Synthesis and biological evaluation of novel phane-structured diazacrowns containing γ-piperidone and pyridine rings

1. Download : Download high-res image (91KB)
2. Download : Download full-size image

     

Synthesis and characterization of novel soluble and thermally stable polyamides based on pyridine monomer

Nucleophilic aromatic substitution reaction of 4-aminophenol and also 5-amino-1-naphthol with 2,6-dichloropyridine in N-methyl-2-pyrrolidone (NMP) as solvent, in the presence of potassium carbonate, afforded two aromatic ether diamines. Eight soluble, thermally stable polyamides were prepared by polycondensation reaction of the obtained diamines with aromatic and aliphatic diacid chlorides including terephthaloyl chloride (TPC), isophthaloyl chloride (IPC), adipoyl chloride (AC), and sebacoyl chloride (SC). The prepared monomers and polymers were characterized by conventional spectroscopic methods. Physical and thermal properties of the polymers, such as thermal behavior, thermal stability, solution viscosity, and solubility behavior were also studied.     

Synthesis and liquid crystalline properties of novel pyridine derivatives

The treatment of 4‐hydroxypyridine with cholestery p‐(ω‐bromoalkyloxy)benzoates in N,N‐dimethylformamide containing K₂CO₃ gave cholestery p‐[ω‐(4‐pyridyloxy)alkyloxy]benzoates, which exhibited liquid crystalline properties     

含吡啶联喹啉羧酸新型配体的合成和表征

以4-乙酰基吡啶(2)、2,6-二乙酰基吡啶(3)为底物分别与靛红及取代靛红(1a-1g)在KOH做催化剂的条件下,以10%的乙醇溶液作为溶剂进行反应,以41.4%-90.5%的产率得到了结构新颖的含氮联喹啉酸有机配体(4a-4g)和(5a-5g),它们的结构均通过红外光谱、核磁共振氢谱、核磁共振碳谱和质谱得以证实。以上制备过程具有反应条件温和、后处理简单、环境友好等优点,为制备含吡啶联喹啉羧酸新型配体提供了简单有效的方法。     

Synthesis and in vitro evaluation of novel tetralin-pyrazolo[3,4-b]pyridine hybrids as potential anticancer agents

New hybrids of tetralin-pyrazolo[3,4-b]pyridine were synthesized in good yields. The structures of newly synthesized compounds were confirmed by IR, NMR, MS, and elemental analyses. Some of the new compounds were in vitro evaluated as antiproliferative candidates against two human cancer cell lines (HCT116 and MCF-7). Most of the examined derivatives showed promising anticancer activity.     

Synthesis,biological evaluation,and molecular docking studies of novel pyrazole,pyrazoline-clubbed pyridine as potential antimicrobial agents

We have prepared 15 hybrid pyrazole, pyrazoline-clubbed pyridine–containing compounds (5a-o) and tested for their antibacterial and antifungal activities for the development of potential antimicrobial agents. The structures of this novel series were characterized by various spectral techniques like IR, ¹H NMR, ¹³C NMR, LC–MS, and elemental analysis. The synthesized compounds 5d, 5e, 5i, 5k, 5m, and 5o exhibited significant antimicrobial activity in the comparison of standard drugs. Molecular docking studies that have been carried out to emphasize the binding orientations of these molecules were in good compliance with crystal structure interactions. The predicted drug-likeness (ADME) properties were found to be in the acceptable range.     

Synthesis and antimicrobial evaluation of some novel pyrido[3,2-f][1,2,3]thiadiazaphosphepinone compounds,bearing a pyridine moiety

Several pyridothiadiazaphosphepinones (3–9) were synthasized by combining tetraphosphorus decasulfide, Lawesson's reagent, phosphorus tribromide, and P,P-dichlorophenyl phosphine with 2-(aminosulfanyl)-6-(3,4-dichlorophenyl)-4-(furan-2-yl)-5-oxo-5,6-dihydropyridine-3-carbonitrile (2). The reaction mechanisms for these products were discussed. On the basis of elemental analysis and spectrum data, the structures of the newly synthesized compounds were determined. The biological activity of every synthesized compound was examined against various microorganisms using the disc diffusion method. The bulk of the microorganisms tested are effectively inhibited by the newly synthesized chemicals.     

Synthesis and biological evaluation of novel imidazole-containing macrocycles

A new family of compounds made of a 5-aryl-1H-imidazole motif included in a macrocycle has been designed and synthesized. The synthesis of the imidazole core makes use of our previously developed method for the regioselective preparation of 1,2,5-trisubstituted imidazoles while the construction of the macrocycle is based on a three steps sequence: S_NAr, Suzuki coupling, and RCM reaction. Biological evaluation of synthesized imidazole-containing macrocycles revealed that they display actual binding activity toward A₃ adenosine (h) receptor, dopamine D₁ (h) receptor, chloride channel (GABA-gated), and choline transporter (h) CHT1.     

Synthesis and evaluation of novel aza-caged Garcinia xanthones

Inspired by the therapeutic potential of the simplified caged xanthones, we have developed a chemical strategy for synthesizing novel aza-caged Garcinia analogues through a regioselective Claisen/Diels-Alder cascade reaction. The origin of regioselectivity has been explained using the DFT method. We have further evaluated the cell proliferation and IKKβ inhibitory activities of these compounds and studied their binding mode with IKKβ by molecular docking. The results suggested that the aza-caged scaffold provides a suitable modification site and the introduction of a hydrophobic moiety leads to improvement in the cytotoxicity and IKKβ inhibitory activity. The aza-caged compound 6c exhibited an IC(50) value of 2.68, 2.10, 8.02 μM against the HepG2, A549 cells and IKKβ, respectively. Mechanism studies with 6c showed that the aza-caged compounds induce apoptosis and cell cycle S phase arrest in A549 cells.     

