Yu, Biao

body text, p. 259 - 269 (2009/06/21)

Candicanoside A (1) and its 4″-O-(p-methoxybenzoate) derivative 2 are congeners of the novel 24(23→22)abeo-cholestane glycosides that occur in the genus Ornithogalum indigenous to Southern Africa and have remarkable cytostatic activities. These two saponi

AMINO DERIVATIVES OF ANDROSTANES AND ANDROSTENES AS MEDICAMENTS FOR CARDIOVASCULAR DISORDERS

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Page/Page column 164, (2008/06/13)

Compounds of formula (I) wherein:the groups are as defined in the description, are useful for the preparation of medicaments for the treatment of cardiovascular disorders, in particular heart failure and hypertension. The compounds are inhibitors of the enzymatic activity of the Na+,K+-ATPase. Said compounds are used for the preparation of a medicament for the treatment of a disease caused by the hypertensive effects of endogenous ouabain, such as renal failure progression in autosomal dominant polycystic renal disease (ADPKD), preeclamptic hypertension and proteinuria and renal failure progression in patients with adducin polymorphisms.

Reactivity of hydroxy and keto groups on C-6 and C-17 of 3α,5α-cycloandrostanes

Kovganko,Kashkan

, p. 47 - 51 (2007/10/03)

Convenient methods for preparing several 3α,5-cycloandrostanes have been developed in order to synthesize the phytoecdysteroid rubrosterone. Certain of their chemical transformations were studied.

Imprinted polymers as protecting groups for regioselective modification of polyfunctional substrates

Alexander, Cameron,Smith, Craig R.,Whitcombe, Michael J.,Vulfson, Evgeny N.

, p. 6640 - 6651 (2007/10/03)

Imprinted polymers were prepared using a functional monomer derived from boronophthalide and a number of steroid templates bearing spatially separated hydroxyl groups. The cooperative nature of the binding interaction was demonstrated in polymers imprinted with androst-5-ene-3β,17β-diol and its structural analogues. The stoichiometry and kinetics of binding were probed using IR spectroscopy, selective solvent extractions, and chemical modification experiments. The feasibility of using imprinted polymers as reusable protecting groups was established by the regioselective acylation of trihydroxysteroids bound to polymers imprinted with structurally related diols. In polymers prepared with tert-butyl ester templates "matched" to the substrate, regioselectivities as high as 23.1:1 (24-acetate:3-acetate) in the monoester products (65% of recovered material) were seen. In the "unmatched" case, the ratio fell to 5.4:1; however, in functionally identical control polymers, imprinted with ethylene glycol, the regioselectivity was completely reversed (1:100), and only poor yields of monoesters (13%) were obtained.

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