103188-44-9

Upstream product

• 60-19-5 tyramine hydrochloride 
• 2757-02-0 C₄H₉C₂O₄C₂H₂C₆H₅ 
• 51-67-2 tyrosamine 
• 140-10-3 (E)-3-phenylacrylic acid 
• 102-92-1 Cinnamoyl chloride 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 

Relevant academic research and scientific papers

Stereoselective formal hydroamidation of si-substituted arylacetylenes with DIBAL-H and isocyanates: Synthesis of (E)- And (Z)-α-Silyl-α,β-unsaturated amides

An efficient and stereoselective method for the synthesis of (E)- and (Z)-α-silyl-α,β-unsaturated amides and its synthetic applications are presented herein. The solvent-controlled hydroaluminations of Si-substituted alkynes with DIBAL-H generate diastereomerically enriched alkenylaluminum reagents that are directly reacted with isocyanates at ambient temperature to afford α-silyl-α,β-unsaturated amides in high yields with retained stereoselectivity. In particular, this process enables the synthesis of a broad range of (E)-α-silyl-α,β- unsaturated amides, which are the less studied isomers. The synthetic utility of this method is highlighted by its short reaction time, ease of purification, easily accessible substrates and reagents, gram-scale synthesis, and the further transformations of C-Si bonds into C-H, C-X, and C-C bonds.

Methods for preparing amide compounds using alkynes and methods for preparing peptides using the same

The present invention relates to a method for preparing an amide compound, which comprises a step of agitating an alkyne and an N-hydroxy compound in an organic solvent in the presence of a transition metal catalyst to form an amide bond, and a method for preparing a peptide using the same. According to the present invention, the amidation reaction does not depend on polar reactivity, such as the conventional simple nucleophilicity and electrophilicity, but is based on a reaction derived from coordination reactivity between an alkyne and a transition metal, and thus shows excellent chemical selectivity. In addition, the method does not require a consumptive step such as attachment and detachment of a protecting group but includes a simple process during the synthesis of a peptide. Thus, the method is very effective for preparing a polypeptide compound. The method also has 100% of atomic economic efficiency since the starting materials are not lost during the reaction.COPYRIGHT KIPO 2017

Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides

Synthetic hydroxycinnamoylamides of amino acids (precursors of aromatic amines) were studied for their antioxidant activity in vitro by two antioxidant assay systems, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and inhibition of lipid peroxidation (LPO). Furthermore, these compounds were tested and compared with their corresponding cinnamoylamides of aromatic amines for their inhibitory activity using mushroom tyrosinase. In addition, five hydroxycinnamoyl amino acid amides were investigated for their antimicrobial effect. Structure-activity relationships analysis disclosed that the presence of catechol rest at amino acid or at benzene moieties of substituted cinnamic acid amides significantly scavenged DPPH radical and inhibited LPO. The results obtained by LPO clearly expressed the positive influence of indole moiety on the activity. Moreover, the existence of p-hydroxy substituted cinnamic acid moiety leads to better tyrosinase inhibition. Amongst the tested compounds, amides of p-coumaroyldopamine or tyramine and their corresponding amino acid precursors are the most potent tyrosinase inhibitors.

Structure-activity relationship of N-(phenylalkyl)cinnamides as novel NR2B subtype-selective NMDA receptor antagonists

A novel series of N-(phenylalkyl)cinnamides related to N-(4- phenylbutyl)-3,4-dihydroxy-β-cyanocinnamide (6, an EGFR-K inhibitor with high antiproliferative activity) was synthesized and tested for antagonism at N-methyl-D-aspartate (NMDA) receptor subtypes. Potency and subunit selectivity were assayed by electrical recordings in Xenopus oocytes expressing three binary combinations of cloned rat NMDA receptor subunits: NR1A expressed in combination with either NR2A, NR2B, or NR2C. The N- (phenylalkyl)cinnamides are selective antagonists of NR1(A)/2B receptors. Assayed under steady-state conditions, N-(4-phenylbutyl)-4-hydroxycinnamide (16) has an IC50 value of 77 nM and > 1000-fold selectivity with respect to NR1(A)/2A and NR1(A)/2C receptors. Potency at α1 adrenergic receptors is low for the four cinnamides tested. Inhibition of NR1(A)/2B receptors does not correlate with EGFR and ErbB2/neu tyrosine kinase inhibitor activity. The N-(phenylalkyl)cinnamide series we describe provides a novel and structurally diverse framework for designing new NR2B-selective NMDA antagonists as potential CNS therapeutics.

N-(2-(4-hydroxyphenyl)ethyl)-4-chlorocinnamide: A novel antagonist at the 1A/2B NMDA receptor subtype

A series of N-(2-phenethyl)cinnamides was synthesized and assayed for antagonism at three N-methyl-D-asparate (NMDA) receptor subtypes (NR1A/2A-C). N-(2-(4-hydroxyphenyl)ethyl)-4-chlorocinnamide (6) was identified as a highly potent and selective antagoni

Isolation and Activity of N-p-Coumaroyltyramine, an α-Glucosidase Inhibitor in Welsh Onion (Allium fistulosum)

A phenolic amide, N-p-coumaroyltyramine (1), was isolated as an α-glucosidase inhibitor from methanol extracts of Welsh onion (Allium fistulosum). The inhibitory activity of 1 against a yeast enzyme was as high as Ki 8.4 × 10-7 M. From a structure-activity relationship study of 1 and its related compounds, the occurrence of α-glucosidase inhibitory activity required a p-coumaramide structure, with an amide hydrogen and alkyl or aralkyl substituent on the amide part.

Inhibition of in vitro prostaglandin and leukotriene biosyntheses by cinnamoyl-β-phenethylamine and N-acyldopamine derivatives

N-trans- and N-cis-Feruloyltyramines were isolated as the inhibitors of in vitro prostaglandin (PG) synthesis from an Indonesian medicinal plant, Ipomoea aquatica (Convolvulaceae). In order to clarify structure activity relationships, cinnamoyl-β-phenethylamines with possible combinations of naturally occurring cinnamic acids and β-phenethylamines were synthesized and tested for their inhibitory activities against PG synthetase and arachidonate 5-lipoxygenase. The compounds containing catechol groups such as N-caffeoyl-β-phenethylamine (CaP) showed higher inhibitory effects on PG synthetase. The catechol group was found to M essential for the inhibition of arachidonate 5-lipoxygenase. The investigation of concentration dependent effects on PG biosynthesis revealed that CaP enhanced PG biosynthesis at a lower concentration range, whereas it inhibited the reaction at a higher concentration. The effects of CaP on each reaction step were investigated with purified PG endoperoxide synthase and microsomal PG synthetase. CaP inhibited the cyclooxygenase reaction, while it enhanced the hydroperoxidase reaction. N-Acyldopamines which contain catechol and lipophylic group were synthesized from dopamine and fatty acids to test their inhibitory effects on arachidonate 5-lipoxygenase. N-Linoleoyldopamine was the most active compound and its IC50 value was 2.3 nM in our assay system, in which an IC50 value of AA 861, a specific inhibitor of 5-lipoxygenase, was 8 nM.