120568-11-8Relevant articles and documents
Regio- and Enantioselective Synthesis of Azole Hemiaminal Esters by Lewis Base Catalyzed Dynamic Kinetic Resolution
Piotrowski, David W.,Kamlet, Adam S.,Dechert-Schmitt, Anne-Marie R.,Yan, Jiangli,Brandt, Thomas A.,Xiao, Jun,Wei, Liuqing,Barrila, Mark T.
, p. 4818 - 4823 (2016)
We report a modular three-component dynamic kinetic resolution (DKR) that affords enantiomerically enriched hemiaminal esters derived from azoles and aldehydes. The novel and scalable reaction can be used to synthesize valuable substituted azoles in a regioselective manner by capping (e.g., acylation) of the equilibrating azole-aldehyde adduct. With the use of a prolinol-derived DMAP catalyst as the chiral Lewis base, the products can be obtained in high chemical yield and with high enantiomeric excess. The DKR was performed on a multikilogram scale to produce a tetrazole prodrug fragment for a leading clinical candidate that posed formidable synthesis challenges.
Safe and fast tetrazole formation in ionic liquids
Schmidt, Boris,Meid, Daniela,Kieser, Daniel
, p. 492 - 496 (2007)
The [2+3] cycloaddition of nitriles and azides is reliable for intramolecular reactions, but the hazards with volatile azides in intermolecular reactions are tremendous. Zinc catalysis in aqueous solution is a magnificent improvement, but requires the removal of the zinc salts from the acidic product. Herein, we report safe solvents featuring low vapor pressure and good solubility of NaN3. Ionic liquids based on alkylated imidazoles combined with microwave heating turned out to be a solution for the given tasks.
Synthesis and selective cytotoxicity of novel biphenyl-based tetrazole derivatives
Malani, Mahesh H.,Dholakiya, Bharatkumar Z.,Ibrahim, Ahmed S.,Badria, Farid A.
, p. 4427 - 4435 (2014)
Cancer today represents a significant public health problem worldwide, and the challenge is to produce cost-effective drugs. Recently, biphenyl compounds as well as tetrazole derivatives is known for their potential nonselective anticancer activities. In search of novel selective anticancer agents, a series of newly hybrid molecules was designed and synthesized by combining the structural features of biphenyl and tetrazole moieties. The structures of newly synthesized compounds were characterized using spectroscopic techniques (FT-IR, 1H NMR, 13C NMR, and HMBC). Cytotoxic evaluations of these novels compound on human cancer cell lines showed a significant anticancer activity against more than one tested cell lines. Compounds 5n, 5j, and 5o proved to exhibit the strongest and selective cytotoxic effect on HepG2 and MCF-7 lines. Taken together, this study has led to the development of promising leads for cancer therapy.
Efficient Synthesis of 5-(4'-Methyl-2-yl)-1H-tetrazole
Russel, Ronald K.,Murray, William V.
, p. 5023 - 5024 (1993)
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Synthesis and characterization of 4′-bromomethyl-2-(N-trityl-1H- tetrazol-5-yl) biphenyl
Wang, Guo-Xi,Sun, Bao-Ping,Ru, Zong-Ling
, p. 3577 - 3581 (2008)
Biphenyl tetrazole ring is an important component of the Sartan family of novel drugs. 4′-Bromomethyl-2-(N-trityl-1H-tetrazol-5-yl)biphenyl was synthesized in this article from 4′-methyl-2-cyano-biphenyl through three steps. 4′-Methyl-2-cyano-biphenyl was reacted with azide ions with the help of ammonium chloride as catalyst in an autoclave with high conversion to afford the tetrazole compounds in 70.6% yield. After being protected by the trityl group with 92.6% yield, 4′-methyl-2-(N-trityl-1H-tetrazol-5-yl) biphenyl was brominated with N-bromosuccinimide (NBS) in cyclohexane with 2,2′-azo-isobutyronitrile (AIBN) acting as an initiator to provide the title compound in 83.8% yield. Copyright Taylor & Francis Group, LLC.
Detritylation of protected tetrazoles by naphthalene-catalyzed lithiation
Behloul, Cherif,Bouchelouche, Kenza,Guijarro, David,Nájera, Carmen,Yus, Miguel
, p. 2065 - 2070 (2014)
Treatment of N-tritylated tetrazoles bearing aliphatic, aromatic, or heteroaromatic substituents (including functionalized ones) with lithium powder and a catalytic amount of naphthalene led to reductive removal of the trityl group to give excellent yields of the corresponding free tetrazoles without decomposition of the tetrazole ring. The detritylation process was successfully extended to several tetrazoles that are components of sartans, an interesting class of drugs. The chemoselectivity between trityl-tetrazole and trityl-amine bond-cleavage reactions was also studied. This method represents an efficient technique for deprotection of tritylated tetrazoles under non-acidic conditions. Georg Thieme Verlag Stuttgart, New York.
