55121-08-9Relevant academic research and scientific papers
Synthesis of 3,4-dihydroisoquinolin-1-ones from N-Boc-(β-Arylethyl) carbamates via isocyanate intermediates
In, Jinkyung,Hwang, Soonho,Kim, Changhun,Seo, Jae Hong,Kim, Sanghee
, p. 965 - 971 (2013/03/14)
Mild reaction conditions for the regioselective synthesis of isoquinolin-1-ones and related fused-ring heterocycles from N-Boc-protected (β-arylethyl)carbamates are described. The reactions involved the use of Tf2O and 2-chloropyridine and isocyanates are likely to be key intermediates. The method was extended to substrates bearing less nucleophilic aryl moieties by using Lewis acid additives, such as BF3· Et2O, to enhance the Friedel-Crafts-type cyclization of the isocyanate intermediates. This method allowed the synthesis of various substituted isoquinolin-1-ones, β-carbolines, thiophene-fused ring systems and tetrahydrobenzoazepin-1-ones in good yields and with high regioselectivities. Copyright
Anticonvulsant properties of histamine H3 receptor ligands belonging to N-substituted carbamates of imidazopropanol
Sadek, Bassem,Shehab, Safa,Wiecek, Malgorzata,Subramanian, Dhanasekaran,Shafiullah, Mohamed,Kiec-Kononowicz, Katarzyna,Adem, Abdu
supporting information, p. 4886 - 4891 (2013/09/02)
Ligands targeting central histamine H3 receptors (H 3Rs) for epilepsy might be a promising therapeutic approach. Therefore, the previously described and structurally strongly related imidazole-based derivatives belonging to carbamate
New N-arachidonoylserotonin analogues with potential "dual" mechanism of action against pain
Ortar, Giorgio,Cascio, Maria Grazia,De Petrocellis, Luciano,Morera, Enrico,Rossi, Francesca,Schiano-Moriello, Aniello,Nalli, Marianna,De Novellis, Vito,Woodward, David F.,Maione, Sabatino,Di Marzo, Vincenzo
, p. 6554 - 6569 (2008/09/17)
N-Arachidonoylserotonin (AA-5-HT, 1a) is an inhibitor of fatty acid amide hydrolase (FAAH) that acts also as an antagonist of transient receptor potential vanilloid-type 1 (TRPV1) channels and is analgesic in rodents. We modified the chemical structure of 1a with the aim of developing "hybrid" FAAH/TRPV1 blockers more potent than the parent compound or obtaining analogues with single activity at either of the two targets to study the mechanism of the analgesic action of 1a. Thirty-eight AA-5-HT analogues, containing a serotonin "head" bound to a variety of lipophilic moieties via amide, urea, or carbamate functionalities, were synthesized. Unlike 1a, most of the new compounds possessed activity at only one of the two considered targets. The amides 1b and 1c of α- and γ-linolenic acid, however, showed "hybrid" activity similar to 1a. The carbamate 3f (OMDM106), although unable to antagonize TRPV1 receptors, was the most potent FAAH inhibitor in this study (IC50 = 0.5 μM). Compounds 3f and 1m (OMDM129), which exhibited activity at only FAAH or TRPV1, respectively, were 10-fold less potent than 1a at preventing formalin-induced hyperalgesia in mice.
Bronchorelaxing agents based on indol- and isoquinoline derivatives
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Page/Page column 11-13, (2010/11/25)
A compound of formula (I) and its acid addition salts, wherein R1-FIj are H, lower (CrC6) alkyl; halogen; NR5R6, wherein R5, R6 are H, lower alkyl, C2-C6 acyl, SO2R7, wherein R7 is lower alkyl, CF3, aryl, substituted aryl; CN; COR8, wherein R8 is H, OH, lower alkyl, lower alkoxy; SO2R9, wherein R9 is OR10, wherein R10 is H, lower alkyl or NRnR12, wherein R11 and R12 is H or lower alkyl; ORi3, wherein R13 is H, lower alkyl, C2-C6 acyl, C1-C8 carboxy, C1-C8 carbamoyl; X is O or S; A is H, lower alkyl; B is C1-C18 alkyl optionally substituted; M is zero or 1; with the proviso that no more than three of R1-R4 are H, for treating and preventing bronchoconstructive pulmonary disease.
Unexpected enhancement of thrombin inhibitor potency with o-aminoalkylbenzylamides in the P1 position
Rittle, Kenneth E.,Barrow, James C.,Cutrona, Kellie J.,Glass, Kristen L.,Krueger, Julie A.,Kuo, Lawrence C.,Lewis, S. Dale,Lucas, Bobby J.,McMasters, Daniel R.,Morrissette, Matthew M.,Nantermet, Philippe G.,Newton, Christina L.,Sanders, William M.,Yan, Youwei,Vacca, Joseph P.,Selnick, Harold G.
, p. 3477 - 3482 (2007/10/03)
Thrombin inhibitors incorporating o-aminoalkylbenzylamides in the P1 position were designed, synthesized and found to have enhanced potency and selectivity in several different structural classes. X-ray crystallographic analysis of compound 24 bound in the α-thrombin-hirugen complex provides an explanation for these unanticipated results.
