TY - JOUR
T1 - Design and synthesis of naphthalene-pregnen derivative using some strategies
AU - Figueroa-Valverde, Lauro
AU - Díaz-Cedillo, Francisco
AU - García-Cervera, Elodia
AU - Pool-Gómez, Eduardo
AU - López-Ramos, Maria
AU - Rosas-Nexticapa, Marcela
AU - Hau-Heredia, Lenin
AU - Sarabia-Alcocer, Beatriz
AU - Marquez-Estrella, Gabriela
PY - 2016
Y1 - 2016
N2 - In this study, a naphthalene-pregnen derivative was synthesized using several strategies. The first step was achieved by the synthesis of 3,5-bis(2-naphthyloxy)benzoic acid (2) via displacement of nitro group from 3,5-dinitrobenzoic acid. In the second stage, N-(2-aminoethyl)- 3,5-bis-(naphthalen-2-yloxy)benzamide (4) was synthesized by the reaction of 2 with ethylenediamine using boric acid as catalyst. Also 4 was developed by the reaction of N-(2-aminoethyl)-3,5-dinitrobenzamide with β-naphthol in presence of dimethyl sulfoxide. Third stage, was achieved by preparation of 3,20-bis-{2-[3,5-bis-(naphthalen-2-yloxy)benzoylamino]ethylimino}pregnene (5) by the reaction of 4 with progesterone using boric acid as catalyst. Additionally 5 was prepared by the reaction of N-[2-(1-{3-[2-(2,4-dinitrobenzenecarbonylamino) ethylimino]-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren- 17-yl}-ethylideneamino)ethyl]-2,4-di-nitro-benzamidewith β-naphthol in presence of dimethyl sulfoxide. Finally, other experiment involves the synthesis of 4-chloro-1-{(2-[3,5-bis-(naphthalen-2-yloxy)benzoylamino])ethyl}-1H,2H-spiro[azetidine-3,3′-17-(4-chloro-1-methyl- 3-oxo-2-{(2-[3,5-bis-(naphthalene-2-yloxy)benzoylamino])ethyl}-2-aza-cyclobutyl)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17- tetradecahydro-1H-cyclopenta[a]phenanthren]-2-one by the reaction of 5 with chloroacetyl chloride in the presence of triethylamine. The structure of all compounds obtained was confirmed by spectroscopic and spectrometric methods.
AB - In this study, a naphthalene-pregnen derivative was synthesized using several strategies. The first step was achieved by the synthesis of 3,5-bis(2-naphthyloxy)benzoic acid (2) via displacement of nitro group from 3,5-dinitrobenzoic acid. In the second stage, N-(2-aminoethyl)- 3,5-bis-(naphthalen-2-yloxy)benzamide (4) was synthesized by the reaction of 2 with ethylenediamine using boric acid as catalyst. Also 4 was developed by the reaction of N-(2-aminoethyl)-3,5-dinitrobenzamide with β-naphthol in presence of dimethyl sulfoxide. Third stage, was achieved by preparation of 3,20-bis-{2-[3,5-bis-(naphthalen-2-yloxy)benzoylamino]ethylimino}pregnene (5) by the reaction of 4 with progesterone using boric acid as catalyst. Additionally 5 was prepared by the reaction of N-[2-(1-{3-[2-(2,4-dinitrobenzenecarbonylamino) ethylimino]-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren- 17-yl}-ethylideneamino)ethyl]-2,4-di-nitro-benzamidewith β-naphthol in presence of dimethyl sulfoxide. Finally, other experiment involves the synthesis of 4-chloro-1-{(2-[3,5-bis-(naphthalen-2-yloxy)benzoylamino])ethyl}-1H,2H-spiro[azetidine-3,3′-17-(4-chloro-1-methyl- 3-oxo-2-{(2-[3,5-bis-(naphthalene-2-yloxy)benzoylamino])ethyl}-2-aza-cyclobutyl)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17- tetradecahydro-1H-cyclopenta[a]phenanthren]-2-one by the reaction of 5 with chloroacetyl chloride in the presence of triethylamine. The structure of all compounds obtained was confirmed by spectroscopic and spectrometric methods.
KW - Benzoic acid
KW - Ethylenediamine
KW - Naphthalene
KW - Progesterone
UR - http://www.scopus.com/inward/record.url?scp=84954190810&partnerID=8YFLogxK
U2 - 10.14233/ajchem.2016.19054
DO - 10.14233/ajchem.2016.19054
M3 - Artículo
SN - 0970-7077
VL - 28
SP - 1
EP - 5
JO - Asian Journal of Chemistry
JF - Asian Journal of Chemistry
IS - 1
ER -