Isohistamine

Buschauer, Armin; Wegner, K.; Schunack, Walter

doi:10.1002/ardp.19843170104

Cited by 9 publications

(3 citation statements)

References 10 publications

(1 reference statement)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The structural analogues of impromidine described in the literature include, for example, chiral compounds with branched cimetidine-like or homohistamine partial structures [44,45] or substances characterised by other substructures from H 2 R antagonists like thiazoles and furans derived from tiotidine, nizatidine and ranitidine [46,47]. Completely different structures replacing the 5-methylimidazole group are present in the case of hybrid molecules combining the imidazolylpropylguanidine moiety with, for example, arylalkyl [48][49][50][51][52][53][54][55][56], diarylalkyl originating from H 1 R antagonists [57][58][59][60][61], dihydropyridine from calcium channel blockers [62,63] and benzoylimidazolone groups [64] from phosphodiesterase inhibitors (for reviews see [15,65,66]). Examples of H 2 R-selective guanidine-type agonists are depicted in (Fig.…”

Section: Amines As H 2 Receptor Agonistsmentioning

confidence: 99%

Structure-Activity Relationships of Histamine H2 Receptor Ligands+

Dove¹,

Elz²,

Seifert³

et al. 2004

MRMC

Self Cite

View full text Add to dashboard Cite

Recent research on histamine H2 receptor agonists was focused on quantitative structure-activity relationships and receptor models explaining the activity of imidazolylpropylguanidines. Their selectivity for guinea pig vs. human isoforms was investigated using H2 receptor-Gsalpha fusion proteins and attributed to amino acid differences in transmembrane domains 1 and 7. New antagonists result from approaches to improve pharmacokinetic properties and to design hybrid drugs which additionally have gastroprotective or anti H. pylori activity.

show abstract

Section: Amines As H 2 Receptor Agonistsmentioning

confidence: 99%

Structure-Activity Relationships of Histamine H2 Receptor Ligands+

Dove¹,

Elz²,

Seifert³

et al. 2004

MRMC

Self Cite

View full text Add to dashboard Cite

show abstract

“…Compounds that gave even very hygroscopic picrates were characterized only by spectral methods. Benzoyl-N -[3-(1 -triphenylmethyl-1 H-imidazol-4-yl)-2-propen-l -yl]-0-phenylisourea (14) A mixture of 30 mmoll3 and 30 mmol2 is stirred in CH2C12 (70 ml) for 15 min at mom temp. and smoothly evaporated to dryness.…”

Section: General Procedures For the Synthesis Of N-benroyl Guanidines mentioning

confidence: 99%

The Effect of Lipophilic Substituents on the H₂‐Histaminergic Activity of Some Close Analogues of Impromidine

Sellier

Elz

Buschauer

et al. 1992

Archiv der Pharmazie

Self Cite

View full text Add to dashboard Cite

The cimetidine-like moiety of the potent H2-agonist impromidine (9a) and three closely related guanidines (10a, 11a, and 12a) which are modified in the imidazolylpropyl portion, has been replaced by 2-[(2-pyridyl)methylthio]ethyl, 2-(benzylthio)ethyl and 3,3-diphenylpropyl substituents. Guanidines 10-12 were obtained from acidic hydrolysis of corresponding N-benzoyl guanidines 7, 8, and 15, accessible by successive aminolysis of diphenyl N-benzoyl carbonimidate (2) according to known methods. Compared with leads 10a and 11a lipophilic substitution affords almost equipotent H2-agonists 10b-d and 11b-d, while substituents with increasing lipophilicity enhance both intrinsic activity and potency of the weak partial agonist 12a at guinea-pig atrial H2-receptors. Guanidines 10-12 are weak H1-antagonists on the isolated guinea-pig ileum.

show abstract

“…9'9, die durch zweifache Aminolyse von 7 oder 8 zuganglich sind, uberlegen, da die Trennung der Ammoniumsalze von den polaren Guanidiniumsalzen entfallt. Beiden Synthesewegen ist jedoch gemeinsam, daf3 die unmittelbaren Guanidin-Vorstufen (5, 9) durch Kristallisation oder Chromatographie gut isolierbar sind, so da13 die Reindarstellung von Guanidinen einfacher ist als durch Aminolyse von S-Methylisothiuroniumsalzen.…”

