- Pyrazolo[4,3-a]quinindoline as a new highly fluorescent heterocyclic system: Design, synthesis, spectroscopic characterization and DFT calculations
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(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.
- Alikhani, Elaheh,Pordel, Mehdi,Daghigh, Leila Rezaei
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- Synthesis of indoles from N-substituted anilines and triethanolamine by a homogeneous ruthenium catalyst
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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.
- Shim,Youn,Lee,Kim,Cho,Uemura,Watanabe
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- 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
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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.
- Barry, J.,Bram, G.,Decodts, G.,Loupy, A.,Pigeon, P.,Sansoulet, J.
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- Design, synthesis, biological evaluation and molecular modelling studies of conophylline inspired novel indolyl oxoacetamides as potent pancreatic lipase inhibitors
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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.
- Palawat, Saksham,Paul, Atish T.,Sridhar, S. N. C.
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- Palladium catalyzed dual C-H functionalization of indoles with cyclic diaryliodoniums, an approach to ring fused carbazole derivatives
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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.
- Wu, Yongcheng,Peng, Xiaopeng,Luo, Bingling,Wu, Fuhai,Liu, Bo,Song, Fenyun,Huang, Peng,Wen, Shijun
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- A tandem carbonylation/cyclization radical process of 1-(2-iodoethyl)indoles and pyrrole
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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.
- Miranda, Luis D.,Cruz-Almanza, Raymundo,Pavon, Miriam,Alva, Edith,Muchowski, Joseph M.
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- Programmed synthesis of triarylnitroimidazoles via sequential cross-coupling reactions
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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.
- Raina, Gaurav,Kannaboina, Prakash,Mupparapu, Nagaraju,Raina, Sushil,Ahmed, Qazi Naveed,Das, Parthasarathi
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- Imidazo[4,5-a]quinindolines as highly effective antibacterial agents
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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.
- Pordel, Mehdi,Ramezani, Shirin,Jajarmi, Maryam,Sokhanvar, Mina
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- Phase-Transfer Alkylation of Heterocycles in the Presence of 18-Crown-6 and Potassium tert-Butoxide
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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.
- Guida, Wayne C.,Mathre, David J.
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- Sequential one-pot synthesis of bis(indolyl)glyoxylamides: Evaluation of antibacterial and anticancer activities
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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.
- Tantak, Mukund P.,Gupta, Vishakha,Nikhil, Kumar,Arun,Singh, Rajnish Prakash,Jha, Prabhat Nath,Shah, Kavita,Kumar, Dalip
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- Palladium-catalyzed amination of aryl dibromides with secondary amines: Synthetic and mechanistic aspects
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Diaminobenzenes are obtained starting from m- and p-dibromobenzenes and secondary amines in the presence of Pd(dba)2/P(o-tolyl)3 and sodium tert- butoxide in moderate to good yields. Reductive dehalogenation of aryl dibromides is a major side reaction under these conditions. The study of this reaction has shown that the formation of reductive dehalogenation products occurs according to two independent ways. The first one proceeds via the well-known β-hydride elimination from amido-coordinated palladium complexes. The second one involves the formation of hydrido palladium complexes from amino-coordinated derivatives. Although our results do not allow us to propose a detailed mechanistic scheme, they clearly show that the deprotonation step of the catalytic amination cycle has a major effect on the amine/arene ratio.
- Beletskaya, Irina P.,Bessmertnykh, Alla G.,Guilard, Roger
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- N-Alkylation of Pyrrole, Indole, and Several Other Nitrogen Heterocycles Using Potassium Hydroxide as a Base in the Presence of Polyethylene Glycols or Their Dialkyl Ethers
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The alkylation of pyrrole and indole in aqueous potassium hydroxide-organic two-phase systems in the presence of polyethylene glycols (PEG) or their dialkyl ethers (PEG-ether) as phase transfer catalysts (PTC) gave substantial quantities of the C-alkylated and C,N-polyalkylated products as well as the N-alkylated products.This fact is similar to that obtained in the presence of quaternary ammonium salts as PTC.In powdered potassium hydroxide-organic two-phase system, the yields of the N-alkylated products were generally high.Especially, when PEG-ether were employed as solvents, the N-alkylated products were obtained in excellent yields under mild conditions.Imidazole, benzimidazole, carbazole, 2-methylindole, and benzotriazole were similarly N-alkylated in high yields by this method.
- Sukata, Kazuaki
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- Organic Reactions in Ionic liquids: N-Alkylation of Phthalimide and Several Nitrogen Heterocycles
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N-Alkylation of heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen with alkyl halides is accomplished in ionic liquids ([bmim]BF4= 1-butyl-3-methylimidazolium te trafluoroborate, [bmim]PF6 = 1-butyl-3-methylimidazolium hexafluorophosphate, [buPy]BF4 = butylpyridiniurri tetrafluoroborate) in the presence of potassium hydroxide as a base. In this manner, phthalimide, indole, benzimidazole, succinimide can be successfully alkylated. The procedure is convenient, efficient, and generally affords the N-alkylated product exclusively.
