Notes - Some 4(or 5)-(2'-Aminopropyl)imidazoles

Alles, Gordon A.; Wisegarver, Burnett B.; Chapman, N. B.; Tompsett, A. L. L.

doi:10.1021/jo01353a601

Cited by 6 publications

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“…d^d-Dimethylhistamine (24) was prepared as reported by Jonsson.32 a-Methylhistamine (25) was prepared as reported by Alies et al 33 with the exception that the dihydrochloride was characterized. Alternatively, 25 may be prepared from histidine by reduction to histidinol, conversion into abromomethylhistamine, and hydrogenolysis, as described recently by Ison and Casy348 and performed independently in these laboratories by Suschitsky.34b…”

Section: Tpcv = Tv X Pcvmentioning

confidence: 99%

Potential histamine H2-receptor antagonists. 3. Methylhistamines

Gj¹,

Jc²,

Cr³

et al. 1976

J. Med. Chem.

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Syntheses are described for all the mono- and some di- and trimethylhistamines. New methods are given for the known Npi, Ntau-, Nalpha-, 2-, and 4-methylhistamines and for the novel compounds, beta-methyl-, 4,Nalpha-dimethyl-, and 4,Nalpha,Nalpha-trimethylhistamines. Agonist activities are reported for stimulation of histamine H1 (guinea-pig ileum) and H2 (rat gastric acid secretion) receptors. H2-Receptor agonist activities indicate that a methyl group is more readily accommodated at the 4 and Nalpha positions than elsewhere in the histamine molecule and that receptor binding is substantially retained with a methyl substituent in these positions. Thus, for the design of potential antagonists, two sites are identified as being worthwhile exploring for the introduction of lipophilic substituents.

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Section: Tpcv = Tv X Pcvmentioning

confidence: 99%

Potential histamine H2-receptor antagonists. 3. Methylhistamines

Gj¹,

Jc²,

Cr³

et al. 1976

J. Med. Chem.

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“…°At 0 °C, from 1 mmol of 1--5 in 5 mL of CH3CN. 6 Two millimoles of N02BF4, 2 mmol of Me2S, and 2 mmol of py per CONH group. "Four to five millimoles of N02BF4/Me2S/py for 1-3, 6-7 mmol for 4 and 5. dTwo millimoles of NOBF4 and 2 mmol of py per CONH group.…”

