- SBA-15-Pr-SO3H catalyzed one-pot synthesis of indole derivatives via Fischer indole pathway
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In this work, an efficient, user-friendly, and simple procedure was reported for the preparation of indole derivatives catalyzed by the heterogeneous SBA-15-Pr-SO3H via Fischer indole pathway. The title compounds were synthesized from various arylhydrazines and ketones in the presence of 3 mol% of the catalyst in the refluxing ethanol.
- Ghiyasabadi, Zahra,Bahadorikhalili, Saeed,Saeedi, Mina,Karimi-Niyazagheh, Mona,Mirfazli, Seyedeh Sara
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- 5,6-Bis(9-(2-decyltetradecyl)-6-fluoro-9H-carbazol-3-yl)naphtho[2,1-b:3,4-b']dithiophene as a Promising Donor Structure for D–A Conjugated Copolymers with a Narrow Bandgap
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A new carbazole-containing naphthodithiophene derivative—heteroaromatic compound 5,6- bis[9-(2-decyltetradecyl)-9H-carbazol-3-yl]naphtho[2,1-b:3,4-b']dithiophene (M1)—has been synthesized. The compound will be used by us as a weak donor structural block for fabricating narrow-bandgap D–A conjugated polymers. The composition and structure of M1 have been confirmed by elemental analysis data, IR spectroscopy, and 1H and 13C NMR. The synthesized compound has a low HOMO energy (–5.4 eV), which is favorable for a high open-circuit voltage. Monomer M1 can be used as a promising weak donor moiety in D–A conjugated polymers for solar photovoltaics.
- Keshtov,Kuklin,Konstantinov,Peregudov,Xie, Zhi-Yuan,Ostapov,Makhaeva,Khokhlov
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- Tetrahydrocarbazoles by mechanochemical Fischer indolisation
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The Fischer indolisation (FI) typically proceeds in the presence of a Br?nsted or Lewis acid in an organic solvent at elevated temperatures. Herein, we report that tetrahydrocarbazoles (THCs) are accessible by mechanochemical FI at ambient temperature. Using phenylhydrazine hydrochlorides in the presence of silica is critical for this solid-state variant of the FI.
- Qiu, Yichen,Puni, Kararaina Te,Duplan, Clotilde C.,Lindsay, Ashley C.,Sperry, Jonathan
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supporting information
(2021/05/26)
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- Design, synthesis, in vivo and in vitro studies of 1,2,3,4-tetrahydro-9H-carbazole derivatives, highly selective and potent butyrylcholinesterase inhibitors
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Abstract: Inhibition of butyrylcholinesterase (BChE) might be a useful therapeutic target for Alzheimer’s disease (AD). A new series of 1,2,3,4-tetrahydro-9H-carbazole derivatives were designed synthesized and evaluated as BChE inhibitors. While all of the derivatives have shown for AChE IC50 values below the detectable limit (> 100?μM), they were selective potent BChE inhibitors. 1-(2-(6-fluoro-1,2,3,4-tetrahydro-9H-carbazole-9-yl)ethyl)piperidin-1-ium chloride (15?g) had the most potent anti-BChE activity (IC50 value = 0.11?μM), the highest BChE selectivity and mixed-type inhibition. Pharmacokinetic properties were accordant to Lipinski rule and compound 15g demonstrated neuroprotective and inhibition of β-secretase (BACE1) activities. Furthermore, in vivo study of compound 15g in Morris water maze task has confirmed memory improvement in scopolamine-induced impairment. All results suggest that new sets of potent selective inhibitors of BChE have a therapeutic potential for the treatment of AD. Graphical abstract: A new series of 1,2,3,4-tetrahydro-9H-carbazole derivatives were designed synthesized and evaluated as BChE inhibitors. While all of the derivatives have shown for AChE IC50 values below the detectable limit, they were selective potent BChE inhibitors. Compound 15g had the most potent anti-BChE activity. All results suggest that new sets of potent selective inhibitors of BChE have a therapeutic potential for the treatment of AD.[Figure not available: see fulltext.]
- Ghobadian, Roshanak,Esfandyari, Roghaieh,Nadri, Hamid,Moradi, Alireza,Mahdavi, Mohammad,Akbarzadeh, Tahmineh,Khaleghzadeh-Ahangar, Hossein,Edraki, Najmeh,Sharifzadeh, Mohammad,Amini, Mohsen
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p. 211 - 223
(2019/04/17)
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- PYRIDINE BASED IONIC FLUORIDE FOR CATALYZING INDOLE AND TETRAZOLE FORMATION
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A pyridine based ionic liquid with a fluoride counter anion which catalyzes Fischer indole reaction and click chemistry. Methods of preparing the ionic liquid, and methods of utilizing the ionic liquid as a catalyst to synthesize indoles/indolenines and tetrazoles are also provided.
