139260-65-4

Upstream product

• 75-16-1 methylmagnesium bromide 
• 143706-87-0 3-carboxy-4-pyridyl 1'-(phenylsulfonyl)-5'-methoxy-2'-indolyl ketone 
• 139260-70-1 4-<1-Hydroxy-1-(5-methoxy-1-phenylsulphonylindol-2-yl)-ethyl>-N,N-diisopropylnicotinamide 
• 4664-08-8 cinchomeronic anhydride 
• 56995-12-1 1-benzenesulfonyl-5-methoxy-1H-indole 
• 59-67-6 nicotinic acid 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 490-11-9 3,4-pyridinecarboxylic acid 
• 38173-40-9 4-methoxycarbonyl-3-pyridylcarbonyl chloride 
• 24202-74-2 4-(methoxycarbonyl)nicotinic acid 
• 139125-05-6 4-Acetyl-N,N-diisopropylnicotinamide 
• 139260-68-7 Methyl 3-(Diisopropylcarbamoyl)isonicotinate 

Downstream Products

• 139260-71-2 4-<1-(5-Methoxy-1-phenylsulphonylindol-2-yl)ethyl>nicotinic Acid 
• 139260-72-3 4-[1-(1-Benzenesulfonyl-5-methoxy-1H-indol-2-yl)-ethyl]-N-(2-dimethylamino-ethyl)-nicotinamide 
• 139260-59-6 4-[1-(1-Benzenesulfonyl-5-methoxy-1H-indol-2-yl)-ethyl]-N-(3-diethylamino-propyl)-nicotinamide 

Relevant academic research and scientific papers

N-methylcarbamate derivatives of ellipticine and olivacine with cytotoxic activity against four human lung cancer cell lines

A series of analogues of the antitumor alkaloids ellipticine and olivacine were tested for cytotoxicity against four human lung cancer cell lines: H69, N417, H460, and H358. Adriamycin (doxorubicin), ellipticine, olivacine, and celiptinium were used as standards. Adriamycin was cytotoxic at 2 μM and celiptinium was inactive at the highest concentrations tested (IC50 > 48 μM). N-methylcarbamates of 9-methoxy-6H-pyrido[4,3-b]carbazole 1-,5-, and 11-methanols gave IC50 values ranging from 0.02 to 0.11 μM against N417, H460, and H358 and were only slightly less effective against H69.

Synthesis of 11-Amino-substituted-9-methoxy-5-methyl-6H-pyridocarbazoles

A route to 11-amino-substituted-6H-pyridocarbazoles has been studied.Thus, condensation of 2-(4-lithiopyridine-3-yl)-4,4-dimethyloxazoline with 2-acetyl-5-methoxy-1-phenylsulphonylindole led to a low yield of the expected alcohol, which upon hydrolysis gave a complex mixture.A better starting building block was 4-acetyl-N,N-diisopropylnicotinamide obtained either from N,N-diisopropyl-4-lithionicotinamide (low yield) or from pyridine-3,4-dicarboxylic anhydride, using a 4-step sequence.This compound was treated with 2-lithio-5-methoxy-1-phenylsulphonylindole, affording N,N-diisopropyl-4-nicotinamide.Hydrolysis and then reduction led to 4-nicotinic acid whose amides were cyclized by phosphorus trichlorideoxide.Finally, the title compounds were obtained by Raney-nickel reduction-elimination of the 6-phenylsulphonyl protecting group.