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194490-15-8

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194490-15-8 Usage

General Description

3-Cyano-5-fluoro-1H-indole is a chemical compound with the molecular formula C9H5FN2. It is a member of the indole family with a cyano group at the 3-position and a fluorine atom at the 5-position of the indole ring. Indoles are aromatic heterocyclic organic compounds that have been associated with a wide range of biological activities, making them important in medicinal chemistry. However, specific information about the properties and potential applications of 3-cyano-5-fluoro-1H-indole is limited, as it is a less common type of indole derivative. Like other indoles, it can potentially be used for various research and chemical reactions, although its toxicity and safety characteristics need comprehensive studies.

Check Digit Verification of cas no

The CAS Registry Mumber 194490-15-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,4,4,9 and 0 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 194490-15:
(8*1)+(7*9)+(6*4)+(5*4)+(4*9)+(3*0)+(2*1)+(1*5)=158
158 % 10 = 8
So 194490-15-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H5FN2/c10-7-1-2-9-8(3-7)6(4-11)5-12-9/h1-3,5,12H

194490-15-8Relevant articles and documents

3-(6-phenylimidazo [2,1-b][1,3,4]thiadiazol-2-yl)-1HIndole derivatives as new anticancer agents in the treatment of pancreatic ductal adenocarcinoma

Arizza, Vincenzo,Carbone, Daniela,Cascioferro, Stella,Cirrincione, Girolamo,Diana, Patrizia,El Hassouni, Btissame,Funel, Niccola,Giovannetti, Elisa,Padova, Alessandro,Parrino, Barbara,Perricone, Ugo,Peters, Godefridus J.,Petri, Giovanna Li

, (2020)

A new series of imidazo[2,1-b][1,3,4]thiadiazole derivatives was efficiently synthesized and screened for their in vitro antiproliferative activity on a panel of pancreatic ductal adenocarcinoma (PDAC) cells, including SUIT-2, Capan-1 and Panc-1. Compounds 9c and 9l, showed relevant in vitro antiproliferative activity on all three pre-clinical models with half maximal inhibitory concentration (IC50) ranging from 5.11 to 10.8 μM, while the compounds 9e and 9n were active in at least one cell line. In addition, compound 9c significantly inhibited the migration rate of SUIT-2 and Capan-1 cells in the scratch wound-healing assay. In conclusion, our results will support further studies to increase the library of imidazo [2,1-b][1,3,4] thiadiazole derivatives for deeper understanding of the relationship between biological activity of the compounds and their structures in the development of new antitumor compounds against pancreatic diseases.

1,2,4-Oxadiazole Topsentin Analogs with Antiproliferative Activity against Pancreatic Cancer Cells, Targeting GSK3β Kinase

Carbone, Daniela,Parrino, Barbara,Cascioferro, Stella,Pecoraro, Camilla,Giovannetti, Elisa,Di Sarno, Veronica,Musella, Simona,Auriemma, Giulia,Cirrincione, Girolamo,Diana, Patrizia

, p. 537 - 554 (2020/12/01)

A new series of topsentin analogs, in which the central imidazole ring of the natural lead was replaced by a 1,2,4-oxadiazole moiety, was efficiently synthesized. All derivatives were pre-screened for antiproliferative activity against the National Cancer Institute (NCI-60) cell lines panel. The five most potent compounds were further investigated in various pancreatic ductal adenocarcinoma (PDAC) cell lines, including SUIT-2, Capan-1, and Panc-1 cells, eliciting EC50 values in the micromolar and sub-micromolar range, associated with significant reduction of cell migration. These remarkable results might be explained by the effects of these new topsentin analogues on epithelial-to-mesenchymal transition markers, including SNAIL-1/2 and metalloproteinase-9. Moreover, flow cytometric analysis after Annexin V-FITC and propidium iodide staining demonstrated that these derivatives enhanced apoptosis of PDAC cells. Keeping with these data, the PathScan intracellular signaling and ELISA array revealed cleavage of caspase-3 and PARP and a significant inhibition of GSK3β phosphorylation, suggesting this kinase as a potential downstream target of our novel compounds. This was further supported by a specific assay for the evaluation of GSK3β activity, showing IC50 values for the most active compounds against this enzyme in the micromolar range.

Efficient construction of diverse 3-cyanoindoles under novel tandem catalysis

Wu, Jun,Liu, Jiabin,Zhou, Kerui,He, Zhenni,Wang, Qian,Wu, Fen,Miao, Tingting,Qian, Jinjie,Shi, Qian

supporting information, p. 12660 - 12663 (2020/11/02)

A novel and rapid construction of 3-cyanoindoles by palladium-catalyzed tandem reactions has been developed. "N-H"free unprotected, N-alkyl and N-aryl 3-cyanoindoles are obtained with good to excellent yields. The usefulness of this synthetic approach is further demonstrated by the successful synthesis of practical compounds such as the therapeutic estrogen receptor ligand A precursor. Mechanism study shows that the tandem catalysis exploits a Suzuki cross-coupling with subsequent base-induced isoxazole fragmentation, followed by the aldimine condensation.

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