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Paragraph 0031; 0115; 0116; 0118
(2020/01/02)
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- Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids
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An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.
- Dalvi, Bhakti A.,Lokhande, Pradeep D.
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supporting information
p. 2145 - 2149
(2018/05/08)
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- An Electrophilic Bromine Redox Catalysis for the Synthesis of Indole Alkaloid Building Blocks by Selective Aliphatic C?H Amination
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A new homogeneous bromine(?I/I) redox catalysis is described, which is based on monomeric bromine(I) compounds containing transferable phthalimidato groups. These catalysts enable intermolecular C?H amination reactions at previously unaccessible aliphatic positions and thus enlarge the synthetic potential of direct C?N bond formation, including its application in the synthesis of alkaloid building blocks. This aspect is demonstrated by a new synthetic approach to aspidospermidine. In addition to the development of the catalyst system, the structures of the involved bromine(I) key catalysts were fully elucidated, including by X-ray analyses.
- Bergès, Julien,García, Belén,Mu?iz, Kilian
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supporting information
p. 15891 - 15895
(2018/11/23)
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- Design, synthesis and pharmacological evaluation of some novel tetrahydrocarbazoles as potential COX-2 inhibitors
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Background: NSAIDs have been extensively used for the treatment of pain and inflammation. There are about 30 different NSAIDs available in market and about 80 percent of prescriptions throughout the world contains one or the other painkiller. Chronic use of these drugs has many side effects such as gastric ulceration and the COX-2 inhibitors suffer from major drawback of cardiac toxicity. The need for a potential and safe NSAIDs has always led to the development of newer, better and safer drug molecules. In this article design and development of tetrahydrocarbazole derivatives with very low ulcerative index is reported. Methods: Fifteen tetrahydrocarbazole derivatives were synthesized on the basis of structural homology to indomethacin. Compounds were synthesized and characterized on the basis of spectral data. These were studied for their analgesic, anti-inflammatory and ulcerogenic activities. These compounds were subjected to molecular docking studies for understanding the possible mechanism of action and target. Results: The designed compounds were synthesized successfully in good yield and purity without much efforts. All compounds were evaluated by in vitro and in vivo assay, molecular modelling studies and ulcerative index. One of the compound (3-Aminophenyl) (6-chloro-1,2,3,4-tetrahydro-9H-carbazol-9-yl) methanone 13 was found to be highly active in the in vitro and in vivo assessment also it was found to be highly safe on ulcerogenic index compared to the standard drugs. Conclusion: Tetrahydrocarbazoles were found to be promising scaffolds which can be developed into safe and potential non-steroidal anti-inflammatory agents.
- Sakinala, Padmavathi,Chikhale, Rupesh,Tajne, Madhukar
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p. 437 - 449
(2018/04/20)
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- N, N -Dimethylpyridin-4-amine (DMAP) based ionic liquids: Evaluation of physical properties via molecular dynamics simulations and application as a catalyst for Fisher indole and 1 H -tetrazole synthesis
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The last few decades have seen a rapid increase in the use of ionic liquids (ILs) as a green alternative to traditional solvents in organic synthesis. The use of ILs as catalysts has also increased in recent years. Herein we the report synthesis of new N,N-dimethylpyridin-4-amine (DMAP) based ionic liquids (ILs) as new and efficient catalysts for the facile synthesis of indoles (via Fischer indole synthesis), and 1H-tetrazoles (via click chemistry). The method is environmentally friendly, requiring only minimum catalyst loading (0.2 equiv. for Fischer indole synthesis). In the case of 1H-tetrazole formation (via click chemistry), the reaction was carried out under a solvent free environment. Moreover, thermal studies (TGA, DTG and DSC) of DMAP-ILs (2, 3) have also been carried out to elicit their stability for temperature dependent reactions. Application of molecular dynamics simulations provided valuable insights into the structural and transport properties of these ionic liquids. An MP2 method was applied to evaluate the stability of the compound via binding energy calculations.
- Ghumro, Sarfaraz Ali,Saleem, Sana,Al-Rashida, Mariya,Iqbal, Nafees,Alharthy, Rima D.,Ahmed, Shakil,Moin, Syed Tarique,Hameed, Abdul
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p. 34197 - 34207
(2017/07/17)
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- Microwave-Assisted Rapid One-Pot Synthesis of Fused and Non-Fused Indoles and 5-[18F]Fluoroindoles from Phenylazocarboxylates
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Substituted indoles can be prepared from phenylazocarboxylates through a rapid one-pot sequence featuring a microwave-assisted Fischer indole synthesis as a key step. Considering that the phenylazocarboxylates may beforehand be modified by mild nucleophilic aromatic substitution, including the introduction of [18F]fluoride, the overall strategy offers an attractive new access to 5-[18F]fluoroindoles.
