120908-66-9

Upstream product

• 61-54-1 tryptamine 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 1383850-14-3 1-(2-chlorophenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole 
• 1383850-08-5 C₂₄H₂₁ClN₂O₂S 

Relevant academic research and scientific papers

Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives

The synthesis of twelve tetrahydro-β-carboline derivatives 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l prepared via the Pictet-Spengler reaction is described. The reaction of tryptamine and a variety of arylaldehydes were carried out under ultrasonic irradiation and trifluoracetic acid catalysis at room temperature. These tetrahydro-β-carbolines have been synthesized in higher yields and shorter reaction times compared to the conventional method. Moreover, the reaction proceeded successfully even employing arylaldehydes with electron-donating or electron-attracting substituents which did not react under conventional method.

Synthesis and Investigation of Tetrahydro-β-carboline Derivatives as Inhibitors of the Breast Cancer Resistance Protein (ABCG2)

The breast cancer resistance protein (ABCG2) transports chemotherapeutic drugs out of cells, which makes it a major player in mediating multidrug resistance (MDR) of cancer cells. To overcome this mechanism, inhibitors of ABCG2 can be used. Only a few potent and selective ABCG2 inhibitors have been discovered, i.e., fumitremorgin C (FTC), Ko143, and the alkaloid harmine, which contain a tetrahydro-β-carboline or β-carboline backbone, respectively. However, toxicity and or instability prevent their use in vivo. Therefore, there is a need for further potent inhibitors. We synthesized and pharmacologically investigated 37 tetrahydro-β-carboline derivatives. The inhibitory activity of two compounds (51, 52) is comparable to that of Ko143, and they are selective for ABCG2 over ABCB1. Furthermore, they are able to reverse the ABCG2-mediated resistance toward SN-38 and inhibit the ATPase activity. The cytotoxicity data show that their inhibitory effect is substantially higher than their toxicity.

A facile and efficient synthesis of tetrahydro-β-carbolines

This Letter describes a convenient, efficient, and clean synthesis of various tetrahydro-β-carbolines catalyzed by propane phosphonic acid anhydride T3P under microwave irradiation.