β-carboline (norgarman) - 9H-pyrido [3,4-b] indole. The β-carboline structure is the basis for a number of alkaloids isolated from plants ( harmala , etc.), commonly known as β-carbolines.
| Beta carboline | |
|---|---|
 | |
| Are common | |
| Chem. formula | C 11 H 8 N 2 |
| Rat formula | 9 H -pyrido [3,4-b] indole |
| Physical properties | |
| Molar mass | 168.19462 g / mol |
| Classification | |
| Reg. CAS number | 244-63-3 |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| Chebi | |
| ChemSpider | |
Isomeric to α-carboline (1H-pyrido [2,3-b] indole) and γ-carboline (5H-pyrido [4,3-b] indole).
Content
Synthesis
A common method for the synthesis of β-carbolines is the Picte-Spengler reaction - the interaction of substituted tryptamines with aromatic and aliphatic aldehydes. In this synthesis, at the first stage, Schiff bases are formed, followed by an electrophilic attack of an imino group according to the Mannich reaction at position 3 of the indole core with the formation of the spiroindolenine intermediate and its further rearrangement to tetrahydro-β-carboline.
Α- keto acids and their esters can act as a functional equivalent of aldehydes, tryptophan and its esters can serve as an indole component; tetrahydrocarbolines formed during the reaction can then be dehydrogenated to β-carbolines.
Another method for synthesizing the β-carboline skeleton is to modify the synthesis of isoquinolines according to Bischler-Napiralsky , in which N- acyltryptamines are used instead of N-acyl-β-phenylethylamines; this synthesis method leads to 3,4-dihydro-β-carbolines:
Pharmacology
Substances containing a β-carboline moiety can exhibit the following pharmacological properties:
- Antimalarial activity [1] .
Structure
Some beta carbolines
The table below lists the best known beta-carbolines and their structural formulas.
| Short name | R1 | R6 | R7 | Structure | ||
|---|---|---|---|---|---|---|
| Beta carboline | ||||||
| Triptolin | ||||||
| Pinolin | ||||||
| Garman | ||||||
| Garmin | ||||||
| Garmalin | ||||||
| Tetrahydroharmine |
Being in nature
β-carbolines are found in various plants:
- In harmala ( lat. Peganum harmala ) - a perennial herbaceous plant of the family of leaf leaves ( lat. Zygophyllaceae );
- In a number of representatives of the order Malpighiotsvetnyh ( lat. Malpighiáles ):
- In the South American liana Banisteriopsis caapi of the Malpigian family ( lat. Malpighiaceae );
- In passion flowers (passiflora, lat. Passiflora );
- In tobacco , especially the species Nicotiana rustica ;
as well as animals (for example, in sea sponges [2] ).
Literature
- Dulenko V.I., Komissarov I.V., Dolzhenko A.T. Beta-carbolines. Chemistry and neurobiology. - Kiev: Naukova Dumka, 1992 - ISBN 5-12-003118-8
Notes
- ↑ Kenny KH Ang, Michael J. Holmes, Tatsuo Higa, Mark T. Hamann, and Ursula AK Kara. In Vivo Antimalarial Activity of the Beta-Carboline Alkaloid Manzamine A // Antimicrobial Agents and Chemotherapy. - 2000. - T. 44 , No. 6 . - S. 1645-49 .
- ↑ Karumanchi V. Rao, Marwa S. Donia, Jiangnan Peng, Esther Garcia-Palomero, Diana Alonso, Ana Martinez, Miguel Medina, Scott G. Franzblau, Babu L. Tekwani, Shabana I. Khan, Subagus Wahyuono, Kristine L. Willett , and Mark T. Hamann. Manzamine B and E and Ircinal A Related Alkaloids from an Indonesian Acanthostrongylophora Sponge and Their Activity against Infectious, Tropical Parasitic, and Alzheimer's Diseases // J. Nat. Prod .. - 2006. - T. 69 , No. 7 . - S. 1034-40 .