Design, Synthesis and Cytotoxicity Evaluation of Tetrahydro β‐Carboline‐Attached Spiroindolones/ Spiroacenapthylene by Using Lemon Juice as a Green Biocatalyst System.

Abstract

An easy atom-economic methodology for the synthesis of tetrahydro-β-carbolino-spiroindolone/ spiroacenapthylene scaffold in one step from tryptamine and isatin have been done via Pictet-Spengler Reaction using lemon juice as a biocatalyst system. The reaction is clean and convenient for the synthesis of spiroindolones. The product was separated via easy chromatographic technique (column/flash) and characterized by 1D NMR (1H, 13 C and DEPT) and HRMS analysis. Bio evaluation against four cancer cell lines (MCF-7, SH-SY5Y, HepG2 and HEK 293) shows good positive indication of activity for 3 g, 3 h and 3 i.

The Progress in Pictet‐Spengler β‐Carboline Synthesis under Green Conditions

“…The biocatalyst used (lemon juice) was widely available and it was responsible for the acid catalysis and the reduction of nanoparticles formation (Scheme 31). [56] …”

“…The biocatalyst used (lemon juice) was widely available and it was responsible for the acid catalysis and the reduction of nanoparticles formation (Scheme 31). [56] Gholap et al prepared a solution of Acacia concinna pods. The aqueous extract was acidic due to presence of high amount of saponin.…”

Synthesis of Tetrahydro-β-carboline Derivatives under Electrochemical Conditions in Deep Eutectic Solvents

“…The β-carboline ring is present in many naturally occurring alkaloids with variable biological activities such as anticancer, antimicrobial, anti-Alzheimer, antimalarial, anti-inflammatory, antihypertensive, analgesic, and vasorelaxant activities. − There is a wide interest in the development of novel synthetic approaches, , especially green methods for the preparation of β-carboline derivatives . The green methods used for the synthesis of β-carbolines include the use of microwave , and ultrasonic irradiation, as well as the use of various types of catalysts including heterogeneous, organometallic, , inorganic salts, organic, , natural, , and enzymatic catalysis . However, most of these methods require hazardous and corrosive reagents, long reaction times, expensive catalysts, or complicated apparatus.…”

Evaluation of the anti-proliferative activity of 2-oxo-pyridine and 1′H-spiro-pyridine derivatives as a new class of EGFRWtand VEGFR-2 inhibitors with apoptotic inducers

“…Moreover, spirooxindole is present in many alkaloids with therapeutic values, such as mitraphylline, strychnofoline, and spirotryprostatin A and B that have excellent anticancer activity. 33,34 Finally, one of the most efficient and interesting methods for discovering and designing a new bioactive agent is the molecular hybridization approach that combines two pharmacophores to form a new bioactive core. [35][36][37][38][39][40] Additionally, forming new pyridine derivatives with different substituents on its main core and the presence of N-(ethyl benzoate) at N1 of pyridine or adding pyridine heterocycles to the spirooxindole core is expected to increase the potency of anticancer therapeutics in medicinal chemistry.…”

“…Moreover, spirooxindole is present in many alkaloids with therapeutic values, such as mitraphylline, strychnofoline, and spirotryprostatin A and B that have excellent anticancer activity. 33,34…”