1169-54-6Relevant articles and documents
17β-Hydroxy-11α-(3'-sulfanylpropyl)oxy-estra-1,3,5(10)-trien-3-yl sulfamate - A novel hapten structure: Toward the development of a specific enzyme immunoassay (EIA) for estra-1,3,5(10)-triene-3-yl sulfamates
Schwarz, Sigfrid,Schumacher, Matthias,Nanninga, Anita,Weber, Gisela,Thieme, Ina,Undeutsch, Bernd,Elger, Walter
, p. 460 - 471 (1999)
The title compound 17 has been synthesized for the use as hapten in the development of a competitive enzyme immunoassay for estrogen sulfamates. The synthesis started from estradiol diacetate 2. Oxyfunctionalization at C-11 to give 11α-hydroxy steroid 8 was accomplished by hydroboration/alkaline hydrogen peroxide oxidation of the 9(11)-dehydro derivative 7, which was obtained from compound 2 via 9-hydroxylation with dimethyldioxirane. After transformation of compound 8 into the allyl ether 9, the side chain was thio- functionalized at the ω-position affording the thioate 11 in two steps. Selective silylether deprotection at position 3 followed by sulfamoylation gave the sulfamate 19, which in turn was demasked at position 17 and treated with sodium borohydride/aluminum chloride to liberate the side chain thiol. Alternatively, title compound 17 was synthesized via the disulfides 13-16. For the preparation of the immunogen the title compound 17 was coupled to bovine gamma globulin in a two-step procedure using an amine and thiol specific bifunctional crosslinker. The immunization of rabbits resulted in the formation of antibodies which clearly discriminated the sulfamoylated estrogens from the non-esterified estrogens. The use of a biotinylated hapten derivative as a tracer in combination with a streptavidin-peroxidase- tetramethylbenzidine based detection system allowed the measurement of estradiol 3-sulfamate (1) in the range of about 1 to 1000 pg/well.
Synthesis of novel steroidal inhibitors of HIV-1 protease
Harburn, James J.,Loftus, Gabrielle C.,Marples, Brian A.
, p. 11907 - 11924 (2007/10/03)
The design and synthesis of potential steroidal HIV-1 protease inhibitors is described. Compounds derived from 1 [-amino-12-keto-cholanic acid derivatives show modest activity.
