SVIBOR - Project code: 1-07-333

MINISTRY OF SCIENCE AND TECHNOLOGY

Strossmayerov trg 4, HR - 10000 ZAGREB
tel.: +385 1 459 44 44, fax: +385 1 459 44 69
E-mail: ured@znanost.hr

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Project code: 1-07-333


SYNTHESIS AND STEREODYNAMIC STUDIES OF CHIRAL AND PHARMACOLOGICALLY INTERESTING COMPOUNDS


Main researcher: MINTAS, MLADEN (31831)



Assistants
Type of research: basic
Duration from: 09/01/93. to 12/31/96.

Papers on project (total): 42
Papers on project quoted in Current Contents: 15
Institution name: Fakultet kemijskog inženjerstva i tehnologije, Zagreb (125)
Department/Institute: Department of Organic Chemistry
Address: 41000 Zagreb, Marulićev trg 20, Croatia
City: 10000 - Zagreb, Croatia
Communication
Phone: 385- 1- 4552 477/ext.23
Fax: 385-1-4550725

Summary: The synthesis ot the following classes of model chiral molecules is proposed: singly- and doubly bridged biphenyls with heteroatoms or functional groups in the bridge, 2H-chromenes and atropisomeric heterocyclic biaryls. The main purpose of the cited compounds preparation is resolution of their enantiomers and study of stereodynamic and chirooptic properties. The ultimate aim of the studies concerned with bridged biphenyls is to develop the method to establish configuration of molecules in solution on the basis of correlative informations from the experimental and calculated circular dichroism and ultraviolet spectral data. Furthermore, the synthesis of the acyclic purine nucleoside and nucleotide analogues as well as related molecules containing other heterocyclic ring systems is proposed. The main reason for this novel compounds preparation is their evaluation on antiviral and particularly anti-HIV activities.The ultimate purpose is to establish structure activity relationship in this class of compounds in order to find more efficacious and selective antiviral drugs. Our studies will also be concerned with the regiospecific synthesis of trifluoromethyl substituted dibenzosemibullvalenes. It is known on the basis of patent literature that related representatives of this clas of compounds possess pharmacological properties as antidepresive agents. The reason for these novel compounds preparation is therefore their screening on the cited activities.

Keywords: Bridged biphenyls, 2H-chromenes, atropisomeric heterocyclic biphenyls, barriers to racemization, Gibbs energy of activation, absolute configuration determination, acyclic purine nucleoside and nucleotide analogues, antiviral activities, anti- HIV drugs, dibenzosemibullvalenes, anti-depressive drugs.

Research goals: The following goals of the proposed studies are: A. Preparation of the model chiral organic molecules: a) 2,2'-singly and 2,2',6,6'-doubly bridged biphenyls containing heteroatoms or functional groups in the bridge; b) 2H-chromenes and c) atropisomeric heterocyclic biaryls. The main and common aim of the preparation of suitably substituted compounds a)-c) is to resolve their enantiomers in order to apply optically active compounds thus obtained in stereodynamic and chiroptical studies. In the part of research concerned with chiral bridged biphenyls we expect that comparison between experimental and calculated circular dichroism and ultraviolet spectral data will permit assignment of absolute configuration. We expect in the field of chiral chromenes to find such molecular system that will enable separation of their enantiomers and determination of thermodynamic parameters for racemization. The principal aim of the studies of atropisomeric heterocyclic biaryls is determination of the unknown Gibbs energies of activation for restricted rotation about the C-N bond; B. Synthesis of the acyclic purine nucleoside and nucleotide analogues as well as related molecules containing other heterocyclic ring systems. The main purpose of these studies is evaluation of the novel compounds on antiviral and particularly anti HIV activities. The purpose of this evaluation is to establish structure activity relationship in this class of compounds with the final goal to find more efficacious and selective antiviral drugs; C. Regiospecific synthesis of trifluoromethyl substituted dibenzosemibullvalenes. Related representatives of this class of compounds possess on the basis of patent literature pharmacological properties as antidepressive agents. We expect therefore that newly prepared compounds with trifluoromethyl groups will also exert such activities. The principal goal of these studies is to test the novel compounds on the cited activities.


COOPERATION - PROJECTS


  1. Name of project: "CHIRAL HETEROCYCLYC BIARYLS AND HELICENES" joint research project with Prof. A. Mannschreck (University of Regensburg) within German-Croatian scientific co-operation program "Juelich"
    Name of institution: Institut fuer Organische Chemie, Universitaet Regensburg
    City: D-93053 - Regensburg, Deutschland

  2. Name of project: "SYNTHESIS ENANTIOMERIC RESOLUTION,BARRIERS TO RACEMIZATION AND ABSOLUTE CONFIGURATION OF SOME CHIRAL 2,2'-BRIDGED AND 2,2',6,6'-DOUBLY BRIDGED BIPHENYLS" joint project with Prof. J. Sandstroem within "Royal Swedish Academy of Engineering Sciences"
    Name of institution: Organic Chemistry 1, Chemical Center, University of Lund
    City: S-22100 - Lund, Sweden

  3. Name of project: > "SYNTHESIS, ENANTIOMERIC RESOLUTION, BARRIERS TO RACEMIZATION AND ABSOLUTE CONFIGURATION OF SOME CHIRAL 2,2'-BRIDGED AND 2,2',6,6'-DOUBLY BRIDGED BIPHENYLS"
    Name of institution: University of Lund, Chemical Center, Organic Chemistry 3,
    City: S-22100 - Lund, Sweden


COOPERATION - INSTITUTIONS


  1. Name of institution: Zavod za opću i anorgansku kemiju, Prirodoslovno-matematički fakultet, Sveučilište u Zagrebu
    Type of institution: University/Faculty
    Type of cooperation: Joint publishing of scientific papers
    City: 10000 - Zagreb, Croatia

  2. Name of institution: Institut Ruđer Bošković
    Type of institution: State institute
    Type of cooperation: Joint publishing of scientific papers
    City: 10000 - Zagreb, Croatia

  3. Name of institution: Department of Chemistry, Brown University
    Type of institution: University/Faculty
    Type of cooperation: Joint publishing of scientific papers
    City: 02912 - Providence, Rhode Island, USA

  4. Name of institution: Chemistry Department, Lousiana State University
    Type of institution: University/Faculty
    Type of cooperation: Joint publishing of scientific papers
    City: LA - Baton Rouge, Lousiana, USA

  5. Name of institution: Pliva istraživački institut
    Type of institution: Economical/Production
    Type of cooperation: Joint publishing of scientific papers
    City: 10000 - Zagreb, Croatia

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Last update: 10/09/95
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