144838-82-4Relevant articles and documents
A precisely positioned chiral center in an: I, i + 7 tether modulates the helicity of the backbone peptide
Hu, Kuan,Sun, Chengjie,Yang, Dan,Wu, Yujie,Shi, Chuan,Chen, Longjian,Liao, Tao,Guo, Jialin,Liu, Yinghuan,Li, Zigang
, p. 6728 - 6731 (2017)
In some cases, helical peptides stabilized by an i, i + 7 tether exhibit better target binding and cellular functions compared to their i, i + 4 analogues. Herein, we carried out a systematic study of the effects of an in-tether chiral center on the i, i + 7 system. We screened the optimal cross linking mode, tether length, in-tether chiral center positions, and absolute configurations. From these studies, we determined that a chiral center of R absolute configuration at the γ-position to the C-terminal of a 10-membered tether could function to efficiently induce helicity of the backbone peptides. This is an important addition to the current i, i + 4 in-tether chiral center induced helicity strategy (CIH strategy), and could have broad biological applications.
GUANIDINE DERIVATIVES AS TRPC MODULATORS
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Page/Page column 56-57, (2014/02/16)
The present invention is directed to guanidine derivatives as inhibitors of transient receptor potential canonical channels (TRPC channels), in particular TRPC3 and/or TRPC6 and/or TRPC7 activity, more particularly TRPC6 activity. Also provided herein are processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders mediated by TRPC channels (Formula (I))
Carbon-carbon bond-forming reactions of α-carbonyl carbocations: Exploration of a reversed-polarity equivalent of enolate chemistry
Lai, Ping-Shan,Dubland, Joshua A.,Sarwar, Mohammed G.,Chudzinski, Michael G.,Taylor, Mark S.
supporting information; experimental part, p. 7586 - 7592 (2011/10/12)
Carbon-carbon bond-forming reactions of putative α-carbonyl carbocation intermediates generated by Lewis acid- or silver-promoted ionizations of toluenesulfonate or halide leaving groups are described. This under-exploited mode of reactivity represents an 'umpolung' of conventional enolate chemistry, and enables C-C bond construction in both intra- and intermolecular contexts. Attempts to develop diastereoselective variants of this process using chiral ester and oxazolidinone-based auxiliaries are discussed.
Potent Kv1.3 inhibitors from correolide - Modification of the C18 position
Bao, Jianming,Miao, Shouwu,Kayser, Frank,Kotliar, Andrew J.,Baker, Robert K.,Doss, George A.,Felix, John P.,Bugianesi, Randal M.,Slaughter, Robert S.,Kaczorowski, Gregory J.,Garcia, Maria L.,Ha, Sookhee N.,Castonguay, Laurie,Koo, Gloria C.,Shah, Kashmira,Springer, Marty S.,Staruch, Mary Jo,Parsons, William H.,Rupprecht, Kathleen M.
, p. 447 - 451 (2007/10/03)
Correolide (1) was converted to a new series of tetracyclic Kv1.3 blockers 2. SAR for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. Kv1.3, the voltage-gated potassium channel in human T cells, represents a new target for treating immunosuppression and autoimmune diseases. Correolide (1), a pentacyclic natural product, is a potent and selective Kv1.3 channel blocker. Simplification of correolide via removal of its E-ring generates enone 4, whose modification produced a new series of tetracyclic Kv1.3 blockers. The structure-activity relationship for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. The most potent analog 43 is 15-fold more potent than correolide as inhibitor of human T cell proliferation.
Stereospecific syntheses of 2-alkyl and 2-phenyl substituted 3-(2,6-dimethyl-4-hydroxyphenyl)propanoic acids
Lu,Schiller
, p. 1639 - 1644 (2007/10/03)
Stereospecific syntheses of 2-methyl-, 2-ethyl-, 2-cyclohexyland 2-phenyl- substituted 3-(2,6-dimethyl-4-hydroxyphenyl)propanoic acids were developed. The key steps for the formation of the stereogenic centers involved the utilization of Evans' 4-benzyl-2-oxazolidinone chiral auxiliary. These compounds were designed to replace the N-terminal tyrosine residue in opioid peptides.
Stereoselective synthesis of isoflavonoids. (R)- and (S)-isoflavans
Versteeg, Marietjie,Bezuidenhoudt, Barend C. B.,Ferreira, Daneel
, p. 3365 - 3376 (2007/10/03)
α-Benzylation of (+)- and (-)-N-phenylacetyl imidazolidinones with 2- O-methoxy-methylbenzyl bromides, followed by reductive removal of the chiral auxiliary and cyclization, afforded oxygenated isoflavans in excellent enantiomeric excess and yield.
A convenient and practical method for N-acylation of 2 oxazolidinone chiral auxiliaries with acids
Prashad, Mahavir,Kim, Hong-Yong,Har, Denis,Repic, Oljan,Blacklock, Thomas J.
, p. 9369 - 9372 (2007/10/03)
A one-pot, convenient and practical method for N-acylation of 2- oxazolidinone chiral auxiliaries directly with acids in the presence of pivaloyl chloride and triethylamine is described.
