1040724-73-9Relevant articles and documents
An Efficient and Facile Synthesis of Functionalized Indole-3-yl Pyrazole Derivatives Starting from 3-Cyanoacetylindole
El-Mekabaty, Ahmed,Mesbah, Ahmed,Fadda, Ahmed A.
, p. 916 - 922 (2017)
The versatile hitherto reported 3-(1H-indol-3-yl)-1H-pyrazol-5-amine (4) was synthesized by the reaction of 3-cyanoacetylindole (3) with hydrazine hydrate in refluxing ethanol and used as a key intermediate for the synthesis of novel pyrazolo[1,5-a]pyrimidines via its reactions with appropriate 1,3-biselectrophilic reagents or through three-component condensations with triethyl orthoformate and compounds possessing an activated methylene group. Besides, the applicability and synthetic potency of (4) to attain polyfunctionally substituted imidazo[1,2-b]pyrazole, pyrazolo[1,5-a][1,3]diazepine and pyrazolo[1,5-c][1,3,5]thiadiazine derivatives of an expected pharmaceutical interest have been investigated. The mechanistic aspects for the formation of the newly synthesized compounds are discussed.
5-(1H-Indol-3-yl)-pyrazolyl derivatives as colorimetric sensor for anions
Ahmad, Israr,Mishra, Neeraj Kumar,Ghosh, Tamal
, p. 183 - 191 (2013)
The synthesis, characterisation and binding and deprotonation studies with anions for four 5-(1H-indol-3-yl)-pyrazolyl derivatives (2-5) have been described. It is worthy to mention that sensor 2 shows a drastic change in absorption spectrum (ca. 335 nm) and colour (colourless to blue) upon addition of F- in DMSO solution due to the deprotonation of indole -NH proton, as confirmed by 1H NMR titration. Sensor 4 recognizes F- and CN- ions by deprotonation mechanism with visible colour change of the solution in a similar manner to that of 2. However, in contrary to 2 and 4, sensor 3 binds with F-, CN-, H2PO4 -, AcO- and PhCOO- ions exploiting hydrogen-bonding interaction with the shifting of absorption band to longer wavelength and subsequent colour change of the solution. Compound 5 recognizes F- without any visual colour change and its binding is studied by 1H NMR titration to acquire the important information about the nature of binding between F- and 5.
Synthesis and cytotoxicity evaluation of novel indole derivatives as potential anti-cancer agents
Abdel-hameid, Mohamed K.,El-Khouly, Eman A.,El-Nassan, Hala B.,Kamel, Mona M.
, p. 873 - 882 (2020/01/25)
Background: Marine sponges and tunicates have been a wealthy source of cytotoxic compounds such as indole alkaloids. Most of the indole alkaloids show in vitro cytotoxic and antineoplastic activities against a wide range of cancer cell lines. Objective: Three series of bioisosteres of marine indole alkaloids (meridianins) were synthesized and the compounds were tested for their in vitro anti-proliferative activity against HCT-116 cellline. In the design of the targeted analogues, the 2-aminopyrimidine ring of merdianins was replaced with 5-aminopyrazole, pyrazolo[1,5-a]pyrimidine and pyrazolo[3,4-b]pyridine rings. Results: The cytotoxic screening of the synthesized compounds revealed that pyrazolo[1,5- a]pyrimidines (compounds 9c and 11a) had the most potent cytotoxic activity with IC50 = 0.31 μM and 0.34 μM respectively. Compounds 9c and 11a were further investigated for their kinase inhibitory potencies toward six kinases (CDK5/p25, CK1e/ε, GSK-3α/β, Dyrk1A, Erk2, and CLK1). They exhibited effective inhibition of GSK-3α/β (IC50 = 0.196 μM and 0.246 μM, respectively) and Erk2 (IC50 = 0.295 μM and 0.376 μM, respectively). Conclusion: Meridianins emerged as promising lead structures that need further development to obtain more selective and potent cytotoxic agents. One of these modifications involved the replacement of 2-aminopyrimidinyl ring of meridianins with other heterocyclic rings. Both pyrazolo[ 1,5-a]pyrimidine and pyrazolo[3,4-b]pyridine rings showed promising cytotoxic activity compared to the five membered 5-aminopyrazole.
