TY - JOUR
T1 - Synthesis, characterization and in silico screening of potential biological activity of 17α-ethynyl-3β, 17β, 19-trihydroxyandrost-5-en acetylated derivatives
AU - Ochoa, Ma Eugenia
AU - Farfán, Norberto
AU - Labra-Vázquez, Pablo
AU - Soto-Castro, Delia
AU - Santillan, Rosa
N1 - Publisher Copyright:
© 2020 Elsevier B.V.
PY - 2021/2/5
Y1 - 2021/2/5
N2 - The synthesis of 17α-ethynyl-3β,17β,19-trihydroxyandrost-5-en derivatives diacetylated at position 3- and 19- (2a), or monoacetylated at position 3 (2b) or 19 (2c), obtained by Grignard reaction over 3β,19-diacetoxyandrost-5-en-17-one (1a), is described. The characterization (NMR, IR, HRMS) and structural analysis of the target molecules are presented, with support from SXRD diffraction studies for three derivatives and DFT computations at the B3LYP/6-31+G(d,p) level of theory, featuring Hirshfeld surface analyses and ESP computations. The impact of these structural derivatizations was further analyzed employing a theoretical evaluation of the potential biological activity of these molecules through the PASS test, envisioning a potential use of these new steroids as lipid metabolism regulators and anti-inflammatory agents.
AB - The synthesis of 17α-ethynyl-3β,17β,19-trihydroxyandrost-5-en derivatives diacetylated at position 3- and 19- (2a), or monoacetylated at position 3 (2b) or 19 (2c), obtained by Grignard reaction over 3β,19-diacetoxyandrost-5-en-17-one (1a), is described. The characterization (NMR, IR, HRMS) and structural analysis of the target molecules are presented, with support from SXRD diffraction studies for three derivatives and DFT computations at the B3LYP/6-31+G(d,p) level of theory, featuring Hirshfeld surface analyses and ESP computations. The impact of these structural derivatizations was further analyzed employing a theoretical evaluation of the potential biological activity of these molecules through the PASS test, envisioning a potential use of these new steroids as lipid metabolism regulators and anti-inflammatory agents.
KW - 19-Dehydroepidandrosterone
KW - Anti-inflammatory activity
KW - DFT
KW - Hirshfeld surface analyses
KW - X-ray
UR - http://www.scopus.com/inward/record.url?scp=85090009357&partnerID=8YFLogxK
U2 - 10.1016/j.molstruc.2020.129167
DO - 10.1016/j.molstruc.2020.129167
M3 - Artículo
AN - SCOPUS:85090009357
SN - 0022-2860
VL - 1225
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
M1 - 129167
ER -