68981-85-1Relevant academic research and scientific papers
Identification and characterization of m1 selective muscarinic receptor antagonists1
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.
, p. 356 - 363 (1999)
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
Nicotinic acid adenine dinucleotide phosphate analogues containing substituted nicotinic acid: Effect of modification on Ca2+ release
Jain, Pooja,Slama, James T.,Perez-Haddock, Leroy A.,Walseth, Timothy F.
experimental part, p. 7599 - 7612 (2011/02/22)
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.
Convergent and Efficient Synthesis of Spiro
Rosenberg, Saul H.,Rapoport, Henry
, p. 56 - 62 (2007/10/02)
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.
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
Hauck, Albert E.,Giam, C. S.
, p. 2227 - 2232 (2007/10/02)
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
Substitutions on Pyridines Activated by Oxazolines via Nucleophilic Additions or Metalation-Alkylation
Meyers, A. I.,Gabel, Richard A.
, p. 2633 - 2637 (2007/10/02)
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.
Regioselective Nucleophilic Addition of Organolithium Compounds to 3-(4,4-Dimethyloxazolin-2-yl)pyridine
Hauck, Albert E.,Giam, Choo-Seng
, p. 2070 - 2076 (2007/10/02)
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-
