- An Efficient, Eco-Friendly Synthesis of Pyran Annulated Indole Analogs under Conventional Heating and Microwave Irradiation, and Their Anticancer and Antioxidant Activity
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A rapid, facile, green, eco-friendly, cost effective, and efficient method for the synthesis of pyran annulated indole analogs via one-pot, three components reaction is developed. According to the developed method 2,5-disubstituted-1H-indol-3-carboxaldehyde, malononitrile and various phenols react under MW assisted solvent-free conditions. These compounds can be also prepared under a conventional method that is characterized by some disadvantages in comparison with the above approach. Structures of products are confirmed by FT-IR, 1H and 13C NMR, and mass spectral data. The in vitro antioxidant and cytotoxic activities of the products are evaluated against three tumor cell lines and discussed in terms of structure―activity analysis. Among the screened compounds 3d, 4a, 4b, 5a, and 5b exhibit excellent antioxidant activity. Compounds 4b, 5a, and 5b demonstrate strong cytotoxic activity.
- Rathod,Biradar
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- A CONVENIENT SYNTHETIC METHOD OF 2-SUBSTITUTED INDOLES AND ITS APPLICATION FOR THE SYNTHESIS OF NATURAL ALKALOID, BORRERINE
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A simple synthetic method of 2-substituted indoles is developed.Total synthesis of natural alkaloid, borrerine, is also reported
- Somei, Masanori,Sayama, Shinsuke,Naka, Katsumi,Yamada, Fumio
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- Molecular iodine mediated oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups into aldehydes
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The oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups is achieved by employing molecular iodine as a mild oxidizing agent under ambient conditions in the presence of a mild base. The important reaction of C3 formylation of free NH and substituted indoles containing various substituents is accomplished from the corresponding Mannich bases. This methodology can also be extended for the synthesis of aryl and other heteroaryl aldehydes and ketones. Furthermore, the usefulness of the method is successfully demonstrated on a gram scale.
- Mandrekar, Ketan S.,Tilve, Santosh G.
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supporting information
p. 4152 - 4155
(2021/03/15)
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- Investigation of indole functionalized pyrazoles and oxadiazoles as anti-inflammatory agents: Synthesis, in-vivo, in-vitro and in-silico analysis
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There are several potential side and adverse effects are found to be associated with the anti-inflammatory drugs in clinical practice. The long-term use of these clinical agents highly unsafe. It encouraged the development of novel heterocyclic compounds with potential anti-inflammatory activity and low to no toxicity. In present investigation, a total of 12 indole functionalized pyrazole and oxadiazole derivatives were designed, synthesized and evaluated for the in-vivo anti-inflammatory and analgesic potential. These compounds displayed comparable anti-inflammatory and analgesic potential to the reference drugs. Finally, molecular docking analysis was performed considering different anti-inflammatory targets to determine the mechanistic target of the designed molecules. Detailed analysis suggested that the molecules inhibit COX-2, preferably over other anti-inflammatory targets. The results suggested that two compounds (15c and 15f) were found promising candidates for the development of novel anti-inflammatory agents.
- Kumar, Devendra,Kumar, Ravi Ranjan,Pathania, Shelly,Singh, Pankaj Kumar,Kalra, Sourav,Kumar, Bhupinder
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- Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide
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Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.
- Lin, Jin-Hong,Xiao, Ji-Chang,Zhu, Yu-Rong
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supporting information
(2021/11/22)
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- C3-Formylation of Indoles in Continuous Flow
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We have developed a continuous flow C3-formylation technique for indoles using hexamethylenetetramine (HMTA) and iodine. A mixed solvent system of DMF–H2O (1:1, vol/vol) completely dissolves reagents and prevents clogging of microchannels during fluid flow. The continuous flow technique provides maximized mixing and excellent heat transfer efficiency. Thus, flow chemistry accelerates the rate of C3-formylation of indoles in the absence of a strong acid, base, or metal catalyst. We show that high yields of C3-formylated indoles (up to 83%) can be obtained at 150°C when the residence time is as low as 8 min.
