Study On The Synthesis And Crystal Structure Of Guanidine Derivatives

Organic compounds containing nitrogen have been received extensive attention inthe academic and industrial fields, due to their important building blocks in theconstruction of amino acids, peptides and proteins, which are closely related to the life.They include nitro compound, amine, amine derivative and heterocyclic compoundbearing nitrogen according to the classification of functional group sequence. Aminederivatives such as nucleic acids, peptides and proteins have also been a very activearea of research to the chemistry and biology, and the interest continues to expand.Recently, the topic of these studies is emphasized on the guanidines.The guanidine is one of the strongest bases being of the biological activity, andeasy to protonate in pH of the physiological medium to form guanidinium group withpositive charge. These groups can bind to the substrate through static attraction.Hydrogen and nitrogen atoms of the guanidinium group are high affinity tocarboxylates, phosphates and peptides to construct the hydrogen-bonding pattern,even a geometry pattern with the substrates. The drugs containing guanidinium groupsare not only easy to transport, but also make the functions of absorb and osmosis moreselectivity in the body because of their various acid salts being easy soluble inaqueous solution. A series of biological functions such as anti-inflammation, nervestimulus and inhibit, antihistamine, hypertension, anti-diabetes can be generated in thebody through the interactions of guanidinium group; hence the guanidinium group inthe drug design has been an alternative group frequently. The guanidine has also beenemployed as a broad-spectrum anti-microbial and fungicide activity in the agriculturalchemicals and water treatment agents. New function, new compound design, newsynthetic method, and mechanism studies at molecular level may be frontier field inthe research of the guanidines.The recent progresses in the research of guanidine are reviewed comparatively inthe pharmaceutical activities of the natural products, mechanism of enzyme, drug andbactericide and syntheses of guanidines in this dissertation. Based on these researchesand trends of academic develop as well as the industrial need, guanidine compoundscontaining quinolinyl and fluorine atom have been designed. The new process andtechnology are found use in the research of the synthesis process, molecular structure,intermolecular action and biological activity. These studies can be provide the newtarget and new idea for the drug design and may be found new use in the future.Based on the analog design principle, the aromatic guanidine, quinolinylguanidine and ferulyl guanidine were designed and synthesized, and characterized bythe means of the IR, NMR, MS and EA, in which the p-fluorophenylguanidine andferulylguanidine were first reported by us up to now. The preliminary biologicalexperimental results indicated these guanidines have some antibacterial activity.The microstructure and interaction of the molecules for the chemical substancescan be investigated at atomic level by single crystal analysis, which is one of theimportant technological tools in the research of modern chemistry. As we know, thesingle crystal of guanidine is not easily obtained due to its easy soluble in water, i韦长梅 胍基化合物的合成与生物活性研究 2004 年 5 月strong base and having positive charge. However, the novel single crystals for the sixguanidine compounds,being of the super molecular structure, were crystallized out byevaporation of their salt solutions, which the pH and concentration were carefullyadjusted trial and error. Their crystal structural data were yielded after X-ray analysisand structural refinements. The CCDC numbers have been given to us when wesubmitted the CIF files of the crystals to the CCDC Cambridge in UK. Theseindicated the crystal structures of these guanidines are of original and first reportedaccording to our knowledge.From the X-ray analysis, w...