Novel System for Decarboxylative Bromination of .ALPHA.,.BETA.-Unsaturated Carboxylic Acids with Diacetoxyiodobenzene

Fursule, Ravindra A.; Patil, Pravin O.; Shewale, B. D.; Kosalge, Satish B.; Deshmukh, Prashant K.; Patil, Dilip A.

doi:10.1248/cpb.57.1243

Cited by 18 publications

(10 citation statements)

References 21 publications

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“…This peak was attributed to the formation of C=C due to formation of enol in the keto-enol tautomerism reaction as the peak for C=C transition occurs traditionally in between 1620-1680 cm -1 for unsaturated carboxylic acids. 252,254 This transition have been found for the solutions of 12.9, 4.6 and 3.6 WSRs; whereas it was absent for the solution with 55.5 WSR, supporting same keto-enol tautomerism reaction for the highly concentrated solutions.…”

Section: Solution Phase Ftir Spectra Of Supersaturated Malonic Acidsupporting

confidence: 57%

Chemical, physical and mechanical properties of nanomaterials and its applications

Ghorai¹

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The contribution of atmospheric aerosols towards radiative forcing has a very high uncertainty due to their short atmospheric lifetime. The aerosol effects are largely controlled by the density, elemental composition, and hygroscopic properties of the aerosol particles. Therefore, we have performed designed new methodology using Scanning Transmission X-ray Microscopy (STXM), Atomic force spectroscopy (AFM), micro-FTIR spectroscopy and Scanning Electron Microscopy (SEM) to quantify these important aerosol properties. Hygroscopic properties are quantified by plotting the mass of water on a single particle basis, calculated from STXM, as a function of relative humidity. Alternatively, micro-FTIR spectra have been used to study the effect of composition of aerosol particles on the hygroscopic properties of NaCl. Moreover, a unique combination of STXM and AFM has been utilized to quantify density and elemental composition of micrometer dimensional particles. This method has also been extended towards exploring mixing state of particles, consisting of heterogeneously mixed inorganic and organic compounds. In addition to these above mentioned vii 3.3.1 Morphology and hygroscopic properties of pure NaCl particles .

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Section: Solution Phase Ftir Spectra Of Supersaturated Malonic Acidsupporting

confidence: 57%

Chemical, physical and mechanical properties of nanomaterials and its applications

Ghorai¹

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“…Peptides (Table ) were synthesized by manually applying the standard Fmoc methodology by 2-chlorotrityl chloride resin and Fmoc-protected amino acids, as we reported before . The synthesized peptides were purified by semipreparative reversed-phase high-performance liquid chromatography (RP-HPLC).…”

Section: Resultsmentioning

confidence: 99%

Neuroprotective Effect of N-Cyclohexylethyl-[A/G]-[D/E]-X-V Peptides on Ischemic Stroke by Blocking nNOS–CAPON Interaction

Qin

Feng

Fan

et al. 2020

ACS Chem. Neurosci.

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The protein−protein interaction between neuronal nitric oxide syntheses (nNOS) and the carboxy-terminal PDZ ligand of nNOS (CAPON) is a potential target for the treatment of ischemic stroke. Our previous study had identified ZLc-002 as a promising lead compound for inhibiting nNOS−CAPON coupling. To find better neuroprotective agents disrupting the ischemia-induced nNOS−CAPON interaction, a series of N-cyclohexylethyl-[A/G]-[D/E]-X-V peptides based on the carboxy-terminal tetrapeptide of CAPON was designed, synthesized, and evaluated in this study. Herein, we reported an affinity-based fluorescence polarization (FP) method using 5-carboxyfluorescein (5-FAM) labeled CAPON (496−506) peptide as the probe for high-throughput screening of the small-molecule inhibitors of the PDZ domain of nNOS. N-Cyclohexylethyl-ADAV displayed the most potent affinity for the nNOS PDZ domain in the FP and isothermal titration calorimetry (ITC) (ΔH = −1670 ± 151.0 cal/mol) assays. To improve bioavailability, lipophilicity, and membrane permeability, the Asp methylation was employed to get N-cyclohexylethyl-AD(OMe)AV, which possesses good blood−brain barrier (BBB) permeability in vitro parallel artificial membrane permeability assay (PAMPA)-BBB (Pe = 6.07 cm/s) and in vivo assays. In addition, N-cyclohexylethyl-AD(OMe)AV (10 mg/kg body weight, i.v., immediately after reperfusion) substantially reduced infarct size in rats, which was measured 24 h after reperfusion and subjected to 120 min of middle cerebral artery occlusion (MCAO).

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“…Remarkably, the reaction is efficient regardless of the nature of the substituents on the aromatic ring or double bond (Scheme ). Saturated aliphatic acids (e.g., butanoic, pentanoic, 2-(phenyl)-propionic acids) did not undergo this bromodecarboxylation protocol.…”

Section: Halodecarboxylation Of αβ-Unsaturated Carboxylic Acidsmentioning

confidence: 99%

Decarboxylative Halogenation of Organic Compounds

2020

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Decarboxylative halogenation, or halodecarboxylation, represents one of the fundamental key methods for the synthesis of ubiquitous organic halides. The method is based on conversion of carboxylic acids to the corresponding organic halides via selective cleavage of a carbon–carbon bond between the skeleton of the molecule and the carboxylic group and the liberation of carbon dioxide. In this review, we discuss and analyze major approaches for the conversion of alkanoic, alkenoic, acetylenic, and (hetero)aromatic acids to the corresponding alkyl, alkenyl, alkynyl, and (hetero)aryl halides. These methods include the preparation of families of valuable organic iodides, bromides, chlorides, and fluorides. The historic and modern methods for halodecarboxylation reactions are broadly discussed, including analysis of their advantages and drawbacks. We critically address the features, reaction selectivity, substrate scopes, and limitations of the approaches. In the available cases, mechanistic details of the reactions are presented, and the generality and uniqueness of the different mechanistic pathways are highlighted. The challenges, opportunities, and future directions in the field of decarboxylative halogenation are provided.

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Novel System for Decarboxylative Bromination of .ALPHA.,.BETA.-Unsaturated Carboxylic Acids with Diacetoxyiodobenzene

Cited by 18 publications

References 21 publications

Chemical, physical and mechanical properties of nanomaterials and its applications

Chemical, physical and mechanical properties of nanomaterials and its applications

Neuroprotective Effect of N-Cyclohexylethyl-[A/G]-[D/E]-X-V Peptides on Ischemic Stroke by Blocking nNOS–CAPON Interaction

Decarboxylative Halogenation of Organic Compounds

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