1. SURF-CSI KEENE Undergraduate Fellowship Research Summer Crystal Structure Investigators Curt Guild, Jerry Jasinski Summer 2010 Keene State College Image Credit: http://www.sportsdesktopwallpaper.net/surfing/default.asp?pindex=7

2. Investigation of structural activity of a variety of pharmaceutically and biologically significant molecules Use of industry standard software suite in analysis of X-ray diffraction results Preparation and publication of final data in the Acta Crystallographica E: Structure Reports Online journal SURF Objectives

3. Types of Structures Chalcones HSY-853: Published Structure HSY-857: Published Structure Schiff Bases YHS-25: Under Review Hantzsch 1,4-dihydropyridines HSY-880: Under Review Pyrazolines HSY-829: Published Structure Overview- Research Progress

4. Chalcone 1,3-Diphenyl-2-propen-1-one Solid State Reaction- GREEN CHEMISTRY Antitumor, Antifungal, Anti-inflammatory properties Several derivatives synthesized Compound Type

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

6. Schiff Bases C=N bond with nitrogen bonded to aryl or alkyl group. Used in biology and catalysis NLO (Non-linear optical) properties Coordinates well to metal ions Compound Type

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

8. Hantzsch 1,4-dihydropyridines Substituted Dihydro-pyradine ring antimutagenic, 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 Type 1(Bocker & Guengerich, 1986; Gordeevet al., 1996).

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

10. Pyrazolines Cyclo-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 chemistry Compound Type

11. HSY-829 Published IUPAC name: 3,5-Bis(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole Pyrazole ring with two p-flourophenyl subsitutents and a phenyl group off the nitrogen Two π-ring interactions stabilize crystal structure Jasinski, Guild, Samshuddin, Narayana, Yathirajan Acta Cryst. (2010). E66, o1948-o1949

12. Progress Update Published HSY-829 HSY-853 HSY-857 Under Review YHS-25 HSY-879 HSY-880 HSY-830 CHEM 461 HSY-835 CHEM 461

13. Coming soon… HSY-885 HSY-881

14. Synthesis HernmigeYathirajan- University of Mysore, India B. Narayana- Mangalore University, India S.Samshuddin- Mangalore University, India ParakashNayak- Mangalore University, India Data Collection Dr. Mathias Zeller- Youngstown State University, USA Dr. Ray Butcher- Howard University, USA Mentor Dr. Jerry Jasinski, Keene State College, USA Acknowledgements