- Sung, Ha Kyoung,Kim, Dong Hyun,Kim, Joon Seok,Park, Chan Pil
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supporting information
p. 388 - 392
(2020/12/30)
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- ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present application relates to an organic electroluminescent compound represented by chemical formula 1, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present application having good thermal stability, it is possible to provide the organic electroluminescent device having lower driving voltage, high luminous efficiency and/or long lifespan characteristics compared with an existing organic electroluminescent device.COPYRIGHT KIPO 2020
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- Discovery of novel multi-substituted benzo-indole pyrazole schiff base derivatives with antibacterial activity targeting DNA gyrase
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The design and synthesis of novel multi-substituted benzo-indole pyrazole Schiff base derivatives of potent DNA gyrase inhibitory activity were the main aims of this study. All the novel synthesized compounds were examined for their antibacterial activities against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, and Salmonella. In addition, we selected 20 compounds for the in vitro antibacterial activities assay of 6 drug-resistant bacteria strains. The result revealed compound 8I-w exhibited excellent antibacterial activity against 4 drug-resistant E. coli bacteria strains with IC50 values of 7.0, 17.0, 13.5, and 1.0 μM, respectively. In vitro enzyme inhibitory assay showed that compound 8I-w displayed potent inhibition against DNA gyrase with IC50 values of 0.10 μM. The molecular docking model indicated that compounds 8I-w can bind well to the DNA gyrase by interacting with various amino acid residues. This study demonstrated that the compound 8I-w can act as the most potent DNA gyrase inhibitor in the reported series of compounds and provide valuable information for the commercial DNA gyrase inhibiting bactericides.
- Cao, Hai-Qun,Chu, Zhi-Wen,Liu, Hao,Lv, Xian-Hai,Xia, Dong-Guo
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- Method for microwave-assisted preparation of 2-phenyl-3-formylindole compound
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The invention discloses a method for microwave-assisted preparation of a 2-phenyl-3-formylindole compound. The method comprises: carrying out a complete reaction on an aniline compound, acrolein and abrominated benzene compound by using an organic solvent
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Paragraph 0017-0018
(2019/08/01)
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- Anti-cancer, anti-oxidant and molecular docking studies of thiosemicarbazone indole-based derivatives
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Based on the structural elements of bioactive 3-substituted indoles, a new series of indole–thiosemicarbazone hybrid derivatives were designed, synthesized, and well-characterized using different spectral techniques. The intended scaffolds were screened for their in vitro anti-proliferative activities against breast cancer (MCF-7), lung cancer (A-549), and liver cancer (Hep-G2) cell lines, as well as their anti-oxidant properties. Cytotoxicity studies revealed that compound 6n was the most potent, at least threefold more potent than the commercially available reference drug etoposide, against A-549. In addition, morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis confirmed induction of apoptosis in the A-549 cells by compound 6n. In order to validate the experimental results, molecular studies were performed to achieve the possible binding interactions of the most potent compound (6n) and colchicine with tubulin as well as ANP with ATPase domain of topoisomerase IIα active sites. Moreover, the radical scavenging potential of the final derivatives was found to be excellent with the range of 0.015–0.630?μM, comparable to the standard ascorbic acid (0.655?μM).
- Bakherad, Zohreh,Safavi, Maliheh,Fassihi, Afshin,Sadeghi-Aliabadi, Hojjat,Bakherad, Mohammad,Rastegar, Hossein,Ghasemi, Jahan B.,Sepehri, Saghi,Saghaie, Lotfollah,Mahdavi, Mohammad
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p. 2827 - 2854
(2019/03/13)
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- Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study
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In this work, two novel series of indole-thiosemicarbazone derivatives were designed, synthesized, and evaluated for their cytotoxic activity against MCF-7, A-549, and Hep-G2 cell lines in comparison to etoposide and colchicine as the reference drugs. Generally, the synthesized compounds showed better cytotoxicity towards A-549 and Hep-G2 than MCF-7. Among them, (2E)-2-{[2-(4-chlorophenyl)-1H-indol-3-yl]methylidene}-N-(4-methoxyphenyl)hydrazinecarbothioamide (8l) was found to be the most potent compound against A-549 and Hep-G2, at least three times more potent than etoposide. The morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that compound 8l induced apoptosis in A-549 cells. Moreover, molecular docking methodology was exploited to elucidate the details of molecular interactions of the studied compounds with putative targets.
