51505-76-1Relevant articles and documents
PRODRUGS OF FUSED HETEROCYCLIC INHIBITORS OF D-AMINO ACID OXIDASE
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Page/Page column 91, (2011/02/26)
The invention relates to prodrugs of fused heterocyclic inhibitors of D-amino oxidase (DAAO) and methods of treating diseases and conditions, wherein modulation of D-amino acid oxidase activity, D-serine levels, D-serine oxidative products and NMDA receptor activity in the nervous system of a mammalian subject is effective.
Facile synthesis of a family of H8BINOL-amine compounds and catalytic asymmetric arylzinc addition to aldehydes
Deberardinis, Albert M.,Turlington, Mark,Ko, Jason,Sole, Laura,Pu, Lin
experimental part, p. 2836 - 2850 (2010/08/05)
A family of optically active H8BINOL-AM compounds containing 3,3′-bis-tertiary amine substituents are synthesized by using a one-step reaction of H8BINOL with amino methanols that were in situ generated from various cyclic or acyclic secondary amines and paraformaldehyde. The H 8BINOL-AM compounds are used to catalyze the reaction of functional arylzincs, in situ prepared from the reaction of aryliodides with ZnEt 2, with aldehydes to produce chiral diaryl carbinols and a few arylalkyl carbinols. Through this study, highly enantioselective catalysts were identified. It was found that the H8BINOL-AM compounds with sterically less congested cyclic or acyclic amino methyl substituents were more enantioselective than those with more bulky substituents. The pyrrolidinyl derivative (S)-12 in most cases showed greater enantioselectivity than other H8BINOL-AM compounds, especially for the challenging ortho-substituted aromatic aldehydes. A H8BINOL-AM with 3,3′-bis-sec-amine substituents, prepared by a multistep method, was also used to catalyze the arylzinc addition to aldehydes, but it showed enantioselectivity lower than that of the compounds with tertiary amine groups. It was found for the first time that an aryl bromide, 2-bromothiophene, could be used to prepare an arylzinc reagent by reaction with ZnEt2. The addition of this heteroarylzinc reagent to an aldehyde in the presence of (S)-12 proceeded with good enantioselectivity.
α-(1H-Imidazol-1-yl)alkyl (IMIDA) carboxylic acid esters as prodrugs of carboxylic acid containing drugs
Majumdar, Susruta,Spaeth, Maren Mueller,Sivendran, Sashikala,Juntunen, Juha,Thomas, Joshua D.,Sloan
, p. 4609 - 4611 (2008/02/06)
Synthesis of α-(1H-imidazol-1-yl)alkyl (IMIDA) carboxylic acid esters have been reported in 2-3 simple steps. α-(1H-Imidazol-1-yl)alkyl (IMIDA) carboxylic acid esters were found to be chemically labile and thus serve as novel prodrugs of carboxylic acids.
MUSCARINIC RECEPTOR ANTAGONISTS
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Page/Page column 33, (2010/11/28)
This present invention generally relates to muscarinic receptor antagonists, which are useful, among other uses, for the treatment of various diseases of the respiratory, urinary and gastrointestinal systems mediated through muscarinic receptors. The inve
Synthesis of soft alkyl phenolic ether prodrugs using Mitsunobu chemistry
Majumdar, Susruta,Juntunen, Juha,Sivendran, Sashi,Bharti, Neelam,Sloan
, p. 8981 - 8982 (2007/10/03)
The synthesis of soft alkyl phenolic ether prodrugs in excellent yields has been reported by coupling a phenol with a hydroxymethylimide using Mitsunobu chemistry. The imides used in this study include saccharin, phthalimide, succinimide and two other compounds containing acidic imide-like N-H groups, benzotriazole, and imidazole.
Synthesis of ω-carbamoyloxyalkylimidazolium salts for evaluation as protective agents against acetylcholinesterase intoxication by soman
Sundberg, Richard J.,Van Nguyen, Phuoc
, p. 123 - 136 (2007/10/03)
A series of N-methyl and N,N-dimethylcarbamoyloxyalkylimidazolium salts has been prepared. The carbamoyloxyalkyl groups are varied from methyl through propyl at the 1,2 or 4 positions of the imidazolium ring. The 2- and 4-substituted series show modest activity as inhibitors of acetylcholinesterase. Several of the compounds show prophylactic activity against soman toxicity but there is no correlation between AChE inhibitory activity and the prophylatic effect, suggesting that reversible carbamoylation is not the basis for the prophylactic effect.