68969-82-4Relevant academic research and scientific papers
Practical Chemoselective Acylation: Organocatalytic Chemodivergent Esterification and Amidation of Amino Alcohols with N-Carbonylimidazoles
Brown, Hailee,Heller, Stephen T.,Light, Christina,Medlin, Abigail,Nelson, Hope,Richard, William
supporting information, p. 22818 - 22825 (2021/09/13)
Chemoselective transformations are a cornerstone of efficient organic synthesis; however, achieving this goal for even simple transformations, such as acylation reactions, is often a challenge. We report that N-carbonylimidazoles enable catalytic chemodivergent aniline or alcohol acylation in the presence of pyridinium ions or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), respectively. Both acylation reactions display high and broad chemoselectivity for the target group. Unprecedented levels of chemoselectivity were observed in the DBU-catalyzed esterification: A single esterification product was obtained from a molecule containing primary aniline, alcohol, phenol, secondary amide, and N?H indole groups. These acylation reactions are highly practical as they involve only readily available, inexpensive, and relatively safe reagents; can be performed on a multigram scale; and can be used on carboxylic acids directly by in situ formation of the acylimidazole electrophile.
A green method for selective acetylation of primary alcohols using ethyl acetate and solid potassium carbonate
Mallesha,Rao, S. Prahlada,Suhas,Gowda, D. Channe
experimental part, p. 536 - 539 (2011/11/30)
A simple and selective acetylation of primary alcohols in the presence of other reactive functionalities such as secondary alcohol, phenol, acetonide and amine is described using mild ethyl acetate as the acetyl-transfer agent and solid potassium carbonate as the catalyst.
HALOETHYL UREA COMPOUNDS AND THE USE THEREOF TO ATTENUATE, INHIBIT OR PREVENT CANCER CELL MIGRATION
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Page 81, (2010/02/09)
The present invention provides haloethyl urea compounds as described in Formula (I) and their use as therapeutic agent in the attenuation, inhibition, or prevention of cancer cell migration and cancer cell proliferation.
Discovery of 1,5-benzodiazepines with peripheral cholecystokinin (CCK-A) receptor agonist activity (II): Optimization of the C3 amino substituent
Hirst, Gavin C.,Aquino, Christopher,Birkemo, Lawrence,Croom, Dallas K.,Dezube, Milana,Dougherty Jr., Robert W.,Ervin, Gregory N.,Grizzle, Mary K.,Henke, Brad,James, Michael K.,Johnson, Michael F.,Momtahen, Tanya,Queen, Kennedy L.,Sherrill, Ronald G.,Szewczyk, Jerzy,Willson, Timothy M.,Sugg, Elizabeth E.
, p. 5236 - 5245 (2007/10/03)
Analogs of the previously reported 1,5-benzodiazepine peripheral cholecystokinin (CCK-A) receptor agonist 1 were prepared which explore substitution and/or replacement of the C-3 phenyl urea moiety. Agonist efficacy on the isolated guinea pig gallbladder (GPGB) was retained with a variety of substituted ureas and amide analogs. Three compounds were identified which were orally active in the mouse gallbladder emptying assay (MGBE). The 2-indolamide (52) and N-(carboxymethyl)-2-indolamide (54) derivatives had improved affinity for the human CCK-A receptor but reduced agonist efficacy on the GPGB. Neither indolamide was orally active in a rat feeding assay. In contrast, the (3-carboxyphenyl)urea derivative (29, GW7854) had moderately increased affinity for the human CCK-B receptor but was a potent full agonist on the GPGB and was orally active in both the MGBE and rat feeding assays. GW7854 was a full agonist (EC50 = 60 nM) for calcium mobilization on CHO K1 cells expressing hCCK-A receptors and a potent antagonist of CCK-8 (pA2 = 9.1) on CHO K1 cells expressing hCCK-B receptors. GW7854 is a potent mixed CCK-A agonist/CCK-B antagonist which is orally active in two in vivo models of CCK-A-mediated agonist activity.