- Bakherad, Zohreh,Safavi, Maliheh,Fassihi, Afshin,Sadeghi-Aliabadi, Hojjat,Bakherad, Mohammad,Rastegar, Hossein,Saeedi, Mina,Ghasemi, Jahan B,Saghaie, Lotfollah,Mahdavi, Mohammad
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- Preparation of some novel imidazopyridine derivatives of indole as anticancer agents: one-pot multicomponent synthesis, biological evaluation and docking studies
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A series of novel imidazopyridine derivatives of indole has been synthesized. All the synthesized derivatives were evaluated for their antiproliferative activity against A-549, T-47D, Hep-G2 and MCF-7 human cancer cell lines. The results demonstrated that some of these derivatives exhibited moderate to excellent cytotoxic activities. Compounds 7a having a cyclohexyl ring substituted to the second amine of imidazopyridyl moiety and phenyl ring of the C-2 indole ring and 7f with a para-methylphenyl ring at the same position exhibited the highest activity against the A-594 cell line with IC50 of 11.48?μM and 10.66?μM, respectively. The results indicate that compounds 7a and 7f are more cytotoxic towards cancer cell lines compared with etoposide in vitro. In addition, compounds, 7d and 7j showed the most potent activity against Hep-G2, equal to etoposide as the standard drug. Also, most of the compounds were inactive against the T-47D and MCF-7 cell lines. The morphological analysis by the acridine orange/ethidium bromide double-staining test and flow cytometry analysis indicated that compounds 7a and 7f induced apoptosis in A-549 cells. Furthermore, in silico and in vitro results of the synthesized compounds showed good correlation with each other. Molecular docking results of the compounds of the 7a–k series with the cyclohexyl ring substituted to the second amine of the imidazopyridyl moiety compared with the 7l–t members with the t-butyl group at the same position confirmed the effect of the higher lipophilicity on hydrophobic interactions with the studied enzymes. Moreover, all the compounds showed higher affinity to tubulin than topoisomerase IIα enzyme.
- Bakherad, Zohreh,Safavi, Maliheh,Sepehri, Saghi,Fassihi, Afshin,Sadeghi-Aliabadi, Hojjat,Bakherad, Mohammad,Rastegar, Hossein,Larijani, Bagher,Saghaie, Lotfollah,Mahdavi, Mohammad
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p. 5261 - 5290
(2019/07/19)
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- Green approach for the synthesis of 3-methyl-1-phenyl-4-((2-phenyl-1H-indol 3-yl)methylene)-1H-pyrazole-5(4H)-ones and their DNA Cleavage, antioxidant, and antimicrobial activities
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3-Methyl-1-phenyl-4-((2-phenyl-1H-indol-3-yl)methylene)-1H-pyrazol-5(4H)-ones (5a-i) was prepared by the condensation reaction of different 3-formyl-2-phenylindole derivatives (2a-i) and 3-methyl-1-phenyl-2-pyrazoline-5-one in quantitative yield by applying various green synthetic methods as grinding, microwave irradiation using different catalysts under solvent-free mild reaction conditions with high product yields. The structures of the synthesized compounds were characterized on the basis of elemental analysis, infrared, 1HNMR, 13C NMR, and mass spectral data. The synthesized compounds were screened for free radical scavenging, antimicrobial, and DNA cleavage activities. Most of the tested compounds belonging to the 3-methyl-1-phenyl-4-((2-phenyl-1H-indol-3-yl)methylene)-1H-pyrazol-5(4H)-ones series exhibited promising activities.
