Literature DB >> 17975906

Verification of a designed intramolecular hydrogen bond in a drug scaffold by nuclear magnetic resonance spectroscopy.

Ariane Jansma1, Qiong Zhang, Bing Li, Qiang Ding, Tetsuo Uno, Badry Bursulaya, Yi Liu, Pascal Furet, Nathanael S Gray, Bernhard H Geierstanger.   

Abstract

2D 1H-15N HMBC NMR acquired at natural abundance and DMSO titration monitored by 1D 1H NMR verified the existence of an intramolecular hydrogen bond that was designed to mimic the pyrimidinone ring of a class of kinase inhibitors. A scalar coupling across the hydrogen bond was detected in organic and aqueous solvent, suggesting a simple and general approach for testing the propensity of intramolecular hydrogen bonds to stabilize pseudo-rings in drug scaffolds.

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Year:  2007        PMID： 17975906     DOI： 10.1021/jm700983a

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  6 in total

1.  Intramolecular hydrogen bonding: a potential strategy for more bioavailable inhibitors of neuronal nitric oxide synthase.

Authors:  Kristin Jansen Labby; Fengtian Xue; James M Kraus; Haitao Ji; Jan Mataka; Huiying Li; Pavel Martásek; Linda J Roman; Thomas L Poulos; Richard B Silverman
Journal:  Bioorg Med Chem       Date:  2012-02-07       Impact factor: 3.641

2.  Development of covalent inhibitors that can overcome resistance to first-generation FGFR kinase inhibitors.

Authors:  Li Tan; Jun Wang; Junko Tanizaki; Zhifeng Huang; Amir R Aref; Maria Rusan; Su-Jie Zhu; Yiyun Zhang; Dalia Ercan; Rachel G Liao; Marzia Capelletti; Wenjun Zhou; Wooyoung Hur; NamDoo Kim; Taebo Sim; Suzanne Gaudet; David A Barbie; Jing-Ruey Joanna Yeh; Cai-Hong Yun; Peter S Hammerman; Moosa Mohammadi; Pasi A Jänne; Nathanael S Gray
Journal:  Proc Natl Acad Sci U S A       Date:  2014-10-27       Impact factor: 11.205

3.  N-N bond-forming cyclization for the one-pot synthesis of N-aryl[3,4-d]pyrazolopyrimidines.

Authors:  Lindsay E Evans; Matthew D Cheeseman; Keith Jones
Journal:  Org Lett       Date:  2012-06-26       Impact factor: 6.005

4.  B-norsteroids from Hymenoscyphus pseudoalbidus.

Authors:  Pierre F Andersson; Stina Bengtsson; Jan Stenlid; Anders Broberg
Journal:  Molecules       Date:  2012-06-25       Impact factor: 4.411

5.  Impact of stereospecific intramolecular hydrogen bonding on cell permeability and physicochemical properties.

Authors:  Björn Over; Patrick McCarren; Per Artursson; Michael Foley; Fabrizio Giordanetto; Gunnar Grönberg; Constanze Hilgendorf; Maurice D Lee; Pär Matsson; Giovanni Muncipinto; Mélanie Pellisson; Matthew W D Perry; Richard Svensson; Jeremy R Duvall; Jan Kihlberg
Journal:  J Med Chem       Date:  2014-02-26       Impact factor: 7.446

6.  Controlling Intramolecular Interactions in the Design of Selective, High-Affinity Ligands for the CREBBP Bromodomain.

Authors:  Michael Brand; James Clayton; Mustafa Moroglu; Matthias Schiedel; Sarah Picaud; Joseph P Bluck; Anna Skwarska; Hannah Bolland; Anthony K N Chan; Corentine M C Laurin; Amy R Scorah; Larissa See; Timothy P C Rooney; Katrina H Andrews; Oleg Fedorov; Gabriella Perell; Prakriti Kalra; Kayla B Vinh; Wilian A Cortopassi; Pascal Heitel; Kirsten E Christensen; Richard I Cooper; Robert S Paton; William C K Pomerantz; Philip C Biggin; Ester M Hammond; Panagis Filippakopoulos; Stuart J Conway
Journal:  J Med Chem       Date:  2021-07-13       Impact factor: 7.446
  6 in total

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