- Le, Zhang-Gao,Chen, Zhen-Chu,Hu, Yi,Zheng, Qin-Guo
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- Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes
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The following work presents three general approaches allowing, for the first time, the synthesis of 5,10-diheterotruxene derivatives containing two identical heteroatoms, namely, oxygen OOC, nitrogen NNC, or sulfur SSC. Two of described pathways involve the photocyclization of the corresponding triene 2 as a key step leading to a heptacyclic aromatic system. The third approach is based on the acidic condensation between ninhydrin 14 and benzo[b]heteroole 15. Typical functionalizations of the 5,10-diheterotruxene core have also been presented. In addition, the article discusses the advantages and limitations of the three suggested paths for receiving specific 5,10-diheterotruxene derivatives because the universal method suitable for obtaining molecules with any type of heteroatoms is not known so far.
- Górski, Krzysztof,Mech-Piskorz, Justyna,Le?niewska, Barbara,Pietraszkiewicz, Oksana,Pietraszkiewicz, Marek
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- Probing the molecular and structural elements of ligands binding to the active site versus an allosteric pocket of the human farnesyl pyrophosphate synthase
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In order to explore the interactions of bisphosphonate ligands with the active site and an allosteric pocket of the human farnesyl pyrophosphate synthase (hFPPS), substituted indole and azabenzimidazole bisphosphonates were designed as chameleon ligands. NMR and crystallographic studies revealed that these compounds can occupy both sub-pockets of the active site cavity, as well as the allosteric pocket of hFPPS in the presence of the enzyme's Mg2+ ion cofactor. These results are consistent with the previously proposed hypothesis that the allosteric pocket of hFPPS, located near the active site, plays a feed-back regulatory role for this enzyme.
- Gritzalis, Dimitrios,Park, Jaeok,Chiu, Wei,Cho, Hyungjun,Lin, Yih-Shyan,De Schutter, Joris W.,Lacbay, Cyrus M.,Zielinski, Michal,Berghuis, Albert M.,Tsantrizos, Youla S.
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- Ruthenium Complex Catalyzed N-Heterocyclization. Syntheses of Quinolines and Indole Derivatives from Aminoarenes and 1,3-Propanediol of Glycols
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Aniline reacts with 1,3-propanediol under reflux in diglyme with spontaneous hydrogen evolution in the presence of a catalytic amount of ruth enium trichloride hydrate ( RuCl3*nH2O)-tributylphosphine (PBu3) to give quinoline in good yield.The yield of quinoline was markedly affected by the molar ratios of aniline to 1,3-propanediol and PBu3 to RuCl3*nH2O.The best yield (76percent) was achieved at the molar ratios of 2.5 of aniline / 1,3-propanediol and 2.0 of PBu3 / RuCl3*nH2O.Also, N-substituted anilines react with ethylene glycol in the presence of a catalytic amount of dichlor otris(triphenylphosphine)ruthenium (RuCl2(PPh3)3) to give N-substituted indole derivatives.The reactions were carried out at 180 deg C in dioxane with spontaneus hydrogen evolution.Aminoarenes also react with 2,3-butanediol and 1,2-cyclohexanediol ( mixture of cis and trans ) in the presence of RuCl2(PPh3)3 to give the corresponding 2,3-dimethylindoles and 1,2,3,4-tetrahydrocarbazoles in good to excellent yields.As the key intermediates of the reactions, N,N'-diarylpropylenediamine (5a) and N,N'-diarylethylenediamine (5b) and their dehydrogenated imine derivatives are postulated.
- Tsuji, Yasushi,Huh, Keun-Tae,Watanabe, Yoshihisa
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- EASY AND EFFICIENT ANION ALKYLATIONS IN SOLID-LIQUID PTC CONDITIONS
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Alkylation of anionic nucleophiles such as potassium acetate or potassium indole can be achieved in good yields without solvent either in the presence of NBu4Br and small amounts of TiO2 or in the presence of Aliquat 336 (Oct3MeN(1+)Cl(1-)).
- Barry, J.,Bram, G.,Decodts, G.,Loupy, A.,Pigeon, P.,Sansoulet, J.
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- Regioselective 2-alkylation of indoles with α-bromo esters catalyzed by Pd/P,P=O system
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A palladium-catalyzed 2-alkylation of indoles with α-bromo esters is developed by employing a P,P=O ligand. The method features excellent regioselectivities, mild reaction conditions, and good functional group compatibility. The employment of the P,P=O ligand as well as 4? molecular sieves were crucial for the success of the transformation. Mechanistic studies indicate the reaction proceed through a radical pathway.