- Modi, Madhuri,Jain, Meenakshi
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p. 3303 - 3312
(2019/11/03)
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- Synthesis of 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed cyclization of indole-3-carbaldehyde oximes
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A new method for synthesizing 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed intramolecular electrophilic amination of 2-arylindole-3-carbaldehyde O-acetyl oximes was developed.
- Aksenov,Gasanova,Prokonov, F. Yu.,Aksenov,Abakarov,Aksenov
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p. 2262 - 2270
(2020/02/15)
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- Access to Polycyclic Sulfonyl Indolines via Fe(II)-Catalyzed or UV-Driven Formal [2 + 2 + 1] Cyclization Reactions of N-((1H-indol-3-yl)methyl)propiolamides with NaHSO3
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A variety of structurally novel polycyclic sulfonyl indolines have been synthesized via FeCl2-catalyzed or UV-driven intramolecular formal [2 + 2 + 1] dearomatizing cyclization reactions of N-(1H-indol-3-yl)methyl)propiolamides with NaHSO3 in an aqueous medium. The reactions involve the formation of one C-C bond and two C-S bonds in a single step.
- Lu, Lin,Luo, Chenguang,Peng, Hui,Jiang, Huanfeng,Lei, Ming,Yin, Biaolin
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supporting information
p. 2602 - 2605
(2019/04/30)
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- A copper(ii)-catalyzed annulative formylation of o-alkynylanilines with DMF: a single-step strategy for 3-formyl indoles
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In this paper, a copper(ii)-catalyzed reaction of o-alkynylanilines with dimethylformamide (DMF) in the presence of oxygen has been developed for synthesizing multisubstituted 3-formyl indole scaffolds. This one-pot reaction proceeds through a cascade 5-endo-dig cyclization followed by formylation to construct 1,2-disubstituted 3-formyl indoles. The key aspects of this synthesis method are the broad substrate scope (with 38 examples), and well tolerating various functional groups. In addition, a detailed mechanism has been proposed, where DMF may serve as a carbon source for the in situ C3 formylation of the obtained indole derivatives.
- Ganesan, Balaji,Senadi, Gopal Chandru,Guo, Bing-Chun,Hung, Min-Yuan,Lin, Wei-Yu
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p. 40968 - 40973
(2019/01/03)
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- Selective nickel-catalyzed dehydrogenative-decarboxylative formylation of indoles with glyoxylic acid
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Herein we present a new strategy for the dehydrogenative-decarboxylative coupling of indoles with glyoxylic acid. A broad range of indoles were transformed into the corresponding 3-formylindoles in moderate to good yields and excellent functional group tolerance. Notably, no N-formylation product was detected under our conditions.
- Yin, Zhiping,Wang, Zechao,Wu, Xiao-Feng
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supporting information
p. 3707 - 3710
(2018/05/31)
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- Method for synthesizing indole -3 - formaldehyde compounds (by machine translation)
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The invention relates to a synthetic indole - 3 - formaldehyde compounds, which belongs to the technical field of organic synthesis. The invention will be indole compound, hexamethylene tetramine, crystalline aluminum trichloride, N, N - dimethyl formamide in proportion in 120 °C reaction under the condition of 1 - 20 the H, then filtered, washing, filtering, concentrating, column chromatography purification and other after-treatment technology, make the refined indole - 3 - formaldehyde compound. The invention overcomes the indole - 3 - benzaldehyde compound of preparation need to use not stabilized peroxide, and for a long time under the high temperature reaction of the defect. And the invention uses the advantages of simple equipment, product yield is high, the resulting yield of a target product can be up to 94%. In addition, the invention relates to a low reaction conditions, less catalyst levels, low energy consumption, the post treatment process is simple and easy to use, without the need of using a high dosage of acid or alkali, post-processing the solvent can be recovered and recycled, industrial "three wastes" is discharged little, suitable for large-scale production. (by machine translation)
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Paragraph 0041-0044; 0048-0049
(2018/08/28)
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- Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air
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An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.
