Indole

indole

1. Dr. Sajid Hussain (Faculty of Pharmacy) The University of Lahore Group#9 Presented by: Mubashar Ali 151 Bilawal Mughal 144 Summer Nisar 251 Rana Muhammad Yasir 244 Shehzad Anwar 247 Umar Hayat 035 M.Asad Iqbal 063 Junaid Ghaffar 134 Organic presentation Presented To:

2. Indole Definition: Indole contains a benzene ring fused with a pyrrole ring at C-2/C-3, and can be described as benzopyrrole. Indole is a ten p electron aromatic system achieved from the delocalization of the lone pair of electrons on the nitrogen atom. Benzofuran and benzothiaphene are very similar to benzopyrrole (indole), with different hetero-atoms, oxygen and sulphur respectively.

3. Structure:

4. General formula: Its chemical formula is C 8 H 7 N. Discovery: Indole as first prepared in 1866 by zinc dust distillation of oxindole.

5. Occurance: indole is a solid at room temperature. It occurs naturally in human feces and has an intense fecal odor. It also occur in coal tar. it is constituent of many flower scents and perfumes.

6. Physical properties: Weak basic compound Conjugate acid of indole is strong acid (pKa = –2.4 ). White solid at room temperature. Boiling point ( 253-254 *C) Melting point (52-54 *C) Slightly soluble in water, readily soluble in organic solvents, e.g. Ethanol,ether and benzene

7. Chemical properties: Solid at room temperature Corresponding substituent is called indolyl. Chemical formula is C 8 H 7 N .

8. Reactions: Electrophilic aromatic substitution Electrophilic aromatic substitution of indole occurs on the five-membered pyrrole ring, because it is more reactive towards such reaction than a benzene ring. As an electron-rich heterocycle, indole undergoes electrophilic aromatic substitution primarily at C-3, for example bromination of indole.

9. Synthesis: Indole is synthesised by these steps: Fischer Indole Synthesis Leimgruber Synthesis

10. Fischer indole synthesis Cyclization of arylhydrazones by heating with an acid or Lewis acid catalyst yields an indole system. The most commonly used catalyst is ZnCl2. The disadvantage of this reaction is that unsymmetrical ketones give mixtures of indoles if R’ also has an ᾱ- methylene group.

11. Leimbruber synthesis: Aminomethylenation of nitrotoluene followed by hydrogenation yield indole.

12. Uses: Preventing breast cancer, colon cancer, and other types of cancer Early research shows that taking indole-3-carbinol by mouth helps treat cervical dysplasia Fibromyalgia.

13. Pharmaceutical products: Drug Name Medication Ziprasidone For the treatment of schizophrenia and related psychotic disorders. Molindone Molindone is used for the management of the manifestations of psychotic disorders. Sertindole   Used in the treatment of schizophrenia. Lurasidone Treatment of schizophrenia.