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1.
Bioorg Med Chem Lett ; 19(3): 597-601, 2009 Feb 01.
Article in English | MEDLINE | ID: mdl-19131247

ABSTRACT

A series of trisubstituted cyclohexanes was designed, synthesized and evaluated as CC chemokine receptor 2 (CCR2) antagonists. This led to the identification of two distinct substitution patterns about the cyclohexane ring as potent and selective CCR2 antagonists. Compound 36 exhibited excellent binding (CCR2 IC(50)=2.4 nM) and functional antagonism (calcium flux IC(50)=2.0 nM and chemotaxis IC(50)=5.1 nM).


Subject(s)
Chemistry, Pharmaceutical/methods , Receptors, CCR2/antagonists & inhibitors , Receptors, CCR2/chemistry , Binding Sites , Calcium/chemistry , Chemokine CCL2/chemistry , Chemotaxis , Cyclohexanes/chemistry , Drug Design , Humans , Inhibitory Concentration 50 , Models, Chemical , Molecular Structure , Protein Binding , Structure-Activity Relationship
2.
J Org Chem ; 69(13): 4538-40, 2004 Jun 25.
Article in English | MEDLINE | ID: mdl-15202916

ABSTRACT

Carbocyclic uracil polyoxin C (+)-2 and its alpha-epimer (-)-3 were synthesized in an efficient fashion from cis-4-(N-tert-butylcarbamoyl)cyclopent-2-en-1-ol (+/-)-7. The synthesis incorporates a concise, inexpensive chemoenzymatic synthesis of enantiopure aminocyclopentenols, a Pd(0)-catalyzed substitution reaction, and a mild reduction of an alpha-nitro ester by TiCl(3)/sodium borohydride. Significantly, this process demonstrates the synthetic utility of the versatile enantiopure aminocyclopentenol building block (-)-4.


Subject(s)
Pyrimidine Nucleosides/chemical synthesis , Uracil/analogs & derivatives , Uracil/chemical synthesis , Molecular Conformation , Stereoisomerism
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