Enantioselective recognition of 1,2-aminoalcohols by the binol receptor dangled with pyrrole-2-carboxamide and its analogues

被引：14

作者：

Nandhakumar, Raju ^{[2
]}

Soo, Ahn Yun ^{[2
]}

Hong, Jooyeon ^{[1
]}

Ham, Sihyun ^{[1
]}

Kim, Kwan Mook ^{[2
]}

机构：

[1] Sookmyung Womens Univ, Dept Chem, Seoul 140742, South Korea

[2] Ewha Womans Univ, Biochiral Lab, Dept Chem & Nano Sci, Seoul 120750, South Korea

来源：

TETRAHEDRON | 2009年 / 65卷 / 03期

关键词：

Enantioselective recognition; Aminoalcohol; Pyrrole-2-carboxamide; AMINO-ACID DERIVATIVES; ASSISTED HYDROGEN-BONDS; CHIRAL RECOGNITION; ENANTIOMERIC RECOGNITION; MOLECULAR RECOGNITION; ALCOHOLS; THERMOCHEMISTRY; EXTRACTION; WATER;

D O I：

10.1016/j.tet.2008.11.022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel binol receptor with pyrrole-2-carboxamide moiety and its analogues have been designed, synthesized, and used to enantioselectively recognize 1,2-aminoalcohols via multiple hydrogen bonding. The pyrrole-based binol receptor showed the highest enantioselectivity among the four receptors as determined by the H-1 NMR. The DFT calculation strongly supports complementary hydrogen bonding between alcoholic -OH and Pyrrolyl groups. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：666 / 671

页数：6

共 1 条

[1] Old and New Pharmacology: Positive Allosteric Modulation of the α7 Nicotinic Acetylcholine Receptor by the 5-Hydroxytryptamine2B/C Receptor Antagonist SB-206553 (3,5-Dihydro-5-methyl-N-3-pyridinylbenzo[1,2-b:4,5-b′]di pyrrole-1(2H)-carboxamide)
Dunlop, John
Lock, Tim
Jow, Brian
Sitzia, Fabrizio
Grauer, Steven
Jow, Flora
Kramer, Angela
Bowlby, Mark R.
Randall, Andrew
Kowal, Dianne
Gilbert, Adam
Comery, Thomas A.
LaRocque, James
Soloveva, Veronica
Brown, Jon
Roncarati, Renza
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2009, 328 (03): : 766 - 776

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