PTP‐1B Inhibitors: Cyclopenta[d][1,2]‐oxazine Derivatives.

Choi, Joong-Kwon; al., et

doi:10.1002/chin.200618158

Cited by 4 publications

(4 citation statements)

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“…3,11,12 In addition, mb can bind Cd(II), Co(II), Fe(III), Mn(II), Ni(II), Zn(II), and Pb(II) and can bind and reduce Ag(I), Au(III), and possibly Hg(II). 14 The best characterized mb peptide is isolated from Methylosinus trichosporium OB3b. 2,11 It contains seven amino acids and two unusual chromophoric residues, each containing a thiocarbonyl/ enethiol attached to a conjugated ring system.…”

mentioning

confidence: 99%

NMR, Mass Spectrometry and Chemical Evidence Reveal a Different Chemical Structure for Methanobactin That Contains Oxazolone Rings

et al. 2008

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Methanobactin (mb) is a small copper-binding peptide produced by methanotrophic bacteria and is intimately involved in both their copper metabolism and their role in the global carbon cycle. The structure for methanobactin comprises seven amino acids plus two chromophoric residues that appear unique to methanobactin. In a previously published structure, both chromophoric residues contain a thiocarbonyl attached to a hydroxyimidazolate ring. In addition, one is attached to a pyrrolidine ring, while the other to an isopropyl ester. A published X-ray determined structure for methanobactin shows these two chromophoric groups forming an N2S2 binding site for a single Cu(I) ion with distorted tetrahedral geometry. In this report we show that NMR, mass spectrometry, and chemical data, reveal a chemical structure that is significantly different than the previously published one. Specifically, the 1H and 13C NMR assignments are inconsistent with an N-terminal isopropyl ester and point instead to a 3-methylbutanoyl group. Our data also indicate that oxazolone rings instead of hydroxyimidazolate rings form the core of the two chromophoric residues. Because these rings are directly involved in the binding of Cu(I) and other metals by methanobactin, and are likely involved in the many chemical activities displayed by methanobactin, their correct identity is central to developing an accurate and detailed understanding of methanobactin’s many chemical and biological roles. For example, the oxazolone rings make methanobactin structurally more similar to other bacterially produced bactins and siderophores and suggest pathways for its biosynthesis.

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confidence: 99%

NMR, Mass Spectrometry and Chemical Evidence Reveal a Different Chemical Structure for Methanobactin That Contains Oxazolone Rings

et al. 2008

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“…A series of 2H-pyridazine-3-one and 1,2-oxazine derivatives have anti-inflammatory activity was tested in vitro on superoxide formation and effects on lipid peroxidation [27], as antioxidants in natural rubber [28,29], pyridazinone PDE inhibitors [30], 1,2-oxazine as PTP 1B inhibitors [31]. An authentic reaction was done by refluxing the acids hydrochloride (1.5 g; 0.04 mol) in boiling pyridine (30 mL) and then refluxed for 3 h. The reaction mixture was pour into ice/HCl and the solid that separated was re-crystallized.…”

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confidence: 99%

Utility of Benzimidazoles in Synthesis of New Bases of Nucleoside Moieties, and as Antioxidant in Lubricant Oils

Rizk¹

2013

J Chem Eng Process Technol

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The treatment of 4-(4-Chloro-3-methylphenyl)-4-oxobut-2-enoic acid with benzimidazole, and 2-mercapto benzimidazole afforded aza-and thia-Michael adduct as unnatural α-amino acid 1 and α-thiaacid 6 respectively. Micheal adducts 1 and 6 are used to synthesize some antioxidant heterocycles. TAN study can be confirmed, the fused heterocycles has a lower antioxidant expt that contain sulfur atom. Quantum chemical studies of 2-mercaptobezimidazole, and its amide long chain, confirmed that N-butyl-S-benzimidazol-2-ylthioglycolate at 400 ppm was more effective antioxidant heterocycles.

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“…Also, mice lacking PTP 1B showed improved insulin sensitivity and resistance to weight gain . Enhanced IR and IR substrate‐1 phosphorylation have been observed in liver and skeleton muscles of PTP 1B knockout mice.…”

Section: Introductionmentioning

confidence: 97%

Accounting of ligand–receptor interactions to explore and design novel architecture for PTP 1B inhibition: a legitimate approach

Malla

Kumar

2012

Journal of Chemometrics

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Computer‐aided drug design was performed on a diverse set of 103 biphenyl derivatives that demonstrated antidiabetic activity by restraining the protein tyrosine phosphatase 1B (PTP 1B) receptor. A four‐point pharmacophore hypothesis using the PHASE module of Schrödinger suite with one hydrogen bond acceptor (A) and three aromatic rings (R) as pharmacophoric features was generated. The hypothesis, ARRR.2, considered the best hypothesis in the present study is characterized by survival score (3.553), cross‐validated r2 (Q2) (0.722), regression coefficient (0.949), Pearson R (0.867), and F value (492.6). The developed pharmacophore model was externally validated by predicting the activity of test set molecules. Docking algorithm combined with the drug–receptor binding free energetic and pharmacokinetic drug profile envisaged a novel concept, which may provide structural insights for the development of potential PTP 1B inhibitors. The study also provided a valid rapport between pharmacophore drug mapping, atom‐based three‐dimensional quantitative structure–activity relationship, molecular docking, sitemap, molecular simulations, and pharmacokinetic prediction approaches demonstrating the trends in activity. The results of these ligand–receptor relationship studies may account to design a legitimate template for the development and optimization of highly selective and potent PTP 1B inhibitors. Copyright © 2012 John Wiley & Sons, Ltd.

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PTP‐1B Inhibitors: Cyclopenta[d][1,2]‐oxazine Derivatives.

Cited by 4 publications

References 1 publication

NMR, Mass Spectrometry and Chemical Evidence Reveal a Different Chemical Structure for Methanobactin That Contains Oxazolone Rings

NMR, Mass Spectrometry and Chemical Evidence Reveal a Different Chemical Structure for Methanobactin That Contains Oxazolone Rings

Utility of Benzimidazoles in Synthesis of New Bases of Nucleoside Moieties, and as Antioxidant in Lubricant Oils

Accounting of ligand–receptor interactions to explore and design novel architecture for PTP 1B inhibition: a legitimate approach

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