- Tian, Wei,Li, Bowen,Tian, Duanshuai,Tang, Wenjun
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supporting information
p. 197 - 200
(2021/08/13)
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- Preparation method of nitrogen-alkyl (deuterated alkyl) aromatic heterocycle and alkyl (deuterated alkyl) aryl ether compound
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The invention provides a method for preparing nitrogen-alkyl(deuterated alkyl)aromatic heterocycle and alkyl(deuterated alkyl)aryl ether compounds. The method adopted in the invention specifically comprises the following steps: firstly, adding an alkoxy base (MOR') or a combination reagent Q (comprising a base M'X, an alcohol C and a molecular sieve E) into a solvent B to be stirred; then, addingan aromatic compound D of nitrogen sulfonyl or oxygen sulfonyl into a mixture; separating and purifying after reaction to obtain nitrogen-alkyl(deuterated alkyl)aromatic heterocycle or alkyl(deuterated alkyl)aryl ether. The method can realize one-step conversion from an electron withdrawing benzenesulfonyl protecting group on a nitrogen or oxygen atom to an electron donating alkyl protecting group, avoids using highly toxic alkyl halide, and has advantages of being efficient, economical, environmentally friendly, mild in condition, good in substrate universality and high in yield; the prepareddeuterated compounds can be widely applied to the fields of pharmaceutical chemistry and organic chemistry synthesis.
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Paragraph 0026-0029
(2021/04/03)
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- Copper-Catalyzed Synthesis of Indolyl Benzo[b]carbazoles and Their Photoluminescence Property
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A copper-catalyzed cascade cyclization of dihydroisobenzofurans with indoles for the rapid construction of indoly benzo[b]carbazoles has been reported, providing the desired products in moderate to good yields under mild conditions along with a broad substrate scope and good functional group tolerance. The photoluminescence property of these indoly benzo[b]carbazoles has also been investigated.
- Hao, Tonggang,Huang, Long,Wei, Yin,Shi, Min
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supporting information
p. 5133 - 5137
(2021/07/19)
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- Application of biomass-supported copper-catalyzed three-component reaction in preparation of fluorine-containing drugs
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The invention relates to an application of a biomass-supported copper-catalyzed three-component reaction in preparation of a fluorine-containing drug. The indole and its derivatives and are synthesized 3 - (2 - (trifluoromethyl) - indo -3 -yl) quinoxaline -2 - ketone derivatives by one-pot synthesis by three-component one-pot method. To the invention, the heterogeneous biological substance carried copper catalyst is adopted to catalyze the reaction, and the problems that a traditional homogeneous catalyst cannot be recovered, metal residues are left and the like are solved. 3 - (2 - (Trifluoromethyl) - indo -3 -yl) quinoxaline -2 - ketone compounds with different substituents are expanded, and the biomass supported copper catalyst can be cyclically and catalytically reacted.
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Paragraph 0066-0068
(2021/09/29)
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- Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors
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The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.
- Chen, Zhe-Sheng,Dai, Qing-Qing,Li, Guo-Bo,Liu, Hong-Min,Liu, Hui,Wang, Bo,Wang, Shaomeng,Yu, Bin,Yuan, Shuo,Zhang, Jing-Ya,Zhang, Xiao-Nan,Zuo, Jia-Hui
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p. 14895 - 14911
(2021/10/12)
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- Nickel-Catalyzed Hydrodeoxygenation of Aryl Sulfamates with Alcohols as Mild Reducing Agents
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The nickel-catalyzed hydrodeoxygenation of aryl sulfamates has been developed with alcohols as mild reductants. A variety of functional groups and heterocycles were tolerated in this reaction system to give the desired products in high yields. In addition, the gram-scale process and stepwise cine-substitution were also achieved with high efficiency.
- Matsuo, Kasumi,Kuriyama, Masami,Yamamoto, Kosuke,Demizu, Yosuke,Nishida, Koyo,Onomura, Osamu
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p. 4449 - 4460
(2021/08/25)
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- Replacing halogenated solvents by a butyl acetate solution of bisphenol S in the transformations of indoles
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A butyl acetate solution of bisphenol S (BPS) was proved to be able to replace hazardous halogenated solvents in the transformation of indoles. Measurement with Kamlet-Taft solvatochromic parameters disclosed that the polarity of the BPS-containing butyl acetate was enhanced greatly. The protocol not only conferred a convenient way to minimize the use of halogenated solvents in the synthesis of indole derivatives, but also enabled successful recycling of both the butyl acetate solvent and BPS additive, strengthening the greenness of the reaction systems.
- Bai, Rongxian,Ferlin, Francesco,Gao, Feng,Gu, Yanlong,Li, Minghao,Vaccaro, Luigi
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supporting information
p. 3588 - 3594
(2021/06/06)
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- Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations
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Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.
- Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo
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supporting information
p. 7738 - 7744
(2021/05/07)
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- Manganese(III) Acetate Catalyzed Aerobic Dehydrogenation of Tertiary Indolines, Tetrahydroquinolines and an N-Unsubstituted Indoline
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A Mn(OAc)3 ? 2H2O-catalyzed aerobic dehydrogenation of five and six-membered N-heterocycles for the synthesis of N-heteroarenes is reported. Of note, this protocol can be applied to the dehydrogenation of tertiary indolines with various electron-deficient N-substituents. Preliminary mechanistic investigations support that a single-electron transfer pathway might be involved. (Figure presented.).
- Niu, Xiaokang,Yang, Lei
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supporting information
p. 4209 - 4215
(2021/08/06)
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- Straightforward access to novel indolo[2,3-: B] indoles via aerobic copper-catalyzed [3+2] annulation of diarylamines and indoles
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Herein, we report an unprecedented aerobic copper-catalyzed [3+2] annulation reaction of diarylamines with indoles, which allows direct access to novel 2-diarylaminoindolo[2,3-b]indoles, a class of potential photoelectric device molecules. The developed transformation proceeds with broad substrate scope, good functional group tolerance, high chemo-selectivity, and no need for pre-preparation of specific agents, which offers a practical route for diverse and atom-economic synthesis of the desired products that are difficult to prepare with the conventional approaches.