- Wang, Qing-Dong,Zhou, Bin,Yang, Jin-Ming,Fang, Dong,Ren, Jiangmeng,Zeng, Bu-Bing
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supporting information
p. 2670 - 2674
(2017/10/06)
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- Chiral Phosphoric Acid Catalyzed Intramolecular Dearomative Michael Addition of Indoles to Enones
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An enantioselective intramolecular dearomative Michael addition of indolyl enones is presented. In the presence of catalytic amount of chiral phosphoric acid, various enantioenriched spiro-indolenines bearing a quaternary stereogenic center were obtained
- Zhou, Yong,Xia, Zi-Lei,Gu, Qing,You, Shu-Li
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supporting information
p. 762 - 765
(2017/03/01)
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- An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives
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An environmentally friendly and efficient protocol (KX/oxone) for oxidative halocyclization of tryptamine/tryptophol derivatives was developed and demonstrated with 28 examples and concise total synthesis of cyclotryptamine alkaloid protubonines A and B. The distinct advantage of this protocol over all previous methods is that no organic byproduct is generated from a halogenating agent or oxidant, thus greatly reducing the environmental impact of halocyclization and facilitating the post-reaction purification.
- Xu, Jun,Tong, Rongbiao
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supporting information
p. 2952 - 2956
(2017/07/24)
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- Iodine-catalyzed C3-formylation of indoles using hexamethylenetetramine and air
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An efficient iodine-catalyzed chemoselective 3-formylation of free (N–H) and N-substituted indoles was achieved by using hexamethylenetetramine (HMTA) in the presence of activated carbon under air atmosphere. This new method could provide 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this catalytic formylation of indoles procedure can be applied to gram-scale synthesis.
- Wang, Qing-Dong,Yang, Jin-Ming,Fang, Dong,Ren, Jiangmeng,Zeng, Bu-Bing
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supporting information
p. 2877 - 2880
(2017/07/11)
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- Selective synthesis of indazoles and indoles via triazene-alkyne cyclization switched by different metals
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We described two orthogonal heterocycle syntheses, where an arene bearing both an alkyne and a triazene functionality underwent two distinct cyclization pathways mediated by different transition metals. Starting from the same substrates, a synthesis of 2H
- Fang, Yan,Wang, Chengming,Su, Shengqin,Yu, Haizhu,Huang, Yong
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p. 1061 - 1071
(2014/02/14)
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- Silica-supported ceric ammonium nitrate catalyzed chemoselective formylation of indoles
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Selective formylation of free (N-H) indoles at C3 can be achieved by using formylating species generated from hexamethylenetetramine (HMTA) and silica-supported ceric ammonium nitrate (CAN-SiO2). The use of a catalytic amount of this solid-supported reagent was found to be compatible with a range of substituents on the indoles and generated the corresponding products with good yields. A plausible mechanism for the formylation involving an electron transfer process is discussed.
- Tongkhan, Sukanya,Radchatawedchakoon, Widchaya,Kruanetr, Senee,Sakee, Uthai
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p. 3909 - 3912
(2014/07/08)
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- Unconventional stereoselective one-pot synthesis of Knoevenagel-type indoles via in situ condensation of iminium salts with active methylene reagents in memory of Professor Angelo Ranise
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A simple one-pot procedure for the stereoselective synthesis of Knoevenagel-type indoles is described. The method is based on the in situ reaction of indole iminium salts (four of them are fully characterized) with acyclic symmetrical and unsymmetrical active methylene reagents in the presence of triethylamine. In general, the overall yields are moderate to good. Some of relevant reaction parameters and steric effects affecting stereoselectivity are discussed.
