10604-59-8Relevant articles and documents
Pyrazolo[4,3-a]quinindoline as a new highly fluorescent heterocyclic system: Design, synthesis, spectroscopic characterization and DFT calculations
Alikhani, Elaheh,Pordel, Mehdi,Daghigh, Leila Rezaei
, p. 1484 - 1490 (2015)
(Chemical Equation Presented) After obtaining the desired precursors in several reactions, new N-alkyl-substituted heterocyclic system pyrazolo[4,3-a]quinindolines (pyrazolo[4,3-f]-indolo[2,3-b]quinolines) were synthesized by one-pot reaction of 1-alkyl-5-nitro-1H-indazole with 2-(1-alkyl-1H-3-indolyl)acetonitrile in MeOH/KOH solution via the nucleophilic substitution of hydrogen in excellent yields. Spectral (UV-Vis, FT-IR, NMR and fluorescence) and analytical data allowed the structures of the synthesized compounds to be established. The values of absorption and fluorescence maxima, extinction coefficients and fluorescence quantum yield of these new heterocyclic fluorophores were obtained and they show highlighting interesting photophysical properties. Density functional theory (DFT) calculations of one structure by using the B3LYP hybrid functional and the 6-311 + G(d,p) basis set were performed to provide the optimized geometry, relevant frontier orbitals and the prediction of 1H NMR chemical shifts. Calculated electronic absorption spectrum of one structure was also obtained by time-dependent density functional theory (TD-DFT) method. Solvatochromic properties of these dyes have been discussed and the results showed that the absorption and emission bands in polar solvents undergo a modest red shift.
Synthesis of indoles from N-substituted anilines and triethanolamine by a homogeneous ruthenium catalyst
Shim,Youn,Lee,Kim,Cho,Uemura,Watanabe
, p. 1349 - 1353 (1996)
N-substituted anilines react with triethanolamine in the presence of a catalytic amount of a homogeneous ruthenium catalyst to give the corresponding 1-substituted indoles in good yields.
ALKYLATIONS EN ABSENCE DE SOLVANT ORGANIQUE. EFFETS D'ADDITION D'OXYDES MINERAUX ET DE SELS D'AMMONIUM - I. N-ALKYLATION DE L'INDOLE EN MILIEU BASIQUE
Barry, J.,Bram, G.,Decodts, G.,Loupy, A.,Pigeon, P.,Sansoulet, J.
, p. 2669 - 2672 (1983)
Indole alkylation, after anion formation (KOH+1percent NBu4Br) is achieved without any solvent in the presence or in the absence of solid mineral supports.N-Ethyl or octyl derivatives are thus obtained quantitatively under very mild conditions.
Design, synthesis, biological evaluation and molecular modelling studies of conophylline inspired novel indolyl oxoacetamides as potent pancreatic lipase inhibitors
Palawat, Saksham,Paul, Atish T.,Sridhar, S. N. C.
, p. 12355 - 12369 (2020)
A novel series of 21 indolyl oxoacetamide analogues was designed based on the natural product lead conophylline, and evaluated for their pancreatic lipase inhibitory activity using porcine pancreatic lipase (Type II). Analogues 12c and 12b exhibited comparatively greater potential (IC50 values of 2.95 and 3.26 μM) than conophylline (IC50-3.31 μM), while the standard drug, orlistat, exhibited a potent IC50 value of 0.99 μM. Further, analogues 12b and 12c exhibited reversible competitive inhibition similar to orlistat and conophylline, and possessed Ki values of 1.89 and 1.69 μM, respectively. Molecular docking of these analogues was in agreement with the in vitro results, wherein the MolDock scores exhibited significant correlation with their inhibitory activity. A 10 ns molecular dynamics simulation of 12c complexed with pancreatic lipase confirmed the role of extended alkyl interactions, along with π-π stacking and π-cation interactions, in stabilising the ligand in the active site (maximum observed RMSD ≈ 3.5 ?). ADMET prediction indicated the GI absorption of these analogues to be high; however, they did not possess carcinogenicity and hepatotoxicity in contrast to orlistat and conophylline.
Palladium catalyzed dual C-H functionalization of indoles with cyclic diaryliodoniums, an approach to ring fused carbazole derivatives
Wu, Yongcheng,Peng, Xiaopeng,Luo, Bingling,Wu, Fuhai,Liu, Bo,Song, Fenyun,Huang, Peng,Wen, Shijun
, p. 9777 - 9780 (2014)
Palladium(ii)-catalyzed dual C-H functionalization of indoles with cyclic diaryliodoniums was successfully achieved, providing a concise method to synthesize dibenzocarbazoles. In a single operation, two C-C bonds and one ring were formed. The reaction was ligand free and tolerated air and moisture conditions.
