16423-76-0

Upstream product

• 15933-07-0 Ethyl 2-oxobutanoate 
• 621-94-3 1-(4-methylphenyl)-2-phenylhydrazine 
• 31750-57-9 ethyl (E)-2-chloro-3-(phenylamino)but-2-enoate 
• 106-49-0 p-toluidine 
• 607-97-6 ethyl 2-ethyl-3-oxobutanoate 
• 95239-03-5 tert-butyl 2-(4-ethoxy-4-oxobut-2-en-2-yl)diazene-1-carboxylate 

Downstream Products

• 132870-72-5 1-(4-Chloro-2-nitro-phenyl)-3,5-dimethyl-1H-indole-2-carboxylic acid ethyl ester 
• 78580-36-6 3,5-Dimethyl-1-(2-nitro-phenyl)-1H-indole-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Ethyl 1-(2-cyanoethyl)-3,5-dimethyl-1Hindole-2-carboxylate

The title compound, C16H18N2O2, is an important precursor in the synthesis of 1,2,3,4-tetrahydropyrazinoindoles, which show excellent antihistamine, antihypertensive and central nervous system depressant properties. The carbethoxy group attached to C2 and the planar cyanoethyl group attached to N1 make dihedral angles of 11.0(4) and 75.0(3) °, respectively, with the mean plane of the indole ring. The C - C=N chain is linear with a bond angle of 179.3(4) °.

Metal and Oxidant Free Construction of Substituted- and/or Polycyclic Indoles: A Useful Alternative to Bischler and Related Syntheses

A wide range of substituted indoles or polycyclic derivatives containing the indole core are easily accessible by acidic treatment of aromatic amines and 1,2-diaza-1,3-dienes. Unlike the related indole-Bischler synthesis, the regioselectivity of the method here reported is unique and predictable, the yields are generally good and also electron withdrawing substituted indoles are smoothly recovered.

Cytotoxic N-unsubstituted indoles and cyclopent(b)indoles and method of making and using same

The merits of N-unsubstituted indoles and cyclopent[b]indoles as DNA-directed reductive alkylating agents are described. These systems represent a significant departure from N-substituted and pyrrolo[1,2-a] fused systems such as the mitomycins and mitosenes. The cyclopent[b]indole—based aziridinylquinone, when bearing an acetate leaving group, was found to be cytotoxic and displayed significant in vivo activity against syngeneic tumor implants. This particular analogue was unexpectedly superior to the others studied, both in terms of high specificity for the activating enzyme DT-diaphorase and in high % DNA alkylation. Alkylation by a quinone methide intermediate as well as by the aziridinyl group were examined for crosslinking. The possible metabolites of the most active indole species were prepared and found to retain cytotoxicity, strongly suggesting that in vivo activity could also be sustained. The indole systems in the present invention display selectivity for melanoma and for non small cell lung, colon, renal, and prostate cancers when administered in an effective amount. The cancer specificity observed is believed to pertain to differential substrate specificity for DT-diaphorase.

Design of cancer-specific antitumor agents based on aziridinylcyclopent[b]indoloquinones

The merits of N-unsubstituted indoles and cyclopent[b]indoles as DNA- directed reductive alkylating agents are described. These systems represent a departure from N-substituted and pyrrolo[1,2-a]-fused systems such as the mitomycins and mitosenes. The cyclopent[b]indole-based aziridinylquinone system, when bearing an acetate leaving group with or without an N-acetyl group, was cytotoxic and displayed significant in vivo activity against syngeneic tumor implants. These analogues were superior to the others studied in terms of both high specificity for the activating enzyme DT-diaphorase and high percent DNA alkylation. Alkylation by a quinone methide intermediate as well as by the aziridinyl group could lead to cross-linking. The possible metabolites of the most active indole species were prepared and found to retain cytotoxicity, suggesting that in vivo activity could be sustained. The indole systems in the present study display selectivity for melanoma and, depending on the substituents present, selectivity for non-small-cell lung, colon, renal, and prostate cancers. The cancer specificities observed are believed to pertain to differential substrate specificities for DT- diaphorase.

3-(Arylamino)quinolin-2(1H)- and -4(1H)-ones: Reinvestigation of the reaction between ethyl 2-chloro-3-(phenylamino)but-2-enoate and arylamines

The reaction between ethyl 2-chloro-3-(phenylamino)but-2-enoate (5) and aniline gave 4-methyl-3-(phenylamino)quinolin-2(1H)-one (6) and not, as reported earlier in the literature, the isomeric 2-methyl-3- (phenylamino)quinolin-4(1H)-one (1). The latter co