4588-81-2

Usage

InChI:InChI=1/C21H29BrO3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(25-19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18H,3-10,12H2,1-2H3/t15-,16-,17-,18?,20-,21-/m0/s1

Upstream product

• 22118-09-8 2-bromoacetyl chloride 
• 58-22-0 testosterone 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 1255-49-8 testosterone 17β-phenylpropionate 
• 131447-69-3 testosterone triphenylphosphoranylideneacetate 

Relevant academic research and scientific papers

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

Testosterone prodrugs for improved drug delivery

Compositions and methods are provided for enhanced transdermal electrotransport of 17-hydroxy sterol compounds, including testosterone. The parent sterols are modified at the 17-hydroxy position by covalent attachment of a charged chemical modifier. The chemical modifier provides the parent sterol with enhanced transport properties and is hydrolyzed under physiological conditions to release the active parent compound. The composition comprises a 17-hydroxy sterol/chemical modifier complex, more generally represented by the formula (sterol--O--)C(O)--R--N(R1)(R2)(R3)+. The portion of the complex derived from the chemical modifier is indicated by "C(O)--R--N(R1)(R2)(R3)+ ", where N(R1)(R2)(R3)+ represents a quaternary ammonium group and R1, R2, and R3 are independently selected from the group consisting of lower alkyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroalkyl, and heteroarylalkyl; or R1 and R2 together with the nitrogen to which they are attached form a substituted heterocycle and R3 is lower alkyl, and R is a linking moiety, linking the (sterol--O)--C(O)-- to the nitrogen atom.

Long-acting contraceptive agents: testosterone esters of unsaturated acids

The synthesis of 13 new esters of testosterone is described, with the esterifying acids bearing acetylenic, olefinic, or polyunsaturated functions in the chain, for evaluation as long-acting androgens.

Brain-specific drug delivery

The subject compounds, which are adapted for the site-specific/sustained delivery of centrally acting drug species to the brain, are: (a) compounds of the formula wherein [D] is a centrally acting drug species, and [DHC] is the reduced, biooxidizable, blood-brain barrier penetrating lipoidal form of a dihydropyridine pyridinium salt redox carrier, with the proviso that when [DHC] is STR1 wherein R is lower alkyl or benzyl and [D] is a drug species containing a single NH2 or OH functional group, the single OH group when present being a primary or secondary OH group, said drug species being linked directly through said NH2 or OH function group to the carbonyl function of [DHC], then [D] must be other than a sympathetic stimulant, steroid sex hormone or long chain alkanol; and (b) non-toxic pharmaceutically acceptable salts of compounds of formula (I) wherein [D] is a centrally acting drug species and [DHC] is the reduced, biooxidizable, blood-brain barrier penetrating lipoidal form of a dihydropyridine pyridinium salt redox carrier. The corresponding ionic pyridinium salt type drug/carrier entitles [D--QC]+ X- are also disclosed.

SYNTHESIS AND EVALUATION OF BROMOACETOXY 4-ANDROSTEN-3-ONES AS ACTIVE SITE-DIRECTED INHIBITORS OF HUMAN PLACENTAL AROMATASE

2α-Bromoacetoxy (II), 6-bromoacetoxy (VII and X), and 19-bromoacetoxy (XII) derivatives of androstenedione and 17β-bromoacetoxy compounds (III, IV, XIII-XVI) were synthesized as potential affinity-labeling reagents for aromatase. 6α-Bromoacetoxy derivative VII was the most potent inhibitor of human placental microsomal aromatase activity among this series.Its inhibitory activity was higher than that of the parent 6α-hydroxy compound V, although other bromoacetates showed weaker inhibition of aromatase than the corresponding alcohols.The bromoacetates (except the 6β-bromoacetate X) inhibited aromatase activity in a time-dependent manner in the absence of NADPH, and the enzyme inactivation was blocked by the addition of androstenedione to the incubates.Kinetic analysis of the time- and concentration-dependent inhibition by the 6β-bromo-17β-bromoacetoxy compound XV gave an apparent Ki of 25 μM and Kinact of 0.027 min-1.