On December 15, 2011, Zhang, Hesheng; Chen, Yingwei; He, Qingchao published a patent.Safety of 6-Chloro-2,3-dihydro-1H-indole The title of the patent was Cyanoquinoline derivatives as tyrosine kinase receptor inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cancer. And the patent contained the following:
Disclosed are Cyanoquinoline derivatives compounds of formula I and their stereoisomers, cis-/trans-isomers, tautomers or mixtures thereof, or pharmaceutically acceptable salts, solvates or prodrugs thereof. Compounds of formula I, wherein R1 is (un)substituted alkylcarbonylamino, (un)substituted alkenylcarbonylamino, (un)substituted alkynylcarbonylamino, (un)substituted arylcarbonylamino, (un)substituted amino and (un)substituted alkoxy; R2 and R3 are independently H, (un)substituted arylalkyl and (un)substituted (hetero)aryl; R2R3 may be taken together with the nitrogen atom attached to form (un)substituted heterocyclyl; R4 (un)substituted heterocyclyl and (un)substituted heteroaryl; and their stereoisomers, cis-/trans-isomers, tautomers or mixtures thereof, or pharmaceutically acceptable salts, solvates or prodrugs thereof, are claimed. Compounds of formula I were prepared via nitration of Me 2-(acetylamino)-4-fluorobenzoate; the resulting Me 2-(acetylamino)-4-fluoro-5-nitrobenzoate underwent condensation with alcs. followed by decarboxylation and deacetylation to give 3-alkoxy-4-nitroanilines, which underwent condensation with Et 2-cyano-2-(ethoxymethylene)acetate to give Et 2-cyano-3-[(3-alkoxy-4-nitrophenyl)amino]acrylates, which underwent intramol. cyclization to give 7-alkoxy-3-cyano-4-hydroxy-6-nitroquinolines, which underwent chlorination to give 7-alkoxy-3-cyano-4-chloro-6-nitroquinolines, which underwent condensation with amines to give 7-alkoxy-3-cyano-4-amino-6-nitroquinolines, which underwent reduction to give 7-alkoxy-3-cyano-4,6-diaminoquinolines, which underwent N-alkylation to give I. All the invention compounds were evaluated for their tyrosine kinase receptor inhibitory activity. From the assay, it was determined that example compound I (R1 = [(E)-4-(dimethylamino)-2-butenoyl]amino, R2 = H, R3 = 3-ethynylphenyl and R4 = tetrahydrofuran-3-yl) exhibited the IC50 value of 0.024 μM with the inhibition of 85% against A431 cell lines. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Safety of 6-Chloro-2,3-dihydro-1H-indole
The Article related to cyano quinoline preparation tyrosine kinase receptor inhibitor treatment cancer, Heterocyclic Compounds (One Hetero Atom): Quinolines and Isoquinolines and other aspects.Safety of 6-Chloro-2,3-dihydro-1H-indole
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Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles