TY - JOUR
T1 - Design and synthesis of new steroid-cyclobutanone derivative
AU - Figueroa-Valverde, Lauro
AU - Diaz-Cedillo, Francisco
AU - Rosas-Nexticapa, Marcela
AU - Mendoza-Lôpez, R.
AU - Garcia-Cervera, Elodia
AU - Pool-Gômez, Eduardo
AU - Lopez-Ramos, Maria
PY - 2013
Y1 - 2013
N2 - In this study, a prednisone derivative was synthetized; the first stage involve the reaction of the compound 1 (11 -Bis-(2-amino-ethylimino)-1 7-[1 -(2-amino-ethylimino)-2-hydroxy-ethyl]- 10,1 3-dimethyl-6,7,8,9,1 0,11,1 2,13,14,15,16,1 7-dodecahydro-3H-cyclopenta[a]phe- nanthren-1 7- ol)withchloroacetyl chloride in presence of triethylamineto form2[(3-chloro-2- oxo-cyclobutyl)(1 - {3, 11 -bis-(2-[{2-[(chlorocarbonyl)amino]-ethyl}(3-chloro- 2-oxocy-clobutyl)amino]-1 7-hydroxy- 10,1 3-dimethyl-6,7,8,9, 10,11,12,13,14,15,16,1 7-dodecahydro-3H-cyclopenta[a]phenantren-1 7- yl})-2-hydroxyethyl)-amino]ethylcarbamic chloride (3). The second stage was achieved by the reaction of 3 with thiourea in methanol to form the compound 5(2-{(2-Amino-ethyl)-[1-(3,11-bis- [(2-amino-ethyl)-(3-chloro-2-oxo-cyclo- butyl)-amino]-l 7-hydroxy-l 0,1 3-dimethyl-6,7,8,9,l 0, 11,12,13,14,15,16,1 7-dode-cahydro-3H-cyclopenta[a]phenantren-l 7-yl)-2-hydroxy-ethyl]-amino}- 4-chloro-cyclobuta-none). The structure of compounds obtainedwas confirmed by elemental analysis, spectroscopy and spectrometry data. In conclusion, this method offers some advantages such as good yields, simple procedure, low cost, and ease of workup.
AB - In this study, a prednisone derivative was synthetized; the first stage involve the reaction of the compound 1 (11 -Bis-(2-amino-ethylimino)-1 7-[1 -(2-amino-ethylimino)-2-hydroxy-ethyl]- 10,1 3-dimethyl-6,7,8,9,1 0,11,1 2,13,14,15,16,1 7-dodecahydro-3H-cyclopenta[a]phe- nanthren-1 7- ol)withchloroacetyl chloride in presence of triethylamineto form2[(3-chloro-2- oxo-cyclobutyl)(1 - {3, 11 -bis-(2-[{2-[(chlorocarbonyl)amino]-ethyl}(3-chloro- 2-oxocy-clobutyl)amino]-1 7-hydroxy- 10,1 3-dimethyl-6,7,8,9, 10,11,12,13,14,15,16,1 7-dodecahydro-3H-cyclopenta[a]phenantren-1 7- yl})-2-hydroxyethyl)-amino]ethylcarbamic chloride (3). The second stage was achieved by the reaction of 3 with thiourea in methanol to form the compound 5(2-{(2-Amino-ethyl)-[1-(3,11-bis- [(2-amino-ethyl)-(3-chloro-2-oxo-cyclo- butyl)-amino]-l 7-hydroxy-l 0,1 3-dimethyl-6,7,8,9,l 0, 11,12,13,14,15,16,1 7-dode-cahydro-3H-cyclopenta[a]phenantren-l 7-yl)-2-hydroxy-ethyl]-amino}- 4-chloro-cyclobuta-none). The structure of compounds obtainedwas confirmed by elemental analysis, spectroscopy and spectrometry data. In conclusion, this method offers some advantages such as good yields, simple procedure, low cost, and ease of workup.
KW - Chloroacetyl chloride
KW - Prednisone
KW - Thiourea
KW - Triethylamine
UR - http://www.scopus.com/inward/record.url?scp=84894253399&partnerID=8YFLogxK
U2 - 10.13005/ojc/290309
DO - 10.13005/ojc/290309
M3 - Artículo
SN - 0970-020X
VL - 29
SP - 921
EP - 925
JO - Oriental Journal of Chemistry
JF - Oriental Journal of Chemistry
IS - 3
ER -