7703-91-5

Upstream product

• 52351-75-4 6-methoxyisatin 
• 35162-27-7 6-methoxy-1-methyl-1H-indole-2,3-dione 
• 14318-66-2 3-methoxy-N-methylaniline 
• 29242-84-0 2-chloro-4-methoxyaniline 
• 156267-21-9 (5-Methoxy-2-methyl-phenyl)-methyl-carbamic acid benzyl ester 
• 156267-17-3 (5-Methoxy-2-methyl-phenyl)-carbamic acid benzyl ester 
• 156267-11-7 5-methoxy-2-methyl-N-methylaniline 
• 124-38-9 carbon dioxide 
• 93646-24-3 N-(2-Chloro-4-methoxy-phenyl)-N-methyl-acetamide 
• 65836-81-9 N-chloroacetyl-N-methyl-m-anisidine 

Downstream Products

• 13383-73-8 6-hydroxy-1-methyl-indolin-2-one 
• 1373243-45-8 5'-(1-(4-fluorobenzyl)-3-hydroxy-2-oxoindolin-3-yl)-6'-hydroxy-1'-methyl spiro[cyclopropane-1,3'-indolin]-2'-one 
• 1373243-46-9 5'-(1-(4-fluorobenzyl)-2-oxoindolin-3-yl)-6'-hydroxy-1'-methyl-spiro[cyclopropane-1,3'-indolin]-2'-one 
• 1373242-16-0 C₂₇H₂₁FN₂O₃ 
• 158719-26-7 2,2'-dithiobis [N-phenyl-6-acetoxy-1-methylindolyl-3-carboxamide] 
• 1026065-90-6 Acetic acid 1-methyl-3-phenylcarbamoyl-2-thioxo-2,3-dihydro-1H-indol-6-yl ester 

Relevant academic research and scientific papers

SPIROCYCLIC COMPOUNDS AS VOLTAGE-GATED SODIUM CHANNEL MODULATORS

The present invention relates to compounds of Formula (I) along with processes for their preparation that are useful for treating, preventing and/or managing the diseases, disorders, syndromes or conditions modulated by VGSCs. The invention further relates to methods of treating, preventing managing and/or lessening the diseases, disorders, syndromes or conditions by modulators of VGSC of Formula (I).

Tyrosine kinase inhibitors. 3. Structure-activity relationships for inhibition of protein tyrosine kinases by nuclear-substituted derivatives of 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)

A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H- indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3- dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity. While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20- fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC50s in the range 2-25 μM, the most active being 4- substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF- mediated phosphorylation.

LITHIATION ROUTES TO OXINDOLES AND 2-INDOLINETHIONES: PRECURSORS TO 2,2'-DITHIOBISINDOLES WITH TYROSINE KINASE INHIBITORY PROPERTIES

N-Substituted oxindoles and 2-indolinethiones can be prepared by lithiation of carboxyl protected N,2-dimethylanilines followed by quenching with CO2 or CS2 respectively. 2-Indolinethione derivatives are also available via demethylation of 2-methylthioindoles, which are prepared by lithiation of N-substituted indoles and treatment with dimethyl disulfide.

Photoinduced Cyclizations of Mono- and Dianions of N-Acyl-o-chloroanilines and N-Acyl-o-chlorobenzylamines as General Methods for the Synthesis of Oxindoles and 1,4-Dihydro-3(2H)-isoquinolinones

Formation of the monoanions of a series of N-acyl-N-alkyl-o-chloroanilines by means of LDA in THF followed by irradiation with near-UV light affords 1,3-dialkyloxindoles in good yields.Similar photoinduced cyclizations of dianions derived from N-acyl-o-chloroanilines leads to 3-alkyloxindoles.Photocyclizations of mono- and dianion prepared from α,β-unsaturated o-haloanilides proceed to form 3-alkylideneoxindoles.Carbanions derived from N-acyl-o-chlorobenzylamines also undergo photoassisted ring closure to afford 1,4-dihydro-3(2H)-isoquinolinones.The influence of near-UV light and the effect of inhibitors implicate a radical-chain mechanism as the major reaction pathway in this convenient new method for oxindole and isoquinolinone synthesis.