Inhibitors of Monoamine Oxidase

Ho, Beng T.; McIsaac, William M.; Walker, K. E.; Estevez, Vicente

doi:10.1002/jps.2600570205

Cited by 106 publications

(19 citation statements)

References 10 publications

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“…[1][2][3] In order to address generality of the methods, these reactions were also conducted with tryptamine. Cyclization reactions of 5-chlorotryptamine hydrochloride and tryptamine hydrochloride with [ 14 C]-paraformaldehyde in 3 M acetate buffer provided the desired b-carbolines in yields of 51 and 67%, Y. LI AND S. R. PRAKASH respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of C-14-labeled novel IKK inhibitor: 2-[14C]-N-(6-chloro-9H-pyrido [3,4-b]indol-8-yl)-3-pyridinecarboxamide

Prakash

2005

J Label Compd Radiopharm

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Section: Resultsmentioning

confidence: 99%

Synthesis of C-14-labeled novel IKK inhibitor: 2-[14C]-N-(6-chloro-9H-pyrido [3,4-b]indol-8-yl)-3-pyridinecarboxamide

Prakash

2005

J Label Compd Radiopharm

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“…It was apparently bound to the enzyme by the formation of a chargetransfer complex (9). When a methyl (IX), and ethyl (X), or a propyl (XI) group was placed in Position 3 of VIII, an increase in inhibitory activity of four-, seven-, and tenfold was observed, respectively.…”

Section: Discussionmentioning

confidence: 97%

Hydroxyindole-O-Methyltransferase I: Substrate Binding

McIsaac

Tansey

1969

Journal of Pharmaceutical Sciences

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“…R.A. sulfuric acid was purchased from Merck. N,N'-Dimethylharmane 6 sulfate was synthesized by known procedures (14).…”

Section: Methodsmentioning

confidence: 99%

Sulfonation reactions of (β-carbolines

Guzman¹,

Almeida²,

Toledo³

et al. 1989

Can. J. Chem.

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Can. J. Chem. 67,720 (1989).The homogeneous sulfonations of P-carboline derivatives norharmane 2, harmane 3, harmine 4, harm01 5, N,N1-dimethylharmane 6, arid harmaline 7 have been studied in 80-90% w/w sulfuric acid solutions at 25OC. Ultraviolet-visible and I3C nuclear magnetic resonance spectra and chemical analysis of the reaction mixtures show that for all the substrates studied only C-6 sulfonated products are obtained. The sulfonation reactions of the benzene unsubstituted substrates 2 , 3 , and 6 and the partially aromatic substrate 7 proceed by direct electrophilic attack of the H3SO4+ cation on the benzene ring of the P-carboline skeleton. Sulfonation of 4 and 5 at the lower sulfuric acid concentrations is effected by the H3S04+ entity. With increasing sulfuric acid concentration there is a gradual changeover of the sulfonating entity from H3S04+ to H2S207. The different mechanisms of sulfonation are discussed. Can. J. Chem. 67, 720 (1989).OpCrant ?I 25"C, dans des solutions ?I 80-90% P/P d'acide sulfurique, on a ttudit les sulfonations homogknes des derives de la P-carboline que sont le norharmane (2), l'harmane (3), l'harmine (4), l'harmol (S), le N,Nf-dimtthylharmane (6) et l'harmaline (7). Les spectres ultraviolet-visible et rksonance magnCtique nucltaire du I3C et les analyses chimiques des mClanges rtactionnels montrent que tous les substrats CtudiCs ne fournissent que les produits substituis en C-6. Les rCactions de sulfonation des substrats qui ne sont pas substituCs sur le noyau benzinique ( 2 , 3 et 6) ou qui ne sont que partiellement aromatiques (7) se produisent par une attaque Clectrophile directe du cation H3S04+ sur le noyau benzknique du squelette de la P-carboline. La sulfonation des composCs 4 et 5 aux concentrations les plus faibles d'acide sulfurique se produisent sous l'effet de l'entitt H3SO4+ Avec une augmentation de la concentration d'acide sulfurique, il se produit un changement graduel de I'entitC responsable de la sulfonation, de H3S04+ ?I H2S207. On discute des divers mtcanismes de sulfonation.

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Inhibitors of Monoamine Oxidase

Cited by 106 publications

References 10 publications

Synthesis of C-14-labeled novel IKK inhibitor: 2-[14C]-N-(6-chloro-9H-pyrido [3,4-b]indol-8-yl)-3-pyridinecarboxamide

Synthesis of C-14-labeled novel IKK inhibitor: 2-[14C]-N-(6-chloro-9H-pyrido [3,4-b]indol-8-yl)-3-pyridinecarboxamide

Hydroxyindole-O-Methyltransferase I: Substrate Binding

Sulfonation reactions of (β-carbolines

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