- Gong, Lingzhen,Jiang, Huanfeng,Liang, Taoyuan,Zhang, Min,Zhao, He
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supporting information
p. 2807 - 2810
(2020/03/13)
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- γ-Carboline synthesis enabled by Rh(iii)-catalysed regioselective C-H annulation
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A redox-neutral Rh(iii)-catalyzed C-H annulation of indolyl oximes was developed. Relying on the use of various alkynyl silanes as the terminal alkyne surrogates, the reaction exhibited a reverse regioselectivity, thus giving an exclusive and easy way for the synthesis of a wide range of substituent free γ-carbolines at C3 position with high efficiency. Deuterium-labelling experiments and kinetic analysis have preliminarily shed light on the working mode of this catalytic system. This journal is
- Jiang, Bo,Jia, Jingwen,Sun, Yufei,Wang, Yichun,Zeng, Jing,Bu, Xiubin,Shi, Liangliang,Sun, Xiaoying,Yang, Xiaobo
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supporting information
p. 13389 - 13392
(2020/11/10)
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- A rhodium(ii) catalysed domino synthesis of azepino fused diindoles from isatin tethered: N -sulfonyl-1,2,3-triazoles and indoles
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An efficient and convenient protocol for the synthesis of a novel class of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles has been disclosed. The reaction proceeds via denitrogenative aza-vinyl rhodium carbene formation to give a carbonyl ylide, which with indole results in 1,3-dipolar cycloaddition followed by sequential semipinacol rearrangement/ring expansion/oxidation to produce azepino fused diindoles. The reaction shows a broad substrate scope giving up to 81% yield. Furthermore, reversible catalytic hydrogenation and photophysical studies were carried out to demonstrate the application of these molecules.
- Kahar, Nilesh,Jadhav, Pankaj,Reddy, R. V. Ramana,Dawande, Sudam
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supporting information
p. 1207 - 1210
(2020/02/04)
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- Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine
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The polystyrene-cross-linking bisphosphine ligand PS-DPPBz was effective for the Ir-catalyzed reversible acceptorless dehydrogenation/hydrogenation of N-heterocycles. Notably, this protocol is applicable to the dehydrogenation of N-substituted indoline derivatives with various N-substituents with different electronic and steric natures. A reaction pathway involving oxidative addition of an N-adjacent C(sp3)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates.
- Zhang, Deliang,Iwai, Tomohiro,Sawamura, Masaya
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supporting information
p. 5240 - 5245
(2020/07/03)
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- Microwave-assisted synthesis method for ethylation reaction
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The invention relates to a microwave-assisted synthesis method for an ethylation reaction. The method is characterized in that a reaction substrate is in an organic solvent, trifluoroacetic acid ethyl ester is taken as an ethylation reagent, in the presence of an alkali, microwave-assisted heating is carried out for 2 minutes, and a corresponding ethylation product can be obtained. The invention provides a new method for the ethylation reaction. The reaction rate of the method is several times higher than that of a traditional method, the operation is simple and convenient, the cost is low, the reaction time is short, the application range of the substrate is wide, the use of the expensive or hypertoxic ethylation reagent can also be avoided, and the method has higher application value.
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Paragraph 0012
(2019/10/05)
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- Cobalt-Catalyzed Regioselective Direct C-4 Alkenylation of 3-Acetylindole with Michael Acceptors Using a Weakly Coordinating Functional Group
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Herein, we disclosed the first report on the selective C(4)-H functionalization of 3-acetylindole derivatives using first-row transition metal cobalt where an acetyl group is acting as a weakly coordinating directing group. Selective C(4)-H functionalization has been achieved using diverse Michael acceptors (acrylate and maleimide) simply by switching the additive from copper acetate to silver carbonate. Further the formation of a cobaltacycle intermediate was also detected through HRMS for mechanistic insight.
- Banjare, Shyam Kumar,Nanda, Tanmayee,Ravikumar
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supporting information
p. 8138 - 8143
(2019/10/14)
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- Replacement of Stoichiometric DDQ with a Low Potential o-Quinone Catalyst Enabling Aerobic Dehydrogenation of Tertiary Indolines in Pharmaceutical Intermediates
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A transition-metal/quinone complex, [Ru(phd)3]2+ (phd = 1,10-phenanthroline-5,6-dione), is shown to be effective for aerobic dehydrogenation of 3° indolines to the corresponding indoles. The results show how low potential quinones may be tailored to provide a catalytic alternative to stoichiometric DDQ, due to their ability to mediate efficient substrate dehydrogenation while also being compatible with facile reoxidation by O2. The utility of the method is demonstrated in the synthesis of key intermediates to pharmaceutically important molecules.
- Li, Bao,Wendlandt, Alison E.,Stahl, Shannon S.
