76403-12-8Relevant articles and documents
Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters
Greenhalgh, Mark D.,Laina-Martín, Víctor,Neyyappadath, Rifahath M.,Qu, Shen,Smith, Andrew D.,Smith, Samuel M.
, p. 16572 - 16578 (2020/09/09)
A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.
N-PHENYL-LACTAM DERIVATIVES CAPABLE OF STIMULATING NEUROGENESIS AND THEIR USE IN THE TREATMENT OF NEUROLOGICAL DISORDERS
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, (2015/08/03)
The present invention relates to compounds of the general formula I wherein Het is oxazole-5-yl, pyridin-4-yl, or pyrazol-4-yl; R1/ R2 are, independently from each other, hydrogen, lower alkyl, lower alkoxy, or halogen; W is -CH2- or -CH2CH2-; X is CR3R4 or NR5; R3 is hydrogen or lower alkyl; R4 is -(CH2)n-phenyl, optionally substituted by halogen, lower alkoxy, lower alkyl substituted by halogen, lower alkoxy substituted by halogen or lower alkyl; R5 is CHR-phenyl or CH2CHR-phenyl, optionally substituted by halogen, lower alkoxy, lower alkyl substituted by halogen, lower alkoxy substituted by halogen or lower alkyl, or is CHR-pyridin-2, 3 or 4 -yl; R is hydrogen or lower alkyl; n is 0 or 1; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to its corresponding enantiomer and/or optical isomer thereof. The compounds may be used for the treatment of schizophrenia, obsessive-compulsive personality disorder, depression, bipolar disorders, anxiety disorders, normal aging, epilepsy, retinal degeneration, traumatic brain injury, spinal cord injury, post-traumatic stress disorder, panic disorder, Parkinson's disease, dementia, Alzheimer's disease, cognitive impairment, chemotherapy-induced cognitive dysfunction, Down syndrome, autism spectrum disorders, hearing loss, tinnitus, spinocerebellar ataxia, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of neuro-active drugs, selected from alcohol, opiates, methamphetamine, phencyclidine and cocaine.
Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 2: Structure-activity relationships for substituted 2-aryl-1-[N-(methyl)-N-(phenylsulfonyl)amino]-4-(piperidin-1-yl)butanes
Finke, Paul E.,Meurer, Laura C.,Oates, Bryan,Mills, Sander G.,MacCoss, Malcolm,Malkowitz, Lorraine,Springer, Martin S.,Daugherty, Bruce L.,Gould, Sandra L.,DeMartino, Julie A.,Siciliano, Salvatore J.,Carella, Anthony,Carver, Gwen,Holmes, Karen,Danzeisen, Renee,Hazuda, Daria,Kessler, Joseph,Lineberger, Janet,Miller, Michael,Schleif, William A.,Emini, Emilio A.
, p. 265 - 270 (2007/10/03)
(2S)-2-(3,4-Dichlorophenyl)-1-[N-(methyl)-N-(phenylsulfonyl)amino]-4-[spiro(2 ,3-dihydrobenzthiophene-3,4′-piperidin-1′yl)]butane S-oxide (3) has been identified as a potent CCR5 antagonist lead structure having an IC50 = 35 nM. Herein, we describe the structure-activity relationship studies directed toward the requirement for and optimization of the C-2 phenyl fragment. The phenyl was found to be important for CCR5 antagonism and substitution was limited to small moieties at the 3-position (13 and 16: X = H, 3-F, 3-Cl, 3-Me).
