1201-73-6Relevant academic research and scientific papers
Synthesis of indolo[2,3-a]quinolizine and hexahydro-1H-indolizino[8,7-b] indole derivatives by cascade condensation, cyclization, and Pictet-Spengler reaction: An application to the synthesis of (±)-harmicine
Sanaboina, Chakrapani,Jana, Samaresh,Chidara, Sridhar,Patro, Balaram,Raolji, Gajendrasinh Balvantsinh,Eppakayala, Laxminarayana
supporting information, p. 5027 - 5029,3 (2020/07/30)
Synthesis of indole alkaloid related compounds using Schiff base formation, intramolecular cyclization (or N-alkylation), and Pictet-Spengler reaction as a cascade one pot condensation has been reported. The cascade chemistry has been applied to the synthesis of (±)-harmicine as a key step.
Discovery of novel non-peptide CCR1 receptor antagonists
Ng, Howard P.,Karen, May,Bauman, John G.,Ghannam, Ameen,Islam, Imadul,Liang, Meina,Horuk, Richard,Hesselgesser, Joseph,Snider, R. Michael,Perez, H. Daniel,Morrissey, Michael M.
, p. 4680 - 4694 (2007/10/03)
Ligands for the CCR1 receptor (MIP-1α and RANTES) have been implicated in a number of chronic inflammatory diseases, most notably multiple sclerosis and rheumatoid arthritis. Because these ligands share a common receptor, CCR1, we sought to discover antagonists for this receptor as an approach to treating these disorders. A novel series of 4-hydroxypiperidines has been discovered by high throughput screening (HTS) which potently inhibits the binding of MIP-1α and RANTES to the recombinant human CCR1 chemokine receptor. The structure-activity relationships of various segments of this template are described as the initial HTS lead 1 was optimized synthetically to the highly potent receptor antagonist 6s. This compound has been shown to have at least 200-fold selectivity for inhibition of CCR1 over other human 7- TM receptors, including other chemokine receptors. In addition, data obtained from in vitro functional assays demonstrate the functional antagonism of compound 6s and structurally related analogues against the CCR1 receptor in a concentration dependent manner. The discovery and optimization of potent and selective CCR1 receptor antagonists represented by compound 6s potentially represent a novel approach to the treatment of chronic inflammatory diseases.
Intramolecular Nucleophilic Acyl Substitution Reactions of Halo-Substituted Esters and Lactones. New Applications of Organosamarium Reagents
Molander, Gary A.,McKie, Jeffrey A.
, p. 7216 - 7227 (2007/10/02)
Intramolecular nucleophilic acyl substitution reactions involving a broad range of halo substituted carboxylic acid derivatives have been accomplished in excellent yield employing samarium(II) iodide as the reductive coupling agent.Although particular substrates cyclized most effectively in THF in the presence of tripiperidinophosphine oxide, carboxylic acid esters, the focus of this report, cyclize equally well without such an additive in the presence of a catalytic quantity of iron(III) complexes.Thus a comprehensive series of halo substituted esters were cyclized in excellent yield to the corresponding 4-, 5-, and 6 -membered carbocycles.The reaction is extremely mild and selective as demonstrated by experiments wherein alkyl chlorides, acetals, and olefins remain completely intact under the reaction conditions.In addition to introducing a convenient procedure for preparing stereodefined spirocyclic systems, a new ring expansion sequence has been developed that appears extremely general for the preparation of various ring systems.
