140421-65-4

Basic information

• Product Name: 6-hydroximino-4-androstene-3,17-dione
• Synonyms: 6-hydroximino-4-androstene-3,17-dione
• CAS NO: 140421-65-4
• Molecular Formula: C₁₉H₂₅NO₃
• Molecular Weight: 0
• Mol File: 140421-65-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Refractive Index: 1.673
• CAS DataBase Reference: 6-hydroximino-4-androstene-3,17-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 6-hydroximino-4-androstene-3,17-dione(140421-65-4)
• EPA Substance Registry System: 6-hydroximino-4-androstene-3,17-dione(140421-65-4)

Safety Data

• Hazardous Substances Data: 140421-65-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H25NO3/c1-18-7-5-11(21)9-15(18)16(20-23)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14,23H,3-8,10H2,1-2H3/t12-,13-,14-,18+,19-/m0/s1

Upstream product

• 140421-63-2 (E)-6-(hydroxyimino)androst-4-ene-3β,17β-diol 
• 633-34-1 androst-4,6-diene-3,17-dione 
• 952747-80-7 3,3:17,17-bis(ethylendioxy)-5α-hydroxy-6-(E)-hydroxyiminoandrostane 
• 3044-38-0 3β,17β-diacetoxy-androst-4-en-6-one 
• 39933-12-5 3β,5,17β-trihydroxy-5α-androstan-6-one 3β,17β-diacetate 
• 140421-62-1 3β,17β-dihydroxyandrostan-4-en-6-one 
• 1588513-84-1 3β,17β-diacetoxy-6E-hydroximino-androst-4-ene 
• 853-23-6 prasterone acetate 
• 1639-43-6 androstenediol-3-acetate 
• 2099-26-5 androstenediol-3,17-diacetate 
• 97948-19-1 3b,17b-diacetoxy-5a-hydroxy-androstan-6-one 

Relevant articles and documents

Synthesis and antiproliferative activity of some androstene oximes and their O-Alkylated derivatives

In order to study the structure-activity relationship with respect to the cytotoxicity of steroidal oximes, several 6E-hydroximino-4-ene steroids and their O-alkylated derivatives were synthesized. The oxime ethers were solidified and purified by preparing their corresponding oxalate salts. The new derivatives as well as some previously synthesized ones were evaluated for in vitro antineoplastic activity against a panel of 60 cancer cell lines at 10 μM. The oximes and oxime ethers were found to have moderate to good antiproliferative activity against various leukemia, colon, melanoma, and renal cancer cell lines. Several 6E-hydroximino-4-ene steroids and their O-alkylated derivatives were synthesized. Their structure-activity relationship with respect to the cytotoxicity of steroidal oximes was studied. The oximes and oxime ethers were found to have moderate-to-good antiproliferative activity against various leukemia, colon, melanoma, and renal cancer cell lines.

Synthesis of cytotoxic 6E-hydroximino-4-ene steroids: Structure/activity studies

In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioctivity than other structural motifs.

Synthesis of 6-Hydroximino-3-oxo Steroids, aNew Class of Aromatase Inhibitor

(E)-3β,17β-Dihydroxyandrost-4-en-6-one oxime has been converted into (E)-6-hydroximinotestosterone and (E)-6-hydroximinoandrost-4-ene-3,17-dione by chemical methods, and into (E)-6-hydroximinoandrosta-1,4-diene-3,17-dione by biotransformation using Arthrobacter simplex ATCC 6946.