ºÝºÝߣ

ºÝºÝߣShare a Scribd company logo

Organic chemistry

•
•
A
Anam Ilyas

The document discusses the Pinner pyrimidine synthesis reaction, which involves the condensation of 1,3-dicarbonyl compounds with amidines catalyzed by acids or bases to form pyrimidine derivatives. It then discusses the historical background of the reaction discovered by Pinner in the 1880s. The document also discusses the synthetic utility of the Pinner pyrimidine synthesis and provides examples of reactions. Finally, the document discusses the synthesis, mechanisms, and uses of the drugs sulfamerazine and trimethoprim, which are synthesized using the Pinner pyrimidine synthesis reaction.

1 of 19
Pinner Pyrimidine Synthesis Presentedby: Anam Ilyas M.Pharm. 1st semester (Pharm chemistry) JAMIA HAMDARD
Pinner Pyrimidine Synthesis: ï‚´ The condensation of 1,3-dicarbonyl compounds with amidines catalysed by acids or bases to give pyrimidine derivatives is regarded as the Pinner pyrimidine synthesis.
HISTORICALPERSPECTIVE: ï‚´ In the 1880s, Pinner found that the amidine derivativereacted with acetoacetic ester to give 2-substituted-6-hydroxy-4-methylpyrimidine.
MECHANISM
Organic chemistry
SYNTHETIC UTILITY OF PINNER PYRIMIDINE SYNTHESIS ï‚´ Many pyrimidine derivatives have been prepared viathe pinner procedure. 1. Amidines react with Acetylacetone to form 2,4,6-Trisubstitutedpyrimidines. K2CO3
2. Amidines react with B-ketoester to provide hydroxypyrimidines.
SULFAMERAZINE ï‚´ Molecular formula: C11H12N4O2S ï‚´ Sulfamerazine is also known as solumedine. ï‚´ Sulfamerazine belongs to antimicrobial drugs that contain sulfonamide as a parent structure.
ï‚´USES OF SULFAMERAZINE: It is used as an antibacterial agent. It can be used to treat : 1. bronchitis 2. Prostatitis 3. urinary tract infections. SIDE EFFECTS OF SULFAMERAZINE: 1. Nausea 2. Vomiting 3. Diarrhea 4. hypersensitivity reactions. 5. Hematologic effects such as anemia.
ï‚´ MECHANISM OF ACTION: ï‚´ Sulfamerazine act by inhibiting bacterial folic acid synthesis by competing PABA with Dihydrofolate Synthetase. ï‚´ It is a competitive inhibitor of dihydrofolate synthetase, this enzyme is used in folate synthesis is bacteria and therefore sulfamerazine interferes with this pathway and ultimately decreasing the synthesis of bacterial nucleotides and DNA.
SYNTHESIS OF SULFAMERAZINE ➢ It is a 3 step process:  Preparation of ASC(p-Acetamidobenzne chloride)  2-Preparation of 2-Amino-4-methyl pyrimidine  Condensation of ASC and 2-Amino-4-methyl pyrimidine followed by alkaline hydrolysis
ï‚´ STEP1: Preparation of ASC(p-Acetamidobenzne chloride)
ï‚´ STEP2: 2-Preparation of 2-Amino-4-methyl pyrimidine It is achived by the interation of sodium derivative of Formyl acetone with guanidine.
ï‚´ STEP 3:Alkaline Hydrolysis: condensation of ACE and 2-Amino-4-methyl Pyrimidine takesplace followed by Alkaline Hydrolysis.
TRIMETHOPRIM 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine MOLECULAR FORMULA: C14H18N4O3
ï‚´USES OF TRIMETHOPRIM: Trimethoprim is a bacteriostatic antibiotic. 1. It is active against many aerobic gram negetive bacilli and a few gram positive organism. 2. trimethoprim is indicated for the treatment of acute episodes of uncomplicated urinary tract infections. ï‚´SIDE EFFECTS OF TRIMETHOPRIM: 1. Folate deficiency result in megaloblastic anaemia. 2. Nausea, Vomitting, Skin rashes.
Mechanism Of Action: ï‚´ Trimethoprim is a bacteriostatic antibiotic. ï‚´ It is active against many aerobic gram negative bacilli ï‚´ It is >50,000 more active against Bacterial DHFRase than Mammalian enzyme. ï‚´ It selectively inhibits bacterial dihydrofolate reductase (DHFRase).
SYNTHESIS OF TRIMETHOPRIM:
THANK YOU

