Linked Life Data

19499574

Source:http://linkedlifedata.com/resource/pubmed/id/19499574

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
2009-11-30
pubmed:abstractText
An improved medium scale synthesis of 3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine (MTEP), a selective and potent metabotropic glutamate subtype 5 (mGlu5) antagonist, has allowed thorough characterisation of the crystal structures of the free base and the previously unreported hydrochloride (MTEP.HCl). Hirshfeld surface analysis has revealed that molecules in crystalline MTEP are weakly polar, and aggregate through nonclassical C--H...N hydrogen bonds. A strong ionic N--H(+)...Cl(-) hydrogen bond dominates the crystal packing in MTEP.HCl. Despite significant differences in the crystal packing, the molecular structures of MTEP and MTEP.HCl are very similar. The acid dissociation constants for MTEP were investigated using (1)H NMR spectroscopy. The second acid dissociation constant (pK(a2)), associated with the pyridine nitrogen, was determined to be 3.40 +/- 0.01, whilst pK(a1), associated with the thiazole nitrogen, was estimated to be 0.2. The low pK(a) values make it unlikely that MTEP is protonated in its biologically active form.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jan
pubmed:issn
1520-6017
pubmed:author
pubmed:issnType
Electronic
pubmed:volume
99
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
234-45
pubmed:meshHeading
pubmed:year
2010
pubmed:articleTitle
Physical and crystallographic characterisation of the mGlu5 antagonist MTEP and its monohydrochloride.
pubmed:affiliation
School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, Crawley, WA 6009, Australia.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't