Section: Syntheseunclassified

Synthese positiv inotroper Substanzen: Aryloxyalkylguanidine

Buschauer

1988

Archiv der Pharmazie

Self Cite

View full text Add to dashboard Cite

' Es wurden Guanidine ausgehend von N-Benzoyl-oder N-Cyano-diphenylimidocarbonat durch zweifache Aminolyse und anschlieflende saure Hydrolyse hergestellt. a-Hydroxyamine konnen mit Benzoyldiphenylimidocarbonat oder Benzoylisocyaniddichlorid zu Oxazolidinen cyclisiert und nach nucleophiler Ringoffnung mit prim. Aminen hydrolytisch in Guanidine ubergefuhrt werden. Am isolierten rechten MeerschweinchenAtrium sind die Substanzen bei unterschiedlicher intrinsic activity bis zu 20mal starker H,-agonistisch wirksam als Histamin. Am isoliert perfundierten Meerschweinchenherzen bewirkt 15b etwa den gleichen maximalen Frequenzanstieg wie Impromidin, wahrend die Kontraktilitatszunahme etwa 50 % des Impromidin-Vergleichswertes entspricht. Synthesis of Positive Inotropic Substances: AryloxydkylguanidinesStarting with diphenyl N-benzoyl carbonimidate or diphenyl N-cyanocarbonimidate guanidine derivatives were prepared by two-fold aminolysis and subsequent acidic hydrolysis. a-Hydroxy amines can be cyclized with diphenyl benzoyl carbonimidate or benzoyl isocyanid dichloride affording oxazolidines, which were reacted with amines and subsequently hydrolysed to yield guanidines. At the isolated guinea-pig right atrium the guanidines are up to 20 times more potent HI-agonists than histamine associated with varying intrinsic activities. At the isolated perfused guinea-pig-heart 15b and impromidine induced about the same maximal increase in heart rate whereas the increase in contractility effected by 15b was about 50 % of the maximal response of impromidine. Die vorliegende Arbeit beschaftigt sich rnit Methoden zur Synthese von Guanidinen, die als Leitstrukturen fur die Entwicklung einer neuen Klasse positiv inotrop wirksamer Sub~t a n z e n~-~' dienen sollen. SyntheseZur Synthese von Guanidinen ist das im Formelschema 1 gezeigte Verfahren unter Verwendung von N-Benzoyl-diphenylimidocarbonat (2)7' als zentralem Synthon besonders geeignet'! Das primare Amin 1')reagiert rnit 2 in inerten Losungsmitteln wie Methylenchlorid, Ether oder Acetonitril innerhalb weniger min zu dem Benzoylisoharnstoff 3'). Die anschliefiende Aminolyse rnit den Imidazolylalkylaminen 4a-c erfoigt vorzugsweise in siedendem Acetonitril oder Pyridin. Die Verwendung von Ethanol oder tert. Butanol als Reaktionsmedium gab bei der Synthese von 5a vergleichbare Ausbeuten. Die Hydrolyse in SM-HC1 liefert praktisch nebenproduktfrei die Guanidine 6 3HC1. Die anfallende Benzoesaure lafit sich durch Extraktion leicht entfernen. Dieses Verfahren ist der Hydrolyse von Cyanoguanidinen (vgl. 9'9, die durch zweifache Aminolyse von 7 oder 8 zuganglich sind, uberlegen, da die Trennung der Ammoniumsalze von den polaren Guanidiniumsalzen entfallt. Beiden Synthesewegen ist jedoch gemeinsam, daf3 die unmittelbaren Guanidin-Vorstufen (5, 9) durch Kristallisation oder Chromatographie gut isolierbar sind, so da13 die Reindarstellung von Guanidinen einfacher ist als durch Aminolyse von S-Methylisothiuroniumsalzen. HI 2 CH,

show abstract

Isohistamine

Cited by 9 publications

References 10 publications

Structure-Activity Relationships of Histamine H2 Receptor Ligands+

Structure-Activity Relationships of Histamine H2 Receptor Ligands+

The Effect of Lipophilic Substituents on the H₂‐Histaminergic Activity of Some Close Analogues of Impromidine

Synthese positiv inotroper Substanzen: Aryloxyalkylguanidine

Contact Info

Product

Resources

About

Isohistamine

Cited by 9 publications

References 10 publications

Structure-Activity Relationships of Histamine H2 Receptor Ligands+

Structure-Activity Relationships of Histamine H2 Receptor Ligands+

The Effect of Lipophilic Substituents on the H2‐Histaminergic Activity of Some Close Analogues of Impromidine

Synthese positiv inotroper Substanzen: Aryloxyalkylguanidine

Contact Info

Product

Resources

About

The Effect of Lipophilic Substituents on the H₂‐Histaminergic Activity of Some Close Analogues of Impromidine