Syntheses of 2-(3,4-Dimethoxyphenyl)ethylamine Derivatives and Their Antiulcer Activities.

Hosokami, Toru; Kuretani, Masahiko; Higashi, Kunio; Asano, Masahide; Ohya, Kazumi; Takasugi, Norio; Mafune, Eiichi; Miki, Tosaku

doi:10.1248/cpb.40.2712

Cited by 16 publications

(6 citation statements)

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“…The utility of the present reaction could be illustrated by some reaction products. For example, N -phenyl- l -proline ( 3 ), the direct coupling product of l -valine with iodobenzene, was found as a key precursor for synthesizing antiulcer agents, while the original synthesis for this compound took several steps to give racemic product. N -(2,6-Dimethylphenyl)- d -alanine ( 12 ) could be used in synthesizing Ciba's phenylamide fungicide ( R )-metalaxyl .…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, chiral N -aryl-α-amino acids are of the common core structures for a number of synthetically challenging and medicinally important agents. These agents include protein kinase C (PKC) activators, indolactam-V, and its analogue benzolactam-V8; (see Figure ) Ciba's phenylamide fungicides ( R )-metalaxyl; fibrinogen receptor antagonist SB 214857; NMDA receptor antagonist L689560 and tricyclic quinoxalinediones; ACE inhibitors; and antiulcer agents . In the past two decades, these structures were assembled via several steps to get the enantiomerically pure form.…”

Section: Introductionmentioning

confidence: 99%

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Accelerating Effect Induced by the Structure of α-Amino Acid in the Copper-Catalyzed Coupling Reaction of Aryl Halides with α-Amino Acids. Synthesis of Benzolactam-V8

et al. 1998

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The coupling of optically pure R-amino acids with aryl halides produces enantiopure N-aryl-Ramino acids with retention of configuration under the catalysis of CuI. This reaction can complete at much lower temperature than typical Ullmann condensation even for electron-rich aryl halides, which indicates that an accelerating effect induced by the structure of the R-amino acid exists in this reaction. R-Amino acids with larger hydrophobic groups give higher coupling yields, while those with smaller hydrophobic groups only deliver lower yields and no coupling products were detected for those with hydrophilic groups. No racemization was observed in most cases of this coupling reaction. After some controlled experiments, a possible mechanism including the π-complex and the intramolecular substitution reaction is proposed. Based on this catalyzed reaction, a facile and stereoselective synthesis of benzolactam-V8, a new PKC activator, is achieved.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Accelerating Effect Induced by the Structure of α-Amino Acid in the Copper-Catalyzed Coupling Reaction of Aryl Halides with α-Amino Acids. Synthesis of Benzolactam-V8

et al. 1998

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“…DQ-2511 is a substituted benzamide (3-[[[2-(3,4dimethoxyphenyl)ethyl]carbamoyl]methyl]amino-Nmethylbenzamide) originally developed as an antiulcer drug (Asano et al, 1990;Hosokami et al, 1992;Hirohashi et al, 1993a,b) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Effects of DQ‐2511 on neutral activity in afferent and efferent loops of gastric vagovagal reflex pathways in the rat

Niijima

Hatanaka²,

Furuhama³

1996

Journal of Autonomic Pharmacology

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1. DQ-2511 is a new substituted benzamide compound that has gastric prokinetic properties. Actions of the drug on neural discharge in the innervation of the stomach of anaesthetized rats were studied. Standard extracellular methods of multi-unit recording were used to study rates of firing in afferent and efferent filaments teased from gastric branches of the vague nerve. 2. Decreased firing in gastric vagal efferents was associated with increased rates of discharge in the gastric afferents. 3. Intravenous application of DQ-2511 resulted in increased frequency of firing in the efferents in association with decreased rate of discharge in afferent fibres. 4. Application of cholecystokinin octapeptide (CCK8) suppressed activity in the gastric efferents which occurred coincident with the elevated discharge in the afferents. Pretreatment with DQ-2511 blocked the actions of CCK8. 5. The results suggest that the gastric prokinetic action of DQ-2511 may involve suppression of activation of afferents in the sensory component of gastric inhibitory vago-vagal reflex pathways.

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“…With the aim of further extending the scope of N -substituted vinyl glycine products that may be accessed using the [2,3]-sigmatropic rearrangement of allylic selenides, we reasoned that aromatic amines may also be suitable reaction partners. Use of aromatic amines would provide access to N -arylated α-amino acids, common motifs found in a number of medicinally important and synthetically interesting biological agents; examples are found in hepatitis C virus replicator inhibitors, ACE inhibitors, anticoagulant factor Xa inhibitors, the GPIIb/IIIa fibrinogen receptor antagonist Lotrafiban, and compounds with antiulcer agent activity . The majority of reported preparations of N -aryl amino acids rely upon metal-catalyzed Ullman-like reactions. − While these provide an efficient synthetic route, the formation of enantioenriched N -aryl amino acids requires enantioenriched amino acid starting materials; in addition, while chiral pool amino acids are easily obtained, unnatural amino acids require enantioselective synthesis which can be nontrivial.…”

Section: Resultsmentioning

confidence: 99%

“…Finally, the use of aromatic amines would provide access to a wide range of N -aryl vinyl glycine derivatives (path c). N -Arylated amino acids are synthetically useful targets found in a broad range of biologically active compounds. − …”

Section: Introductionmentioning

confidence: 99%

[2,3]-Sigmatropic Rearrangement of Allylic Selenimides: Strategy for the Synthesis of Peptides, Peptidomimetics, and N-Aryl Vinyl Glycines

et al. 2014

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The scope of the NCS-mediated amination/[2,3]-sigmatropic rearrangement of enantioenriched allylic selenides has been expanded to provide access to three new product classes. The use of N-protected amino acid amides provides a novel strategy for accessing peptide chains containing unnatural vinyl glycine amino acid residues. Also reported is the use of amino acid esters, allowing the diastereoselective synthesis of N,N-dicarboxymethylamines, a motif found in a number of pharmaceuticals. Furthermore, use of a range of N-aromatic and N-heteroaromatic amines allows the formation of enantioenriched N-arylamino acids, a motif found in a number of synthetically and biologically interesting compounds.

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Syntheses of 2-(3,4-Dimethoxyphenyl)ethylamine Derivatives and Their Antiulcer Activities.

Cited by 16 publications

References 0 publications

Accelerating Effect Induced by the Structure of α-Amino Acid in the Copper-Catalyzed Coupling Reaction of Aryl Halides with α-Amino Acids. Synthesis of Benzolactam-V8

Accelerating Effect Induced by the Structure of α-Amino Acid in the Copper-Catalyzed Coupling Reaction of Aryl Halides with α-Amino Acids. Synthesis of Benzolactam-V8

Effects of DQ‐2511 on neutral activity in afferent and efferent loops of gastric vagovagal reflex pathways in the rat

[2,3]-Sigmatropic Rearrangement of Allylic Selenimides: Strategy for the Synthesis of Peptides, Peptidomimetics, and N-Aryl Vinyl Glycines

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