72648-46-5

Usage

Uses

Used in Pharmaceutical Industry:
6-Oxo Boldione is used as an aromatase inhibitor for its ability to inhibit the aromatase enzyme, which is responsible for converting androgens to estrogens. This inhibition is crucial in the treatment of hormone-sensitive conditions and cancers, such as breast cancer.
Used in Cancer Treatment:
6-Oxo Boldione is used as an anticancer agent, particularly in the treatment of hormone receptor-positive breast cancer. By inhibiting the aromatase enzyme, it helps to reduce the levels of estrogen in the body, thereby limiting the growth and progression of cancer cells that rely on estrogen for their survival and proliferation.
Used in Hormone Therapy:
6-Oxo Boldione is used as a hormone therapy agent for managing conditions related to hormonal imbalances, such as endometriosis and certain gynecological disorders. Its aromatase inhibitory action helps to regulate hormone levels and alleviate symptoms associated with these conditions.

InChI:InChI=1/C19H22O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h5,7,9,12-14H,3-4,6,8,10H2,1-2H3/t12-,13-,14-,18+,19-/m0/s1

Upstream product

• 897-06-3 Androsta-1,4-diene-3,17-dione 
• 7745-40-6 3β-hydroxy-17,17-ethylenedioxo-5-androstene 
• 53-43-0 dehydroepiandrosterone 
• 67737-88-6 1α,3-dipyrrolidinylandrosta-3,5-dien-17-one 
• 121021-51-0 6β-hydroxymethylandrosta-1,4-diene-3,17-dione 
• 174507-19-8 17-(ethylenedioxy)-Δ⁴-3,6-androstenedione 

Relevant academic research and scientific papers

Derivatives of exemestane - Synthesis and evaluation of aromatase inhibition

The irreversible aromatase inhibitor exemestane (6) reacts with nitromethane and sodium ethanolate to yield the Michael adduct 9. The aldehyde 10 is obtained by Nef reaction of the nitro compound 9 and affords the 1,4-dihydropyridine (DHP) 11 by Hantzsch reaction using methyl β-aminocrotonate in acetic acid. The new compounds showed a reduced inhibitory potency towards aromatase (IC50 values: 9, 0.91 μM; 10, 2.5 μM; 11, 10 μM) compared to 6 (IC50 = 0.23 μM). The 1,4-DHP 11 was dehydrogenated with CAN or electrochemically (E1/2 = 1.18 V) to yield the corresponding pyridine 12.

Expeditious synthetic route to B-ring functionalised 2-oxa-steroids: Synthesis of 17-ethylenedioxy-6α-hydroxy-2-oxa-4-androsten-3-one as key synthon

The easily prepared 17-ethylenedioxy-4-androsten-3,6-dione 8 is transformed to 17-ethylenedioxy-6α-hydroxy-2-oxa-4-androsten-3-one 15 in a few steps with complete stereo- and regio-control. The hydroxylactone 15 provides an easy entry to B-ring functionalised 2-oxa-androgens for evaluation as potential aromatase inhibitors and anabolic agents.

Synthesis and aromatase inhibition by potential metabolites of exemestane (6-methylenandrosta-1,4-diene-3,17-dione)

Exemestane (6-methylenandrosta-1,4-diene-3,17-dione; FCE 24304) is an orally active irreversible aromatase inhibitor which is in phase II clinical evaluation for the potential therapy of postmenopausal breast cancer. A series of exemestane analogs, with modifications at the 6-methylene group and with additional reduction at the 17-keto group, were synthesized as potential metabolites and tested in vitro for their effect on human placental aromatase. All these new analogs were found to be less potent in inhibiting aromatase than exemestane. The most effective compound was the 17β-hydroxy- derivative (compound 2), which is 2.6-fold less potent than exemestane [50% inhibitory concentration (IC50) 69 and 27 nM, respectively]. The various C- 6 modified derivatives of the 17-oxo series were found to inhibit the aromatase enzyme in the following descending order: 6-methylene (exemestane) > 6-spirooxirane (6) > 6β-hydroxymethyl (11) > 6-hydroxymethyl (7) > 6β- carboxy (13), showing IC50 values of 27, 206, 295, 2,300, and 7,200 nM, respectively. The 17β-hydroxy analogs of some of the above mentioned compounds were also synthesized (3, 4, 12) and found to be 3-8-fold less potent than the corresponding 17-keto analogs.