Synthesis and .beta.-lactamase inhibitory properties of 2.beta.-[(1,2,3-triazol-1-yl)methyl]-2.alpha.-methylpenam-3.alpha.-carboxylic acid 1,1-dioxide and related triazolyl derivatives

Micetich, Ronald G.; Maiti, Samarendra N.; Spevak, Paul; Hall, T. W.; Yamabe, Shigeru; Ishida, N; Tanaka, Motoaki; Yamazaki, Tomio; Nakai, Akira; Ogawa, Kazuo

doi:10.1021/jm00391a032

Cited by 105 publications

(27 citation statements)

References 2 publications

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“…Diazotization is mostly commonly performed with nitrous acid, generated in situ from sodium nitrite and a mineral acid source such as nitric, sulfuric, or acetic acids. A range of various 1-substituted benzotriazoles 92 can be prepared from the corresponding benzene-1,2-diamine derivatives 91 (Table 12. 9). 1-Substituted benzotriazoles can be prepared from various azides with a benzyne intermediate generated in situ from 2-aminobenzoic acid (Table 12.10).…”

Section: Other Methods For Preparations Of 123-triazolesmentioning

confidence: 99%

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

Yet

2011

Modern Heterocyclic Chemistry

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Section: Other Methods For Preparations Of 123-triazolesmentioning

confidence: 99%

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

Yet

2011

Modern Heterocyclic Chemistry

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“…SEPT. 1994 l-Methoxybenzyl (3>S?5i?,6Z) In a similar manner, the following compounds 12a, lib and 12b were obtained from the corresponding 9b,and 10b,5i?,3, Anhydrous aluminum chloride (0.31 g, 2.32mmol) was added to a stirred solution of 9a (0.60g, 0.92mmol) in an anhydrous mixture ofdichloromethane (6ml) and anisole (25 ml) at -40~-45°C under a nitrogen atmosphere. After 1 hour, the reaction was quenched by adding water and the pH was adjusted to pH 7.1 with 0.1 n NaOH.…”

Section: Methodsmentioning

confidence: 98%

“…The resulted solution was freeze-dried to give a solid, which was purified by reverse phase chromatography using water-acetonitrile, 10: 1 (v/v) In an analogous manner, the following compounds 14a, 15a, 16a, 13b, 14b, 15b and 16b were prepared from the corresponding PMBester compounds 10a, lla, 12a, 9b, 10b, lib, and 12b, respectively. Sodium (3^,5i?,3, …”

Section: Methodsmentioning

confidence: 99%

Synthesis and .BETA.-lactamase inhibitory activity of 6-((1-heteroarylthioethyl-1,2,3-triazol4-yl)methylene)-penam sulfones.

Maiti²,

Micetich

et al. 1994

J. Antibiot.

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The synthesis of /Mactamase inhibitory activity of a series of sodium 6-[(l-heteroarylthioethyll ,2,3-triazol-4-yl)methylene]penicillanate 1 , 1-dioxides are described. Their activity was compared with tazobactam and sulbactam. The Z-isomers were moreactive than the Is-isomers. The in vitro activity of the Z-isomers of the phenylthiadiazole derivatives (13a and 15a) was better than sulbactam against the tested /Mactamases and comparable to tazobactam especially against TEM-2 and cephalosporinase. But their synergistic activity with five antibiotics was inferior to tazobactam.A successful approach to overcoming the bacterial resistance to /Mactam antibiotics caused by /Mactamase production is to develop agents that can inhibit the action of the /Mactamase. The success of clavulanic acid1} stimulated extensive research leading to the discovery of other /Mactamase inhibitors such as sulbactam2) and tazobactam3). A number of 6-(substituted methylene)penams have been reported in the literature4'5) as potent inhibitors of cell free /Mactamases, but were ineffective in synergistic antibacterial tests probably because of poor penetration through the bacterial cell wall. More recently, 6-triazolylmethylenepenem (1)6'7), BRL-42715, has been shown to be a very potent inhibitor of most bacterial /Mactamases including the class I /Mactamase, which is resistant to other /Mactamase inhibitors.

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13] The conventional method for the synthesis of the 1,2,3-triazole ring system is based on the thermal 1,3-dipolar Huisgen cycloaddition between azides 1 and alkynes 2 (Scheme 1, a). [14] However, this non-cata-Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Immobilization of Porphyrinatocopper Nanoparticles onto Activated Multi‐Walled Carbon Nanotubes and a Study of its Catalytic Activity as an Efficient Heterogeneous Catalyst for a Click Approach to the Three‐Component Synthesis of 1,2,3‐Triazoles in Water

et al. 2009

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An efficient, regioselective, one-pot and two-step synthesis of b-hydroxy 1,4-disubstituted 1,2,3-triazoles from a wide range of non-activated terminal alkynes and epoxides and sodium azide by way of a three-component click reaction using a catalytic amount of [meso-tetrakis(o-chlorophenyl)porphyrinato]copper(II) (5 mol%) in excellent isolated yields is described. The reactions were performed in water as a green solvent at ambient temperature without any additives. By performing two reaction steps in one pot and purifying only at the final step, this procedure excludes any interim purification of in situ generated organic azide intermediates, which significantly improves the overall yield and reduces the reaction time. To benefit from the recovery and reuse of the catalyst, a new heterogeneous catalyst was prepared by simple and successful impregnation of the catalyst onto activated multi-walled carbon nanotubes (AMWCNT). The heterogeneous catalyst was characterized by powder X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), atomic forced microscopy (AFM), and thermogravimetric (TG) analysis to estimate the amount of nitrogen adsorption, and Raman and FT-IR spectroscopy. Leaching experiments after ten successive cycles showed that the catalyst is most strongly anchored to the AMWCNT support. Mechanistically, porphyrinatocopper catalyzes each step of the reaction in different ways as a bifunctional catalyst including epoxide ring opening by azide delivery to epoxide, forming in situ generated 2-azido alcohols followed by activation of the C C triple bond of the starting terminal alkynes by forming a porphyrinatocopper-acetylide intermediate and thereby promoting the [3 + 2]-cycloaddition reaction as the key step to form the tri-

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Synthesis and .beta.-lactamase inhibitory properties of 2.beta.-[(1,2,3-triazol-1-yl)methyl]-2.alpha.-methylpenam-3.alpha.-carboxylic acid 1,1-dioxide and related triazolyl derivatives

Cited by 105 publications

References 2 publications

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

Synthesis and .BETA.-lactamase inhibitory activity of 6-((1-heteroarylthioethyl-1,2,3-triazol4-yl)methylene)-penam sulfones.

Immobilization of Porphyrinatocopper Nanoparticles onto Activated Multi‐Walled Carbon Nanotubes and a Study of its Catalytic Activity as an Efficient Heterogeneous Catalyst for a Click Approach to the Three‐Component Synthesis of 1,2,3‐Triazoles in Water

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