103335-54-2

Basic information

• Product Name: 3-OXO-4-AZAANDROST-5-EEN-17-BETA-CARBONZUUR
• Synonyms: 3-OXO-4-AZAANDROST-5-EEN-17-BETA-CARBONZUUR;4-AZA-5-ANDROSTEN-3-ONE-17-BETA-CARBOXYLIC ACID;delta-5 aza acid;3-Oxo-4-aza-5-androstene-17b-carboxylic acid;4-aza-5-androsten-3-oxo-17β-carboxylic acid;4-Azaandrost-5-ene-17-carboxylic acid, 3-oxo-, (17β)-;1H-Indeno[5,4-f]quinoline-7-carboxylicacid, 2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-4a,6a-diMethyl-2-oxo-,(4aR,4bS,6aS,7S,9aS,9bS)-;4-aza-5-androsten-3-oxo-17beta-carboxylicacid
• CAS NO: 103335-54-2
• Molecular Formula: C₁₉H₂₇NO₃
• Molecular Weight: 317.42
• Mol File: 103335-54-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: >308℃
• Boiling Point: 541.405 °C at 760 mmHg
• Flash Point: 281.232 °C
• Appearance: /
• Density: 1.21
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.534
• Solubility: 1.27 in mg/100g standard fat at 20 ℃
• PKA: 4.79±0.60(Predicted)
• Water Solubility: 1.46mg/L
• CAS DataBase Reference: 3-OXO-4-AZAANDROST-5-EEN-17-BETA-CARBONZUUR(CAS DataBase Reference)
• NIST Chemistry Reference: 3-OXO-4-AZAANDROST-5-EEN-17-BETA-CARBONZUUR(103335-54-2)
• EPA Substance Registry System: 3-OXO-4-AZAANDROST-5-EEN-17-BETA-CARBONZUUR(103335-54-2)

Safety Data

• RIDADR: 3077
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 103335-54-2(Hazardous Substances Data)

Usage

Description

3-OXO-4-AZAANDROST-5-EEN-17-BETA-CARBONZUUR, also known as 3-Oxo-4-aza-5-androstene-17β-carboxylic acid, is an organic compound that serves as an intermediate in the synthesis of pharmaceuticals. It is characterized by its unique molecular structure, which includes an oxo group, an aza group, and an androstene backbone with a carboxylic acid at the 17β position.

Uses

Used in Pharmaceutical Industry:
3-OXO-4-AZAANDROST-5-EEN-17-BETA-CARBONZUUR is used as a key intermediate in the synthesis of 5β-Finasteride (F342030), an azasteroid and 5β-isomeric impurity of Finasteride (F342000). 3-OXO-4-AZAANDROST-5-EEN-17-BETA-CARBONZUUR plays a crucial role in the development of medications for treating various conditions, such as benign prostatic hyperplasia and androgenetic alopecia, by inhibiting the conversion of testosterone to dihydrotestosterone.

InChI:InChI=1/C19H29NO3/c1-18-9-7-13-11(12(18)4-5-14(18)17(22)23)3-6-15-19(13,2)10-8-16(21)20-15/h11-15H,3-10H2,1-2H3,(H,20,21)(H,22,23)/t11-,12-,13-,14+,15+,18-,19+/m0/s1

Upstream product

• 145-13-1 Pregnenolone 
• 73672-02-3 pregnenolone 21-pyridinium iodide 
• 302-97-6 androst-4-en-3-one-17β-carboxylic acid 
• 2681-55-2 3-oxo-androst-4-ene-17β-carboxylic acid methyl ester 
• 85541-82-8 methyl 5-androsten-3β-ol-17β-carboxylate 
• 76763-14-9 (3S,3aS,5aS,6R,9aS,9bS)-6-(2-carboxyethyl)-3a,6-dimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalene-3-carboxylic acid 

