Exploring Pyrrolo-Fused Heterocycles as Promising Anticancer Agents: An Integrated Synthetic, Biological, and Computational Approach.

Five new series of pyrrolo-fused heterocycles were designed through a scaffold hybridization strategy as analogs of the well-known microtubule inhibitor phenstatin. Compounds were synthesized using the 1,3-dipolar cycloaddition of cycloimmonium N-ylides to ethyl propiolate as a key step. Selected compounds were then evaluated for anticancer activity and ability to inhibit tubulin polymerization in vitro.

Exploring Pyrrolo-Phenanthrolines as Semiconductors for Potential Implementation in Organic Electronics.

This paper describes the synthesis and characterization of new organic semiconductors based on pyrrolo[1,2-i][1,7]phenanthrolines in the form of thin layers. The thin layers, produced via the spin coating method (with a thickness of 10-11 μm), were investigated for their electrical and optical properties. After heat treatment at temperatures ranging from 210 to 240 °C, the layers displayed consistent and reproducible properties.

Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity.

This study presents the synthesis, structural characterization, and in vitro evaluation of anticancer activity of some newly benzo[]quinoline derivatives. The synthesis is facile and efficient, involving two steps: quaternization of nitrogen heterocycle followed by a [3+2] dipolar cycloaddition reaction. The synthesized compounds were characterized by FTIR, NMR, and X-ray diffraction on monocrystal in the case of compounds and .

Hybrids Diazine: Recent Advancements in Modern Antimicrobial Therapy.

Nowadays, antimicrobial therapies have become a very challenging issue because of a large diversity of reasons such as antimicrobial resistance, over consumption and misuse of antimicrobial agents, . A modern, actual and very useful approach in antimicrobial therapy is represented by the use of hybrid drugs, especially combined five and six-membered ring azaheterocycles. In this review, we present an overview of the recent advanced data from the last five years in the field of hybrid diazine compounds with antimicrobial activity.

Structural, Electrical and Optical Properties of Pyrrolo[1,2-][1,7] Phenanthroline-Based Organic Semiconductors.

This work reports a study on structural, electrical and optical properties of some recently synthesized pyrrolo[1,2-][1,7] phenanthrolines derivatives in thin films. The thin films were deposited onto glass substrates by spin coating technique, using chloroform as solvent. The obtained films exhibited a polycrystalline structure with an -type semiconductor behavior after heat treatment in the temperature range 293-543 K, specific to each sample.

Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives.

Several new cyano-substituted derivatives with pyrrolo[1,2-]quinoline and pyrrolo[2,1-]isoquinoline scaffolds were synthesized by the [3 + 2] cycloaddition of (iso)quinolinium ylides to fumaronitrile. The cycloimmonium ylides reacted in situ as 1,3-dipoles with fumaronitrile to selectively form distinct final compounds, depending on the structure of the (iso)quinolinium salt. Eleven compounds were evaluated for their anticancer activity against a panel of 60 human cancer cell lines.

New 2,9-disubstituted-1,10-phenanthroline derivatives with anticancer activity by selective targeting of telomeric G-quadruplex DNA.

Fifteen new 1,10-phenanthrolines disubstituted at positions 2 and 9 via amide bonds with different heterocycles have been designed and synthesized as G-quadruplex DNA stabilizers. Ten compounds were evaluated for the in vitro anticancer activity against 60 human tumor cell lines panel, four of them showing a very good inhibitory activity on several cell lines. To assess the ability of the most active compounds to interact with G-quadruplex DNA (G4-DNA), circular dichroism experiments were performed.

Huisgen [3 + 2] Dipolar Cycloadditions of Phthalazinium Ylides to Activated Symmetric and Non-Symmetric Alkynes.

We present herein a straightforward and efficient pathway for the synthesis of pyrrolophthalazine cycloadducts via Huisgen [3 + 2] dipolar cycloaddition reactions of phthalazinium ylides to methyl propiolate or dimethyl acetylenedicarboxylate (DMAD). A thoroughly comparative study concerning the efficiency of synthesis, conventional thermal heating (TH) versus microwave (MW) and ultrasound (US) irradiation, has been performed. The cycloaddition reactions of phthalazinium ylides to methyl propiolate occur regiospecific, with a single regioisomer being obtained.

