Pyridine and quinoline molecules as crucial protagonists in the never-stopping discovery of new agents against tuberculosis.

Tuberculosis (TB) disease remains to be an alarming infection worldwide with nearly 1.6 million deaths per year ranking above HIV/AIDS. Although Mycobacterium tuberculosis (Mtb), which causes TB, was identified more than 130 years ago, nowadays only old vaccine (Bacillus Calmette-Guérin vaccine) and classical toxic drugs that are losing its effectiveness are available in clinic practice.

Recent synthetic efforts in the preparation of 2-(3,4)-alkenyl (aryl) quinoline molecules towards anti-kinetoplastid agents.

Leishmaniasis, Chagas disease and African sleeping sickness have been considered some of the most important tropical protozoan afflictions. As the number of drugs currently available to treat these human illnesses is severely limited and the majority has poor safety profiles and complicated administration schedules, actually there is an urgent need to develop new effective, safe and cost-effective drugs. Because quinoline alkaloids with antiprotozoal activity (quinine, chimanine, cryptolepine or huperzine groups) were historically and are still essential models for drug research to combat these parasitic infections, synthetic or semi-synthetic quinoline-based molecules are important for anti-kinetoplastid drug design approaches and synthetic methods of their preparation become a key task that is the central subject of this review.

Bioactivity of semisynthetic eugenol derivatives against (Lepidoptera: Noctuidae) larvae infesting maize in Colombia.

The anti-acetylcholinesterase, larvicidal, antifeedant activities and general toxicity of 15 semisynthetic eugenol derivatives based on clove oil (including the own oil), were evaluated against the maize armyworm, (J.E. Smith).

Synthesis, Biological Evaluation and In Silico Computational Studies of 7-Chloro-4-(1-1,2,3-triazol-1-yl)quinoline Derivatives: Search for New Controlling Agents against (Lepidoptera: Noctuidae) Larvae.

The insecticidal and antifeedant activities of five 7-chloro-4-(1-1,2,3-triazol-1-yl)quinoline derivatives were evaluated against the maize armyworm, (J.E. Smith).

Semisynthetic eugenol derivatives as antifungal agents against dermatophytes of the genus Trichophyton.

Purpose: Eugenol, the main component of clove bud essential oil (Eugenia caryophyllus), has been linked to antimicrobial, anti-inflammatory, insecticidal and immunomodulatory properties. The purpose of this study was to evaluate the antifungal and cytotoxic activity of eugenol, the essential oil of Eugenia caryophyllus, and some semisynthetic derivatives of eugenol against dermatophytes of the genus Trichophyton.

Methodology: We evaluated the antifungal effect of the compounds, determining the minimum inhibitory concentrations (MICs) by the microdilution method and the minimum fungicidal concentrations by cultures from the inhibitions.

Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever.

Girgensohnine alkaloid was used as a natural model in the design and generation of new alkaloid-like α-aminonitrile series that was completed by the use of SSA-catalyzed Strecker reaction between commercial and inexpensive substituted benzaldehydes, piperidine (pyrrolidine, morpholine and N-methylpiperazine) and acetone cyanohydrin. Calculated ADMETox parameters of the designed analogs revealed their good pharmacokinetic profiles indicating lipophilic characteristics. In vitro AChE enzyme test showed that obtained α-aminonitriles could be considered as AChEIs with micromolar IC50 values ranging from 42.

Cantharidin-based small molecules as potential therapeutic agents.

Chemical and pharmacological information on cantharidin-based small molecules was analyzed. The review summarizes new facts about blister beetles' metabolites for the period 2006-2012. General synthetic approaches to cantharidin-based small molecules as well as their chemical transformations and biological activities related to cantharidin, norcantharidin, cantharidimide, and norcantharimide analogs, especially their inhibitory activity of phosphoprotein phosphatases in cancer treatment, were discussed in this mini review, which could help to design new small molecule modulators for other biological models.

Cytotoxic and Antifungal Activities of Diverse α-Naphthylamine Derivatives.

Diverse α-naphthylamine derivatives were easily prepared from corresponding aldimines derived from commercially available α-naphthaldehyde and anilines or isomeric pyridinecarboxyaldehydes and α-naphthylamine. The secondary amines obtained were tested as possible antifungal and cytotoxic agents. The diverse N-aryl-N-[1-(1-naphthyl)but-3-enyl]amines obtained were active (IC(50) < 10 μg/mL) against breast (MCF-7), non-small cell lung (H-460), and central nervous system (SF-268) human cancer cell lines, while N-(pyridinylmethyl)-naphthalen-1-amines resulted in activity against (MIC 25-32 μg/mL) some human opportunistic pathogenic fungi including yeasts, hialohyphomycetes, and dermatophytes.

Scavenger Activity Evaluation of the Clove Bud Essential Oil (Eugenia caryophyllus) and Eugenol Derivatives Employing ABTS Decolorization.

The essential oil (EO) of clove bud dried fruits from Eugenia caryophyllus was obtained by a conventional hydrodistillation process in an excellent yield (11.7 %). Its chemical composition was analyzed by GC-MS, identifying eugenol as a main constituent (60.

Efficient synthesis and free-radical scavenging capacity of new 2,4-substituted tetrahydroquinolines prepared via BiCl₃-catalyzed three-component Povarov reaction, using N-vinylamides.

Efficient synthesis of new structurally different 2-(het)aryl-4-amidyl-substituted tetrahydroquinolines 8-29 is reported. The synthesis based on BiCl(3)-catalyzed three-component Povarov reaction between anilines, (het)aryl aldehydes and enamides offers a fast, safe, and cheap way for efficient tetrahydroquinoline libraries construction. Using N-vinylamides (N-vinylpyrrolidin-2-one and N-vinylacetamide) in this reaction, it was possible to obtain two series of different cis tetrahydroquinolines with antioxidant properties.

Challenges and perspectives of chemical biology, a successful multidisciplinary field of natural sciences.

Objects, goals, and main methods as well as perspectives of chemical biology are discussed. This review is focused on the fundamental aspects of this emerging field of life sciences: chemical space, the small molecule library and chemical sensibilization (small molecule microassays).

Antifungal and cytotoxic activities of some N-substituted aniline derivatives bearing a hetaryl fragment.

Diverse N-substituted anilines bearing hetaryl fragments were easily prepared from corresponding aldimines derived from commercially available aromatic aldehydes and anilines. 2-Furyl substituted anilines showed very good antifungal activities against dermatophytes, particularly against Trichophyton rubrum (MIC=3.12-6.

4,6-Dimethyl-2-(3-pyridyl)quinolin-5-amine.

The title compound, C(16)H(15)N(3), shows a hindrance effect between adjacent amino and methyl groups that leads to a structural distortion, which is reflected in the non-planarity of the quinoline entity and in the bond angles and distances. The crystal packing consists of chains along the b axis sustained by an intermolecular hydrogen bond between the amino group and the N atom of the pyridyl ring.

4-Aryl(benzyl)amino-4-heteroarylbut-1-enes as building blocks in heterocyclic synthesis. 4. Synthesis of 4, 6-dimethyl-5-nitro(amino)-2-pyridylquinolines and their antiparasitic activities.

New nitro- and aminoquinoline derivatives containing a pyridyl nucleus were synthesized from 6, 8-disubstituted 4-methyl-2-pyridylquinolines, which were prepared from N-pyridylmethylidenanilines. The anti-chagasic and trichomonacidal in vitro activity, as well as the cytotoxic properties towards macrophages of some of these compounds were evaluated. Although some of the compounds showed only moderate activity it was possible to establish some structure-activity relationships.