7738-80-9Relevant academic research and scientific papers
Efficient syntheses of 17-β-amino steroids
Taylor, Scott D.,Harris, Jesse
experimental part, p. 1098 - 1102 (2011/08/22)
17β-Amino steroids such as 17β-amino-1,3,5(10)-estratrien-3-ol (1), 17β-amino-5α-androstan-3β-ol (2) and, 17β-amino- 3β-hydroxyandrost-5-ene (3) have been widely used as a key intermediates in the synthesis of a variety of biologically active steroid derivatives though concise, high yielding syntheses of these compounds has yet to be reported. 17β-Amino-1,3,5(10)-estratrien-3-ol (1) and 17β-amino-5α- androstan-3β-ol (2) were prepared in high yield by reductive amination of estrone and epiandrosterone using benzylamine and sodium triacetoxyborohydride followed by catalytic hydrogenolysis of the resulting 17β-benzylamino derivatives. Attempts to prepare 17β-amino-3β-hydroxyandrost-5-ene (3) from dehydroepiandosterone using a similar approach resulted in partial reduction of the double bond. 17β-Amino-3β-hydroxyandrost-5-ene (3) was ultimately obtained in high yield by reductive amination of dehydroepiandosterone using allylamine and sodium triacetoxyborohydride followed by removal of the allyl group from the resulting 17β-allylamino derivative with dimethylbarbituric acid and Pd(PPh3)4 as catalyst.
Oligonucleotide having enhanced binding affinity
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, (2008/06/13)
The present invention relates to an oligonucleotide or analog thereof conjugated to a molecule comprising a structure, which structure (a) is of substantially fixed conformation; (b) contains, is directly attached to, or is attached to a carbon atom that is directly attached to, an first amine; and (c) contains, is directly attached to, or is attached to an atom that is directly attached to a phosphate, a second amine, or a cationic sulfur. In a preferred embodiment, the structure consists of at least a nonaromatic cyclic portion or substituted derivative thereof. In a specific embodiment, the structure is a nonaromatic cyclic compound. In another embodiment, the molecule is a steroid. In yet another particular aspect, the structure is an aromatic compound. In another embodiment, the structure can bind to a nucleic acid sequence in a nonintercalative manner. The invention also relates to a conjugate comprising a steroid or substituted derivative thereof containing, or attached directly or through a carbon atom to, an amine, which steroid or substituted derivative is conjugated to at least one hydrogen-phosphonate and a cation; such a conjugate may be used as an intermediate in synthesis. The oligonucleotide conjugates of the invention can have a number of uses. For example, the conjugates may be used for diagnostic purposes by detecting a nucleic acid sequence.
Steroids, LIII: New Routes to Aminosteroids [1]
Szendi,Dombi,Vincze
, p. 1189 - 1196 (2007/10/03)
Steroid ketoximes were reduced with sodium tetrahydroborate in the presence of nickel chloride or molybdenum trioxide. These processes yielded 17α- and 20α- aminosteroids (1c-5c) in higher yields than common reduction methods.
STEROIDS .LIII. TRANSFORMATION OF 3β-ACETOXY-5α-ANDROSTAN-17-ONE INTO 17α- AND 17β-AMINO DERIVATIVES OF 5α-ANDROSTAN-3β-OL
Nadaraia, N. Sh.,Sladkov, V. I.,Kuleshova, L. N.,Suvorov, N. N.
, p. 481 - 485 (2007/10/02)
The epimeric 17α- and 17β-amino-5α-androstan-3β-ols were synthesized from 3β-acetoxy-5α-androstan-17-one.The configurations at the C17 atom were demonstrated by the 1H NMR method.
