TY - JOUR
T1 - Design and synthesis of two chrysene derivatives using estrone and androsterone as chemical tools
AU - Figueroa-Valverde, Lauro
AU - Diaz-Cedillo, Francisco
AU - Hau-Heredia, Lenin
AU - Rosas-Nexticapa, Marcela
AU - Otto-Ortega, Benjamin
AU - Garcia-Cervera, Elodia
AU - Pool-Gomez, Eduardo
AU - Lopez-Ramos, Maria
N1 - Publisher Copyright:
© 2016 Bentham Science Publishers.
PY - 2016/5/1
Y1 - 2016/5/1
N2 - Background: Several crysene derivatives have been prepared using different protocols; however some require special reagents and conditions. The aim of study involved the synthesis of two crysene,derivative using androsterone and estrone as chemical tool. Methods: Crysene derivatives were prepared by a series of reactions that involve; 1) Synthesis of two isoquinolinone derivatives by reaction of androsterone or estrone with p-nitrobenzoyl azide using imidazole as catalyst; 2) Reaction of the isoquinoline derivatives with ethylenediamine to form two chrysenol using boric acid as catalyst; 3) Synthesis of chrysene-carbaldehyde derivatives via oxidation of hydroxyl groups from chrysenol derivatives with DMSO; 4) Reaction of chrysene-carbaldehyde derivatives with phenylpropanone to form two chrysene-phenylpropenone analogs; 5) Preparation of chrisene-allylic alcohol derivatives by reaction of chrysene-phenylpropenones with benzaldehyde using imidazole as catalyst; 6) Synthesis of two chrisene-dione derivatives through oxidation of chrisene-allylic alcohols with DMSO; 7) Reaction of the chrisene-diones with ethylenediamine for preparation of two diazepin-chrisene derivatives using boric acid as catalyst. The chemical structure of compounds was determined by spectroscopic and spectrometric methods. Results: The 1H NMR spectrum for the chrysene derivatives showed signals at 4.50-4.76 ppm for azepine rings and at 6.50 and 7.46-8.36 ppm for phenyl groups. Conclusion: In conclusion, in this work were prepared two crysene derivatives using several chemical techniques, which are simple procedures and very ease of workup.
AB - Background: Several crysene derivatives have been prepared using different protocols; however some require special reagents and conditions. The aim of study involved the synthesis of two crysene,derivative using androsterone and estrone as chemical tool. Methods: Crysene derivatives were prepared by a series of reactions that involve; 1) Synthesis of two isoquinolinone derivatives by reaction of androsterone or estrone with p-nitrobenzoyl azide using imidazole as catalyst; 2) Reaction of the isoquinoline derivatives with ethylenediamine to form two chrysenol using boric acid as catalyst; 3) Synthesis of chrysene-carbaldehyde derivatives via oxidation of hydroxyl groups from chrysenol derivatives with DMSO; 4) Reaction of chrysene-carbaldehyde derivatives with phenylpropanone to form two chrysene-phenylpropenone analogs; 5) Preparation of chrisene-allylic alcohol derivatives by reaction of chrysene-phenylpropenones with benzaldehyde using imidazole as catalyst; 6) Synthesis of two chrisene-dione derivatives through oxidation of chrisene-allylic alcohols with DMSO; 7) Reaction of the chrisene-diones with ethylenediamine for preparation of two diazepin-chrisene derivatives using boric acid as catalyst. The chemical structure of compounds was determined by spectroscopic and spectrometric methods. Results: The 1H NMR spectrum for the chrysene derivatives showed signals at 4.50-4.76 ppm for azepine rings and at 6.50 and 7.46-8.36 ppm for phenyl groups. Conclusion: In conclusion, in this work were prepared two crysene derivatives using several chemical techniques, which are simple procedures and very ease of workup.
KW - Allyl alcohol
KW - Androsterone
KW - Crysene
KW - Estrone
KW - Isoquinoline
UR - http://www.scopus.com/inward/record.url?scp=84964810658&partnerID=8YFLogxK
U2 - 10.2174/1570178613666160128232738
DO - 10.2174/1570178613666160128232738
M3 - Artículo
SN - 1570-1786
VL - 13
SP - 237
EP - 248
JO - Letters in Organic Chemistry
JF - Letters in Organic Chemistry
IS - 4
ER -