Synthesis of (.+-.)-cryptowoline iodide

Benington, F.; Morin, R. D.

doi:10.1021/jo01279a040

Cited by 28 publications

(16 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The residue obtained on evaporation was dried in vacuo over P205 to remove the last traces of D M F and finally crystallized from benzene/petroleum ether (30-40 "C) to give an amorphous white solid (640 mg, 83%), mp 65-67 "C [lit. (Benington & Morin, 1967) 69-70 "C].…”

Section: Enzymesmentioning

confidence: 99%

Stereochemistry and kinetic isotope effects in the bovine plasma amine oxidase catalyzed oxidation of dopamine

Summers¹,

Marković²,

Klinman³

1979

Biochemistry

View full text Add to dashboard Cite

The stereochemistry of the bovine plasma amine oxidase catalyzed oxidation of 2-(3,4-dihydroxyphenyl)-ethylamine (domapine) has been investigated by comparing 3H/14C ratios of 3,4-dibenzyloxyphenethyl alcohols, derived from 3,4-dihydroxyphenylacetaldehydes, to starting dopamines chirally labeled at C-1 and C-2. The oxidation of [2RS-3H]-, [2R-3H]-, and [2S-3H]dopamine leads to products which have retained 53, 59, and 47% of their tritium. Similarly, oxidation of [1RS-3H]-, [1R-3H]-, and [1S-3H]dopamine leads to an 80, 80, and 92% retention of tritium. The configurational purity of tritium at C-2 of dopamine and C-1 of the dopamine precursor 3-methoxy-4-hydroxyphenethylamine has been confirmed employing dopamine-beta-hydroxylase (specific for the pro-R hydrogen at C-2) and pea seedling amine oxidase (specific for the pro-S hydrogen at C-1). In addition, chromatographically resolved isozymes of bovine plasma amine oxidase have been demonstrated to lead to the same stereochemical result as pooled enzyme fractions. We have been able to rule out carbon interchange and tritium transfer in the ethylamine side chain of dopamine as the source of the apparent nonstereospecificity. Estimated primary tritium isotope effects are 1 for [2-3H]dopamines and 5--6 and 26--34 for [1R-3H]- and [1S-3H]dopamine, respectively. We propose the presence of alternate dopamine binding modes, characterized by absolute but opposing stereochemistries and differential primary tritium isotope effects at C-1.

show abstract

Section: Enzymesmentioning

confidence: 99%

Stereochemistry and kinetic isotope effects in the bovine plasma amine oxidase catalyzed oxidation of dopamine

Summers¹,

Marković²,

Klinman³

1979

Biochemistry

View full text Add to dashboard Cite

show abstract

“…In principle, the total amount of starting material can be transformed into a desired target molecule. The preparation according to [16] via reduction of a triple bond seemed to us too cumbersome. Therefore, we investigated the inversion of the double bond of dimethyl (E)-3-hexendioate (20) (Scheme 3) by the method described by Sonnet and Oliver [17].…”

Section: *Cooh Oh H H 1mentioning

confidence: 99%

3‐Hydroxyglutarate and β,γ‐Epoxy Esters as Substrates for Pig Liver Esterase (PLE) and α‐Chymotrypsin

Mohr

Rösslein

Tamm

1987

Helvetica Chimica Acta

View full text Add to dashboard Cite

Scheme I / a-Chy or PLE 2 5 MeOOC COOMs 3 9 4 C13CCH200C COOMe 8 6 7a) (t-Bu)Me,reagent in order to obtain diastereoisomeric mixtures, which can be analyzed by appropriate techniques. According to Scheme I , the (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropionyl derivative 4 [6] and the camphanoates 6 and 7 were prepared via bromide 5 and via acylation of the diesters 8 and 9, respectively, using routine t-ransformations. Whereas 4 showed clear splittings in the 90-MHz 'H-NMR spectrum which allowed the calculation of the e.e. value, neither the 'Hnor the 13C-NMR spectra of 6 and 7 were suited for the determination of the e.e. Ester 6 was decomposed during GC analysis, too. However, the diastereoisoineric triester 7, obtained from 2 in two steps without crystalline intermediate, could be analyzed accurately by HPLC (Partisil-5 NO,, hexane/Et,O).

show abstract

“…[ 1–5 ] Some of them have been shown to exhibit interesting biological activities [ 6‐12 ] including antileukemic and antitumor activities, [ 6‐8 ] nonsteroidal antiestrogen, [ 10 ] and anti‐tubulin activity. [ 11 ] Most of the reported methods for the synthesis of such alkaloids and related indolo[2,1‐ a ]isoquinolines [ 6‐59 ] involve the procedures ending up with the formation of the fused indole ring, such as benzyne method, [ 6–11 , 13–26 ] oxidative coupling, [ 27‐30 ] Bischler‐Napieralski cyclization, [ 31 ] photocyclization, [ 32 ] anionic cyclization, [ 33,34 ] radical cyclization, [ 34‐36 ] Pschorr cyclization, [ 37,38 ] Ni or Pd‐catalyzed intramolecular amination, [ 39,40 ] other metal‐catalyzed cycloaddition, [ 41‐50 ] and other methods. [ 12,51‐59 ] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of indolo[2,1‐a]isoquinolines by CF₃COOH‐induced cyclization

Wada

Kurono

Senboku

et al. 2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Indolo[2,1-a]isoquinoline alkaloids and related compounds have been known to have interesting biological activities, such as antileukemic and antitumor activities. We found that 1-(3,4-dimethoxyphenethyl)indole gave 2,3-dimethoxyindolo [2,1-a]isoquinoline and 1-(3,4-dimethoxyphenylacetyl)indole gave 2,3-dimethoxy-6-oxoindolo[2,1-a]isoquinoline, respectively, by an intramolecular cyclization carried out in boiling trifluoroacetic acid.

show abstract

Synthesis of (.+-.)-cryptowoline iodide

Cited by 28 publications

References 0 publications

Stereochemistry and kinetic isotope effects in the bovine plasma amine oxidase catalyzed oxidation of dopamine

Stereochemistry and kinetic isotope effects in the bovine plasma amine oxidase catalyzed oxidation of dopamine

3‐Hydroxyglutarate and β,γ‐Epoxy Esters as Substrates for Pig Liver Esterase (PLE) and α‐Chymotrypsin

Synthesis of indolo[2,1‐a]isoquinolines by CF₃COOH‐induced cyclization

Contact Info

Product

Resources

About

Synthesis of (.+-.)-cryptowoline iodide

Cited by 28 publications

References 0 publications

Stereochemistry and kinetic isotope effects in the bovine plasma amine oxidase catalyzed oxidation of dopamine

Stereochemistry and kinetic isotope effects in the bovine plasma amine oxidase catalyzed oxidation of dopamine

3‐Hydroxyglutarate and β,γ‐Epoxy Esters as Substrates for Pig Liver Esterase (PLE) and α‐Chymotrypsin

Synthesis of indolo[2,1‐a]isoquinolines by CF3COOH‐induced cyclization

Contact Info

Product

Resources

About

Synthesis of indolo[2,1‐a]isoquinolines by CF₃COOH‐induced cyclization