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Molecular Biology

Sulfur-containing-antimicrobial-ester-amides

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Sulfur-containing antimicrobial ester-amides

Details

Inventors: Mod, Robert R.; Magne, Frank C.; Sumrell, Gene; Novak, Arthur F.;
Assignee: The United States of America as represented by the Secretary of (Washington, DC)
Primary Examiner: Jiles; Henry R.
Assistant Examiner: Ramsuer; R. W.
Attorney, Agent or Firm: Silverstein; M. Howard, McConnell; David G., Cangemi; Salvadore J.

Sulfur-containing long chain fatty ester-amides have been prepared by the addition of mercaptoacetic acid to the terminal and nonterminal double bonds of unsaturated amides followed by esterification of the carboxyl group with the appropriate alcohol. These compounds exhibit antimicrobial activity and have properties making them useful as antimicrobial agents.

DETAILED DESCRIPTION We claim: 1.
A sulfur-containing ester amide having antimicrobial activity and the general structure: ##STR2## where R.
sub.
1 is a lower alkyl or alkenyl group of 1 to 6 carbons; R.
sub.
2 and R.
sub.
3 cojointly form a morpholine ring; n + m add up to 15 and n = m plus or minus 1.
2.
The ester amide of claim 1 wherein the compound is 9(10)-(carbomethoxymethylthio)stearoylmorpholine.
3.
The ester amide of claim 1 wherein the compound is 9(10)-(carbethoxymethylthio)stearoylmorpholine.
4.
The ester amide of claim 1 wherein the compound is 9(10)-(carbopropoxymethylthio)stearoylmorpholine.
5.
The ester amide of claim 1 wherein the compound is 9(10)-(carbopentoxymethylthio)stearoylmorpholine.
6.
The ester amide of claim 1 wherein the compound is 9(10)-(carbo-3-methyl-1-butoxymethylthio)stearoylmorpholine.
7.
The ester amide of claim 1 wherein the compound is 9(10)-(carbohexoxymethylthio)stearoylmorpholine.
8.
The ester amide of claim 1 wherein the compound is 9(10)-(carballyloxymethylthio)stearoylmorpholine.
9.
A sulfur-containing ester amide having antimicrobial activity and the general structure: ##STR3## wherein R.
sub.
1 is a lower alkyl or alkenyl group of 1 to 6 carbons; and R.
sub.
2 and R.
sub.
3 cojointly form a morpholine ring.
10.
The ester amide of claim 9 wherein the compound is 11-(carbethoxymethylthio)undecanoylmorpholine.

Description:
BACKGROUND OF THE INVENTION 1.
Field of the Invention This invention relates to certain new sulfur-containing organic compounds which have exhibited antimicrobial activity.
More particularly, this invention relates to reaction products of mercaptoacetic acid with N,N-disubstituted long chain aliphatic amides.
2.
Description of the Prior Art It is known to the art that a variety of N-substituted fatty amides show antimicrobial activity.
However, many are not antimicrobially active and there is a wide difference in the activity of those which are active.
Some are active against only one, or a small number of microorganisms, while others show a broad spectrum of activity against many types or organisms

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