The taste of 1‐alkoxy‐ and 1‐halogeno‐2‐amino‐4‐cyano‐benzenes

Blanksma, J. J.; Petri, E. M.

doi:10.1002/recl.19470660604

Cited by 3 publications

(2 citation statements)

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“…Eleven compounds were highly active against T. brucei rhodesiense, with IC 50 values less than 10 nM ( 50 values less than 10 nM as well as cytotoxic indices between 10 and 25 times higher than that of furamidine.…”

Section: Antiprotozoal Activities and Cytotoxicitymentioning

confidence: 99%

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Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

et al. 2007

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3,5-bis(4-amidinophenyl)isoxazole (3)-an analogue of 2,5-bis(4-amidinophenyl)furan (furamidine) in which the central furan ring is replaced by isoxazole-and 42 novel analogues were prepared by two general synthetic pathways. The 43 isoxazole derivatives were assayed against Trypanosoma brucei rhodesiense (T. brucei rhodesiense) STIB900, Plasmodium falciparum (P. falciparum) K1, and rat myoblast L6 cells (for cytotoxicity) in vitro. Eleven compounds (3, 13, 16-18, 22, 26, 29, 31, 37, and 41) exhibited antitrypanosomal IC50 values less than 10 nM, five of which displayed cytotoxic indices (ratios of cytotoxic IC50 to antiprotozoal IC50 values) at least 10 times higher than that of furamidine. Eighteen compounds (4-8, 12, 14, 18-22, 25, 26, 28, 29, 32, and 43) were more active against P. falciparum than furamidine, with IC50 values less than 15 nM. Fourteen of these compounds had cytotoxic indices ranging between 10 and 120 times higher than that of furamidine, and five analogues exhibited high selectivity for P. falciparum over T. brucei rhodesiense.

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Section: Antiprotozoal Activities and Cytotoxicitymentioning

confidence: 99%

“…The nitration of bromobenzonitrile 68a to 68b 49 and its subsequent reduction to aniline 65 have been reported previously. 49,50 Diazotization of 65 followed by treatment with copper(I) chloride gave chlorobenzene 68c. Methoxy triflate 68d was prepared by treatment of 4-bromo-3-hydroxybenzonitrile with triflic anhydride.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

et al. 2007

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Sweet taste receptor

Tinti

Durozard

Nofre

1980

Naturwissenschaften

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Structural relationships of sugars to taste

1976

C R C Critical Reviews in Food Science and Nutrition

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Chemical modification of sugars and their simple analogues indicates that these types of compound are almost always sweet, bitter, or bitter/sweet; hence, the two basic tastes may be intimately associated features of the same molecule. Stepwise modification at each chiral center around the sugar ring allows the sapid functions in these molecules to be mapped and leads to the inescapable conclusion that sugar molecules may be "polarized" on taste bud receptors, so that one end of the molecule elicits sweetness and the other bitterness. However, more extensive chemical modification evidently causes the molecule to realign itself in entirely different ways on the receptor. In most oligosaccharides only one sugar residue is likely to bind to the taste receptor, and this is probably a nonreducing end group, because the anomeric center of glucopyranose types of structure does not appear to affect sweetness. Sweetness depresses bitterness and bitterness depresses sweetness. Hence, it is not possible to make structural comparisons between analogues without correcting for these effects. However, some semiquantitative studies have established the value of current hydrogen bond theories of sweetness and the ideal oxygen-oxygen interorbital spacings for sweetness criteria in sugar molecules.

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The taste of 1‐alkoxy‐ and 1‐halogeno‐2‐amino‐4‐cyano‐benzenes

Cited by 3 publications

References 6 publications

Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

Sweet taste receptor

Structural relationships of sugars to taste

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