936252-50-5

Basic information

• Product Name: 3-(2-iodoethyl)-5-methoxy-1-(p-toluenesulfonyl)indole
• Synonyms: 3-(2-iodoethyl)-5-methoxy-1-(p-toluenesulfonyl)indole
• CAS NO: 936252-50-5
• Molecular Weight: 455.316
• Mol File: 936252-50-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-(2-iodoethyl)-5-methoxy-1-(p-toluenesulfonyl)indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-iodoethyl)-5-methoxy-1-(p-toluenesulfonyl)indole(936252-50-5)
• EPA Substance Registry System: 3-(2-iodoethyl)-5-methoxy-1-(p-toluenesulfonyl)indole(936252-50-5)

Safety Data

• Hazardous Substances Data: 936252-50-5(Hazardous Substances Data)

Upstream product

• 3471-31-6 5-methoxy-1H-indole-3-acetic acid 
• 712-09-4 5-methoxytryptophol 
• 1026250-24-7 2-(5-methoxy-1-tosyl-1H-indol-3-yl)ethyl 4-methylbenzenesulfonate 

Downstream Products

• 936252-74-3 6-chloro-2-(3''-(5''-methoxy-1''-(p-toluenesulfonyl)indolyl)ethyloxy)-3',4',5'-triacetyladenosine 
• 936252-90-3 2-(3''-(5''-methoxy-1''-(p-toluenesulfonyl)indolyl)ethyloxy)adenosine 

Relevant articles and documents

A Photoredox-Induced Stereoselective Dearomative Radical (4+2)-Cyclization/1,4-Addition Cascade for the Synthesis of Highly Functionalized Hexahydro-1H-carbazoles

A stereoselective synthesis of functionalized hexahydrocarbazoles was developed based on an unprecedented photoredox-induced dearomative radical (4+2)-cyclization/1,4-addition cascade between 3-(2-iodoethyl)indoles and acceptor-substituted alkenes. The title reaction simultaneously generates three C?C bonds and one C?H bond, along with three contiguous stereogenic centers. The hexahydro-1H-carbazole products are highly valuable intermediates for the synthesis of novel antibiotics, as well as unnatural ring homologues of polycyclic indoline alkaloids.

Structure-activity relationships of 2,N6,5′-substituted adenosine derivatives with potent activity at the A2B adenosine receptor

2, N6, and 5′-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A2BAR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N6-ethyl or N6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-(3-(indolyl)- ethyloxy)adenosine series. Indole 5″- or 6″-halo substitution was favored at the A2BAR, but a 5′-N-ethylcarboxyamide did not further enhance potency. 2-(3″-(6″-Bromoindolyl)ethyloxy)adenosine 28 displayed an A2BAR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5′-N- ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A 2B and A2AARs and a low efficacy partial agonist at A 1 and A3ARs. Thus, we have identified and optimized 2-(2-arylethyl)oxo moieties in AR agonists that enhance A2BAR potency and selectivity.