A tandem carbonylation/cyclization radical process of 1-(2-iodoethyl)indoles and pyrrole
Miranda, Luis D.,Cruz-Almanza, Raymundo,Pavon, Miriam,Alva, Edith,Muchowski, Joseph M.
, p. 7153 - 7157 (1999)
The AIBN-induced radical reaction of 1-(2-iodoethyl)indoles and pyrroles with Bu3SnH under 80 atm of CO was examined. Carbon monoxide was efficiently trapped by an alkyl radical to form an acyl radical which underwent intramolecular addition to the aromatic system to produce bicyclic aromatic ketones after in situ oxidation.
Programmed synthesis of triarylnitroimidazoles via sequential cross-coupling reactions
Raina, Gaurav,Kannaboina, Prakash,Mupparapu, Nagaraju,Raina, Sushil,Ahmed, Qazi Naveed,Das, Parthasarathi
, p. 2134 - 2147 (2019)
Transition-metal-catalyzed programmed sequential arylation reactions of 2-chloro-4-nitro-1H-imidazoles were achieved. The methods are general and were applied in a chemoselective manner for the synthesis of different multiarylated 4-nitroimidazoles bearing three different aryl groups. A salient feature is Pd-catalyzed hetero-hetero coupling at the C5 position through a NO2 directed cross-dehydrogenative coupling (CDC) approach.
Imidazo[4,5-a]quinindolines as highly effective antibacterial agents
Pordel, Mehdi,Ramezani, Shirin,Jajarmi, Maryam,Sokhanvar, Mina
, p. 106 - 110 (2016)
Resistance to antimicrobial agents is a concern that exists globally and has a considerable impact on human and animal health, so that the discovery of new antibacterial compounds has become increasingly more important in combating infectious disease. In this paper, imidazo[4,5-a]quinindolines are introduced as new antibacterial agents against Gram-positive and Gram-negative bacteria. These pentacyclic compounds are synthesized by the reaction of N-alkyl-5-nitrobenzimidazoles with 2-(1-alkyl-1H-3-indolyl)acetonitrile under basic conditions in excellent yields. The structures of newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectral data. The antibacterial activities of the synthesized compounds were screened against standard strains of two Gram-positive and two Gram-negative bacteria using the broth microdilution method. Most of the compounds studied showed promising activities against both types of bacteria.
Phase-Transfer Alkylation of Heterocycles in the Presence of 18-Crown-6 and Potassium tert-Butoxide
Guida, Wayne C.,Mathre, David J.
, p. 3172 - 3176 (1980)
It has been found that the N-alkylation of heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen can be accomplished in diethyl ether via a phase-transfer process in which 18-crown-6 is employed as the catalyst and potassium tert-butoxide is employed as the base.In this manner, pyrrole (1), indole (2), pyrazole (3), imidazole (4), benzimidazole (5), benzotriazole (6), carbazole (7), and methyl indole-3-acetate (8) can be successfully alkylated.The procedure is convenient and mild and generally gives rise to exclusive N-alkylation.
Sequential one-pot synthesis of bis(indolyl)glyoxylamides: Evaluation of antibacterial and anticancer activities
Tantak, Mukund P.,Gupta, Vishakha,Nikhil, Kumar,Arun,Singh, Rajnish Prakash,Jha, Prabhat Nath,Shah, Kavita,Kumar, Dalip
, p. 3167 - 3171 (2016)
A series of bis(indolyl)glyoxylamides 10a-n has been designed and synthesized. In situ generated indole-3-glyoxalylchloride from the reaction of readily available indole 9 with oxalyl chloride was treated with tryptamine to produce bis(indolyl)glyoxylamides 10a-n in 82-93% yields. All the synthesized bis(indolyl)glyoxylamides were well characterized and tested for their antibacterial activity against Gram-positive and Gram-negative bacterial strains. Compounds 10d, 10g and 10i were found to display potent antibacterial activity against Gram-negative strain. Further, the cytotoxicity of bis(indolyl)glyoxylamides 10a-n were evaluated against a panel of human cancer cell lines. Of the screened analogues, compound 10f (IC50 = 22.34 μM; HeLa, 24.05 μM; PC-3, 21.13 μM; MDA-MB-231 and 29.94 μM; BxPC-3) was identified as the most potent analogue of the series. Exposure of PC-3 cells to either 10a or 10f resulted in increased levels of cleaved PARP1, indicating that bis(indolyl)glyoxylamides induce apoptosis in PC-3 cells. Most importantly, compounds 10d, 10g and 10i were completely ineffective in mammalian cells, suggesting that they target bacterial-specific targets and thus will not display any toxicity in host cells.