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confidence: 99%

Nitrosation of hindered amides

Romea¹,

Urpı́²,

Vilarrasa³

1989

J. Org. Chem.

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N-Nitrosoamides are among the most widely used synthetic intermediates for the preparation of diazo alkanes, generation of aryl radicals, and deamination of aliphatic amines.' More recently, the enhanced reactivity of nitrosoamides and nitroamides with a variety of nucleophiles was utilized for the conversion of RCONHR' into RCONHR", RCON3, and RCOSR",2 and for the cleavage of certain peptide amide bonds3 under mild conditions. In general agreement with the literat~re?~ we found2,38*6 that N204/NaAc0 was an excellent reagent for the nitrosation of amides in cold CH2C12. Nevertheless, under such conditions several hindered peptide bonds could not be nit r o~a t e d .~~In this paper we report the reaction of three nitrosating agents on compounds containing sterically hindered amide bonds: N-cyclohexyl-2,2-dimethylpropanamide ( l ) , Nacetyl-L-valine methyl ester (Ac-Val-OMe, 2) and Nacetyl-L-isoleucine methyl ester (Ac-Ile-OMe, 3). The most promising nitrosating reagents have been then applied to N-benzyloxycarbonyl-L-isoleucyl-L-valine methyl ester (Z-Ile-Val-OMe, 4) and N-benzyloxycarbonyl-L-valyl-Lleucine methyl ester (Z-Val-Leu-OMe, 5). 0 1 2 3 I 4 5When N204/NaAc0 was used, compounds 1-3 gave no detectable amounts of N-nitrosated Substitution of pyridine (py) for NaAcO, which we had shown to improve the nitrosation yields of some moderately hindered peptide bonds,' did not afford any significant (1) For related general reviews, see: (a) Challis, J. A. In The Chemistry of Amides; Zabicky, J., Ed.; Wiley-Interscience: London, 1970. (b) Regitz, M. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Wilev: Chichester. 1978. (c) Challis. B. C.: Challis. J. A. In Comorehenshe Organic CLemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pirgamon Press: Oxford, 1979; Vol. 2. (2) (a) Garcia, J.; Gondez, J.; Segura, R.; Urpi, F.; Vilarrasa, J. J. Org. Chem. 1984, 49, 3322 and references therein. (b) Garcia, J. Doctoral Thesis, Universitat de Barcelona, 1986. (c) Berenauer, R.; Garcia, J.; Vilarrasa, J. Synthesis, in press.(3) (a) Garcia, J.; Gonzblez, J.; Segura, R.; Vilarrasa, J. Tetrahedron 1984, 16, 3121. (b) For related papers on nitrosopeptides, see: Challis, B. C.; Milligan, J. R.; Mitchell, R. C. J. Chem. SOC., Chem. Commun. 1984, 1050 and references therein.(4) (a) White, E. H. J. Am. Chem. SOC. 1955, 77,6008 and references therein; (b) 6011; (c) 6014. (5) France, H.; Heilbron, I. M.; Hey, D. H. 1987, 28, 341. (7) Preliminary experiments with N204/py in CH2C12 were performed by J. Garcia some years ago.2b These conditions have also been employed in another context: Larm, 0. Carbohydr. Res. 1975,43, 192. Forrest, A. K.; Schmidt, R. R. Tetrahedron Lett. 1984,25, 1769.improvement in the cases studied here (1-3). After several trials (changing the base, adding either Me2S or EtSH in different amounts), encouraging yields were attained when 10 equiv of Me,S was added to a solution of the amide in py/CH2Cl2 (60% of nitrosation in the case of 2 and 30% in 3, but 0% in 1).It is known that, upon the oxidation of ...

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“…Ausgehend von 2-Acetyl-4-pentensaureethylester, der aus Acetessigester und Allylbromid nach '*) leicht zuganglich ist, wurde 3-Amino-5-hexen-2-on auf dem in 13) beschriebenen Weg erhalten. Aus diesem ist 4-Allyl-5-methyl-imidazo113) durch Zyklisierung mit NH,SCN und nachfolgende Oxidation erhaltlich.…”

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Struktur‐Wirkungs‐Beziehungen bei Histaminanaloga, 24. Mitt. Absolute Konfiguration und histaminartige Wirkung der Enantiomere von 4‐(2‐Aminopropyl)‐5‐methyl‐imidazol

Schwarz¹,

Schunack²

1982

Archiv der Pharmazie

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Es werden die Racematspaltung von 4-(2-Aminopropyl)-5-methyl-imidazol(l), die Bestimmung der absoluten Konfiguration sowie die histaminartige Wirksamkeit der Enantiomere am Ileum (HI) und Atrium (Hz) des Meerschweinchens beschrieben. Structure-Activity Relationships of Histamine Analogues, XXIV: Absolute Configuration and Histamine-Type Activity of the Enantiomen of 4-(2-Aminopropyl)-5-methylimidazoleThe resolution of 4-(2-aminopropyl)-5-methylimidazole (l), the determination of the absolute configuration and the histamine-type activity of the enantiomers on the guinea pig ileum (HI) and atrium (H2) are reported.

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Notes - Some 4(or 5)-(2'-Aminopropyl)imidazoles

Cited by 6 publications

References 0 publications

Potential histamine H2-receptor antagonists. 3. Methylhistamines

Potential histamine H2-receptor antagonists. 3. Methylhistamines

Nitrosation of hindered amides

Struktur‐Wirkungs‐Beziehungen bei Histaminanaloga, 24. Mitt. Absolute Konfiguration und histaminartige Wirkung der Enantiomere von 4‐(2‐Aminopropyl)‐5‐methyl‐imidazol

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