Cyclodextrin Encapsulated pH Sensitive Dyes as Fluorescent Cellular Probes: Self-Aggregation and In Vitro Assessments.

We have designed and synthesized a series of novel, supramolecular, long-lived fluorescent probes based on the host-guest inclusion complexes formation between fluorescent indolizinyl-pyridinium salts and β-cyclodextrin. Fluorescence and electrospray ionisation mass spectrometry experiments, supported by theoretical molecular docking studies, were utilized in the monitoring of the inclusion complexes formation, evidencing the appearance of corresponding 1:1 and 1:2 species. Additionally, the influence of the guest molecule over the aggregation processes of the cyclodextrin inclusion complexes was investigated by transmission electron microscopy.

Cytotoxic substituted indolizines as new colchicine site tubulin polymerisation inhibitors.

A potential microtubule destabilising series of new indolizine derivatives was synthesised and tested for their anticancer activity against a panel of 60 human cancer cell lines. Compounds , , , and showed a broad spectrum of growth inhibitory activity against cancer cell lines representing leukaemia, melanoma and cancer of lung, colon, central nervous system, ovary, kidney, breast, and prostate. Among them, compound was distinguishable by its excellent cytostatic activity, showing GI values in the range of 10-100 nM on 43 cell lines.

Microwave Assisted Reactions of Azaheterocycles Formedicinal Chemistry Applications.

Microwave (MW) assisted reactions have became a powerful tool in azaheterocycles chemistry during the last decades. Five and six membered ring azaheterocycles are privileged scaffolds in modern medicinal chemistry possessing a large variety of biological activity. This review is focused on the recent relevant advances in the MW assisted reactions applied to azaheterocyclic derivatives and their medicinal chemistry applications from the last five years.

Design, Synthesis, Molecular Modelling and Anticancer Activities of New Fused Phenanthrolines.

Three series of fused pyrrolophenanthroline derivatives were designed as analogues of phenstatin and synthesized in two steps starting with 1,7-phenanthroline, 4,7-phenanthroline and 1,10-phenanthroline, respectively. Two (Compounds and ) of the four compounds tested against a panel of sixty human cancer cell lines of the National Cancer Institute (NCI) exhibited significant growth inhibition activity on several cell lines. Compound showed a broad spectrum in terms of antiproliferative efficacy with GI values in the range of 0.

Synthesis, molecular modelling and anticancer evaluation of new pyrrolo[1,2-b]pyridazine and pyrrolo[2,1-a]phthalazine derivatives.

Two new series of heterocyclic derivatives with potential anticancer activity, in which a pyrrolo[1,2-b]pyridazine or a pyrrolo[2,1-a]phthalazine moiety was introduced in place of the 3'-hydroxy-4'-methoxyphenyl ring of phenstatin have been synthesised and their structure-activity relationship (SAR) was studied. Fourteen of the new compounds were evaluated for their in vitro cytotoxic activity by National Cancer Institute (NCI) against 60 human tumour cell lines panel. The best five compounds in terms of in vitro growth inhibition were screened in the second stage five dose-response studies, three of them showing a very good antiproliferative activity with GI<100 nM on several cell lines including colon, ovarian, renal, prostate, brain and breast cancer, melanoma and leukemia.

Antimycobacterial activity of nitrogen heterocycles derivatives: 7-(pyridine-4-yl)-indolizine derivatives. Part VII.

A series of 13 compounds having a monoindolizine mono-salt skeleton was designed and synthesised in order to evaluate their antimycobacterial activity. The synthesis is efficient, involving only three steps: two alkylations and one 3 + 2 dipolar cycloaddition. The antimicrobial activity against Mycobacterium tuberculosis H37Rv grown under aerobic conditions was evaluated, eight compounds showing a very good antimycobacterial activity.

Synthesis, structure, antimycobacterial and anticancer evaluation of new pyrrolo-phenanthroline derivatives.

