Notes. Thiomethyltetrazole Hypoglycemic Agents

Jm, McManus

doi:10.1021/jm00303a629

Cited by 4 publications

(2 citation statements)

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“…Tetrazoles can be obtained from the corresponding carboxylic acids by reaction of amidrazones with nitrous acid (Pinner, 1897), by reaction of diazonium salts with acylhydrazides or S-diacylhydrazines (Dimroth & de Montmollin, 1910), and by condensation of phenyl azides with the phenylhydrazones of aldehydes in alcoholic sodium alkoxide solutions (Dimroth & Merzbacher, 1910). The synthesis of some arylsulfonylmethyltetrazoles was described previously by MacManus (1969). We slightly modified this procedure by changing the reaction sequence (Polań ski & Jarzembek, 2002), as shown below.…”

Section: Synthesis and Toxicological Testsmentioning

confidence: 99%

Bitter sweeteners: tetrazole derivatives of arylsulfonylalcanoids – synthesis, structure and comparative study

Kalinowska‐Tłuścik

Jarzembek

Śliwiński

et al. 2008

Acta Crystallogr Sect B

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Within a research project aimed at the design of new sweeteners, the tetrazole moiety was introduced to arylsulfonylalkanoic acids (ASA) as a bioisostere of the carboxyl group. The crystal structures of four newly synthesized tetrazole derivatives and one intermediate product of the reaction were determined in order to explain the bitter taste of these compounds. Three chiral compounds crystallize as racemic mixtures in centrosymmetric space groups of the monoclinic system, whereas the non-chiral compound, with a higher dipole moment, crystallizes in the polar space group Cc. Intermolecular N-H...N hydrogen bonds between tetrazole moieties were observed in all four structures and are compared with the analogous interactions observed in tetrazole derivatives deposited in the Cambridge Structural Database (CSD). Specifically, the typical N1-H...N4 as well as N1-H...N3 interactions, which are less abundant in the CSD, are described. The formation of the latter interaction type can be hypothetically explained by an asymmetry of pi-electron distribution in the tetrazole rings caused by the crystalline environment. Important features of the crystal architecture are the chains of molecules linked by N-H...N bonds. A possible reason for the lack of a sweet taste of the tetrazoles investigated may be the improper position of the tetrazole H atom, and the mutual orientation of the proton donor and acceptor in their molecules. This orientation does not allow the tetrazoles to interact with the sweet-taste receptor in a way similar to that of ASA. The bitter taste of the investigated compounds needs further study.

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Section: Synthesis and Toxicological Testsmentioning

confidence: 99%

Bitter sweeteners: tetrazole derivatives of arylsulfonylalcanoids – synthesis, structure and comparative study

Kalinowska‐Tłuścik

Jarzembek

Śliwiński

et al. 2008

Acta Crystallogr Sect B

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“…Generally, we followed a slightly modified procedure described in the reference [4,5,14]. Therefore, the reaction of arylsulfonyl- Table 1.…”

Section: Synthesismentioning

confidence: 99%

Search for new sulfonyl-containing glucophores

Polański

Jarzembek

2002

Pure and Applied Chemistry

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A number of sweeteners contain the sulfur atom and a sulfonyl group. In our current search for new glucophores, several new compounds containing a sulfonyl group were obtained. Synthetic targets have been found both by intuitive modifications of the structural motifs of the known sweet compounds and by the use of molecular modeling techniques. We developed the efficient synthetic routes yielding these compounds and obtained a number of these analogs. We have evaluated the taste quality of the amides and sulfonylated amino acids, finding out that almost all of them are bitter actives. We are now performing basic toxicological tests preceding the systematic taste study within the tetrazoles obtained.

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Recent Advances in Tetrazole Chemistry

Butler

1977

Advances in Heterocyclic Chemistry Volume 21

211

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Notes. Thiomethyltetrazole Hypoglycemic Agents

Cited by 4 publications

References 1 publication

Bitter sweeteners: tetrazole derivatives of arylsulfonylalcanoids – synthesis, structure and comparative study

Bitter sweeteners: tetrazole derivatives of arylsulfonylalcanoids – synthesis, structure and comparative study

Search for new sulfonyl-containing glucophores

Recent Advances in Tetrazole Chemistry

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