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Sulfa Drug Group Project

Sulfa Drug Group Project. Chemistry 258 Loyd D. Bastin. Brief History. 1932-I.G. Farben (dye company in Germany). 1933-Prontosil used against staphylococcal septicemia (blood infection) 1935-Gerhard Domagk Prontosil cured streptococcal infections in mice and rabbits

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Sulfa Drug Group Project

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  1. Sulfa Drug Group Project Chemistry 258 Loyd D. Bastin

  2. Brief History • 1932-I.G. Farben (dye company in Germany) • 1933-Prontosil used against staphylococcal septicemia (blood infection) • 1935-Gerhard Domagk • Prontosil cured streptococcal infections in mice and rabbits • Later shown to have an even broader application • 1939-Domagk earned Nobel Prize in medicine • Hitler did not allow him to accept • Was later awarded the prize

  3. More History • 1935-J. Tréfouël • In vivo (in animals) prontosil effective • In vitro (petri dish) prontosil ineffective WHY? • Tréfouël showed that prontosil was metabolized to sulfanilamide in the body • Sulfanilamide shown to have in vivo and in vitro activity • Led to an explosion in the synthesis of sulfanilamide analogs • Became the wonder drug of the 30s and early 40s (referred to as sulfa drugs)

  4. A Little More History • 1929-Alexander Fleming discovers Penicillin G • 1941-Penicillin G shown to be successful antibacterial agent in humans • Leads to a decline in use of sulfa drugs • However, sulfa drugs are still used for malaria, tuberculosis, leprosy, meningitus, pneumonia, scarlet fever, plague, respiratory, infections, and intestinal/urinary tract infections

  5. Synthesis

  6. Your Task • Groups of 3 or 4 • Select groups • Weekly group meetings with instructor to discuss your progress and future plans • You are a team and it is your job to work together and synthesize the appropriate number of sulfa drugs. • Choose the R groups and synthesize 3 (or 4) different sulfanilamide analogs. • Group of 3 – synthesize 3 different sulfanilamide analogs • Group of 4 – synthesize 4 different sulfanilamide analogs • Design a “greener” method for one of your group C sulfanilamide analogs • If you change your plan, it must be submitted in writing and signed by all group members. • You MUST prove the identity and purity of your compound using mp, 1H-NMR, IR, and/or TLC to receive full credit • We will do1H-NMR once you have purified your product. • Finally, you will test the antibacterial activity of your drugs against E. coli.

  7. Your Task Continued • Here are your possible R groups • It is your job to make the synthesis work. Use the procedures in the lab manualas GUIDELINES. Modifications may/will be necessary. Could be as simple as changing T and/or solvent, or it could require some research on your part. Use your time wisely and multi-task. • Your group must submit IN WRITING during the first lab meeting, which molecules you plan to synthesize, 2-3 procedures that the group will initially dry, and a list of IR peaks you will use to indicate if a reaction occurred. If you have trouble with compounds from Groups B or C, you can update your target molecules and methods. However, you can NOT upgrade your target group after the firstlab meeting. We want to be GREEN.

  8. Rough Schedule Week 1 Groups must submit in writing within the first 1.5 hours of the 1st lab meeting. • List of Group Members • Amines to be used initially and reasoning behind those choices • 2-3 procedures that the group will try initially and the reasoning behind those choices • List of IR peaks that your group will use to indicate if a reaction has occurred. Weeks 1, 2, and 3 Work on step 1. Group meetings Week 4 Work on hydrolysis step. Group meetings Weeks 5 and 6 Work on greener method. Group meetings Week 7 Test antibacterial activity of sulfa drugs. Finish any characterization

  9. Final Report • Each group will submit ONE report. • Each member will submit a peer evaluation sheet for each member of their group The written lab report 60 pts (total possible) Successful synthesis of drug from group A: 4 pts Successful synthesis of drug from group B: 8 pts Successful synthesis of drug from group C: 12 pts Successful “greener” synthesis of a sulfa drug: 12 pts Peer evaluation of group work: 8 pts Instructor evaluation of group work: 4 pts Total points for the report 120 points Examples: The total points possible for doing an amine from group A and 2 amines from group C and devising a greener method would be 112 points (60 + 4 + 12 +12 + 12 + 8 + 4). Total possible for doing 3 amines from group A and devising a greener method would be 96 points (60 + 4 + 4 + 4 + 4 + 8 + 4). • For details please see pg. 181 in the lab manual and then ask me if you have any questions.

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