2‐Substituierte Histamine 3. Mitt. über Struktur‐Wirkungs‐Beziehungen bei Histaminanaloga

Dziuron, P.; Schunack, Walter

doi:10.1002/ardp.19743070203

Cited by 15 publications

(3 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hydrolysis of 11a (1 g) in boiling water for 16 h gave 13 (0.42 g, 60%), after cooling and filtration, and a small amount of the hydrochloride of 12a (0.25 g, 28%), after evaporation of the filtrate and treatment of the residue with EtOH-HCl. lVT-Benzyl-Ar"-carbomethoxyhistamine (14). A solution of the bromide of 11a (0.44 g) in MeOH (50 mL) was heated under reflux for 4 h. Concentration and addition of picric acid and then H20 gave the picrate of 14 (0.66 g, 95%), mp 179-180 °C, identical with the product obtained from the reaction of 12a with methyl chloroformate: NMR (Me2SO-d6) 2.78 (t, CH2Im), 3.22 (t, CH2N), 3.50 (s, CH3), 5.44 (s, CH2Ph), 7.2 (br, NH), 7.41 (s, Ph), 7.55 (d, Im 4 H), 8.66 (s, picrate), 9.11 (d, Im 2 H).…”

Section: Methodsmentioning

confidence: 99%

“…lVT-Benzyl-Ar"-carbomethoxyhistamine (14). A solution of the bromide of 11a (0.44 g) in MeOH (50 mL) was heated under reflux for 4 h. Concentration and addition of picric acid and then H20 gave the picrate of 14 (0.66 g, 95%), mp 179-180 °C, identical with the product obtained from the reaction of 12a with methyl chloroformate: NMR (Me2SO-d6) 2.78 (t, CH2Im), 3.22 (t, CH2N), 3.50 (s, CH3), 5.44 (s, CH2Ph), 7.2 (br, NH), 7.41 (s, Ph), 7.55 (d, Im 4 H), 8.66 (s, picrate), 9.11 (d, Im 2 H). Anal.…”

Section: Methodsmentioning

confidence: 99%

“…An investigation of the stability of the quaternary salt (11a) showed that it was readily ring opened by nucleophiles. Treatment with hot MeOH gave the carbamate (14), and boiling water furnished a mixture of 12a and the urea (13) presumably formed by reaction of unprotonated amine (12a) with 11a. Addition of acid in this hydrolysis favored exclusive formation of 12a, while addition of base (Na2C03) gave the urea (13) as the sole product.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Potential histamine H2-receptor antagonists. 4. Benzylhistamines

Emmett¹,

Durant²,

Ganellin³

et al. 1982

J. Med. Chem.

View full text Add to dashboard Cite

As part of our studies aimed at designing histamine H2-receptor antagonists, the effect on histaminergic activity of introducing benzyl substituents at various positions in the histamine molecule is described. New synthetic methods are reported for the novel 4-benzyl-, beta-benzyl- and 4,N tau-dibenylhistamines and the reported 2-benzylhistamine. The novel N tau-benzylhistamine was synthesized by the versatile route reported by us for the synthesis of N tau-methylhistamine. These benzylhistamines, together with the reported N alpha- and N pi-benzylhistamines, were tested for agonist and antagonist activity at both H1 and H2 receptors. The results obtained indicate that introduction of a benzyl group into the histamine molecule causes a marked reduction in H1- or H2-agonist activity, and none of the compounds showed consistent antagonist activity. Evidently, the sterically demanding benzyl substituent is not easily accommodated in the agonist binding mode and is unable to locate a lipophilic receptor region for potential hydrophobic binding.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Potential histamine H2-receptor antagonists. 4. Benzylhistamines

Emmett¹,

Durant²,

Ganellin³

et al. 1982

J. Med. Chem.

View full text Add to dashboard Cite

show abstract

Imidazol‐4‐carbinole aus Iminoestern und Dihydroxyaceton. 2. Mitt. über Imidazolsynthesen mit flüssigem Ammoniak

Dziuron

Schunack

1974

Archiv der Pharmazie

View full text Add to dashboard Cite

show abstract

Äther und Ester des 4‐(2‐Hydroxyaethyl)‐imidazols und Ester der 4‐Imidazolpropionsäure 4. Mitt. über Struktur‐Wirkungs‐Beziehungen bei Histaminanaloga

Schunack

1974

Archiv der Pharmazie

View full text Add to dashboard Cite

Als potentiell histaminartig wirksame Substanzen wurden Ather und Ester des 4(2-Hydroxy-aethy1)-imidazols und Ester der 4Imidazolpropionsaure dargestellt und am isolierten Ileum des Meerschweinchens und anderen Testobjekten untersucht. Ethers and Esters of 4-(2-Hydroxyethyl)-imidazole and Esters of 4-Imidazolepropionic AcidAs substances with possible histaminelike activity, ethers and esters of 4-(hydroxyethyl)-imi dazole and esters of Cimidazolepropionic acid are prepared and tested o n isolated guinea pig ileum and other objects 1 3. Mitt.: P.

show abstract

2‐Substituierte Histamine 3. Mitt. über Struktur‐Wirkungs‐Beziehungen bei Histaminanaloga

Abstract: Es wurden verschiedene 2‐substituierte Histaminderivate aus den entsprechenden 2‐substituierten Imidazol‐4‐carbinolen dargestellt und am isolierten Ileum des Meerschweinchens auf ihre histaminartige Wirkung untersucht.

Cited by 15 publications

References 8 publications

Potential histamine H2-receptor antagonists. 4. Benzylhistamines

Potential histamine H2-receptor antagonists. 4. Benzylhistamines

Imidazol‐4‐carbinole aus Iminoestern und Dihydroxyaceton. 2. Mitt. über Imidazolsynthesen mit flüssigem Ammoniak

Äther und Ester des 4‐(2‐Hydroxyaethyl)‐imidazols und Ester der 4‐Imidazolpropionsäure 4. Mitt. über Struktur‐Wirkungs‐Beziehungen bei Histaminanaloga

Contact Info

Product

Resources

About