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supporting information
p. 1176 - 1181
(2019/02/14)
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- Chiral N,N′-Dioxide/ScΙΙΙ Complex-Catalyzed Asymmetric Ring-Opening Reaction of Cyclopropyl Ketones with Indoles
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The asymmetric ring-opening reaction of cyclopropyl ketones with indoles has been realized by using a N,N′-dioxide/scandium(ΙΙΙ) complex as catalyst. The corresponding 3-alkylated indole derivatives were obtained in moderate to excellent yields with good ee values. Moreover, a possible transition state was proposed on the basis of experimental studies and X-ray structure of product. (Figure presented.).
- Chang, Fenzhen,Lin, Lili,Xia, Yong,Zhang, Hang,Dong, Shunxi,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 2608 - 2612
(2018/05/30)
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- Directly Bridging Indoles to 3,3′-Bisindolylmethanes by Using Carboxylic Acids and Hydrosilanes under Mild Conditions
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A straightforward Lewis acid-promoted protocol for 3,3′-bisindolylmethanes (BIMs) synthesis by reductive alkylation of indoles at the C3 position with carboxylic acids in the presence of hydrosilane was developed for the first time. Instead of aldehydes, more readily available, stable, and easy-to-handle carboxylic acids have been employed as alternative alkylating agents. As an efficient organocatalyst, B(C6F5)3 enables the reductive alkylation of various substituted indole derivatives with carboxylic acids with up to 98 % yield at room temperature and under neat conditions. This metal-free strategy offers an alternative approach for the direct functionalization of indoles to BIMs with carboxylic acids and such protocol allows selective reduction of carboxylic acid to aldehyde in combination with C?C bond formation.
- Qiao, Chang,Liu, Xiao-Fang,Fu, Hong-Chen,Yang, Hao-Peng,Zhang, Zhi-Bo,He, Liang-Nian
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p. 2664 - 2670
(2018/09/14)
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- Novel indolo-sophoridinic scaffold as Topo I inhibitors: Design, synthesis and biological evaluation as anticancer agents
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Based on the mechanism of action, novel scaffolds as Topo I inhibitors bearing indole and sophoridinine were designed. Preliminary docking study revealed that some molecules among the designed series possessed promising Topo I inhibitor properties. Subsequently, thirty new compounds were synthesized and characterized by 1H NMR, 13C NMR, and Mass spectral analyses. The compounds were then screened for their antiproliferative and enzymatic inhibitory activities. The results affirmed the consistency between docking and activities and the rationality of the design strategy. Furthermore, compound 10b was chosen as a representative compound to test its anticancer effects in vitro and in vivo. The results showed that 10b caused prominent S phase cell cycle arrest and significantly suppressed tumor growth in HepG2 cell derived mouse model. These findings present a promising series of lead molecules which can serve as potential Topo I inhibitors for the treatment of cancer and a theoretical basis for structural modifications.
- Xu, Yiming,Wu, Lichuan,Rashid, Haroon Ur,Jing, Dewang,Liang, Xiaole,Wang, Haodong,Liu, Xu,Jiang, Jun,Wang, Lisheng,Xie, Peng
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p. 479 - 492
(2018/07/25)
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- Boronic Acid Accelerated Three-Component Reaction for the Synthesis of α-Sulfanyl-Substituted Indole-3-acetic Acids
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Boronic acid was used to accelerate a three-component reaction of indoles, thiols, and glyoxylic acids for the synthesis of α-sulfanyl-substituted indole-3-acetic acids. Boronic acid catalysis to activate the α-hydroxy group in α-hydroxycarboxylic acid in
- Das, Amrita,Watanabe, Kenji,Morimoto, Hiroyuki,Ohshima, Takashi
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supporting information
p. 5794 - 5797
(2017/11/10)
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- Divergent dehydrogenative coupling of indolines with alcohols
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The dehydrogenative coupling of indolines with alcohols catalyzed by an iridium complex has been achieved to afford both N- and C3-alkylated indoles selectively, by simply changing the addition time of a base additive. The iridacycle catalyst plays multiple roles in these reactions, which dehydrogenates both amines and alcohols and catalyzes the coupling reactions. Mechanistic studies reveal that a borrowing hydrogen-dehydrogenation process and a dehydrogenationborrowing hydrogen process are involved in N-alkylation and C3-alkylation reactions, respectively. The C3-alkylation reaction involves the direct coupling of two sp3 carbon centers.
- Jiang, Xue,Tang, Weijun,Xue, Dong,Xiao, Jianliang,Wang, Chao
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p. 1831 - 1835
(2017/08/01)
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- Introducing tetramethylurea as a new methylene precursor: a microwave-assisted RuCl3-catalyzed cross dehydrogenative coupling approach to bis(indolyl)methanes
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Herein we report a microwave assisted Ru(iii)/TBHP-mediated reaction of indoles with tetramethylurea (TMU) synthesizing symmetrical as well as unsymmetrical bis(indolyl)methanes, where TMU acts as a methylenating agent. This is the first report where TMU is used as a methylene source. Moreover, the synthesis of unsymmetrical bis(indolyl)methanes by using a carbon precursor is also reported herein for the first time. Various substituted indoles are used for the reaction. The reaction is high yielding and takes a much shorter time to accomplish compared to the existing methods.