- Ranise, Angelo,Lucchesini, Francesco,Caviglia, Matteo,Alfei, Silvana,Spallarossa, Andrea,Caneva, Chiara
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p. 10858 - 10868
(2014/01/06)
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- Synthesis of some bisindolyl analogs for in vitro cytotoxic and DNA cleavage studies
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One-pot, three components, conventional and microwave-assisted synthesis of bisindolyl analogs is described. Michael addition of preformed 2,5-disubstituted indole-3-carboxaldehydes and 3-methyl-1H-pyrazol-5(4H)-one with 2,5-disubstituted indoles under solvent and catalyst-free conditions afforded the hitherto unreported 2,5-disubstituted bisindolyl analogs bearing a pyrazolone moiety in excellent yields. All the synthesized compounds were characterized using IR, 1H NMR, mass spectral, and analytical data. The analogs were screened for in vitro cytotoxic and DNA cleavage studies. Among the screened compounds 4c, 4f, and 4h-4j have emerged as most potent cytotoxic and 4c and 4f-4h as active DNA cleavage analogs.
- Sasidhar,Biradar
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p. 3518 - 3526
(2013/07/11)
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- Synthesis of 1H-Indol-3-ylpyrazole derivatives from 1,3,5-triketones and arylhydrazines: One-pot construction of pyrazole and indole rings
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The reaction of 1,3,5-triketones and arylhydrazines provided indolylpyrazole derivatives in a one-pot reaction in good to moderate yields. Both the pyrazole and indole rings were constructed simultaneously with phenylhydrazine, RCOCH2CO- moiety for the py
- Kim, Sung Hwan,Lee, Sangku,Kim, Se Hee,Kim, Ko Hoon,Kim, Jae Nyoung
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p. 3415 - 3419
(2014/01/06)
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- Cyanine-like dyes with large bond-length alternation
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Herein, the synthesis and properties of alkyne-bridged carbocations, which are analogous in structure to cyanine dyes, are reported. An alkene-bridged dye, linked at the third position of the indole, was also synthesized as a reference compound. These new carbocations are stable under ambient conditions, allowing characterization by UV/Vis and NMR (1H and 13C) spectroscopies. These techniques revealed a large degree of delocalization of the positive charge, similar to a previously reported porphyrin carbocation. The linear and nonlinear optical properties are compared with cyanine dyes and triarylmethyl cations, to investigate the effects of the bond-length alternation and the overall molecular geometry. The value of Re(γ), the real part of the third-order microscopic polarizability, of -1.3×10-33 esu for the alkyne-linked cation is comparable to that of a cyanine dye of similar length. Nondegenerate two-photon absorption spectra showed that the alkene-bridged dye exhibited characteristics of cyanines, whereas the alkyne-bridged dye is reminiscent of octupolar chromophores, such as the triarylmethyl carbocation brilliant green. Such attributes were confirmed and rationalized by quantum chemical calculations. Copyright
- Thorley, Karl J.,Hales, Joel M.,Kim, Hyeongeu,Ohira, Shino,Bredas, Jean-Luc,Perry, Joseph W.,Anderson, Harry L.
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p. 10370 - 10377
(2013/09/02)
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- Regioselective synthesis of 4-substituted indoles via C-H activation: A ruthenium catalyzed novel directing group strategy
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A highly regioselective functionalization of indole at the C-4 position by employing an aldehyde functional group as a directing group, and Ru as a catalyst, under mild reaction conditions (open flask) has been uncovered. This strategy to synthesize 4-substituted indoles is important, as this class of privileged molecules serves as a precursor for ergot alkaloids and related heterocyclic compounds.
- Lanke, Veeranjaneyulu,Ramaiah Prabhu, Kandikere
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supporting information
p. 6262 - 6265
(2014/01/17)
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- Synthesis and biological evaluation of novel indolyl isoxazoline derivatives as analgesic and antiinflammatory agents
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A series of 3-(2-(4-substituted phenyl)-1H-indol-3-yl)-1-(4-substituted phenyl)prop-2-en-1-one 3(a-l) were synthesized from substituted indole aldehydes. Using hydroxylamine hydrochloride the chalcones 3(a-l) were cyclized to afford a novel series of 2-(4-substituted phenyl)-3-(3-(4-substituted phenyl)-4,5-dihydroisoxazol-5-yl)-1H-indole 4(a-l). The structure of all these compounds were established on the basis of spectral (IR, 1H NMR) studies. The compounds 4(a-l) were evaluated for the antiinflammatory and analgesic activity by using different pharmacological models. The most active compounds were subjected to acute ulcerogenesis activity and were found to be less ulcerogenic than the reference drug indomethacin.
