- Identification and characterization of m1 selective muscarinic receptor antagonists1
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A series of esters of 1,4-disubstituted tetrahydropyridine carboxylic acids (I) has been synthesized and characterized as potential ml selective muscarinic receptor antagonists. The affinity of these compounds for the five human muscarinic receptor subtyp
- Augelli-Szafran, Corinne E.,Blankley, C. John,Jaen, Juan C.,Moreland, David W.,Nelson, Carrie B.,Penvose-Yi, Jan R.,Schwarz, Roy D.,Thomas, Anthony J.
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- Nicotinic acid adenine dinucleotide phosphate analogues containing substituted nicotinic acid: Effect of modification on Ca2+ release
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Analogues of nicotinic acid adenine dinucleotide phosphate (NAADP) with substitution at either the 4- or the 5-position position of the nicotinic acid moiety have been synthesized from NADP enzymatically using Aplysia californica ADP-ribosyl cyclase or mammalian NAD glycohydrolase. Substitution at the 4-position of the nicotinic acid resulted in the loss of agonist potency for release of Ca2+-ions from sea urchin egg homogenates and in potency for competition ligand binding assays using [32P]NAADP. In contrast, several 5-substituted NAADP derivatives showed high potency for binding and full agonist activity for Ca2+ release. 5-Azido-NAADP was shown to release calcium from sea urchin egg homogenates at low concentration and to compete with [32P]NAADP in a competition ligand binding assay with an IC50 of 18 nM, indicating that this compound might be a potential photoprobe useful for specific labeling and identification of the NAADP receptor.
- Jain, Pooja,Slama, James T.,Perez-Haddock, Leroy A.,Walseth, Timothy F.
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experimental part
p. 7599 - 7612
(2011/02/22)
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- Convergent and Efficient Synthesis of Spiro
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A synthesis is presented of spiro, tricyclic analogues containing the A, N, and O rings of codeine.Two successive 1,4-additions into a pyridine residue, an intermolecular aryllithium addition followed by an intramolecular ester enolate ring closure, establish the spiro system.Reduction and finally α-methylene lactam rearrangment provide the necessary functionalization for further elaboration and C-ring closure.
- Rosenberg, Saul H.,Rapoport, Henry
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- The Addition-Elimination Mechanism in the Nucleophilic Heteroaromatic Substitution of 3-(4',4'-Dimethyl-4',5'-dihydro-oxazol-2'-yl)pyridine. Solvent Effect on the Regiochemistry of the Addition Reaction
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The nucleophilic heteroaromatic substitution of 3-(4',4'-dimethyl-4',5'-dihydro-oxazol-2'-yl)pyridine (3) with organolithium compounds has been studied.The reaction of (3) with butyl-lithium gave a mixture of the corresponding 2,3-, 3,4-, and 2,5-disubsti
- Hauck, Albert E.,Giam, C. S.
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p. 2227 - 2232
(2007/10/02)
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- Substitutions on Pyridines Activated by Oxazolines via Nucleophilic Additions or Metalation-Alkylation
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Pyridyloxazolines, derived from nicotinic acid or isonicotinic acid, have been shown to metalate at the 4- and 3-positions, respectively.These react with a variety of electrophiles to provide 4- and 3-substituted pyridines in good yield.Alternatively, 3-pyridyloxazolines, when treated with organolithium or Grignard reagents, give addition to the 4-position and provide a series of 4-substituted 1,4-dihydropyridines.
- Meyers, A. I.,Gabel, Richard A.
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p. 2633 - 2637
(2007/10/02)
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- Regioselective Nucleophilic Addition of Organolithium Compounds to 3-(4,4-Dimethyloxazolin-2-yl)pyridine
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The nucleophilic heteroaromatic addition reactions of 3-(4,4-dimethyloxazolin-2-yl)pyridine (8) with organolithium compounds as nucleophilic reagents have been investigated.Strongly nucleophilic reagents have been observed to add preferentially to the γ-
- Hauck, Albert E.,Giam, Choo-Seng
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p. 2070 - 2076
(2007/10/02)
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