TY - JOUR
T1 - Theoretical design of dendrimeric fractal patterns for the encapsulation of a family of drugs
T2 - salicylanilides
AU - Soto-Castro, Delia
AU - Evangelista-Lara, Aurelio
AU - Guadarrama, Patricia
PY - 2006/12/18
Y1 - 2006/12/18
N2 - Four dendrimeric fragments (FPs) were designed to encapsulate a family of drugs known as salicylanilides (importantly acaricides/anthelminthics), mainly by H-bonding. The experimental system: PAMAM-DBNP (2,6-dibromo-4-nitrophenol) was also calculated as a reference. The efficiency of encapsulation is related to the presence of functional groups like amide and alcohol, the flexibility of the aliphatic chains, and efficient pre-organization before the encapsulation. All the geometry optimizations were carried out at DFT/LAV3P* level of theory. Two hybrid functionals were tested: B3LYP and BHandHLYP. The last one shows improved performance in describing close contacts as well as better agreement with experimental observations for the complex PAMAM-BDNP.
AB - Four dendrimeric fragments (FPs) were designed to encapsulate a family of drugs known as salicylanilides (importantly acaricides/anthelminthics), mainly by H-bonding. The experimental system: PAMAM-DBNP (2,6-dibromo-4-nitrophenol) was also calculated as a reference. The efficiency of encapsulation is related to the presence of functional groups like amide and alcohol, the flexibility of the aliphatic chains, and efficient pre-organization before the encapsulation. All the geometry optimizations were carried out at DFT/LAV3P* level of theory. Two hybrid functionals were tested: B3LYP and BHandHLYP. The last one shows improved performance in describing close contacts as well as better agreement with experimental observations for the complex PAMAM-BDNP.
KW - DFT calculations
KW - Dendrimers
KW - H-bonding
KW - Host-guest complexes
KW - Salicylanilides
UR - http://www.scopus.com/inward/record.url?scp=33751217185&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2006.08.053
DO - 10.1016/j.tet.2006.08.053
M3 - Artículo
SN - 0040-4020
VL - 62
SP - 12116
EP - 12125
JO - Tetrahedron
JF - Tetrahedron
IS - 51
ER -