5336-57-2Relevant articles and documents
Palladium-Catalyzed Distal m-C-H Functionalization of Arylacetic Acid Derivatives
Srinivas, Dasari,Satyanarayana, Gedu
supporting information, p. 7353 - 7358 (2021/10/01)
Herein, we present m-C-H olefination on derivatives of phenylacetic acids by tethering with a simple nitrile-based template through palladium catalysis. Notably, the versatility of the method is evaluated with a wide range of phenylacetic acid derivatives for obtaining the meta-olefination products in fair to excellent yields with outstanding selectivities under mild conditions. Significantly, the present strategy is successfully exemplified for the synthesis of drugs/natural product analogues (naproxen, ibuprofen, paracetamol, and cholesterol).
Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes
Bucher, Janina,Wurm, Thomas,Taschinski, Svenja,Sachs, Eleni,Ascough, David,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 225 - 233 (2017/02/05)
1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)–H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H-fluorene and 11H-benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H-benzo[b]fluorene derivatives are obtained in high yield. (Figure presented.).
Inhibitors of Acyl-CoA:Cholesterol Acyltransferase. 4. A Novel Series of Urea ACAT Inhibitors as Potential Hypocholesterolemic Agents
Trivedi, Bharat K.,Holmes, Ann,Stoeber, Terri L.,Blankley, C. John,Roark, W. Howard,et al.
, p. 3300 - 3307 (2007/10/02)
We have synthesized a series of N-phenyl-N'-aralkyl and N-phenyl-N'-(1-phenylcycloalkyl)ureas as inhibitors of acyl-CoA:cholesterol acyltransferase (ACAT).This intracellular enzyme is thought to be responsible for the esterification of dietary cholesterol; hence inhibition of this enzyme could reduce diet-induced hypercholesterolemia.For this series of compounds, the in vitro ACAT inhibitory activity was improved by increasing the bulk of the 2,6-substituents on the phenyl ring.Additionally, we found that spacing of the aromatic rings was critical for ACAT inhibitory activity.A phenyl ring five atoms away from the requiste 2,6-diisopropylphenyl moiety was optimal for in vitro activity.Substitution α to the N'-phenyl moiety enhanced in vitro potency.In the case of phenylcycloalkyl ureas, ACAT inhibitory activity was independent of the size of the cycloalkyl ring.From this series of analogs, compound 25, which had excellent in vitro potency for inhibiting ACAT, was found to lower plasma cholesterol by 73percent in vivo when administrated in the diet at 50 mg/kg in an animal model of hypercholesterolemia.In this model, compound 25 lowered plasma cholesterol dose dependently and was as efficacious as the Lederle ACAT inhibitor CL 277082.
