70547-26-1

Upstream product

• 563-76-8 α-bromopropionyl bromide 
• 2227-79-4 benzenecarbothioamide 
• 535-11-5 Ethyl 2-bromopropionate 
• 79-42-5 2-mercaptopropanoic acid 
• 100-47-0 benzonitrile 

Downstream Products

• 161012-98-2 4-ethoxy-3-methyl-2-phenylthiazole 
• 70547-27-2 (S)-1-tert-Butylamino-3-(5-methyl-2-phenyl-thiazol-4-yloxy)-propan-2-ol 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of novel oxadiazole- and thiazole-based histamine H3R ligands

Histamine H3 receptor (H3R) is largely expressed in the CNS and modulation of the H3R function can affect histamine synthesis and liberation, and modulate the release of many other neurotransmitters. Targeting H3R with antagonists/inverse agonists may have therapeutic applications in neurodegenerative disorders, gastrointestinal and inflammatory diseases. This prompted us to design and synthesize azole-based H3R ligands, i.e. having oxadiazole- or thiazole-based core structures. While ligands of oxadiazole scaffold were almost inactive, thiazole-based ligands were very potent and several exhibited binding affinities in a nanomolar concentration range. Ligands combining 4-cyanophenyl moiety as arbitrary region, para-xylene or piperidine carbamoyl linkers, and/or pyrrolidine or piperidine basic heads were found to be the most active within this series of thiazole-based H3R ligands. The most active ligands were in silico screened for ADMET properties and drug-likeness. They fulfilled Lipinski's and Veber's rules and exhibited potential activities for oral administration, blood–brain barrier penetration, low hepatotoxicity, combined with an overall good toxicity profile.

Enantioselective construction of tetrasubstituted stereogenic carbons through bronsted base catalyzed michael reactions: α′-hydroxy enones as key enoate equivalent

Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C-C bonds in synthesis, but most of the reports claiming high selectivity are limited to some specific combinations of nucleophile/electrophile compound types, and only few successful methods deal with the generation of all-carbon quaternary stereocenters. A contribution to solve this gap is presented here based on chiral bifunctional Bronsted base (BB) catalysis and the use of α′-oxy enones as enabling Michael acceptors with ambivalent H-bond acceptor/donor character, a yet unreported design element for bidentate enoate equivalents. It is found that the Michael addition of a range of enolizable carbonyl compounds that have previously demonstrated challenging (i.e., α-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azlactones) to α′-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts. Experiments show that the α′-oxy ketone moiety plays a key role in the above realizations, as parallel reactions under identical conditions but using the parent α,β-unsaturated ketones or esters instead proceed sluggish and/or with poor stereoselectivity. A series of trivial chemical manipulations of the ketol moiety in adducts can produce the corresponding carboxy, aldehyde, and ketone compounds under very mild conditions, giving access to a variety of enantioenriched densely functionalized building blocks containing a fully substituted carbon stereocenter. A computational investigation to rationalize the mode of substrate activation and the reaction stereochemistry is also provided, and the proposed models are compared with related systems in the literature.

Catalytic enantioselective synthesis of tertiary thiols from 5h-thiazol-4-ones and nitroolefins: Bifunctional ureidopeptide-based bronsted base catalysis

Fully loaded: The ureidopeptide-based bifunctional Bronsted base 1 efficiently promotes the first direct catalytic Michael reaction of α-mercapto carboxylate surrogates with nitroolefins involving a fully substituted α-carbon atom construction. Copyright

Aminothiazole Derivatives. II. A Facile Synthesis of Condensed 4-Aminothiazole Derivatives using α-Bromolactams and Thioamides

The reaction of an α-bromolactam with a thioamide was found to give a cyclic 4-aminothiazole derivative.Novel heterocyclic compounds such as 4,5,6,7-tetrahydrothiazolopyridines 10, 5,6,7,8-tetrahydro-4H-thiazoloazepines 11, 4,5,6,7,8,9-hexahydrothiazoloazocine 12 and 9,10-dihydro-4H-thiazolobenzazepines 18 were thus prepared and the utility of this method in the construction of 4-aminothiazole-containing compounds was suggested.

4-HYDROXYTHIAZOLES AS 5-LIPOXYGENASE INHIBITORS

A composition for the inhibition of lipoxygenase enzymes comprising a pharmaceutically acceptable carrier and a compound of the formula: I wherein R1 and R2 are independently selected from the group consisting of alkyl, alkenyl, cycloalkyl, cycloalkenyl,

4-Hydroxythiazole Inhibitors of 5-Lipoxygenase

4-Hydroxythiazoles have been identified as potent inhibitors of 5-lipoxygenase in vitro exhibiting IC50's of less than 1 μM.An investigation of structure-activity relationships showed that the most potent inhibitors of this series are the 5-phenyl derivatives.The corresponding thiazolidin-4-one analogues were found to be relatively inactive.The 4-hydroxythiazoles were active inhibitors against 5-lipoxygenase in both intact rat polymorphonuclear leukocytes and human whole blood.The compounds were also selective inhibitors of 5-lipoxygenase, displaying only weak activity against other related enzymes, cyclooxygenase and 12- and 15-lipoxygenase.

A facile preparation of 4-thiazolone derivatives from thioamides and various haloacyl halides in a biphase system

The reaction of thioamides (1) with various haloacyl halides (2, 7, 11, 14, 17, and 19) was carried out in sat. NaHCO3-CH2Cl2 and 5% NaOH-CH2C12 to give several kinds of 4-thiazolones (3-5, 10, 12 and