Medicinal chemistry of tetrazoles
TL;DR: In this paper, the properties of responsible for biological activity tetrazoles are considered and examples are given of active pharmaceutical ingredients of modern drugs containing the tetrazole ring in the molecular structure.
Abstract: Properties of responsible for biological activity tetrazoles are considered. Examples are given of active pharmaceutical ingredients of modern drugs containing the tetrazole ring in the molecular structure. New publications on the synthesis and investigations of biological activity of promising tetrazole-containing compounds are cited.
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TL;DR: The use of multicomponent reactions for the preparation of substituted tetrazole derivatives is reviewed and synthetic approaches and their value are discussed by analyzing scope and limitations, and also enlighten their receptor binding mode.
Abstract: Tetrazole derivatives are a prime class of heterocycles, very important to medicinal chemistry and drug design due to not only their bioisosterism to carboxylic acid and amide moieties but also to their metabolic stability and other beneficial physicochemical properties. Although more than 20 FDA-approved drugs contain 1 H- or 2 H-tetrazole substituents, their exact binding mode, structural biology, 3D conformations, and in general their chemical behavior is not fully understood. Importantly, multicomponent reaction (MCR) chemistry offers convergent access to multiple tetrazole scaffolds providing the three important elements of novelty, diversity, and complexity, yet MCR pathways to tetrazoles are far from completely explored. Here, we review the use of multicomponent reactions for the preparation of substituted tetrazole derivatives. We highlight specific applications and general trends holding therein and discuss synthetic approaches and their value by analyzing scope and limitations, and also enlighten their receptor binding mode. Finally, we estimated the prospects of further research in this field.
337 citations
TL;DR: This review describes foundational subjects, methods, and metrics relevant to the energetic materials community and provides an overview of important classes of catenated nitrogen compounds ranging from theoretical investigation of hypothetical molecules to the practical application of real-world energetic materials.
Abstract: The properties of catenated nitrogen molecules, molecules containing internal chains of bonded nitrogen atoms, is of fundamental scientific interest in chemical structure and bonding, as nitrogen i...
134 citations
TL;DR: In this article, a review of α-amino nitriles through the Strecker-type and α-cyanation reactions, their chemical and biological properties, as well as their synthetic application, paying attention on the wonderful capacity for generating novel molecular diversity for pharmacological, biological and agrochemical researches, which ends with the total synthesis of complex alkaloids, preparation of new N-heterocycles and αaminonitrile-containing drugs.
109 citations
TL;DR: A short review compiles the main results of the studies in tetrazole chemistry published in the period 2009-2016 as discussed by the authors, focusing on the structure, reactivity, synthetic problems, functionalization, and also to the application of derivatives of this class of polynitrogen heterocyclic compounds.
Abstract: This short review compiles the main results of the studies in tetrazole chemistry published in the period 2009–2016. Attention is directed to the structure, reactivity, synthetic problems, functionalization, and also to the application of derivatives of this class of polynitrogen heterocyclic compounds. New conditions are revealed of the tetrazole synthesis underpinned by the use of versatile catalytic systems, ionic liquids, superacids, microwave activation, microreactor techniques, etc. Main trends in the development of the tetrazole chemistry that are helping to focus the efforts of researchers on novel, important, and promising directions of study are considered.
103 citations
TL;DR: It is confirmed that H2L could be used to detect Al(3+) and Zn(2+) in cells by bioimaging and the sensing mechanism is the inhibition of excited state intramolecular proton transfer (ESIPT).
Abstract: A tetrazole derivative 1-[(1H-tetrazol-5-ylimino)methyl]naphthalen-2-ol (H2L) as a fluorescent chemosensor for Al3+ in DMSO and Zn2+ in DMF was designed and synthesized. From 1H NMR data, the Job plot and the ESI-MS spectrum, 1:1 stoichiometric complexation between H2L and Al3+/Zn2+ was found in DMSO and DMF, respectively. The theoretical calculations at the level of B3LYP/6-311G** for the ground state and TD-B3LYP/6-311G** for the excited state revealed the sensing mechanism is the inhibition of excited state intramolecular proton transfer (ESIPT). And the possible fluorescent species formed in the DMSO and DMF solutions were deduced to be [Al(HL)(OH)(NO3)(H2O)(DMSO)] and [Zn(HL)(OH)(H2O)(DMF)]. What's more, it is confirmed that H2L could be used to detect Al3+ and Zn2+ in cells by bioimaging.
80 citations
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TL;DR: In this article, the authors present a compendium of all relevant ligands that have been employed to generate coordination polymers and metal-Organic Frameworks (MOFs), and three representative examples for each category are described in detail.
839 citations
TL;DR: A survey of representative literature procedures for the preparation of 5-substituted-1H-tetrazoles, focusing on preparations from aryl and alkyl nitriles, is presented in sections by generalized synthetic methods.
719 citations
487 citations
TL;DR: Docking of the 5CITEP inhibitor to snapshots of a 2 ns HIV-1 integrase MD trajectory indicated a previously uncharacterized trench adjacent to the active site that intermittently opens, which suggests a new target for HIV- 1 therapeutics.
Abstract: Docking of the 5CITEP inhibitor to snapshots of a 2 ns HIV-1 integrase MD trajectory indicated a previously uncharacterized trench adjacent to the active site that intermittently opens. Further docking studies of novel ligands with the potential to bind to both regions showed greater selective affinity when able to bind to the trench. Our ranking of ligands is open to experimental testing, and our approach suggests a new target for HIV-1 therapeutics.
344 citations
TL;DR: In this article, conditions for the transformation of alpha-aminonitriles to the tetrazole analogues of alpha amino acids were described, and the starting material in water/2-propanol at 80 degrees C with sodium azide and catalytic zinc bromide was refluxed.
186 citations