e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Cardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents

MJ Zelesko, DF McComsey, WE Hageman…

Index: Zelesko, Michael J.; McComsey, David F.; Hageman, William E.; Nortey, Samuel O.; Baker, Carol A.; Maryanoff, Bruce E. Journal of Medicinal Chemistry, 1983 , vol. 26, # 2 p. 230 - 237

Full Text: HTML

Citation Number: 10

Abstract

Scheme I. Indole I was reacted with thiourea and Iz/KI, and the thiouronium intermediate product was immediately hydrolyzed with aqueous NaOH to give sodium 3-indolylthiolate I1 in situ.'l The thiolate was alkylated with chloroacetonitrile to give nitrile 111. If desired, N- alkylation could be conducted at this point by reaction of nitrile I11 with an alkyl halide and aqueous NaOH, giving alkylated nitriles IV. Reduction of I11 or IV with BH3. THFlZ or ...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-[1-(2-methoxyethyl)indol-3-yl]sulfanylacetonitrile Structure

2-[1-(2-methoxy...

Indole Structure

~%

2-[1-(2-methoxyethyl)indol-3-yl]sulfanylacetonitrile Structure

2-[1-(2-methoxy...

2-(1H-INDOL-3-YLSULFANYL)-ETHYLAMINE Structure

2-(1H-INDOL-3-Y...

5-ethoxy-1-methyl-3,4-dihydro-2H-pyrrolium, tetrafluoroborate Structure

5-ethoxy-1-meth...

~40%

N-[2-(1H-indol-3-ylsulfanyl)ethyl]-1-methylpyrrolidin-2-imine Structure

N-[2-(1H-indol-...

3-(1H-indol-3-ylsulfanyl)propan-1-amine Structure

3-(1H-indol-3-y...

5-ethoxy-1-methyl-3,4-dihydro-2H-pyrrolium, tetrafluoroborate Structure

5-ethoxy-1-meth...

~%

N-[3-(1H-indol-3-ylsulfanyl)propyl]-1-methylpyrrolidin-2-imine Structure

N-[3-(1H-indol-...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-[1-(cyclopropylmethyl)indol-3-yl]sulfanylacetonitrile Structure

2-[1-(cycloprop...

Indole Structure

~%

2-[1-(cyclopropylmethyl)indol-3-yl]sulfanylacetonitrile Structure

2-[1-(cycloprop...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-(1-octylindol-3-yl)sulfanylacetonitrile Structure

2-(1-octylindol...

Indole Structure

~%

2-(1-octylindol-3-yl)sulfanylacetonitrile Structure

2-(1-octylindol...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-[1-(furan-2-ylmethyl)indol-3-yl]sulfanylacetonitrile Structure

2-[1-(furan-2-y...

Indole Structure

~%

2-[1-(furan-2-ylmethyl)indol-3-yl]sulfanylacetonitrile Structure

2-[1-(furan-2-y...

Indole Structure

~%

3-(1H-indol-3-ylsulfanyl)propan-1-amine Structure

3-(1H-indol-3-y...

2-((5-chloro-2-methyl-1H-indol-3-yl)thio)acetonitrile Structure

2-((5-chloro-2-...

~%

2-[(5-chloro-2-methyl-1H-indol-3-yl)sulfanyl]ethanamine Structure

2-[(5-chloro-2-...

5-Chloro-2-methylindole Structure

5-Chloro-2-meth...

~%

2-[(5-chloro-2-methyl-1H-indol-3-yl)sulfanyl]ethanamine Structure

2-[(5-chloro-2-...

5-Methoxyindole Structure

5-Methoxyindole

~%

2-[(5-methoxy-1H-indol-3-yl)sulfanyl]acetonitrile Structure

2-[(5-methoxy-1...

2-Methylindole Structure

~%

2-[(2-methyl-1H-indol-3-yl)sulfanyl]acetonitrile Structure

2-[(2-methyl-1H...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-(1H-INDOL-3-YLSULFANYL)-ETHYLAMINE Structure

2-(1H-INDOL-3-Y...

Indole Structure

~%

2-(1H-INDOL-3-YLSULFANYL)-ETHYLAMINE Structure

2-(1H-INDOL-3-Y...