More Related Content

Organic chemistry

  • 1. Pinner Pyrimidine Synthesis Presentedby: Anam Ilyas M.Pharm. 1st semester (Pharm chemistry) JAMIA HAMDARD
  • 2. Pinner Pyrimidine Synthesis: ï‚´ The condensation of 1,3-dicarbonyl compounds with amidines catalysed by acids or bases to give pyrimidine derivatives is regarded as the Pinner pyrimidine synthesis.
  • 3. HISTORICALPERSPECTIVE: ï‚´ In the 1880s, Pinner found that the amidine derivativereacted with acetoacetic ester to give 2-substituted-6-hydroxy-4-methylpyrimidine.
  • 6. SYNTHETIC UTILITY OF PINNER PYRIMIDINE SYNTHESIS ï‚´ Many pyrimidine derivatives have been prepared viathe pinner procedure. 1. Amidines react with Acetylacetone to form 2,4,6-Trisubstitutedpyrimidines. K2CO3
  • 7. 2. Amidines react with B-ketoester to provide hydroxypyrimidines.
  • 8. SULFAMERAZINE ï‚´ Molecular formula: C11H12N4O2S ï‚´ Sulfamerazine is also known as solumedine. ï‚´ Sulfamerazine belongs to antimicrobial drugs that contain sulfonamide as a parent structure.
  • 9. ï‚´USES OF SULFAMERAZINE: It is used as an antibacterial agent. It can be used to treat : 1. bronchitis 2. Prostatitis 3. urinary tract infections. SIDE EFFECTS OF SULFAMERAZINE: 1. Nausea 2. Vomiting 3. Diarrhea 4. hypersensitivity reactions. 5. Hematologic effects such as anemia.
  • 10. ï‚´ MECHANISM OF ACTION: ï‚´ Sulfamerazine act by inhibiting bacterial folic acid synthesis by competing PABA with Dihydrofolate Synthetase. ï‚´ It is a competitive inhibitor of dihydrofolate synthetase, this enzyme is used in folate synthesis is bacteria and therefore sulfamerazine interferes with this pathway and ultimately decreasing the synthesis of bacterial nucleotides and DNA.
  • 11. SYNTHESIS OF SULFAMERAZINE ➢ It is a 3 step process: ï‚´ Preparation of ASC(p-Acetamidobenzne chloride) ï‚´ 2-Preparation of 2-Amino-4-methyl pyrimidine ï‚´ Condensation of ASC and 2-Amino-4-methyl pyrimidine followed by alkaline hydrolysis
  • 12. ï‚´ STEP1: Preparation of ASC(p-Acetamidobenzne chloride)
  • 13. ï‚´ STEP2: 2-Preparation of 2-Amino-4-methyl pyrimidine It is achived by the interation of sodium derivative of Formyl acetone with guanidine.
  • 14. ï‚´ STEP 3:Alkaline Hydrolysis: condensation of ACE and 2-Amino-4-methyl Pyrimidine takesplace followed by Alkaline Hydrolysis.
  • 16. ï‚´USES OF TRIMETHOPRIM: Trimethoprim is a bacteriostatic antibiotic. 1. It is active against many aerobic gram negetive bacilli and a few gram positive organism. 2. trimethoprim is indicated for the treatment of acute episodes of uncomplicated urinary tract infections. ï‚´SIDE EFFECTS OF TRIMETHOPRIM: 1. Folate deficiency result in megaloblastic anaemia. 2. Nausea, Vomitting, Skin rashes.
  • 17. Mechanism Of Action: ï‚´ Trimethoprim is a bacteriostatic antibiotic. ï‚´ It is active against many aerobic gram negative bacilli ï‚´ It is >50,000 more active against Bacterial DHFRase than Mammalian enzyme. ï‚´ It selectively inhibits bacterial dihydrofolate reductase (DHFRase).