Carboxylic acid replacement structure-activity relationships in suosan type sweeteners. A sweet taste antagonist. 1.
N-(4-Cyanophenyl)-N'-(2-carboxyethyl)urea (2), an analogue of suosan [1,N-(4-nitrophenyl)-N'-(2-carboxyethyl)urea], is a known high-potency sweetener derived from beta-alanine. Sulfonic and phosphonic acid analogues of 2 were prepared to develop structure-activity relationships through modification of the carboxylic acid region of this family of sweeteners. Neither of the carboxylic acid replacements resulted in sweet analogues. However, we found that N-(4-cyanophenyl)-N'-[(sodiosulfo)methyl]urea (7) is an antagonist of the sweet taste response. The bitter taste response to caffeine, quinine, and naringin was also antagonized. Antagonist 7 was found to inhibit the sweet taste perception of a variety of sweeteners. Antagonist 7 had no effect on the sour or salty taste response.
Muller
G W
GW
NutraSweet Company, Mt. Prospect, Illinois 60056.
Culberson
J C
JC
Roy
G
G
Ziegler
J
J
Walters
D E
DE
Kellogg
M S
MS
Schiffman
S S
SS
Warwick
Z S
ZS
D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D002110:Caffeine / Q000037:antagonists & inhibitors; D002264:Carboxylic Acids / Q000737:chemistry*; D044950:Flavanones; D005419:Flavonoids / Q000037:antagonists & inhibitors; D006801:Humans; D010671:Phenylurea Compounds / Q000737:chemistry / Q000494:pharmacology*; D011803:Quinine / Q000037:antagonists & inhibitors; D013329:Structure-Activity Relationship; D013549:Sweetening Agents; D013649:Taste / Q000187:drug effects*; D015091:beta-Alanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*
D002264:Carboxylic Acids; D044950:Flavanones; D005419:Flavonoids; D010671:Phenylurea Compounds; D013549:Sweetening Agents; C000107:aspartic acid-beta-4-nitroanilide; D015091:beta-Alanine; C074652:N-(4-cyanophenyl)-N'-((sodiosulfo)methyl)urea; D001224:Aspartic Acid; D002110:Caffeine; C074653:N-(4-cyanophenyl)-N'-(2-carboxyethyl)urea; D011803:Quinine; C005274:naringin