Bacterial Peptide Deformylase Inhibition of Tetrazole-Substituted Biaryl Acid Analogs: Synthesis, Biological Evaluations, and Molecular Docking Study
Khan, Firoz A. Kalam,Patil, Rajendra H.,Patil, Manjiri,Arote, Rohidas,Shinde, Devanand B.,Sangshetti, Jaiprakash N.
, p. 934 - 943 (2016)
The synthesis and screening of tetrazole-substituted biaryl acid analogs 7a–l as bacterial peptide deformylase (PDF) enzyme inhibitors is reported. The compounds 7e (IC50 value = 5.50 μM) and 7g (IC50 value = 7.25 μM) showed good PDF inhibition activity. The compounds 7e (MIC range = 10.75–11.66 μg/mL) and 7g (MIC range = 8.91–12.83 μg/mL) also showed potent antibacterial activity when compared with the standard ciprofloxacin (MIC range = 25–50 μg/mL). Thus, the active derivatives were not only potent PDF enzyme inhibitors but also efficient antibacterial agents. In order to gain more insight into the binding mode of the compounds with the PDF enzyme, the most active compounds 7e and 7g, the moderately active compound 7k, and the least active compound 7h were docked against the PDF enzyme of Escherichia coli. The docking study of the most active compounds 7e and 7g against the PDF enzyme exhibited good binding properties. Hence, we believe our synthesized compounds 7a–l could serve as reservoir for bacterial PDF inhibitor development.
Novel synthesis of 5-substituted tetrazoles from nitriles
Koguro, Kiyoto,Oga, Toshikazu,Mitsui, Sunao,Orita, Ryozo
, p. 910 - 914 (1998)
A variety of 5-substituted tetrazoles were prepared through the respective reactions of sodium azide with corresponding nitriles in an aromatic solvent in the presence of an amine salt.
TMSN3-Bu2Sn(OAc)2: A modified and mild reagent system for Wittenberger tetrazole-synthesis
Yoneyama, Hiroki,Oka, Naoki,Usami, Yoshihide,Harusawa, Shinya
, (2020)
Treatments of various nitriles with TMSN3 and Bu2Sn(OAc)2 at 30 °C in benzene for 60 h yielded the corresponding 5-substituted 1H-tetrazoles in good to excellent yields. This method is a mild and efficient alternative reagent system for Wittenberger tetrazole-synthesis that uses TMSN3 and Bu2SnO in toluene at high temperature (93–110 °C) for 24–72 h.
Reductive removal of the pivaloyl protecting group from tetrazoles by a naphthalene-catalyzed lithiation process
Behloul, Cherif,Chouti, Aicha,Guijarro, David,Nájera, Carmen,Yus, Miguel
, p. 507 - 510 (2015)
The reaction of various 1-pivaloyl-1H-tetrazoles with excess lithium and a catalytic amount of naphthalene (20 mol%) led, after treatment with methanol, to the corresponding free tetrazoles through reductive C-N bond cleavage. This methodology represents a reasonable alternative to other nonreductive protocols.
TBAF-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles under Solventless Conditions
Amantini, David,Beleggia, Romina,Fringuelli, Francesco,Pizzo, Ferdinando,Vaccaro, Luigi
, p. 2896 - 2898 (2004)
Tetrabutylammonium fluoride (TBAF) is an efficient catalyst in the [3 + 2] cycloaddition reaction of organic nitriles 1 with trimethylsilyl azide (TMSN3) in solventless conditions. The corresponding 5-substituted 1H-tetrazoles 2 were obtained under mild conditions and in 80-97% yields.
Antimicrobial evaluation of 5-substituted aryl 1H-tetrazoles
Feinn, Liana,Dudley, Joshua,Coca, Adiel,Roberts, Elizabeth L.
, p. 359 - 364 (2017/06/20)
Background: Tetrazole derivatives such as 1-substituted dinitrobenzyl tetrazoles and their oxa and selanyl analogs have previously been studied against drug-susceptible and multidrugresistant mycobacteria. In addition, other tetrazole derivatives have bee
