Cationic chalcone antibiotics. Design, synthesis, and mechanism of action

…, T Boesen, K Schønning, H Kromann

Index: Nielsen, Simon F.; Larsen, Mogens; Boesen, Thomas; Schonning, Kristian; Kromann, Hasse Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2667 - 2677

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Citation Number: 116

Abstract

This paper describes how the introduction of “cationic” aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the B-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an ...

 Related Synthetic Route
methylpiperazine Structure

109-01-3

methylpiperazine

3-Bromo-4-fluorobenzaldehyde Structure

77771-02-9

3-Bromo-4-fluor...

~43%

3-Bromo-4-(4-methyl-1-piperazinyl)benzaldehyde Structure

443777-03-5

3-Bromo-4-(4-me...

4-bromo-2-(chloromethyl)-1-methoxybenzene Structure

7017-52-9

4-bromo-2-(chlo...

~%

1-(3-DIMETHYLAMINOMETHYL-4-METHOXY-PHENYL)-ETHANONE Structure

505070-85-9

1-(3-DIMETHYLAM...

(5-Bromo-2-methoxyphenyl)methanol Structure

80866-82-6

(5-Bromo-2-meth...

~%

1-(3-DIMETHYLAMINOMETHYL-4-METHOXY-PHENYL)-ETHANONE Structure

505070-85-9

1-(3-DIMETHYLAM...

5-Bromo-2-anisaldehyde Structure

25016-01-7

5-Bromo-2-anisa...

~%

1-(3-DIMETHYLAMINOMETHYL-4-METHOXY-PHENYL)-ETHANONE Structure

505070-85-9

1-(3-DIMETHYLAM...

2-Bromo-5-methoxybenzoic acid Structure

22921-68-2

2-Bromo-5-metho...

~%

2-bromo-5-methoxy-N,N-dimethylbenzamide Structure

212908-12-8

2-bromo-5-metho...

5-Bromo-2-anisaldehyde Structure

25016-01-7

5-Bromo-2-anisa...

~%

4-bromo-2-(chloromethyl)-1-methoxybenzene Structure

7017-52-9

4-bromo-2-(chlo...

methylpiperazine Structure

109-01-3

methylpiperazine

5-Bromo-2-fluorobenzaldehyde Structure

93777-26-5

5-Bromo-2-fluor...

~52%

5-BROMO-2-(4-METHYLPIPERAZIN-1-YL)-BENZALDEHYDE Structure

628325-60-0

5-BROMO-2-(4-ME...

m-Bromoacetophenone Structure

2142-63-4

m-Bromoacetophenone

~%

1-[3-(4-Methyl-1-piperazinyl)phenyl]ethanone Structure

56915-80-1

1-[3-(4-Methyl-...

methylpiperazine Structure

109-01-3

methylpiperazine

~%

1-[3-(4-Methyl-1-piperazinyl)phenyl]ethanone Structure

56915-80-1

1-[3-(4-Methyl-...

2-(3-bromophenyl)-2-methyl-[1,3]dioxane Structure

850789-60-5

2-(3-bromopheny...

~%

1-[3-(4-Methyl-1-piperazinyl)phenyl]ethanone Structure

56915-80-1

1-[3-(4-Methyl-...

(5-Bromo-2-methoxyphenyl)methanol Structure

80866-82-6

(5-Bromo-2-meth...

~%

1-(5-Bromo-2-methoxyphenyl)-N,N-dimethylmethanamine Structure

7078-90-2

1-(5-Bromo-2-me...

5-Bromo-2-anisaldehyde Structure

25016-01-7

5-Bromo-2-anisa...

~%

1-(5-Bromo-2-methoxyphenyl)-N,N-dimethylmethanamine Structure

7078-90-2

1-(5-Bromo-2-me...

4-bromo-2-(chloromethyl)-1-methoxybenzene Structure

7017-52-9

4-bromo-2-(chlo...

Dimethylamine Structure

124-40-3

Dimethylamine

~%

1-(5-Bromo-2-methoxyphenyl)-N,N-dimethylmethanamine Structure

7078-90-2

1-(5-Bromo-2-me...

N-Butyl Vinyl Ether Structure

111-34-2

N-Butyl Vinyl Ether

1-(2-bromo-5-methoxyphenyl)-N,N-dimethylmethanamine Structure

10126-37-1

1-(2-bromo-5-me...

~81%

1-(2-FURYL)PROPAN-1-ONE Structure

77973-25-2

1-(2-FURYL)PROP...

2-bromo-5-methoxybenzoyl chloride Structure

56658-04-9

2-bromo-5-metho...

~%

1-(2-FURYL)PROPAN-1-ONE Structure

77973-25-2

1-(2-FURYL)PROP...

2-bromo-5-methoxy-N,N-dimethylbenzamide Structure

212908-12-8

2-bromo-5-metho...

~%

1-(2-FURYL)PROPAN-1-ONE Structure

77973-25-2

1-(2-FURYL)PROP...

2-Bromo-5-methoxybenzoic acid Structure

22921-68-2

2-Bromo-5-metho...

~%

1-(2-FURYL)PROPAN-1-ONE Structure

77973-25-2

1-(2-FURYL)PROP...

3-(4-Methylpiperazin-1-yl)benzaldehyde Structure

628325-62-2

3-(4-Methylpipe...

~93%

2-BROMO-5-(4-METHYL-PIPERAZIN-1-YL)-BENZALDEHYDE Structure

628325-61-1

2-BROMO-5-(4-ME...

3-Bromobenzaldehyde Structure

3132-99-8

3-Bromobenzaldehyde

~%

2-BROMO-5-(4-METHYL-PIPERAZIN-1-YL)-BENZALDEHYDE Structure

628325-61-1

2-BROMO-5-(4-ME...

1,3-Dioxane,2-(3-bromophenyl)-(9CI) Structure

67437-93-8

1,3-Dioxane,2-(...

~%

2-BROMO-5-(4-METHYL-PIPERAZIN-1-YL)-BENZALDEHYDE Structure

628325-61-1

2-BROMO-5-(4-ME...

2-bromo-5-methoxy-N,N-dimethylbenzamide Structure

212908-12-8

2-bromo-5-metho...

~%

1-(2-bromo-5-methoxyphenyl)-N,N-dimethylmethanamine Structure

10126-37-1

1-(2-bromo-5-me...

5-Bromo-2-fluorobenzaldehyde Structure

93777-26-5

5-Bromo-2-fluor...

N-Boc-piperazine Structure

57260-71-6

N-Boc-piperazine

~38%

tert-Butyl 4-(4-bromo-2-formylphenyl)piperazine-1-carboxylate Structure

628326-05-6

tert-Butyl 4-(4...

methylpiperazine Structure

109-01-3

methylpiperazine

4-Bromo-2-fluorobenzaldehyde Structure

57848-46-1

4-Bromo-2-fluor...

~99%

4-Bromo-2-(4-methylpiperazino)benzaldehyde Structure

628326-12-5

4-Bromo-2-(4-me...

3,5-Dibromobenzaldehyde Structure

56990-02-4

3,5-Dibromobenz...

~%

3-Bromo-5-(4-methyl-1-piperazinyl)benzaldehyde Structure

628325-71-3

3-Bromo-5-(4-me...

methylpiperazine Structure

109-01-3

methylpiperazine

~%

3-Bromo-5-(4-methyl-1-piperazinyl)benzaldehyde Structure

628325-71-3

3-Bromo-5-(4-me...


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