- Krüll, Jasmin,Hubert, Anja,Nebel, Natascha,Prante, Olaf,Heinrich, Markus R.
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supporting information
p. 16174 - 16178
(2017/10/30)
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- Novel and Efficient Heterogeneous 4-Methylbenzenesulfonic Acid-Based Ionic Liquid Supported on Silica Gel for Greener Fischer Indole Synthesis
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In this work, a functionalizing active species 4-methylbenzenesulfonic acid-based IL on silica gel (IL-SO3H-SiO2) has been prepared, and characterized by FT-IR, XRD, TGA, SEM and EDX spectra. Then, IL-SO3H-SiO2 was utilized as an efficient and heterogeneous catalyst for the synthesis of indoles via the one-pot Fischer reaction of phenyl hydrazines with ketones or aldehydes at room temperature. The heterogeneous catalyst could be recovered easily by filtration and reused many times without significant loss of its catalytic activity.
- Hu, Yu-Lin,Fang, Dong,Li, Dong-Sheng
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p. 968 - 976
(2016/04/20)
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- Ruthenium-catalyzed synthesis of indoles from anilines and epoxides
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A general synthetic route to indoles from readily available anilines and epoxides by using ruthenium catalysis is described. This straightforward transformation allows a variety of indoles to be obtained in good yields by using [Ru3(CO)12]/1,1-bis(diphenylphosphino)ferrocene as the catalytic system. Water and hydrogen are formed as the only stoichiometric by-products, making this process highly atom efficient.
- Pena-Lopez, Miguel,Neumann, Helfried,Beller, Matthias
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supporting information
p. 1818 - 1824
(2014/03/21)
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- Nickel-catalyzed N-arylation of benzophenone hydrazone with bromoarenes
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A nickel-catalyzed method for the cross-coupling of benzophenone hydrazone with aryl bromides is described. The use of a simple Ni(ii)/NHC catalyst leads to the arylated hydrazones in good or acceptable yields. This protocol provides a simple, convenient alternative to the synthesis of arylhydrazines.
- Wu, Wei,Fan, Xin-Heng,Zhang, Li-Peng,Yang, Lian-Ming
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p. 3364 - 3367
(2014/01/06)
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- Mild, efficient Fischer indole synthesis using 2,4,6-trichloro-1,3,5- triazine (TCT)
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Mild and efficient protocol for the Fischer indole synthesis using TCT has been described. TCT serves as a mild and inexpensive catalyst. Under these conditions several functional groups such as ester, cyano, sulfone, amides, and ethers are tolerated. By this method, many functionalized analytically pure indoles were prepared easily without the need of purification.
- Siddalingamurthy, Eranna,Mahadevan, Kittappa M.,Masagalli, Jagadeesh N.,Harishkumar, Hosanagara N.
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supporting information
p. 5591 - 5596
(2013/09/23)
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- Highly enantioselective hydrogenation of N-unprotected indoles using (S)-C10-BridgePHOS as the chiral ligand
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(S)-C10-BridgePHOS was successfully applied to a highly efficient Pd-catalyzed enantioselective hydrogenation of substituted indoles. The methodology was suitable for the hydrogenation of indoles substituted at the 2-, 3- and 2,3-positions. Products were obtained in quantitative conversion and up to 98% ee. The role the 2-position substituent plays in the hydrogenation process has been proposed. The methodology could be used as an alternative method to synthesize extremely important chiral indolines from N-unprotected indoles.
- Li, Chao,Chen, Jianzhong,Fu, Guanghong,Liu, Delong,Liu, Yangang,Zhang, Wanbin
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supporting information
p. 6839 - 6844
(2013/07/26)
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- A microwave-assisted, propylphosphonic anhydride (T3P) mediated one-pot Fischer indole synthesis
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A rapid, mild, and high yielding protocol for the Fischer indolization of arylhydrazines with T3P under microwave irradiation is described. Significant features of this method include short reaction times and preparative ease.
- Desroses, Matthieu,Wieckowski, Krzysztof,Stevens, Marc,Odell, Luke R.
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supporting information; experimental part
p. 4417 - 4420
(2011/09/19)
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- Efficient and straightforward synthesis of tetrahydrocarbazoles and 2,3-dimethyl indoles catalyzed by CAN
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A simple protocol was established to synthesize 2,3-dialkyl indoles and various tetrahydrocarbazoles via Fischer indole synthesis. This method uses ceric ammonium nitrate as a catalyst for the Fischer indole synthesis with substituted phenyl hydrazine hydrochlorides and 2-butanone, phenyl propanal, and cyclohexanone. This process is a practical synthetic method for the preparation of various 2,3-disubstituted alkyl indoles and tetrahydrocarbazoles. Copyright Taylor & Francis Group, LLC.
