6301-87-7

Usage

Uses

Used in Cancer Treatment:
(17beta)-2-aminoestra-1(10),2,4-triene-3,17-diol is used as an antineoplastic agent for the treatment of hormone-sensitive cancers such as breast and prostate cancer. Its antiangiogenic and antiproliferative properties make it a promising candidate for cancer therapy.
Used in Pharmaceutical Industry:
(17beta)-2-aminoestra-1(10),2,4-triene-3,17-diol is used as a pharmaceutical compound for the development of drugs targeting cancer cells. Its ability to induce apoptosis and inhibit cell cycle progression makes it a valuable component in the creation of novel cancer treatments.

Upstream product

• 25975-57-9 2-Nitro-4-bromo-1,3,5(10)-estratriene-3,17β-diol 
• 6298-51-7 2-Nitroestratriene-3,17beta-diol 
• 19590-55-7 2,4-dibromoestradiol 
• 5976-73-8 2-nitroestrone 
• 53-16-7 Estrone 

Downstream Products

• 362-05-0 2-Hydroxyestradiol 

Relevant academic research and scientific papers

Synthesis and conversion of primary and secondary 2-aminoestradiols into A-ring-integrated benzoxazolone hybrids and theirin vitroanticancer activity

Hybrid systems are often endowed with completely different and improved properties compared to their parent compounds. In order to extend the chemical space toward sterane-based molecular hybrids, a number of estradiol-derived benzoxazol-2-ones with combined aromatic rings were synthesizedviathe corresponding 2-aminophenol intermediates. 2-Aminoestradiol was first prepared from estrone by a two-step nitration/reduction sequence under mild reaction conditions. Subsequent reductive aminations with different arylaldehydes furnished secondary 2-aminoestradiol derivatives in good yields. The proton dissociation processes of the aminoestradiols were investigated in aqueous solution by UV-visible spectrophotometric titrations to reveal their actual chemical forms at physiological pH. The determined pK1and pK2values are attributed to the+NH3or+NH2R and OH moieties, and both varied by the different R substituents of the amino group. Primary and secondary 2-aminoestradiols were next reacted with carbonyldiimidazole as a phosgene equivalent to introduce a carbonyl group with simultaneous ring-closure to give A-ring-fused oxazolone derivatives in high yields. The novel aminoestradiols and benzoxazolones were subjected toin vitrocytotoxicity analysis and were found to exert cancer cell specific activity.

NOVEL AND REGIOSPECIFIC SYNTHESIS OF 2-AMINO ESTROGENS VIA ZINCKE NITRATION

An efficient synthesis of 2-aminoestrone (14), 2-aminoestradiol (15), 2-amino-16α-hydroxyestrone (16) and 2-aminoestriol (17) is described. 2,4-Dibromo estrogens 1 - 4 were regiospecifically converted to the corresponding 2-nitro-4-bromo derivatives 5 - 8 in quantitative yields, with Zincke nitration using sodium nitrite.Catalytic hydrogenation of the 2-nitro-4-bromides 5 - 8 over palladium-on-charcoal gave directly the desired 2-amino estrogens 14 - 17 in high yields.The 2-amino compounds 15 and 17 were also obtained by the reduction of the corresponding 2-nitro-4-bromides 6 and 8 with sodium borohydride in the presence of palladium chloride.