17889-63-3

Upstream product

• 75-00-3 chloroethane 
• 124-38-9 carbon dioxide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 183020-74-8 ethyl-(4,5-dimethoxy-2-(2-phenylacetyl) phenethyl) carbamate 
• 17889-64-4 N-Carbethoxy-2-bromo-4,5-dimethoxyphenylethylamine 
• 493-49-2 6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one 
• 343780-59-6 N-[2-(2-iodo-4,5-dimethoxyphenyl)ethyl]carbamic acid ethyl ester 
• 5884-67-3 armepavine 
• 3472-22-8 N-norarmepavine 
• 23506-74-3 (±)-ethyl 1-(4-hydroxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 73083-05-3 (±)-ethyl 1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 

Relevant academic research and scientific papers

Gene editing and synthetically accessible inhibitors reveal role for TPC2 in HCC cell proliferation and tumor growth

The role of two-pore channel 2 (TPC2), one of the few cation channels localized on endolysosomal membranes, in cancer remains poorly understood. Here, we report that TPC2 knockout reduces proliferation of cancer cells in vitro, affects their energy metabolism, and successfully abrogates tumor growth in vivo. Concurrently, we have developed simplified analogs of the alkaloid tetrandrine as potent TPC2 inhibitors by screening a library of synthesized benzyltetrahydroisoquinoline derivatives. Removal of dispensable substructures of the lead molecule tetrandrine increases antiproliferative properties against cancer cells and impairs proangiogenic signaling of endothelial cells to a greater extent than tetrandrine. Simultaneously, toxic effects on non-cancerous cells are reduced, allowing in vivo administration and revealing a TPC2 inhibitor with antitumor efficacy in mice. Hence, our study unveils TPC2 as valid target for cancer therapy and provides easily accessible tetrandrine analogs as a promising option for effective pharmacological interference.

Catalyst-free cyclization of anthranils and cyclic amines: One-step synthesis of rutaecarpine

An efficient synthesis of a variety of quinazolinone derivatives via a direct cyclization reaction between commercially available anthranils and cyclic amines is described. The developed transformation proceeds with the merits of high step- and atom-efficiency, a broad substrate scope, and good to excellent yields, without additional catalysts, and offers a practical way for the preparation of rutaecarpine and its derivatives with structural diversity.

Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex

Reported herein is a visible-light-driven intramolecular C?N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.

One-pot α-amidosulfone-mediated variation of the pictet-Spengler tetrahydroisoquinoline synthesis, suitable for amide-type substrates

The development of Pictet-Spengler reactions from amide substrates is a challenging problem. We report here that the reaction between amide-type compounds (including carbamates, amides, ureas and diketopiperazines), aldehydes and p-toluenesulfinic acid constitutes an efficient method for the preparation of tetrahydroisoquinolines or pyrazino-[2,1-b]isoquinolines. Unlike previously known methods, this one-pot Pictet-Spengler protocol avoids the need for strong Lewis or Br?nsted acid catalysts.

17a-HYDROXYLASE/C17,20-LYASE INHIBITORS

The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.

17α-HYDROXYLASE/C17,20-LYASE INHIBITORS

The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.

Strategies and synthetic methods directed toward the preparation of libraries of substituted isoquinolines

Strategies for the production of substituted isoquinoline libraries were developed and explored. Routes involving microwave-assisted variants of the Bischler-Napieralski or Pictet-Spengler reaction allowed for cyclization of substituted β-arylethylamine derivatives. The dihydroisoquinolines and tetrahydroisoquinolines thus generated could then be oxidized to their corresponding isoquinoline analogues. An alternate strategy, however, involving the preparation and activation of isoquinolin-1(2H)-ones is demonstrated to be a more practical, rapid, and efficient route to C1- and C4-substituted isoquinoline libraries.

First total syntheses of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines annoretine and litebamine

We describe here the first total synthesis of the two natural 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines, annoretine and litebamine, from [2-(2-styrylphenyl)ethyl]methylcarbamic acid ethyl esters. The key steps were the Bischler-Napieralski cyclization

Electrocatalytical carboxylation of primary and secondary amines; alternative synthesis of urethanes

Electrocatalytical carboxylation of 13 no-reducible primary and secondary amines lead in CO2-saturated DMF to known and new carbamates. Electrochemical results correlated with MNDO-calculation and potential curves proved, that the new, general and regioselective carboxylation method proceed via amin-CO2-radicalanion initiation, followed by SET-reaction inside an self-reproducing process.