synthesis of traube purine , mercaptopurine, theophylline, thioguanine

1. TRAUBE PURINE SYNTHESIS
THAKUR KARANVIR SINGH
M PHARMACY
(PHARMACEUTICAL CHEMISTRY)

2. • This reaction was 1st introduced by Traube in 1900
• Traube purine synthesis is the most versatile method for introduction of one carbon fragment to
bridge the nitrogen atoms of the amino group C-5 and C-6 of the pyrimidine ring
• Preparation of 4,5-diaminopyrimidines by introduction of the amino group into the 5-position of
4-amino-6-hydroxy- or 4,6-diaminopyrimidines by nitrosation and ammonium sulfide reduction,
followed by ring closure with formic acid or chlorocarbonic ester .
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TRAUBE PURINE SYNTHESIS

4. MERCAPTOPURINE
6,7-dihydro-3H-purine-6-thione
Mercaptopurine (6-MP), sold under the brand name Purinethol
Medical uses
 It is used to treat acute lymphocytic leukemia
 Crohn's disease
 Ulcerative colitis.

5.  Mercaptopurine (6-MP), sold under the brand name Purinethol among.
 Mercaptopurine is a medication used for cancer and autoimmune diseases.
 Specifically it is used to treat acute lymphocytic leukemia, chronic myeloid
leukemia, Crohn's disease, and ulcerative colitis.
 Common side effects include bone marrow suppression, liver toxicity, vomiting, and loss
of appetite.
 Other serious side effects include an increased risk of future cancer and pancreatitis.
 Those with a genetic deficiency in thiopurine S-methyltransferase are at higher risk of
side effects.
 Use in pregnancy may harm the baby.
 Mercaptopurine is in the thiopurine and antimetabolite family of medications
MERCAPTOPURINE

6. SYNTHESIS OF MERCAPTOPURINE

7. THEOPHYLLINE
1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dion
Theophylline, also known as 1,3-dimethylxanthine
NATURAL OCCURRENCES
Theophylline is naturally found in cocoa beans.
Trace amounts of theophylline are also found in brewed tea,
Trace amounts of theophylline are also found in guarana (Paullinia
cupana) and in kola nuts cola (plant)

8. Medical uses
The main actions of theophylline involve:
• Relaxing bronchial smooth muscle
• Increasing heart muscle contractility and efficiency (positive inotrope)
• Increasing heart rate (positive chronotropic)[2]
• Increasing blood pressure
• Increasing renal blood flow
• Anti-inflammatory effects
• Central nervous system stimulatory effect mainly on the medullary respiratory center.
The main therapeutic uses of theophylline are aimed at:
• Chronic obstructive pulmonary disease (COPD)
• Asthma
• Infant apnea
• Blocks the action of adenosine; an inhibitory neurotransmitter that induces sleep,
contracts the smooth muscles and relaxes the cardiac muscle.

9. Synthesis of theophylline

10. Thioguanine, also known as Tioguanine or 6-thioguanine (6-TG)
THIOGUANINE
2-amino-6,7-dihydro-3H-purine-6-thione
MEDICAL USES
• Acute leukemias in both adults and children
• Chronic myelogenous leukemia
• Inflammatory bowel disease, especially ulcerative colitis
• Psoriasis

11. SYNTHESIS OF THIOGUANINE

12. REFERENCES
11/22/2018
• Quin D. L. Tyrele A. J. , Fundamental of heterocyclic
chemistry Page number 225 to 240
• https://scholar.google.com date of search 28/09/2018
• https://en.wikipedia.org date of search 27/09/2018
• https://www.google.com date of search 27/09/2018
• https://www.slideshare.net date of search 27/09/2018
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