The document summarizes an undergraduate research fellowship investigating the crystal structures of various biologically significant molecules using X-ray diffraction. It describes research on chalcones, Schiff bases, Hantzsch 1,4-dihydropyridines, and pyrazolines, with several structures already published. The fellowship involves using industry standard software to analyze diffraction results and prepare final data for publication.

1. SURF-CSI KEENEUndergraduateFellowshipResearchSummerCrystalStructureInvestigatorsCurt Guild, Jerry Jasinski Summer 2010Keene State CollegeImage Credit: http://www.sportsdesktopwallpaper.net/surfing/default.asp?pindex=7

2. Investigation of structural activity of a variety of pharmaceutically and biologically significant moleculesUse of industry standard software suite in analysis of X-ray diffraction resultsPreparation and publication of final data in the Acta Crystallographica E: Structure Reports Online journalSURF Objectives

3. Types of StructuresChalconesHSY-853: Published StructureHSY-857: Published StructureSchiff BasesYHS-25: Under ReviewHantzsch 1,4-dihydropyridinesHSY-880: Under ReviewPyrazolinesHSY-829: Published StructureOverview- Research Progress

4. Chalcone1,3-Diphenyl-2-propen-1-oneSolid State Reaction- GREEN CHEMISTRYAntitumor, Antifungal, Anti-inflammatory propertiesSeveral derivatives synthesizedCompound Type

5. IUPAC name: (2E)-3-(4-Methoxyphenyl)-1-(4-piperidin-1-ylphenyl)prop-2-en-1-oneChalcone structure with a piperidine substituent and –methoxy substituentSingle weak H-bond and two π-ring interactions stabilize crystal structure.HSY-857 PublishedJasinski, Guild, Nayak, Narayana, Yathirajan Acta Cryst. (2010). E66

6. Schiff BasesC=N bond with nitrogen bonded to aryl or alkyl group.Used in biology and catalysisNLO (Non-linear optical) properties Coordinates well to metal ionsCompound Type

7. YHS-25 Under ReviewIUPAC name: (1E)-1-(3-Bromophenyl) ethanone (2,4-dinitrophenyl) hydrazone3-bromophenyl and 2,4-dinitrophenyl groups on opposite sides of a hydrazone moietyTwo structures in unit cell, one of which shows a disordered bromine

8. Hantzsch 1,4-dihydropyridinesSubstituted Dihydro-pyradine ringantimutagenic, antihypertensive, bronchodilator, geroprotective and antidiabetic agents“are rapidly emerging as one of the most important classes of drugs for the treatment of cardiovascular diseases including hypertension1”Compound Type1(Bocker & Guengerich, 1986; Gordeevet al., 1996).

9. HSY-880 Under ReviewIUPAC name: Dimethyl 4- (4 -bromophenyl)-2,6-dimethyl-1,4-dihydro pyridine-3,5-dicarboxylateDihydro-pyridine with a p-substituted phenyl groupOne single weak hydrogen bond contributes to crystal packing stability.

10. PyrazolinesCyclo-pentane ring containing two adjacent nitrogens, one of which is bound to an ‘R’ group (here hydrogen)anti-inflammatory, antiarrhythmic, tranquilizing, muscle relaxing, antidiabetic and antibacterial activities.Study contributed to the development of heterocyclic chemistryCompound Type

11. HSY-829 PublishedIUPAC name: 3,5-Bis(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazolePyrazole ring with two p-flourophenyl subsitutents and a phenyl group off the nitrogenTwo π-ring interactions stabilize crystal structureJasinski, Guild, Samshuddin, Narayana, Yathirajan Acta Cryst. (2010). E66, o1948-o1949

12. Progress UpdatePublishedHSY-829HSY-853HSY-857Under ReviewYHS-25HSY-879HSY-880HSY-830 CHEM 461HSY-835 CHEM 461

13. Coming soon…HSY-885HSY-881

14. SynthesisHernmigeYathirajan- University of Mysore, IndiaB. Narayana- Mangalore University, IndiaS.Samshuddin- Mangalore University, IndiaParakashNayak- Mangalore University, IndiaData CollectionDr. Mathias Zeller- Youngstown State University, USADr. Ray Butcher- Howard University, USAMentorDr. Jerry Jasinski, Keene State College, USAAcknowledgements