5-Chloroindole Structure

~%

2-[(5-chloro-1H-indol-3-yl)sulfanyl]acetonitrile Structure

2-[(5-chloro-1H...

5-Ethylindole Structure

~%

2-[(5-ethyl-1H-indol-3-yl)sulfanyl]acetonitrile Structure

2-[(5-ethyl-1H-...

Indole Structure

~%

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-(1-methylindol-3-yl)sulfanylacetonitrile Structure

2-(1-methylindo...

Indole Structure

~%

2-(1-methylindol-3-yl)sulfanylacetonitrile Structure

2-(1-methylindo...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

allyl bromide Structure

~85%

2-(1-prop-2-enylindol-3-yl)sulfanylacetonitrile Structure

2-(1-prop-2-eny...

Indole Structure

~%

2-(1-prop-2-enylindol-3-yl)sulfanylacetonitrile Structure

2-(1-prop-2-eny...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-(1-prop-2-ynylindol-3-yl)sulfanylacetonitrile Structure

2-(1-prop-2-yny...

Indole Structure

~%

2-(1-prop-2-ynylindol-3-yl)sulfanylacetonitrile Structure

2-(1-prop-2-yny...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-[1-(2-methylprop-2-enyl)indol-3-yl]sulfanylacetonitrile Structure

2-[1-(2-methylp...

Indole Structure

~%

2-[1-(2-methylprop-2-enyl)indol-3-yl]sulfanylacetonitrile Structure

2-[1-(2-methylp...

Indole Structure

~%

4-(1H-indol-3-ylsulfanyl)butanenitrile Structure

4-(1H-indol-3-y...

4-(1H-indol-3-ylsulfanyl)butanenitrile Structure

4-(1H-indol-3-y...

~%

4-(1H-indol-3-ylsulfanyl)butan-1-amine Structure

4-(1H-indol-3-y...

Indole Structure

~%

4-(1H-indol-3-ylsulfanyl)butan-1-amine Structure

4-(1H-indol-3-y...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-(1-ethylindol-3-yl)sulfanylacetonitrile Structure

2-(1-ethylindol...

Indole Structure

~%

2-(1-ethylindol-3-yl)sulfanylacetonitrile Structure

2-(1-ethylindol...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-(1-propan-2-ylindol-3-yl)sulfanylacetonitrile Structure

2-(1-propan-2-y...

Indole Structure

~%

2-(1-propan-2-ylindol-3-yl)sulfanylacetonitrile Structure

2-(1-propan-2-y...

2-[(2-methyl-1H-indol-3-yl)sulfanyl]acetonitrile Structure

2-[(2-methyl-1H...

~%

2-(1,2-dimethylindol-3-yl)sulfanylacetonitrile Structure

2-(1,2-dimethyl...

2-Methylindole Structure

~%

2-(1,2-dimethylindol-3-yl)sulfanylacetonitrile Structure

2-(1,2-dimethyl...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-(1-cyclopentylindol-3-yl)sulfanylacetonitrile Structure

2-(1-cyclopenty...

Indole Structure

~%

2-(1-cyclopentylindol-3-yl)sulfanylacetonitrile Structure

2-(1-cyclopenty...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-(1-propylindol-3-yl)sulfanylacetonitrile Structure

2-(1-propylindo...

Indole Structure

~%

2-(1-propylindol-3-yl)sulfanylacetonitrile Structure

2-(1-propylindo...

2-(1H-indol-3-ylsulfanyl)acetonitrile Structure

2-(1H-indol-3-y...

~%

2-(1-benzylindol-3-yl)sulfanylacetonitrile Structure

2-(1-benzylindo...

Indole Structure

~%

2-(1-benzylindol-3-yl)sulfanylacetonitrile Structure

2-(1-benzylindo...

2-[(2-methyl-1H-indol-3-yl)sulfanyl]acetonitrile Structure

2-[(2-methyl-1H...

~%

2-[(2-METHYL-1H-INDOL-3-YL)THIO]ETHANAMINE Structure

2-[(2-METHYL-1H...

2-Methylindole Structure

~%

2-[(2-METHYL-1H-INDOL-3-YL)THIO]ETHANAMINE Structure

2-[(2-METHYL-1H...