A study concerning design, synthesis, structure and in vitro antimycobacterial and anticancer evaluation of new fused derivatives with pyrrolo[2,1-c][4,7]phenanthroline skeleton is described. The strategy adopted for synthesis involves a [3 + 2] dipolar cycloaddition of several in situ generated 4,7-phenanthrolin-4-ium ylides to different substituted alkynes and alkenes. Stereo- and regiochemistry of cycloaddition reactions were discussed.

New indolizines with phenanthroline skeleton: Synthesis, structure, antimycobacterial and anticancer evaluation.

We report herein a feasible study concerning the design, synthesis, structure and in vitro antimycobacterial and anticancer activity of two new classes (containing four and five fused rings) of indolizine with phenanthroline skeleton. The preparation is straight and efficient, involving a Huisgen [3+2] dipolar cycloaddition of cycloimmonium ylides to alkynes or alkenes dipolarophiles. The cycloaddition reactions are highly stereo- or regioselective, according with the dipolarophiles nature.

Antibacterial activity of Pd(II) complexes with salicylaldehyde-amino acids Schiff bases ligands.

Palladium(II) complexes with Schiff bases ligands derived from salicylaldehyde and amino acids (Ala, Gly, Met, Ser, Val) have been synthesized and characterized by Fourier transform (FT)-IR, UV-Vis and (1)H-NMR spectroscopy. The electrospray mass spectrometry (ES-MS) spectrometry confirms the formation of palladium(II) complexes in 1/2 (M/L) molar ratio. All the Pd(II) complexes 1, [Pd(SalAla)2]Cl2; 2, [Pd(SalGly)2]Cl2; 3, [Pd(SalMet)2]Cl2; 4, [Pd(SalSer)2]Cl2; 5, [Pd(SalVal)2]Cl2; have shown antibacterial activity against Gram-positive bacteria Staphylococcus aureus and Gram-negative bacteria Escherichia coli.

Antimycobacterial activity of nitrogen heterocycles derivatives: bipyridine derivatives. Part III.

Three classes of fused bipyridine heterocycles were designed, synthesized and evaluated for their antimycobacterial activities. The method for preparation of fused bipyridine derivatives is straight and efficient. The primary antimycobacterial screening reveals that mono-indolizine mono-salts are displaying potency superior to the second-line antitubercular drugs Cycloserine and Pyrimethamine and, equal as the first line anti-TB Ethambutol.

Synthesis of glucose derivatives modified at the 4-OH as potential chain-terminators of cellulose biosynthesis; herbicidal activity of simple monosaccharide derivatives.

A series of D-glucose derivatives that have been modified at C-4 were synthesised from D-galactose as potential chain terminators of cellulose biosynthesis. Two compounds displayed herbicidal activity in pre-emergence tests and in addition a cell expansion assay at higher concentrations revealed symptomology of a third compound that was indicative of inhibition of cellulose biosynthesis.

Synthesis of UDP-glucose derivatives modified at the 3-OH as potential chain terminators of beta-glucan biosynthesis.

A series of UDP-D-glucose derivatives and precursors that have been modified at C-3 were synthesised from D-glucose as potential chain terminators of beta-glucan biosynthesis. None of the UDP-derivatives or the precursors tested displayed significant anti-fungal activity in a series of germination assays on the dermatophyte Trichophyton rubrum.

[Antimicrobial activity of new 4,4'-bipyridine derivatives: and in vitro study].

The antimicrobial and antifungal activity of some 4,4'-bipyridine derivatives were studied. The diffusimetric gelose surface diffusion method with stainless steel cylinders was used to study bacteria and Sabouraud fields for Candida albicans. Comparative analysis of the results led to the following conclusions.

[In vitro antimicrobial activity of new 1,10-phenantroline derivatives].

The antimicrobial and antifungical activities of some 1,10-phenanthroline derivatives are described. The test was performed using the diffusimetric method with stainless steel cylinders based on diffusion of the substances on the gelose surface for bacteria and Sabouraud field for Candida Albicans yeast. The comparative analysis of the obtained data leads to the following conclusions concerning the relation between structure and activity