TY - JOUR
T1 - A crystallographic investigation of ergolines
AU - Zhu, Naijue
AU - Johnson, L’aurelle
AU - White, Julian
AU - Klein-Stevens, Cheryl L.
N1 - Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
PY - 2002
Y1 - 2002
N2 - The X-ray crystal structures of three ergoline derivatives have been completed and are reported herein. These include mesulergine hydrochloride (III), pergolide methanesulfonate (IV), and dihydroergocriptine hydrate (V). These molecules show dopamine agonist activity at the D2 receptor. These three-dimensional structures were compared to structurally similar molecules with similar pharmacological activity. It was found that ergoline derivatives have rigid fused-ring systems with substituents that can exist in a variety of conformations. The ergoline structures reported here have structural features consistent with other active dopamine agonists. Crystallographic data: (III) C18H26EN4O2S·HCl, monoclinic space group P21, a = 12.183(2) Å, b = 6.174(2) Å, c = 13.649(2) Å, β = 105.55(1)°, Z = 2, final R = 0.071 for 2293 observed reflections [I > 3σ(I)]; (IV) C19H 27N2S·CH3SO3, monoclinic space group P21, a = 8.455(4) Å, b = 29.868(4) Å, c = 8.957(6) Å, β= 111.95(5)°, Z = 4, final R = 0.055 for 3836 observed reflections; (V) C32H43N5O 5·H2O, monoclinic space group P21, a = 12.403(2) Å, b = 18.103(3) Å, c = 15.418(3) Å, β = 113.04(2)°, Z = 4, final R = 0.058 for 3208 observed reflections.
AB - The X-ray crystal structures of three ergoline derivatives have been completed and are reported herein. These include mesulergine hydrochloride (III), pergolide methanesulfonate (IV), and dihydroergocriptine hydrate (V). These molecules show dopamine agonist activity at the D2 receptor. These three-dimensional structures were compared to structurally similar molecules with similar pharmacological activity. It was found that ergoline derivatives have rigid fused-ring systems with substituents that can exist in a variety of conformations. The ergoline structures reported here have structural features consistent with other active dopamine agonists. Crystallographic data: (III) C18H26EN4O2S·HCl, monoclinic space group P21, a = 12.183(2) Å, b = 6.174(2) Å, c = 13.649(2) Å, β = 105.55(1)°, Z = 2, final R = 0.071 for 2293 observed reflections [I > 3σ(I)]; (IV) C19H 27N2S·CH3SO3, monoclinic space group P21, a = 8.455(4) Å, b = 29.868(4) Å, c = 8.957(6) Å, β= 111.95(5)°, Z = 4, final R = 0.055 for 3836 observed reflections; (V) C32H43N5O 5·H2O, monoclinic space group P21, a = 12.403(2) Å, b = 18.103(3) Å, c = 15.418(3) Å, β = 113.04(2)°, Z = 4, final R = 0.058 for 3208 observed reflections.
KW - Dopamine agonists
KW - Ergolines
KW - Mesulergine
KW - Pergolide
KW - X-ray crystallography
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U2 - 10.1023/A:1020521706309
DO - 10.1023/A:1020521706309
M3 - Article
AN - SCOPUS:1842426263
VL - 13
SP - 491
EP - 499
JO - Structural Chemistry
JF - Structural Chemistry
SN - 1040-0400
IS - 5-6
M1 - 450234
ER -