Synthesis and characterization of novel star-shaped pyridine cored compounds with alternating carbazole and triphenylamine moieties

Amorphous 2,4,6-trissubstituted pyridines containing three peripheral carbazole or two triphenylarnine and one carbazole moieties,respectively,have been synthesized and characterized.The properties of the compounds are investigated by UV-vis absorption,photoluminescence spectroscopy,thermal analysis as well as cyclic voltammetry.The results show that the compounds have high thermal stability,emit blue light.Also,the compounds possess the HOMO and LUMO energy levels comparable to those of NPB.The effects of different substituents on the electronic properties of the materials have been discussed.     

Synthesis and characterization of novel star-shaped pyridine cored compounds with altemating carbazole and triphenylamine moieties

Amorphous 2,4,6-trissubstituted pyridines containing three peripheral carbazole or two triphenylamine and one carbazole moieties, respectively, have been synthesized and characterized. The properties of the compounds are investigated by UV-vis absorption, photoluminescence spectroscopy, thermal analysis as well as cyclic voltammetry. The results show that the compounds have high thermal stability, emit blue light. Also, the compounds possess the HOMO and LUMO energy levels comparable to those of NPB. The effects of different substituents on the electronic properties of the materials have been discussed.     

Synthesis and antifungal evaluation of novel dicyanoderivatives of rhodanine

This work describes the synthesis and antifungal evaluation of 5‐arylidene‐(Z)‐2‐(1,1‐dicyanomethylene)‐1,3‐thiazol‐4‐ones 5 obtained from the reaction of 2‐(1,1‐dicyanomethylene)‐1,3‐thiazol‐4‐one 3 and benzaldehydes 4. The starting material 3 was synthesized by a condensation reaction of rhodanine 1 and malononitrile 2. The structures of the obtained products were established by IR, NMR, mass spectrometry, and elemental analysis. J. Heterocyclic Chem., (2011).     

Synthesis and antiproliferative evaluation of novel biheterocycles based on coumarin and 2-aminoselenophene-3-carbonitrile unit

Monatshefte für Chemie - Chemical Monthly - A series of novel coumarins with 2-amino-3-cyanoselenophen-5-yl unit on C-3 have been synthesized. These compounds prepared easily at room...     

Synthesis of a β-strand mimetic based on a pyridine scaffold

A synthetic route to a 2,4-disubstituted pyridine as a potential β-strand mimetic has been developed and applied in the synthesis of a tripeptidomimetic of Leu-Gly-Gly. The pyridine scaffold replaces the central glycine, and is substituted with analogues of leucine and glycine in positions 4 and 2, respectively. 2-Fluoro-4-iodopyridine was chosen as the functionalized scaffold and was substituted with protected leucinal in position 4 via a Grignard exchange reaction using iso-propyl magnesium chloride. The glycine moiety was introduced in position 2 via a nucleophilic aromatic substitution reaction (S_NAr) facilitated by microwave irradiation. The synthetic sequence involved 12 steps with an overall yield of 7%.     

Synthesis and biological evaluation of novel derivatives of desloratadine

Series of novel derivatives of desloratadine designed as arginine vasopressin receptor antagonists were synthesized and structurally characterized by melting points,~1H NMR and HRMS.Their in vivo diuretic activities were evaluated on rats,and several target compounds showed promising diuretic results, especially compounds 8,18,27 and 31.Further in vitro bonding assay and cAMP assay showed that these compounds had a higher affinity to vasopressin V2 receptor than VI a receptor.Our studies indicated that desloratadine may be an active substructure for novel arginine vasopressin receptor antagonist development.     

Synthesis of a new series of pyridine and fused pyridine derivatives

The reaction of 4-methyl-2-phenyl-1,2-dihydro-6-oxo-5-pyridine- carbonitrile (1) with arylidene malononitrile afforded isoquinoline derivatives 2a,b. 6-Chloro-4-methyl-2-phenyl-5-pyridinecarbonitile (3) obtained by chlorination of compound 1 with phosphoryl chloride was converted into 6-amino-4-methyl-2-phenyl-5-pyridinecarbonitrile (4) and 6-hydrazido-4-methyl-2-phenyl-5-pyridinecarbonitrile (5) in good yield, through reactions with ammonium acetate and hydrazine hydrate, respectively. Treatment of 4 with ethyl acetoacetate, acetic anhydride, formic acid, urea and thiourea gave the corresponding pyrido [2,3-d] pyrimidine derivatives 7-10a,b. A new series of 6-substituted-4-methyl-2-phenyl-5-pyridine carbonitriles 11-13 has been synthesized via reaction of 4 with phenyl isothiocyanate, benzenesulphonyl chloride and acetic anhydride. Treatment of 4 with malononitrile gave 1,8-naphthyridine derivative 14. The reactivity of hydrazide 5 towards acetic acid, phenylisothiocyanate and methylacrylate to give pyrazolo-[3,4-b]-pyridine derivatives 15-17 was studied. Treatment of 5 with acetic anhydride, phthalic anhydride and carbon disulphide gave pyridine derivatives 18,19 and 1,2,4-triazolo-[3,4-a]-pyridine derivative 20.     

Synthesis and biological evaluation of novel steroid-linked nitrogen mustards

Two novel steroid-linked nitrogen mustard conjugates 1a and 1b were synthesized by using estrogenic acid 4 coupled with aniline mustard 8 and phenol mustard 13 in an esterification or amidation procedure. Preliminary cytotoxic screening on cancer cell lines in vitro showed that, the steroid-ester linked nitrogen mustard conjugate la exhibited obvious increasing of activities.