- Varma, P. Prabhakara,Sherigara, Bailure S.,Mahadevan, Kittapa M.,Hulikal, Vijaykumar
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experimental part
p. 158 - 165
(2009/04/07)
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- Antimony (III) sulfate catalyzed one-pot synthesis of 2,3- disubstitutedindoles
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A novel one-pot Fischer indole synthesis approach has been developed by using antimony (III) sulfate as the catalyst. Good yields were obtained after reacting phenylhydrazines hydrochlorides and ketones in refluxing methanol. The exclusive formation of 2,3- disubstituted indoles was observed in the reaction of ethyl methyl ketone with phenylhydrazines. One-pot synthesis of indole-3-propanol using dihydropyran has also been described. The use of reusable antimony (III) sulfate as a catalyst makes this method both economically and environmentally friendly.
- Srinivasa,Mahadevan,Varma, P. Prabhakara,Sudhakara
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experimental part
p. 1843 - 1853
(2010/02/28)
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- Bismuth nitrate promoted fischer indole synthesis: A simple and convenient approach for the synthesis of alkyl indoles
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A novel one-pot fisher indole synthesis approach has been developed by using bismuth nitrate as a catalyst. Yields around 90-95% were obtained after reaction in methanol at reflux temperature in 20-40 min. Apart from the mild reaction conditions of the process and its excellent results, the simplicity of product isolation and the possibility to recycle the bismuth nitrate offers a significant advantage.
- Sudhakara, Aralihalli,Jayadevappa, Honnali,Kumar, Hosanagara N.H.,Mahadevan, Kittappa M.
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scheme or table
p. 159 - 164
(2010/04/23)
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- Pyridocarbazole derivatives having cGMP-PDE inhibitory activity
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PCT No. PCT/JP97/01829 Sec. 371 Date Jan. 29, 1998 Sec. 102(e) Date Jan. 29, 1998 PCT Filed May 29, 1997 PCT Pub. No. WO97/45427 PCT Pub. Date Dec. 4, 1997The invention relates to novel pyridocarbazole derivatives having highly selective action in inhibiting cyclic GMP-phosphodiesterase (hereinafter abbreviated as cGMP-PDE), processes for producing such derivatives, agents containing at least one of such derivatives as an active ingredient for preventing and/or treating pulmonary hypertension, ischemic heart diseases or diseases against which the cGMP-PDE inhibitory action is effective, and intermediates useful for the production of pyridocarbazole derivatives.
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- Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles
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The complex base NaNH2-t-BuONa allowed expeditious syntheses of indoles by arynic cyclisation of imines or enaminoketones prepared from halogeno anilines and carbonyl derivatives. Unstable imines may be used without purification, complex bases being unsensitive to impurities. It is showed that this kind of reaction may be applied to mixture of substrates suitably halogenated on the benzene ring. Formation of three components aggregates is proposed to explain a number of observations.
- Caubere, Catherine,Caubere, Paul,Ianelli, Sandra,Nardelli, Mario,Jamart-Gregoire, Brigitte
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p. 11903 - 11920
(2007/10/02)
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- β-Lactam series compound and antibacterial pharmaceutical composition containing the same
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A β-lactam series compound represented by the formula (I): STR1 wherein R1 represents a hydrogen atom or a lower alkyl group; R2 represents a hydrogen atom; R3 represents a halogen atom, a nitro group, an amino group, a hydroxy group, a lower alkyl group, a lower alkoxy group, a lower alkanoylamino group, a lower alkanesulfonyloxy group or a group represented by the formula STR2 where R5 represents a hydrogen atom, a lower alkanoyl group, or a lower alkanesulfonyl group; R4 represents a hydrogen atom or a hydroxy group; n is 0 or 1; l is 0, 1 or 2; and A represents --C(CH3)2 --CH(COOH)-- or --CH2 C(CH2 R6)=C(COOH)-- where R6 represents a lower alkanoyloxy group, a group represented by the formula STR3 where R7 and R8 each represents a lower alkyl group and when n is 0, R1 and R2 can combine to form a cyclohexane ring together with the carbon atoms to which they are attached, and pharmaceutically acceptable salts thereof as well as a method for preparing same are disclosed. These compounds have antimicrobial activity.
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- Pyrido[3,2,1-jk]carbazols
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A pyrido[3,2,1-jk]carbazol derivative represented by the formula (I) STR1 wherein R represents a hydroxy group, an alkoxy group which may be substituted with a halogen atom or with a 4-methyl-1-piperidinyl group, a hydrazino group or a STR2 group, Y represents an alkoxy group, a halogen atom, a nitro group, an amino group, an alkanoylamino group or alkyl group, and n is 0, 1 or 2; and the pharmaceutically acceptable salts thereof having antimicrobial, anti-cancer and antiviral activities, and a process for preparing the same.
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