New polifunctional nitrogen derivatives (heterocycles, podants and macrocycles) as smart versatile building blocks for multiple tasks

2011 (3 months). Stage I.  Synthesis and structural analysis of the necessary intermediary

Synthesis will be performed according to the following scheme:

A.I.1. Synthesis of 6-member ring nitrogen π–deficient and 5-member ring nitrogen π–reach heterocycles by conventional methods

A.I.2. Synthesis of diols with acetophenone skeleton by conventional methods

A.I.3. Elemental and structural analysis of the obtained structures. Final stage report. The structure of the newly compounds will be proven through elemental and structural analysis: IR, NMR.

A final stage report will be accomplished and it will be present on the web page of the project.

2012. Stage II.  Synthesis and structural analysis of intermediars and podant derivatives

In this stage there will be bring it contributions to objectives O1, O2, O5-O7.

A.II.1. Synthesis of 5- and 6- member ring nitrogen heterocycles and diols intermediary (obtained in stage I by conventional methods), using MW and/or US technology.

A.II.2. Synthesis of new polifunctional nitrogen podant type P1 having in the same molecule a π–reach and a π–deficient heterocycle connected via different spacers. In the second step, P1 will be tested as chemosensor (complexation with metals, M^m+) and as logic gate of type NOR (complex either H⁺ or M^m+), P1 being a fluorophore-spacer-receptor system.

A.II.3. Synthesis of new polifunctional nitrogen podant type P2 having in the same molecule a π–reach  and a π–deficient heterocycle connected  via different spacers. In the second step, P2 will be tested as chemosensor (complexation with metals, M^m+) and as logic gate with three inputs (2H⁺ and M^m+) and one output (fluorescence), a fluorophore-spacer-receptor-spacer-fluorophore system.

A.II.4. Synthesis of new polifunctional nitrogen podant type P5 having in molecule only a π–reach

nitrogen heterocycle connected via different spacers with the receptor. In the second step, P5 will be tested as chemosensor (complexation with metals, M^m+) and as logic gate (two input: H⁺ and M^m+and one output: fluorescence), a fluorophore-spacer-receptor system.

A.II.5. Biologically active evaluation. The newly obtained compounds will be tested as follow:  P1 and P2 as DNA intercalators, P5 as antimicrobial.

A.II.6. Elemental and structural analysis of the obtained structures. Final stage report. The structure of the newly compounds will be proven through elemental and structural analysis: IR, NMR, UV-Vis and fluorescence, MS, X-ray. A final stage report will be accomplished and it will be present on the web page of the project. Manuscript preparation for publication.

2013. Stage III.  Synthesis and structural analysis of intermediars and podant derivatives

In this stage there will be bring it contributions to objectives O1, O2, O5-O7.

A.III.1. Synthesis of the necessary intermediary (as we described in stage I)

A.III.2. Synthesis of new polifunctional nitrogen podant type P3 having in the same molecule a π–reach  and a π–deficient heterocycle. In the second step, P3 will be tested as chemosensor (complexation with metals, M^m+) and as logic gate with three inputs (2H⁺ and M^m+) and one output (fluorescence), a fluorophore-spacer-receptor-spacer-fluorophore system.

A.III.3. Synthesis of new polifunctional nitrogen podant type P6 having in molecule only a π–reach nitrogen heterocycle. In the second step, P6 will be tested as chemosensor (complexation with metals, M^m+) and as logic gate (two input: H⁺ and M^m+and one output: fluorescence), a fluorophore-spacer-fluorophore-spacer-receptor system.

A.III.4. Synthesis of new polifunctional nitrogen podant type P4 having in the same molecule a π–reach and a π–deficient heterocycle connected via different spacers. In the second step, P4 will be tested as chemosensor (complexation with metals, M^m+) and as logic gate with three inputs (2H⁺ and M^m+) and one output (fluorescence), a fluorophore-spacer-receptor-spacer-fluorophore system.

A.III.5. Biologically active evaluation. The newly obtained compounds will be tested as follow:  P3 as DNA intercalators and P4 and P6 as DNA intercalators and antimicrobials.

A.III.6. Elemental and structural analysis of the obtained structures. Final stage report. The structure of the newly compounds will be proven through elemental and structural analysis: IR, NMR, UV-Vis and fluorescence, MS, X-ray. A final stage report will be accomplished and it will be present on the web page of the project. Manuscript preparation for publication.

2014. Stage IV.  Synthesis and structural analysis of macrocycles and podant derivatives

In this stage there will be bring it contributions to objectives O3-O7.

A.IV.1. Synthesis of the necessary intermediary (as we described in stage I)

A.IV.2. Synthesis of new polifunctional nitrogen podant type P8 having in molecule a π–deficient heterocycle connected via different spacers with a bis-alkylator unit.

In the second step, P8 will be tested as chemosensor (complexation with metals, M^m+).

A.IV.3. Synthesis of new nitrogen macrocycle type P7 having in the same molecule at a π–reach and a π–deficient heterocycle connected via different spacers. In the second step, P7 will be tested as chemosensor (complexation with metals, M^m+) and as logic gate with three inputs (2H⁺ and M^m+) and one output (fluorescence), a fluorophore-spacer -receptor-spacer-fluorophore system.

A.IV.5. Biologically active evaluation. The newly obtained compounds will be tested as follow:  P7 as DNA intercalator and P8 as DNA alkylator and antimicrobial.

A.IV.6. Elemental and structural analysis of the obtained structures. Final stage and grant report. The structure of the newly compounds will be proven through elemental and structural analysis: IR, NMR, UV-Vis and fluorescence, MS, X-ray. A final stage report will be accomplished and it will be present on the web page of the project. Manuscript preparation for publication.