153683-49-9Relevant articles and documents
Cu-catalyzed synthesis of tetrasubstituted 2,3-allenols through decarboxylative silylation of alkyne-substituted cyclic carbonates
Guo, Kun,Kleij, Arjan W.
supporting information, p. 3942 - 3945 (2020/06/08)
An efficient and mild Cu-catalyzed protocol has been developed for the decarboxylative silylation of alkyne-functionalized cyclic carbonate substrates affording 2,3-allenols featuring four different substituents. This practical methodology gives access to a wide scope of tetrasubstituted functionalized allenes in excellent yields.
Non-imidazole histamine H3 ligands. Part VI. Synthesis and preliminary pharmacological investigation of thiazole-type histamine H3-receptor antagonists with lacking a nitrogen nucleus in the side chain
Guryn, Roman,Staszewski, Marek,Kopczacki, Piotr,Walczyński, Krzysztof
, p. 65 - 76 (2017/06/05)
Background: Antagonists to the H3 receptor are considered to be potential drugs for the treatment of Alzheimer's disease, attention deficit-hyperactive disorder, memory and learning deficits, and epilepsy. The initial development of potent H3 receptor antagonists focused on extensive modification of the natural ligand histamine. However, it has appeared that imidazole-containing ligands are associated with inhibition of cytochrome P450 enzymes, caused by imidazole nitrogen complexation to heme iron in the active site of the enzyme. For these reasons, the development of potent non-imidazole H3 receptor antagonists was eagerly awaited. Objective: Previously, we reported the synthesis and pharmacological in vitro characterization of series of potent histamine H3-receptor non-imidazole antagonists belonging to the class of substituted 2-thiazol-4-n-propylpiperazines. A lead compound 1 of this family was a derivative carrying the ethylaminomethylpropyl chain. Methods: With the aim of increasing lipophilicity, that will help the ligands to cross the blood-brain barrier, we synthesized a series of new 2-thiazol-4-n-propylpiperazines where the ethylaminomethylpropyl moiety was replaced by a p-substituted-, an unsubstituted benzene ring, and ω-phenylalkyl substituent at positions 4 and 5 of thiazole ring, respectively. All compounds were tested for H3 antagonistic effects in vitro using the electrically contracting guinea pig jejunum. Results: The most active compounds of presented series 3d, 3e, and 3j showed lower affinity than the lead compound 1 and additionally, derivatives 3d and 3j possessed weak, competitive H1-antagonistic activity. This is in contrast to the lead compound 1 that has no affinity at H1 receptor. Conclusion: We can conclude that a side chain in the 2-thiazol-4-n-propylpiperazine scaffold should contain a basic center and should be present at a favorable position 5 of thiazole ring.
AUTOTAXIN INHIBITORS
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Paragraph 00406, (2016/09/22)
The present invention relates to compounds of formula (I): wherein R1, R2, R3, R4a, R4b, R4C, R4d, L, A, Q, W and HET are each as defined herein. The compounds of the present inv
Preparation of enantiomerically enriched bromohydrins from [N-(p-tolylsulfonyl)sulfoximino]oxiranes using in situ reduction of α-bromo aldehydes
Bailey, Peter L.,Briggs, Andrew D.,Jackson, Richard F. W.,Pietruszka, Joerg
, p. 3359 - 3363 (2007/10/03)
Treatment of enantiomerically pure [N-(p-tolylsulfonyl)sulfoximino]oxiranes 6 with MgBr2 in the presence of tetrabutylammonium borohydride gives enantiomerically enriched bromohydrins 3, together with small amounts of the primary alcohols 11. The bromohydrins 3 are isolated in good yields with enantiomeric excesses in the range 70% to 91%. This process establishes that α-bromo aldehydes have sufficient configurational stability to be viable synthetic intermediates.
Preparation of enantiomerically enriched bromohydrins by reaction of sulfoximinooxiranes with MgBr2 in the presence of tetra-butylammonium borohydride
Bailey, Peter L.,Briggs, Andrew D.,Jackson, Richard F. W.,Pietruszka, Joerg
, p. 6611 - 6614 (2007/10/02)
Treatment of enantiomerically pure N-tosylsulfoximinooxiranes 6 with MgBr2 in the presence of tetra-butylammonium borohydride gives enantiomerically enriched bromohydrins 3, together with small amounts of the simple primary alcohols. The bromohydrins are isolated in good yields with enantiomeric excess in the range 70% to 91 % (as assessed by enantioselective g.l.c.
