62450-07-1

Usage

Uses

Carcinogen

Safety Profile

Confirmed carcinogen with experimental carcinogenic and neoplastigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,.

InChI:InChI=1/C12H11N3/c1-8-6-15(13)7-10-9-4-2-3-5-11(9)14-12(8)10/h2-7H,13H2,1H3

Upstream product

• 65032-78-2 3-acetylindole-2-acetonitrile 
• 143618-98-8 t-Boc-Trp-P-2 
• 65032-81-7 1-methyl-5H-pyrido<4,3-b>indole-3-carboxylic acid 
• 73-22-3 L-Tryptophan 
• 7210-27-7 2-indoleacetonitrile 
• 75-05-8 acetonitrile 
• 40899-68-1 1-(methoxymethyl)-1H-indole 
• 40899-79-4 1-(methoxymethyl)-1H-indole-2-carbaldehyde 
• 13993-04-9 (1H-indol-2-ylmethyl)dimethylamine 
• 65032-79-3 2-acetamido-3-(2-indolyl)propionic acid 
• 65032-80-6 ethyl 1-methyl-5H-3,4-dihydropyrido<4,3-b>indole-3-carboxylate 
• 95242-11-8 C₁₂H₁₇N₂⁽¹⁺⁾*CH₃O₄S^(1-) 
• 13373-31-4 diethyl 2-acetamido-2-<(2-indolyl)methyl>malonate 
• 96286-14-5 ethyl 2-acetamido-3-(2-indolyl)propionate 

Downstream Products

• 94705-59-6 1-methyl-3-(phenyl-ONN-azoxy)-5H-pyrido<4,3-b>indole 
• 75567-58-7 1-methyl-3-nitro-5H-pyrido<4,3-b>indole 
• 74011-07-7 3-acetylamino-1-methyl-5H-pyrido<4,3-b>indole 
• 70805-81-1 3-(C⁸-guanyl)amino-1-methyl-5H-pyrido<4,3-b>indole 

Relevant academic research and scientific papers

Iminophosphorane-Mediated Synthesis of the Genotoxic Heterocyclic Amine Trp-P-2.

A new eight-step synthesis of the genotoxic amine Trp-P-2 in an overall yield of 14.4 percent is described.The key step, formation of γ-carboline ring, involves a tandem aza Wittig/electrocyclic ring closure process.

Synthesis and characterization of the aqueous solution chemistry of the food-derived carcinogen model N-acetoxy-N-(1-methyl-5H-pyrido[4,5-b]indol-3-yl)acetamide and its N-pivaloyloxy analogue

We report the synthesis of N-acetoxy-N-(1-methyl-5H-pyrido[4,5-b]indol-3-yl)acetamide, 7, its N-pivaloyloxy analogue, 9, and improved synthesis of indole-2-acetonitrile, 3 (70% in five steps from indole-2-carboxylic acid), the carcinogenic amine Trp-P-2, 4 (40% from 3), and the nitro compound, 5 (40% from 4 by oxidation with H2O2 using Mo(CO)6 catalyst). In aqueous solution at neutral pH, 7 primarily undergoes C-O bond cleavage to yield the hydroxamic acid, 8, but under the same conditions the sterically hindered 9 decomposes predominately by N-O bond cleavage with a pH independent rate constant that is 7.5-fold smaller than that for 7. In the pH range 0.5-7.0 three different processes for the decomposition of 9 were detected by kinetics. Only the process that dominates at neutral pH generates a nitrenium species that can be trapped by N3-.

Synthesis of 3-Amino-5H-pyridoindoles, Carcinogenic γ-Carbolines

The carcinogenic γ-carbolines 3-amino-1,4-dimethyl-5H-pyridoindole (1) and 3-amino-1-methyl-5H-pyridoindole (2) were synthesized efficiently by the following procedures.The key method involved the acid-catalyzed cyclization of 2-acetamido-3-(2-indolyl)alkanoic acids to 1,2-dihydro-γ-carbolines.This was followed by dehydrogenation to the γ-carbolinecarboxylates and conversion of the ester group to the carboxyl and finally to the amino one by Curtius rearrangement.Alternative methods involved the thermolysis of 4-(1-benzotriazolyl)-3,6-dimethyl-2-pyridinamine to synthesize 1 and the condensation of 3-acetylindole-2-acetonitrile with ammonia to synthesize 2.The structures of γ-carbolines 1 and 2 were unambiguously established by comparing samples of each synthesized by the two different routes.A selective and one-step synthesis of ethyl 2-acetamido-3-(2-indolyl)alkanoates was newly exploited starting from diethyl acetamidomalonate and quaternary ammonium salts of 2-indoles.