- Deb, Mohit L.,Borpatra, Paran J.,Saikia, Prakash J.,Baruah, Pranjal K.
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supporting information
p. 1435 - 1443
(2017/02/15)
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- Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
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Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.
- Marcum, Justin S.,Roberts, Courtney C.,Manan, Rajith S.,Cervarich, Tia N.,Meek, Simon J.
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supporting information
p. 15580 - 15583
(2017/11/14)
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- THERAPEUTIC COMPOUNDS AND USES THEREOF
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The present invention relates to compounds of formula (I): and to salts thereof, wherein A has any of the values defined in the specification, and compositions and uses thereof. The compounds are useful as inhibitors of CBP and/or EP300. Also included are pharmaceutical compositions comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof, and methods of using such compounds and salts in the treatment of various CBP and/or EP300-mediated disorders.
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Page/Page column 110
(2016/05/02)
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- HETEROARYL COMPOUNDS FOR KINASE INHIBITION
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Compounds and pharmaceutical compositions that modulate kinase activity, including mutant EGFR and mutant HER2 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including mutant EGFRand mutant HER2 activity, are described herein.
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Paragraph 465
(2016/04/26)
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- 9,10-Bis(N-alkylindole-3-yl-vinyl-2)anthracenes as a new series of alkyl length-dependent piezofluorochromic aggregation-induced emission homologues
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The introduction and length-extending of peripheral alkyl chains is usually to improve the solubility of conjugated organic molecules. This article reports the synthesis and optical properties of 9,10-bis(N-alkylindole-3-yl-vinyl-2)anthracenes (IACn) with different alkyl lengths. These homologues exhibit the strong alkyl length-dependent piezofluorochromic (PFC) behaviour, and their PFC spectral shifts are in the range of 27-65 nm. It is found that the shorter the N-alkyl length, the larger the spectral shift upon mechanical grinding or pressing. Wide-angle X-ray diffraction evidenced that the mechanical grinding has resulted in destruction of pristine ordered structures, formation of crystal defects, and appearance of some amorphous states, which is responsible for the PFC behaviour.
- Sun,Liu,Ying,Wang,Xue,Yang
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p. 73046 - 73050
(2015/09/15)
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- An Orally Bioavailable, Indole-3-glyoxylamide Based Series of Tubulin Polymerization Inhibitors Showing Tumor Growth Inhibition in a Mouse Xenograft Model of Head and Neck Cancer
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A number of indole-3-glyoxylamides have previously been reported as tubulin polymerization inhibitors, although none has yet been successfully developed clinically. We report here a new series of related compounds, modified according to a strategy of redu
- Colley, Helen E.,Muthana, Munitta,Danson, Sarah J.,Jackson, Lucinda V.,Brett, Matthew L.,Harrison, Joanne,Coole, Sean F.,Mason, Daniel P.,Jennings, Luke R.,Wong, Melanie,Tulasi, Vamshi,Norman, Dennis,Lockey, Peter M.,Williams, Lynne,Dossetter, Alexander G.,Griffen, Edward J.,Thompson, Mark J.
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p. 9309 - 9333
(2015/12/23)
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- An efficient ultrasound-assisted synthesis of n-alkyl derivatives of carbazole, indole, and phenothiazine
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Heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen such as carbazole, indole, and phenothiazine can be efficiently alkylated in DMSO or N,N-DMF under ultrasonic irradiation in the presence of potassium hydroxide as a base. In almost all cases, a dramatic reduction of the reaction time results and a clear yield increase accompanied by an improved quality of the products occurs.
- Zhao, Sanhu,Kang, Jin,Du, Yuting,Kang, Jingyan,Zhao, Xiaoni,Xu, Yinfeng,Chen, Ruixi,Wang, Qianqian,Shi, Xitao
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supporting information
p. 683 - 689
(2014/06/10)
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- Gold(I)-catalyzed rearrangement of alkynylaziridine indoles for the synthesis of spiro-tetrahydro-β-carbolines
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Functionalized spiro-tetrahydro-β-carbolines were formed by an efficient gold(I)-catalyzed rearrangement reaction of alkynylaziridine indoles. The reaction involved a Friedel-Crafts type intramolecular reaction of alkynylaziridine indoles, following by hydroamination of aminoallene intermediate.
- Yang, Yan-Fang,Li, Lian-Hua,He, Yu-Tao,Luo, Jian-Yi,Liang, Yong-Min
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supporting information
p. 702 - 707
(2014/02/14)
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- Iridium-catalyzed, intermolecular hydroamination of unactivated alkenes with indoles
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The addition of an N-H bond to an olefin is the most direct route for the synthesis of alkylamines. Currently, intermolecular hydroamination is limited to reactions of a narrow range of reagents containing N-H bonds or activated alkenes, and all the examples of additions to unactivated alkenes require large excesses of alkene. We report intermolecular hydroamination reactions of indoles with unactivated olefins. The reactions occur with as few as 1.5 equiv of olefin to form N-alkylindoles exclusively and in good yield. Characterizations of the catalyst resting state, kinetic data, labeling studies, and computational data imply that the addition occurs by olefin insertion into the Ir-N bond of an N-indolyl complex and that this insertion reaction is faster than insertion of olefin into the Ir-C bond of the isomeric C-2-indolyl complex.
