Synthesis and Evaluation of Pyrimidine Steroids as Antiproliferative Agents.
antiproliferative activity
cycloaddition reactions
heterocycle
pyrimidine
steroids
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
12 Oct 2019
12 Oct 2019
Historique:
received:
04
09
2019
revised:
30
09
2019
accepted:
11
10
2019
entrez:
17
10
2019
pubmed:
17
10
2019
medline:
19
2
2020
Statut:
epublish
Résumé
A small and focused library of steroidal non-fused and fused pyrimidines was prepared from pregnenolone acetate and diosgenin, respectively. The key step was the cycloaddition reaction of nitrogen-containing 1,3-binucleophiles with the steroidal α,β-unsaturated ketone. Urea, thiourea and guanidine reacted in a similar manner and afforded the steroidal pyrimidines in good yields. The antiproliferative tests against human tumor cell lines gave GI
Identifiants
pubmed: 31614780
pii: molecules24203676
doi: 10.3390/molecules24203676
pmc: PMC6832952
pii:
doi:
Substances chimiques
Acetates
0
Pyrimidines
0
Steroids
0
Pregnenolone
73R90F7MQ8
pyrimidine
K8CXK5Q32L
Nitrogen
N762921K75
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Conacyt-México
ID : 240329
Organisme : Spanish Government
ID : PGC2018-094503-B-C22
Références
Eur J Med Chem. 2018 Jan 1;143:21-32
pubmed: 29172080
Br J Cancer. 2003 Jun 16;88(12):1963-70
pubmed: 12799644
J Nat Prod. 2016 Mar 25;79(3):629-61
pubmed: 26852623
Mar Drugs. 2016 Dec 14;14(12):
pubmed: 27983614
Steroids. 2014 Sep;87:86-92
pubmed: 24928724
Steroids. 2016 Dec;116:13-19
pubmed: 27692994
J Natl Cancer Inst. 1991 Jun 5;83(11):757-66
pubmed: 2041050
Mar Drugs. 2018 Aug 04;16(8):null
pubmed: 30081568
J Med Chem. 2014 Dec 26;57(24):10257-74
pubmed: 25255204
ChemMedChem. 2006 Mar;1(3):323-9
pubmed: 16892367
Steroids. 2012 Jan;77(1-2):59-66
pubmed: 22061618
Steroids. 2007 May;72(5):459-65
pubmed: 17386937
Int J Biol Macromol. 2018 May;111:52-61
pubmed: 29292141
Steroids. 2014 Jun;84:46-56
pubmed: 24686206
Eur J Med Chem. 2013 Nov;69:323-30
pubmed: 24077182
J Biosci. 2007 Jun;32(4):737-46
pubmed: 17762146
Bioorg Chem. 2017 Aug;73:83-99
pubmed: 28623723
Drug Metab Dispos. 2006 Dec;34(12):1976-84
pubmed: 16997908
Int J Biol Macromol. 2012 May 1;50(4):1127-32
pubmed: 22361454