199603-85-5Relevant academic research and scientific papers
Discovery of 3-Substituted 1H-Indole-2-carboxylic Acid Derivatives as a Novel Class of CysLT1 Selective Antagonists
Chen, Huayan,Yang, Hui,Wang, Zhilong,Xie, Xin,Nan, Fajun
, p. 335 - 339 (2016/03/25)
The indole derivative, 3-((E)-3-((3-((E)-2-(7-chloroquinolin-2yl)vinyl)phenyl)amino)-3-oxoprop-1-en-1-yl)-7-methoxy-1H-indole-2-carboxylic acid (17k), was identified as a novel and highly potent and selective CysLT1 antagonist with IC50 values of 0.0059 ± 0.0011 and 15 ± 4 μM for CysLT1 and CysLT2, respectively.
Synthesis and biological activity of functionalized indole-2-carboxylates, triazino- and pyridazino-indoles
El-Gendy, Adel A.,Said, Mohamed M.,Ghareb, Nagat,Mostafa, Yasser M.,El-Ashry, El Sayed H.
experimental part, p. 294 - 300 (2009/04/11)
Condensation of aryl hydrazines with ethyl pyruvate gave the respective hydrazones 4-6; Fischer indolization led to substituted-1H-indole-2-carboxylic acid ethyl esters 7-9. The Mannich reaction of these compounds with formaldehyde and morpholine yielded ethyl 3-(morpholinomethyl)-substituted-1H-indole-2- carboxylates 10-12. The 5,7-dichloro-1H-indole-2-carbohydrazide 13 was cyclized with methyl orthoformate in DMF to give 6,8-dichloro[1,2,4]triazino[4,5-a]indol- 1(2H)-one 14. Vilsmeier-Haack formylation of 7-9 gave ethyl 3-formyl- substituted-1H-indole-2-carboxylates 15-17 whose 2,2′-((5-chloro-2- (ethoxycarbonyl)-1H-indol-3-yl)methylene)bis-(sulfanediyl) diacetic acid 18 was prepared. The reaction of 15 and 16 with substituted anilines by conventional and microwave methods gave ethyl 3-(N-aryliminomethyl)-5-halo-1H-indole-2- carboxylates 19-29. In a cyclocondensation reaction of 19-25 with thiolactic acid or thioglycolic acid substituted indolylthiazolidinones 30-33 were prepared. Reaction of hydrazine hydrate with 15-17 did not give the respective hydrazones but directly led to the cyclized products substituted-3H- pyridazino[4,5-b]indol-4(5H)-ones 34-36, while a reaction with 2,4-dichlorophenylhydrazine yielded the uncyclized hydrazones. The chlorination of 35 and 36 with POCl3 gave pyridazino[ 4,5-b]indoles 39 and 40, respectively; reaction of the latter compounds with morpholine gave 4-(substituted-5H-pyridazino[4,5-b]indol-4-yl)morpholine 41 and 42. Mannich reaction of 34 with formaldehyde and N-ethylpiperazine gave 8-chloro-3-((4- ethylpiperazin-1-yl)methyl)-3H-pyridazino[ 4,5-b]indol-4(5H)-one 43. The microwave assistance of selected reactions has a profound effect on the reaction speed. The structures of the new compounds were confirmed by both analytical and spectral data. Some compounds were subjected to investigations concerning their antimicrobial, tranquilizing, and anticonvulsant activities.
Synthesis of Substituted 3-Amino-4-cyano-1-oxo-1,2,5,10-tetrahydroazepino[3,4-b]indoles
Troschuetz, Reinhard,Hoffmann, Armin
, p. 1431 - 1440 (2007/10/03)
The preparation of 3-amino- and 3-dialkylamino-4-cyanoazepino[3,4-b]indoles bearing substituents on the aromatic nucleus and N10 is outlined. Starting from suitable substituted ethyl 3-formylindole-2-carboxylates 2, condensation with malononitrile (3) and subsequent sodium borohydride-reduction yielded ethyl 3-(2,2-dicyanoethyl)indole-2-carboxyIates 5 and 19, respectively, which were cyclized in boiling alkoxides to 3-alkoxy-4-cyanoazepino[3,4-b]indoles 10,11,20 and 21. This sequence constitutes a novel and flexible route to functional azepino[3,4-b]indoles. The aminolysis of 10,11,20 and 21 with different amines and ammonia yielded the title compounds which were screened for their possible biological activity.