Downstream Products

• 103335-55-3 3-oxo-4-aza-5α-androstane-17β-carboxylic acid 
• 161511-08-6 (4aR,4bS,6aS,7S,9aS,9bS)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid 
• 142187-11-9 N-[(R)-1,2-Diphenylethyl]-3-oxo-4-azaandrost-5-ene-17β-carboxamide 
• 142187-06-2 N-[(S)-1,2-Diphenylethyl]-3-oxo-4-azaandrost-5-ene-17β-carboxamide 
• 142139-94-4 N,N-Dibenzyl-3-oxo-4-azaandrost-5-ene-17β-carboxamide 
• 142139-73-9 N-(1,1-diphenylethyl)-3-oxo-4-azaandrost-5-ene-17β-carboxamide 
• 142139-69-3 N-(diphenylmethyl)-3-oxo-4-azaandrost-5-ene-17β-carboxamide 
• 142139-67-1 N-(1,2-diphenylethyl)-3-oxo-4-azaandrost-5-ene-17β-carboxamide 
• 1430804-94-6 3-oxo-4-aza-5β-androstane-17β-carboxylic acid 

Relevant articles and documents

A 3-carbonyl-4-aza-5-androstene -17 β method for preparing derivatives of

The invention provides a preparation method of a 3-carbonyl-4-aza-5-androstene-17beta derivative. The preparation method comprises the following steps: suspending an A-nor-3,5-cracking-androstan-5-keto-3-carboxylic acid-17beta derivative II in an aqueous solution of ammonium acetate for performing a ring-closure reaction; cooling a reaction product; adjusting the PH value of the reaction product by using industrial ammonia water; filtering the reaction product by spinning; drying the reaction product by spinning; and washing a filter cake by using water, and drying the filter cake to obtain a 3-carbonyl-4-aza-5-androstene-17beta derivative I, wherein R in a formula II and a formula I is carbonyl, carboxylic acid, carboxylic ester, amide, acetyl, hydroxyl, alkyl, ether or chloro. The preparation method has the advantages of mild reaction condition in the absence of inorganic solvents, low requirements on equipment and pre-treatment, complete reaction, and high product purity of over 99 percent without purification; moreover, a spinning-filtered mother solution is recovered, so that the emission of three wastes is reduced greatly; in the whole reaction, used raw materials are readily available; and meanwhile, the reaction yield is high, and the preparation method is economical and environmentally friendly, and is convenient for industrial implementation.

PROCESS FOR THE PREPARATION OF 4-AZASTEROIDS

The invention relates to a process for the preparation of 4-steroids of the formula (I), R1 and R2 are independently selected from the group consisting of hydrogen, F, Cl, Br, I, C1-6-alkyl and C1-6-alkoxy, and R4 is selected from the group consisting of hydrogen, (N, N-di-C1-6-alkylamino)methyl, 2-(N,N-di-C1-6-alkylamino)ethyl, C1-6alkyl, C1-6-alkoxy, phenyl and benzyl, and Q7 represents a carbonyl oxygen atom or is R7-1 and R7-2, wherein one of R7-1 and R7-2 is hydrogen and the other is selected from the group consisting of hydrogen, F, Cl, Br, I, C1-6-alkyl and C1-6-alkoxy and R9 represents hydrogen or F, and Q11 represents a carbonyl oxygen atom or is R11-1 and R11-2, wherein one of R11-1 and R11-2 is hydrogen and the other is selected from the group consisting of hydrogen, cyano, cyano-C1-3-alkyl, acetoxy, COOH and COO-M+, wherein M+ is Na+, K+ or NH+4, and R16 is selected from the group consisting of hydrogen cyano, C1-3-alkyl, cyano-C1-3-alkyl, acetoxy, COOH and COO-M+, wherein M+ is Na+, K+ or NH+4, and COOR represents COOH or COO-M+, wherein M+ is Na+, K+ or NH+4. The three step process comprises (i) a haloform reaction of a 17-acetyl steroid converting the acetyl group into a -COOR group, (ii) subsequent ozonolysis of the A-ring and (iii) re-closure of the A-ring by reaction with an appropriate nitrogen compound of formula H2NR4 to afford a compound of formula (I) above.

Anti-AIDS agents. Part 36: 17-carboxylated steroids as potential anti-HIV agents

In our search for novel anti-HIV agents, seven 17-carboxylated steroid derivatives were synthesized and evaluated as potential anti-HIV agents. Compound 13 exhibited potent anti-HIV activity in acutely infected H9 lymphocytes with EC50 and therapeutic index values of 0.8 μM and 300, respectively.