Tetrazoles as carboxylic acid isosteres: chemistry and biology

Malik, Maqsood Ahmad; Wani, Mohmmad Younus; Al-Thabaiti, Shaeel A.; Shiekh, Rayees Ahmad

doi:10.1007/s10847-013-0334-x

Cited by 107 publications

(67 citation statements)

References 114 publications

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“…It serves as important structural component in several molecules of pharmaceutical interest. 20 The presence of 1H-tetrazole species in drug molecules has been known to favorably enhance their metabolic resistance and pharmacokinetic properties.…”

Section: 12mentioning

confidence: 99%

N,N-Dimethylpyridin-4-amine (DMAP) based ionic liquids: evaluation of physical properties via molecular dynamics simulations and application as a catalyst for Fisher indole and 1H-tetrazole synthesis

et al. 2017

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The last few decades have seen a rapid increase in the use of ionic liquids (ILs) as a green alternative to traditional solvents in organic synthesis. The use of ILs as catalysts has also increased in recent years.Herein we the report synthesis of new N,N-dimethylpyridin-4-amine (DMAP) based ionic liquids (ILs) as new and efficient catalysts for the facile synthesis of indoles (via Fischer indole synthesis), and 1H-tetrazoles (via click chemistry). The method is environmentally friendly, requiring only minimum catalyst loading (0.2 equiv. for Fischer indole synthesis). In the case of 1H-tetrazole formation (via click chemistry), the reaction was carried out under a solvent free environment. Moreover, thermal studies (TGA, DTG and DSC) of DMAP-ILs (2, 3) have also been carried out to elicit their stability for temperature dependent reactions. Application of molecular dynamics simulations provided valuable insights into the structural and transport properties of these ionic liquids. An MP2 method was applied to evaluate the stability of the compound via binding energy calculations.

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Section: 12mentioning

confidence: 99%

N,N-Dimethylpyridin-4-amine (DMAP) based ionic liquids: evaluation of physical properties via molecular dynamics simulations and application as a catalyst for Fisher indole and 1H-tetrazole synthesis

et al. 2017

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“…9,15,25,156 As mentioned above, NH-unsubstituted tetrazoles and carboxylic acids have similar physicochemical characteristics. 20, 35 Matta and co-workers 33, 34 revealed the similarity in the electrostatic potential and electron density distributions for tetrazolate and carboxylate anions. Allen and co-workers 32 analyzed the crystallographic data and results of theoretical calculations and showed that the following pairs are characterized by similar hydrogen bonding patterns: 1H-tetrazole ± CO 2 H group and tetrazolate anion ± carboxylate anions.…”

Section: Biologically Active Tetrazole-containing Analogues and Dementioning

confidence: 95%

Synthesis and biological properties of amino acids and peptides containing a tetrazolyl moiety

Popova¹,

Trifonov²

2015

Russ. Chem. Rev.

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“…Since the 1960s, tetrazoles witnessed a renaissance but now with their application strongly depending on their isomeric form. In the medicinal chemistry, N2- and especially C5-substituted tetrazoles are used as carboxylic acid bioisosteres [7], as structural motif for angiotensin blockers [8–10], as activator in oligonucleotide synthesis [11] or in the MTT-assay, determining the metabolic cell activity by reduction of a tetrazole-dye to a formazan by living cells [12]. …”

Section: Introductionmentioning

confidence: 99%

Microwave alkylation of lithium tetrazolate

2016

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N1-substituted tetrazoles are interesting ligands in transition metal coordination chemistry, especially in the field of spin crossover. Their synthesis is performed in most cases according to the Franke-synthesis, using a primary amine as reagent introducing the substitution pattern. To enhance flexibility in means of substrate scope, we developed a new protocol based on alkylation of lithium tetrazolate with alkyl bromides. The N1–N2 isomerism of the tetrazole during the alkylation was successfully suppressed by use of highly pure lithium tetrazolate and 30 vol.% aqueous ethanol as solvent, leading to pure N1-substituted products. The feasibility of this reaction was demonstrated by a selection of different substrates.Graphical abstract

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Tetrazoles as carboxylic acid isosteres: chemistry and biology

Cited by 107 publications

References 114 publications

N,N-Dimethylpyridin-4-amine (DMAP) based ionic liquids: evaluation of physical properties via molecular dynamics simulations and application as a catalyst for Fisher indole and 1H-tetrazole synthesis

N,N-Dimethylpyridin-4-amine (DMAP) based ionic liquids: evaluation of physical properties via molecular dynamics simulations and application as a catalyst for Fisher indole and 1H-tetrazole synthesis

Synthesis and biological properties of amino acids and peptides containing a tetrazolyl moiety

Microwave alkylation of lithium tetrazolate

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