978-98-3

Basic information

• Product Name: Progesterone Cyclic 20-(Ethylene Acetal)
• Synonyms: Progesterone Cyclic 20-(Ethylene Acetal);(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS NO: 978-98-3
• Molecular Formula: C₂₃H₃₄O₃
• Molecular Weight: 358.51426
• Mol File: 978-98-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 188-190 °C
• Boiling Point: 471.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.12±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: Progesterone Cyclic 20-(Ethylene Acetal)(CAS DataBase Reference)
• NIST Chemistry Reference: Progesterone Cyclic 20-(Ethylene Acetal)(978-98-3)
• EPA Substance Registry System: Progesterone Cyclic 20-(Ethylene Acetal)(978-98-3)

Safety Data

• Hazardous Substances Data: 978-98-3(Hazardous Substances Data)

Usage

Uses

Progesterone Cyclic 20-(Ethylene Acetal) is an analog of Allopregnanolone (A547100), a GABAA receptor positive allosteric modulator.

Upstream product

• 2415-36-3 (3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 108-94-1 cyclohexanone 
• 116153-06-1 20,20-ethanediyldioxy-3α,6α-bis-(toluene-4-sulfonyloxy)-5β-pregnane 
• 40148-10-5 (3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7, 8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 
• 57-83-0 Progesterone 
• 107-21-1 ethylene glycol 
• 1778-02-5 Pregnenolone acetate 
• 19316-10-0 20,20-ethanediyldioxy-5β-pregnane-3α,6α-diol 
• 145-13-1 Pregnenolone 
• 7381-30-8 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane 

Downstream Products

• 146276-33-7 (20R,23R,24S)-5α-Dinosterane 
• 146276-37-1 (20R,23R,24R)-5α-Dinosterane 
• 146276-36-0 (20R,23S,24S)-5α-Dinosterane 
• 146276-34-8 (20R,23S,24R)-5α-Dinosterane 
• 146201-25-4 Thiocarbonic acid O-phenyl ester O-[(4S,5S,8R,9S,10R,13S,14S,17S)-4,10,13-trimethyl-17-(2-methyl-[1,3]dioxolan-2-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester 
• 57-83-0 Progesterone 
• 146201-22-1 4-((phenylthio)methyl)-4-pregnene-3,20-dione 20-ethylene ketal 
• 122723-79-9 Benzoic acid 10,13-dimethyl-17-(2-methyl-[1,3]dioxolan-2-yl)-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester 

Relevant articles and documents

Progesterone-pyrazinamide compound, preparation method and anti-cancer application thereof

The invention discloses a progesterone-pyrazinamide compound, a preparation method and anti-cancer application thereof. The general structural formula of the compound is shown as a formula (I). The preparation method disclosed by the invention includes: carrying out Boc amino protection, amidation and Boc removal reaction to obtain an amino acid molecular fragment 3a-o; conducting progesterone C-20 carbonyl protection, A ring C-4 site dimethyl introduction and C-2 oxidation to synthesize an intermediate 6 containing 2, 3-o-dicarbonyl; and finally, constructing a pyrazine ring by utilizing diamino of an amino acid fragment and steroid A ring o-dicarbonyl so as to obtain a target molecule. The progesterone-pyrazinamide compound provided by the invention has inhibitory activity on breast cancer, liver cancer and prostate cancer, and especially has more remarkable inhibitory activity on prostate cancer cells.

Method for preparing high quality progesterone

The invention discloses a preparation method of high-quality progesterone, which comprises the following steps: by using pregnenolone as the raw material, sequentially carrying out ketal protection, Oppenauer oxidation and hydrolysis to obtain a progesterone crude product, and recrystalizing to obtain the high-quality progesterone of which the purity is greater than or equal to 99.7% and the single impurity content is less than 0.1%. In the ketal protection process, the pregnenolone and ethylene glycol react in the presence of an organic solvent, triethyl orthoformate and a catalyst; and in the Oppenauer oxidation process, the ketal product obtained by ketal protection reacts with cyclohexanone under reflux conditions in the presence of anhydrous toluene and aluminum isopropoxide. The purity of the prepared progesterone is greater than or equal to 99.7%, the single impurity content is less than 0.1%, and the total weight yield is greater than or equal to 82%, so the method is suitable for industrialized mass production.

Synthesis of E- And Z-isomeric progesterone 3-O-methyloximes

Isomeric E- And Z-3methoxyiminopregn 4-en-20-ones were obtained from progesterone by selective ketalization of 20-oxo group, subsequent oximation of the remaining 3-keto group, removal of the protecting group, and chromatographic separation of isomers.