- Sevov, Christo S.,Zhou, Jianrong,Hartwig, John F.
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supporting information
p. 3200 - 3207
(2014/03/21)
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- Copper nanoparticles from copper aluminum hydrotalcite: An efficient catalyst for acceptor- and oxidant-free dehydrogenation of amines and alcohols
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An efficient and simple process for the preparation of stable nanocopper(0) on alumina [Cu(0)/Al2O3] from the inorganic composite precursor copper aluminum hydrotalcite (Cu-AlHT) by a chemical reduction method is described. Cu(0)/ Al2O3 was employed as an efficient catalyst in the acceptor- and oxidant-free dehydrogenation of various amines and alcohols to their corresponding dehydrogenated products in good to excellent yields. The stability of Cu(0)/Al2O3 was assessed by studying its recoverability and reusability in the dehydrogenation of amines and alcohols for up to five cycles.
- Damodara, Dandu,Arundhathi, Racha,Likhar, Pravin R.
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supporting information
p. 189 - 198
(2014/03/21)
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- Copper-promoted decarboxylative direct C3-acylation of N-substituted indoles with α-oxocarboxylic acids
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A novel and efficient Cu-promoted decarboxylative direct C3-acylation of N-substituted indoles with α-oxocarboxylic acids for the synthesis of 3-acylindoles was developed. The Royal Society of Chemistry.
- Yu, Lin,Li, Pinhua,Wang, Lei
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supporting information
p. 2368 - 2370
(2013/06/27)
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- Indole-based fibrates as potential hypolipidemic and antiobesity agents
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Hypolipidemic and antiobesity effects of the newly synthesized indole-based fibrates were evaluated in Triton WR-1339 and high fat diet (HFD)-induced hyperlipidemic rats. Preliminary screening of all the synthesized compounds was done by using an acute model (Triton model), in which compounds 3f and 3l showed significant antidyslipidemic activity. Furthermore, these compounds 3f and 3l were found to induce significant weight loss in the visceral fat mass of HFD-fed hyperlipidemic rats without affecting the normal feeding behavior. Histological examination of the liver of rats supplemented with 3f and 3l revealed a significant decrease in steatosis when compared to the effect of the standard drug fenofibrate. Additional effects such as an increase in lecithin cholesterol acyl-transferase (LCAT) enzyme level and increased receptor mediated catabolism of I131-low density lipoproteins (LDL) confirm and reinforce the efficacy of both of these compounds as a new class of dual-acting hypolipidemic and antiobesity agents.
- Sashidhara, Koneni V.,Kumar, Manoj,Sonkar, Ravi,Singh, Bhanu Shankar,Khanna,Bhatia, Gitika
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scheme or table
p. 2769 - 2779
(2012/06/04)
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- Cu(ii)-catalyzed C-H (SP3) oxidation and C-N cleavage: Base-switched methylenation and formylation using tetramethylethylenediamine as a carbon source
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Base-switched methylenation and formylation using tetramethylethylenediamine (TMEDA) as a carbon source have been achieved under mild conditions, catalyzed by CuCl2, with atmospheric oxygen as oxidant. Bisindolylmethanes, diphenylmethanes and 3-formylindoles were synthesized with excellent regioselectivity and good yield.
- Zhang, Lei,Peng, Chen,Zhao, Dan,Wang, Yue,Fu, Hai-Jian,Shen, Qi,Li, Jian-Xin
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supporting information; experimental part
p. 5928 - 5930
(2012/07/27)
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- Synthesis of 3,5-diaryl substituted indole derivatives and its selective iodide ion chemosensing
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In this contribution, we have synthesized series of 1-ethyl-3,5-bis[2- (aryl)ethenyl]-1H-indole based derivatives with different functional groups using Wadsworth-Emmons coupling. The sensing ability of the receptors has been studied for halides like tetrabutylammonium fluoride, chloride, bromide, iodide and bisulphate by UV-vis spectroscopy methods. In THF solution, compound A-E exhibits excellent selectivity with iodide ions over the other ions like tetrabutylammonium bromide (TBABr), tetrabutylammonium chloride (TBACl), tetrabutylammonium fluoride (TBAF) and tetrabutylammonium bisulphate (TBAHSO4). The indole cores were observed effectively and selectively recognized biologically important iodide was reported. Significant absorption change was observed only for tetrabutylammonium iodide and no change with other anions. The absorption spectra indicated the formation of complex between host and guest is in 1:1 stoichiometric ratio. The association constants of A-E for iodide ions were found to be 3.2 × 104 M-1, 3.9 × 104 M-1, 4.2 × 103 M -1, 2.9 × 103 M-1 and 2.14 × 103 M-1, respectively.
