4 Medicinal Chemistry of Tetrazoles

Singh, Harkishan; Chawla, Amit Kumar; Kapoor, Vijay K.; Paul, Dharam; Malhotra, Ravinder

doi:10.1016/s0079-6468(08)70159-0

Cited by 319 publications

(146 citation statements)

References 129 publications

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“…Recrystallization from diethyl ether gave the desired compound as colorless needles (25% yield; mp 376-377 K). 1 Infrared Spectroscopy. The IR spectra were obtained using a Mattson (Infinity 60AR Series) Fourier Transform infrared spectrometer, equipped with a deuterated triglycine sulfate (DTGS) detector and a Ge/KBr beam splitter, with 0.5 cm -1 resolution.…”

Section: Methodsmentioning

confidence: 99%

Molecular Structure, Vibrational Spectra and Photochemistry of 2-Methyl-2H-Tetrazol-5-Amine in Solid Argon

et al. 2005

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In this work, the molecular structure, infrared spectrum and UV photochemistry of 2-methyl-2H-tetrazol-5-amine (2MTA) isolated in solid argon (10 K) were investigated. The experimental studies were supported by extensive DFT(B3LYP)/6-311++G(d,p) calculations. The infrared spectrum of matrix-isolated 2MTA was fully assigned and correlated with structural properties. Taking into consideration the observed frequency of the NH 2 wagging mode, it is suggested that, in the matrixes, the amine group becomes slightly more planar than in the gas phase, due to matrix-packing effects. In situ UV irradiation (λ > 235 nm) of the matrixisolated 2MTA monomer is shown to induce three main primary photochemical processes: (1) tautomerization to mesoionic 3-methyl-1H-tetrazol-3-ium-5-aminide; (2) nitrogen elimination, with production of 1-methyl-1H-diazirene-3-amine; (3) ring cleavage leading to production of methyl azide and cyanamide. Following the primary photoproducts, secondary reactions were observed, leading to spectroscopic observation of methylenimine and isocyanidric acid.

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Section: Methodsmentioning

confidence: 99%

Molecular Structure, Vibrational Spectra and Photochemistry of 2-Methyl-2H-Tetrazol-5-Amine in Solid Argon

et al. 2005

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“…Tetrazoles derivatives are an important class of compounds, which can be used in the fields of bioorganic and medicinal chemistry as antibacterials, anti-cancer, heart disease, neurodegenerative disease, and antifungal activity (Smissman et al,1976;McGuire et al, 1990;Lunn et al, 1992;Itoh et al, 1995;Upadhayaya et al, 2004;Wu et al, 2008;Rostom et al, 2009. The tetrazole moiety has long been established as a bioisostere of a carboxyl unit (Burger, 1991). A major advantage of tetrazoles over carboxylic acids is that they are resistant to many biological metabolic degradation pathways (Singh et al, 1980).…”

Section: Methodsmentioning

confidence: 99%

“…For the biological activity and medicinal properties of tetrazole derivatives, see : Smissman et al (1976); McGuire et al (1990); Lunn et al (1992); Itoh et al (1995); Upadhayaya et al (2004); Wu et al (2008); Rostom et al (2009);Burger (1991); Singh et al (1980). For the synthetic procedure, see: Adams & Langley (1941a,b).…”

Section: Related Literaturementioning

confidence: 99%

N-(Cyanomethyl)benzamide

et al. 2010

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Key indicators: single-crystal X-ray study; T = 296 K, P = 0.0 kPa; mean (C-C) = 0.002 Å; R factor = 0.038; wR factor = 0.109; data-to-parameter ratio = 13.6.In the structure of the title compound, C 9 H 8 N 2 O, the amide group is twisted by a dihedral angle of 21.86 (7) with respect to the benzene ring, while the planes of the benzene ring and cyanomethyl group form a dihedral angle of 53.13 (11) . In the crystal structure, molecules are linked via N-HÁ Á ÁO hydrogen bonds, forming a chain running parallel to the a axis. Related literature ExperimentalCrystal data Data collectionBruker X8 APEXII CCD areadetector diffractometer 11132 measured reflections 1920 independent reflections 1433 reflections with I > 2 (I) R int = 0.027

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“…They have long been recognized as carboxylic acid isosteres 2,3 and are important heterocycles in medicinal chemistry, owing to their increased stability towards metabolic degradation pathways 4 . The acidity of the tetrazole NH group corresponds roughly to that of the carboxylic acid 5 .…”

Section: Introductionmentioning

confidence: 99%

Facile One-Pot Multicomponent Synthesis of Biaryl Tetrazoles through In Situ Formed Secondary Amides

2017

Chem Sci Trans

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4 Medicinal Chemistry of Tetrazoles

Cited by 319 publications

References 129 publications

Molecular Structure, Vibrational Spectra and Photochemistry of 2-Methyl-2H-Tetrazol-5-Amine in Solid Argon

Molecular Structure, Vibrational Spectra and Photochemistry of 2-Methyl-2H-Tetrazol-5-Amine in Solid Argon

N-(Cyanomethyl)benzamide

Facile One-Pot Multicomponent Synthesis of Biaryl Tetrazoles through In Situ Formed Secondary Amides

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