Mohammed Abid Shaikh

Georgia Southern University | GSU · Department of Chemistry

The discovery of novel analgesic agents with high potency, low toxicity and low addictive properties remain a priority. This study aims to identify the analgesic potential of quinoline derived α‐trifluoromethylated alcohols (QTA) and their mechanism of action. We synthesized and characterized several compounds of QTAs and screened them for antiepil...

4-Methylcyclohexanemethanol (4-MCHM) spilled into the Elk River in Charleston, WV, USA, in early 2014. While the local human population experienced adverse dermatological and gastrointestinal effects and toxicity assays were performed on a variety of organisms, the full public health and ecological consequences of 4-MCHM exposure remains unknown. T...

In this study the rational design, synthesis, and anticancer activity of quinoline-derived trifluoromethyl alcohols were evaluated. Members of this novel class of trifluoromethyl alcohols were identified as potent growth inhibitors in a zebrafish embryo model. Synthesis of these compounds was carried out with an sp(3) -CH functionalization strateg...

Triflic acid catalyzes both the functionalization of 2-alkyl azaarenes and concomitant N-deprotection of imino ester (II).

A Bronsted acid promoted C-sp3-H functionalization of 2-alkyl azaarenes with alpha-trifluoromethylated imino ester is described. A catalytic amount of triflic acid provided straightforward access to the corresponding trifluoromethylated amino esters via concomitant in situ one step N-alkyl deprotection. On further hydrolysis of ester, synthesis of...

Ytterbium triflate is found to be highly efficient for the title reaction, delivering trifluormethylated alcohols in excellent yields.

A Lewis acid promoted Csp3–H bond functionalization of methyl azaarenes with α-trifluoromethylated carbonyl compounds is described. Catalytic amounts of Yb(OTf)3 provided a straightforward access to the corresponding trifluoromethylated alcohols in excellent yields up to 94% under mild reaction conditions.

A broad group of structurally diverse small organofluorine compounds were synthesized and evaluated as inhibitors of β-amyloid (Aβ) self-assembly. The main goal was to generate a diverse library of compounds with the same functional group and to observe general structural features that characterize inhibitors of Aβ oligomer and fibril formation, ul...

Over the years, ionic liquids have gained significant attention in organic synthesis and other areas of chemistry as environmentally benign solvents. Unlike traditional solvents, ionic liquids offer several advantages such as being nonvolatile, noncorrosive, immiscible in organic solvents, easily stored and handled, producing less hazardous waste,...

A potential therapeutic approach for Alzheimer's disease is to reduce the amount of toxic amyloid-beta oligomers and fibrillar amyloid plaques. In order to contribute to this approach the ability of small organofluorine compounds that were previously reported as successful inhibitors of fibrillogenesis to destabilize preformed fibrils of the amyloi...

The effect of enantiomeric trifluoromethyl-indolyl-acetic acid ethyl esters on the fibrillogenesis of Alzheimer's amyloid beta (Abeta) peptide is described. These compounds have been previously identified as effective inhibitors of the Abeta self-assembly in their racemic form. Thioflavin-T Fluorescence Spectroscopy and Atomic Force Microscopy were...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A rapid, microwave-assisted synthesis of β-carbolines via a successive condensation/cyclization/dehydrogenation approach is described. This methodology involves the coupling of various tryptamines with aromatic aldehydes/glyoxals. The product imine undergoes a Pictet–Spengler cyclization followed by a final dehydrogenation to yield β-carbolines in...

Over the years, microwave-assisted organic synthesis (MAOS) became a commonly applied mainstream tool for the synthesis of heterocyclic compounds. The broad range of emerging applications in this field is mainly due to the significant contribution of MAOS to the development of ecofriendly processes. Various transformations have been developed for t...

Over the years, microwave-assisted organic synthesis (MAOS) became a commonly applied mainstream tool for the synthesis of heterocyclic compounds. The broad range of emerging applications in this field is mainly due to the significant contribution of MAOS to the development of ecofriendly processes. Various transformations have been developed for t...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A simple and efficient synthesis to both enantiomers of highly enantiomerically enriched alpha-trifluoromethyl-alpha-(heteroaryl)-glycine derivatives via highly stereoselective aminoalkylation of indoles and pyrroles is described. The triflic acid-catalyzed reaction of enantiomeric 3,3,3-trifluoro-pyruvate-alpha-methylbenzyl imines with indoles and...

A novel one-pot synthesis of N-acylindoles via tandem cycloalkylation-annelation is described. This approach is based on the use of a strong solid-acid catalyst, montmorillonite K-10, and microwave irradiation under solvent-free conditions. The tandem cycloalkylation of amides and annelation of intermediate pyrroles were completed in minutes and pr...

A novel one-pot synthesis of N-substituted heterocycles via successive cyclization/annelation starting from primary sulfonamides is described. This process leads directly to N-sulfonyl pyrroles, indoles and carbazoles. The selection of appropriate reactant/triflic acid ratio successfully controls the formation of the desired product.

A new solid acid/superacid catalyzed microwave assisted synthesis of trifluoromethyl-imines is described. Various α,α,α-trifluoromethylketones react readily with primary amines to produce the corresponding imines. Two different strategies have been employed; one is the application of microwave irradiation coupled with solvent-free solid acid cataly...

An effective microwave-induced, solid acid-catalyzed, environmentally benign synthesis of substituted pyrroles, indoles and carbazoles under solvent-free conditions is described. The new synthetic methodology is based on the use of a considerably strong solid acid, K-10 montmorillonite. Both the cyclialkylation of amines and annelation of pyrroles...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

The design and application of an effective, new class of organofluorine inhibitors of amyloid fibrillogenesis are described. Based on experimental evidence a core structure containing indol-3-yl, trifluoromethyl, hydroxyl, and carboxylic acid ester functions has been designed. Several substituted derivatives of this core structure have been synthes...

The synthesis of N-heteroaryl(trifluoromethyl)hydroxyalkanoic acid esters by solid acid-catalyzed Friedel–Crafts hydroxyalkylation of indoles and pyrroles with ethyl 3,3,3-trifluoropyruvate and ethyl 4,4,4-trifluoroacetoacetate is described. The inexpensive and readily available K-10 montmorillonite is found to be an efficient catalyst for the synt...

(Chemical Equation Presented) Readily available cinchona alkaloids have been used as organocatalysts in the highly efficient stereoselective hydroxyalkylation of heteroaromatics such as indoles with 3,3,3- trifluoropyruvate (2, see scheme). High yields and ee values of both enantiomers of the products, depending on the catalyst used, indicate the u...

The determination of the enantiomeric composition of α-trifluoromethylated-hydroxyl compounds using cinchona alkaloids as chiral selectors is described. The interaction between the alkaloid and trifluoromethylated-hydroxyl compounds converted the enantiotopic nuclei to diastereotopic nuclei observed by 19F NMR spectroscopy. A wide variety of target...