- Rathikrishnan, Krishnaswamy R.,Indirapriyadharshini, Vellore K.,Ramakrishna, Seeram,Murugan, Rajendiran
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scheme or table
p. 640 - 644
(2012/02/05)
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- Consecutive SNH and Suzuki-Miyaura cross-coupling reactions-an efficient synthetic strategy to pyrimidines bearing pyrrole and indole fragments
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The combination of the Suzuki-Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen reactions is a versatile tool for the syntheses of 4-(1R-pyrrol-2-yl)-and 4-(1R-indol-3-yl)-5-(hetero)aryl-substituted pyrimidines from commercially available 5-bromopyrimidine. The S NH [AE, (addition-elimination)] and SN H [AO, (addition-oxidation)] reactions of 5-bromopyrimidine with pyrroles and indoles were studied by gas chromatography-mass spectrometry. The structures of the intermediate σH adducts as well as the pyrrole-(hetero)arylpyrimidine and indole-(hetero)arylpyrimidine dyads were established for the first time by X-ray crystal structure analysis.
- Verbitskiy, Egor V.,Rusinov, Gennady L.,Charushin, Valery N.,Chupakhin, Oleg N.,Cheprakova, Ekaterina M.,Slepukhin, Pavel A.,Pervova, Marina G.,Ezhikova, Marina A.,Kodess, Mikhail I.
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supporting information
p. 6612 - 6621
(2013/01/15)
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- An efficient synthesis of N-substituted indoles from indoline/indoline carboxylic acid via aromatization followed by C-N cross-coupling reaction by using nano copper oxide as a recyclable catalyst
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A new and elegant protocol for the synthesis of 1-substituted indoles was developed via aromatization of indoline/indoline carboxylic acid followed by C-N cross-coupling with various aryl halides in the presence of nano CuO as a recyclable catalyst, Cs2CO3 as a base in DMSO at 80 °C. 1-Substituted indoles were obtained in good to excellent yields and the catalytic system can be recycled up to four cycles without loss of catalytic activity.
- Reddy, K. Harsha Vardhan,Satish,Ramesh,Karnakar,Nageswar
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supporting information; experimental part
p. 3061 - 3065
(2012/07/27)
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- Synthesis of indole and biindolyl triflones: Trifluoromethanesulfonylation of indoles with Tf2O/TTBP (2,4,6-tri- tert -butylpyridine) system
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A convenient synthesis of indole triflones is reported. N-Alkyl, aryl and N-H indole triflones were obtained in 82-96% yields by the Tf2O/TTBP System. Biindolyl triflones were accessed in 51-81% yields for the first time by simple treatment of the resulting indole triflones with a base and without any use of organometallic chemistry. An environmentally friendly solvent, Solkane 365/227, can be substituted for this process without any loss of efficiency.
- Xu, Xiu-Hua,Liu, Guo-Kai,Azuma, Ayaka,Tokunaga, Etsuko,Shibata, Norio
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supporting information; experimental part
p. 4854 - 4857
(2011/11/06)
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- Structure-Activity Relationship Refinement and Further Assessment of Indole-3-glyoxylamides as a Lead Series against Prion Disease
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Structure-activity relationships within the indole-3-glyoxylamide series of antiprion agents have been explored further, resulting in discovery of several new compounds demonstrating excellent activity in a cell line model of prion disease (EC50 10 nM). After examining a range of substituents at the para-position of the N-phenylglyoxylamide moiety, five-membered heterocycles containing at least two heteroatoms were found to be optimal for the antiprion effect. A number of modifications were made to probe the importance of the glyoxylamide substructure, although none were well tolerated. The most potent compounds did, however, prove largely stable towards microsomal metabolism, and the most active library member cured scrapie-infected cells indefinitely on administration of a single treatment. The present results thereby confirm the indole-3-glyoxylamides as a promising lead series for continuing in vitro and in vivo evaluation against prion disease.Making mad cows a myth! The indole-3-glyoxylamide series of antiprion agents has been further optimised, and characteristics contributing to their activity have been identified by computational studies. Varying the glyoxylamide motif or introducing substitution at N-1 gave analogues with lower efficacy.
- Thompson, Mark J.,Louth, Jennifer C.,Ferrara, Steven,Sorrell, Fiona J.,Irving, Benjamin J.,Cochrane, Edward J.,Meijer, Anthony J. H. M.,Chen, Beining
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p. 115 - 130
(2013/01/09)
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- BICYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME
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Disclosed herein are compounds that may be modulators of 5-HT receptors, and methods of making and using same.
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Page/Page column 35
(2010/06/20)
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- NOVEL INDOLIC DERIVATIVES, THEIR PREPARATION PROCESSES AND THEIR USES IN PARTICULAR AS ANTIBACTERIALS
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The invention relates to the use of at least one compound of the formula (I), in which R and R3 are particularly a hydrogen atom, R1 is particularly a hydrogen atom or a methyl, ethyl or isobutyl mi group, R4, R5, R6 and R7 are independently a hydrogen atony, an alkoxyl group with 1 to 7 carbon atoms or a halogen atom, R2 is a hydrogen atom, an O? group or an OH group, B is an N-GP1 or NRc, group, GP1 being a Boc or Cbz group, and Rc is a hydrogen atom or a methyl or t-butyl group, for preparing a drug for treating conditions associated with bacterial infections, in particular for treating bacterial diseases.
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Page/Page column 43
(2010/06/19)
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