SURF-CSI KEENE

Curt Guild, Jerry Jasinski Summer 2010Keene State College

Crystal

Structure

Investigators

Image Credit: http://www.sportsdesktopwallpaper.net/surfing/default.asp?pindex=7

Undergraduate

Fellowship

ResearchSummer

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

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

Chalcone

◦ 1,3-Diphenyl-2-propen-1-one

◦ Solid State Reaction- GREEN CHEMISTRY

◦ Antitumor, Antifungal, Anti-inflammatory properties

◦ Several derivatives synthesized

Compound Type

O

OO

H H3C

O

+NaOH

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

O

N O

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

NC

R R'

R''' R''

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

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

N

O O

1(Bocker & Guengerich, 1986; Gordeev et al., 1996).

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.

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

HN

N

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 

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

Coming soon…

HSY-885HSY-881

Synthesis◦ Hernmige Yathirajan- University of Mysore, India◦ B. Narayana- Mangalore University, India◦ S.Samshuddin- Mangalore University, India◦ Parakash Nayak- 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