Improved synthesis, molecular modeling and anti-inflammatory activity of new fluorinated dihydrofurano-naphthoquinone compounds.

A series of new fluorinated dihydrofurano-napthoquinone compounds were sucessfully synthesized in good yields using microwave-assisted multi-component reactions of 2-hydroxy-1,4-naphthoquinone, fluorinated aromatic aldehydes, and pyridinium bromide. The products were fully characterized using spectroscopic techniques and evaluated for their anti-inflammatory activity using lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. Among 12 new compounds, compounds 8b, 8d, and 8e showed high potent NO inhibitory activity in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells with IC50 values ranging from 1.54 to 3.92 µM. The levels of pro-inflammatory cytokines IL-1ß and IL-6 in LPS-stimulated RAW264.7 macrophages were remarkably decreased after the application of 8b, 8d, 8e and 8k. Molecular docking simulations revealed structure-activity relationships of 8b, 8d, and 8e toward NO synthase, cyclooxygenase (COX-2 over COX-1), and prostaglandin E synthase-1 (mPGES-1). Further physicochemical and pharmacokinetic computations also demonstrated the drug-like characteristics of synthesized compounds. These findings demonstrated the importance of fluorinated dihydrofurano-napthoquinone moieties in the development of potential anti-inflammatory agents.

Synthesis, in vitro Α-Glucosidase, and acetylcholinesterase inhibitory activities of novel Indol-Fused Pyrano[2,3-D]Pyrimidine compounds.

In this study, new indol-fused pyrano[2,3-d]pyrimidines were designed and synthesized. These products were obtained in moderate to good yields and their structures were assigned by NMR, MS, and IR analysis. Afterwards, the biological important of the products was highlighted by evaluating in vitro for α-glucosidase inhibitory activity as well as acetylcholinesterase (AChE) inhibitory activity. Eleven products revealed substantial inhibitory activity against α-glucosidase enzyme, among which, two most potent products 11d,e were approximately 93-fold more potent than acarbose as a standard antidiabetic drug. Besides that, product 11k exhibited good AChE inhibition. The substituents on the 5-phenyl ring, attached to the pyran ring, played a critical role in inhibitory activities. The biological potencies have provided an opportunity to further investigations of indol-fused pyrano[2,3-d]pyrimidines as potential anti-diabetic agents.

Microwave-Assisted Three-Component Synthesis of Novel N-Arylated-Dihydrobenzo[g]quinoline-5,10-Diones and Their Potential Cytotoxic Activity.

A convenient three-component synthetic approach was developed en route to new and significative N-arylated-dihydrobenzo[g]quinoline-5,10-diones using 2-hydroxy-1,4-naphthoquinone, a variety of aromatic aldehydes, and 4-(arylamino)furan-2(5H)-ones. A sequence of steps including Knoevenagel condensation, Michael addition, [1,3]-hydrogen shift, intramolecular cyclization and dehydration led to the formation of products. All the products were structurally characterized by spectroscopic techniques and assessed in terms of their cytotoxicity profile against four cancer cell lines (KB, HepG2, A549, and MCF7), and human embryonic kidney (Hek-293) cell lines.

Application of Fe-based metal-organic framework and its pyrolysis products for sulfonamide treatment.

The occurrence and fate of antibiotic compounds in water can adversely affect human and animal health; hence, the removal of such substrates from soil and water is indispensable. Herein, we described the synthesis method of mesoporous carbon (MPC) via the pyrolysis route from a coordination polymer Fe-based MIL-53 (or MIL-53, shortly). The MPC structure was analyzed by several physical techniques such as SEM, TEM, BET, FT-IR, VSM, and XRD. The response surface methodology (RSM) was applied to find out the effects of initial concentration, MPC dosage, and pH on the removal efficiency of trimethoprim (TMP) and sulfamethoxazole (SMX) antibiotics in water. Under the optimized conditions, the removal efficiencies of TMP and SMX were found to be 87% and 99%, respectively. Moreover, the adsorption kinetic and isotherm studies showed that chemisorption and the monolayer adsorption controlled the adsorption process. The leaching test and recyclability studies indicated that the MPC structure was stable and can be reused for at least four times without any considerable change in the removal efficiency. Plausible adsorption mechanisms were also addressed in this study. Because of high maximum adsorption capacity (85.5 mg/g and 131.6 mg/g for TMP and SMX, respectively) and efficient reusability, MPC is recommended to be a potential adsorbent for TMP and SMX from water media.

Crystal structure of 22,24,25-trimethyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.02,7.015,20]penta-cosa-2,4,6,15(20),16,18-hexaen-23-one.

The title compound, C24H29NO4, is the product of a Petrenko-Kritchenko condensation of 1,5-bis-(2-formyl-phen-oxy)-3-oxa-pentane, pentan-3-one and methyl-ammonium acetate in ethanol. The mol-ecule has mirror symmetry. The aza-14-crown-3 ether ring adopts a bowl conformation stabilized by a weak intra-molecular C-H⋯O hydrogen bond. The conformation of the C-O-C-C-O-C-C-O-C polyether chain is t-g+-t-t-g--t (t = trans, 180°; g = gauche, ±60°). The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether moiety is 72.68 (4)°. The piperidinone ring adopts a chair conformation. The nitro-gen atom has a trigonal-pyramidal geometry, the sum of the bond angles being 335.9°. In the crystal, the mol-ecules are linked by weak C-H⋯O inter-actions, forming zigzag chains propagating along the [100] direction.

Synthesis of new simplified hemiasterlin derivatives with α,ß-unsaturated carbonyl moiety.

In this Letter, we report a convenient and efficient method for the synthesis of new simplified derivatives of hemiasterlin in which the α,α-dimethylbenzylic moiety A is replaced by α,ß-unsaturated aryl groups as Michael acceptor. Most of these derivatives have a strong cytotoxic activity on three human tumor cell lines (KB, Hep-G2 and MCF7). Analogs 17b and 17f showed a high cytotoxicity against KB and Hep-G2 cancer cell lines comparable to paclitaxel and ellipticine.

Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone.

An efficient and straightforward approach towards the synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone via imination, α-chlorination, hydride reduction and ring closure was developed. In addition, novel primary ß-iodo amines were obtained by regioselective ring opening of these 2-(trifluoromethyl)aziridines using alkyl iodides, and their synthetic potential was demonstrated by converting them into novel α-CF(3)-ß-phenylethylamines upon treatment with lithium diphenylcuprate.