Malaysian Journal of Analytical Sciences Vol 26 No 1 (2022): 1 - 7

 

 

 

 

SYNTHESIS AND MECHANISM STUDY OF NEW BIVALENT β-CARBOLINE DERIVATIVES

 

(Kajian Sintesis dan Mekanisma Derivatif Bivalen β-karbolin Baharu)

 

Nurul Tasnim Noor Aaisa^1,2, Karimah Kassim², Nur Azzalia Kamaruzaman³, Mazlin Mohideen¹*

 

¹Faculty of Pharmacy and Health Sciences,

Universiti Kuala Lumpur Royal College of Medicine Perak, 30450 Ipoh, Perak, Malaysia

²Institute of Science,

Universiti Teknologi MARA, 40450 Puncak Alam, Selangor, Malaysia

³National Poison Centre,

Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia

 

*Corresponding author:  mazlin.mohideen@unilkl.edu.my

 

 

Received: 15 September 2021; Accepted: 30 December 2021; Published:  25 February 2022

 

 

Abstract

This study reports simple and straightforward methods for synthesizing new bivalent β-carboline compounds using L-tryptophan as a starting material with 1,4-dibromobutane as a dimerization linker. The synthetic route began with coupling L-tryptophan with formaldehyde via Pictet-Spengler condensation to afford tetrahydro-β-carboline, T1 as the key intermediate. The reaction proceeded with decarboxylation of T1 using potassium dichromate with acetic acid to afford β-carboline, T2. Subsequent alkylation of T2 using 1,4-dibromobutane as the linker yielded intermediate T3, followed by dimerization to furnish the new bivalent β-carboline, T4. ¹H and ¹³C NMR confirmed all the synthesized compounds. In addition, this study includes the proposed mechanism for the synthesis of a new bivalent β-carboline compound.

 

Keywords: synthesis, bivalent β-carboline, L-Tryptophan, Pictet-Spengler condensation, dimerization

 

Abstrak

Abstract in Bahasa Malaysia/English Kajian ini melaporkan kaedah mudah dan secara terus untuk mensintesis sebatian baru bivalen β-karbolin menggunakan L-tryptofan sebagai bahan pemulaan dengan 1,4-dibromobutana sebagai penghubung dimerisasi. Laluan sintesis bermula dengan gandingan L-tryptofan dengan formaldehid melalui pemeluwapan Pictet-Spengler untuk mendapatkan tetrahidro-β-karbolin, T1 sebagai kunci perantaraan. Tindak balas diteruskan dengan pendekarboksilan T1 menggunakan kalium dikromat dengan asid asetik untuk menghasilkan β-karbolin, T2. Seterusnya alkilasi T2 menggunakan 1,4-dibromobutana sebagai penghubung menghasilkan perantara T3, diikuti dengan dimerisasi untuk menghasilkan bivalen β-karbolin baharu, T4. Semua sebatian yang disintesis disahkan dengan ¹H NMR dan ¹³C NMR. Sebagai tambahan, kajian ini merangkumi mekanisma yang dicadangkan untuk sintesis sebatian bivalen β-karbolin baharu.

 

Kata kunci: sintesis, bivalen β-Karbolin, L-Tryptofan, pemeluwapan Pictet-Spengler, dimerisasi

 

 

Graphical Abstract

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