- Chavan,Khadke
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p. 2711 - 2716
(2012/09/10)
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- Microwave-Assisted synthesis of 30-indolyl substituted 4H-chromenes catalyzed by DMAP and their antimicrobial activity
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A new series of indole-based chromene derivatives 4a-4p has been synthesized by one pot cyclocondensation reaction of 2-phenyl-1H-indole-3- carbaldehyde 1a-1h; malononitrile 2; and 1,3-cyclohexanedione/dimedone 3a/b under microwave irradiation catalyzed by an organocatalyst 4-(N,N-dimethylamino) pyridine. Easy experimental procedure, high yield, selectivity, and shorter reaction time are the imperative features of this method. All the compounds were screened against a representative panel of bacteria and fungi. Some of the compounds are found to be equipotent or more potent than that of standard drugs as evident from SAR study. Springer Science+Business Media, LLC 2011.
- Kathrotiya, Harshad G.,Patel, Manish P.
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p. 3406 - 3416
(2013/02/25)
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- Synthesis, single crystal X-ray studies and antimicrobial activities of novel Indole barbiturates
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A novel series of N-substituted 2-phenyl indole derivatives incorporating barbituric acid have been synthesised and the chemical structures of the resulting molecules were characterised by means of IR, NMR and mass spectra. The antimicrobial activities of these compounds were investigated. Significant improvement in the antimicrobial activity can be achieved, in the presence of Cl and Br substituents on phenacyl moiety at para position. Single crystal X-ray analysis was also performed for the compound 6b in order to determine the crystal structure. Springer Science+Business Media, LLC 2011.
- Laxmi, S. Vijaya,Janardhan,Rajitha,Raghavaiah,Srinivas, Prathima
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p. 2896 - 2901
(2012/10/30)
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- The copper-catalyzed C-3-formylation of indole C-H bonds using tertiary amines and molecular oxygen
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A copper-catalyzed formylation reaction has been developed by employing oxygen (O2) as the clean oxidant. The C-H bonds of indoles were C-3-formylated by tetramethylethylenediamine (TMEDA) and water (H2O; in situ formed and external added water) as the carbonyl source in moderate to good yields with good functional group tolerance. Thus, it represents a facile procedure leading to 3-formylindoles. Copyright
- Chen, Jianbin,Liu, Bin,Liu, Dongfang,Liu, Shan,Cheng, Jiang
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supporting information
p. 2438 - 2442
(2012/11/07)
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- 2-Indolyl Imidazo [4,5-d] Phenanthroline Derivatives and Their Use in the Treatment for Cancer
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2-indolyl imidazo[4,5-d]phenanthroline compounds of Formula I that are capable of intracellular chelation of transition metals and of exerting antiproliferative effects in cancer cells, that are cytostatic and/or cytotoxic, are provided. Compounds of Form
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Page/Page column 32
(2010/07/08)
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- Novel benzofuran-3-one indole inhibitors of PI3 kinase-α and the mammalian target of rapamycin: Hit to lead studies
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A series of benzofuran-3-one indole phosphatidylinositol-3-kinases (PI3K) inhibitors identified via HTS has been prepared. The optimized inhibitors possess single digit nanomolar activity against p110α (PI3K-α), good pharmaceutical properties, selectivity versus p110γ (PI3K-γ), and tunable selectivity versus the mammalian target of rapamycin (mTOR). Modeling of compounds 9 and 32 in homology models of PI3K-α and mTOR supports the proposed rationale for selectivity. Compounds show activity in multiple cellular proliferation assays with signaling through the PI3K pathway confirmed via phospho-Akt inhibition in PC-3 cells.
- Bursavich, Matthew G.,Brooijmans, Natasja,Feldberg, Lawrence,Hollander, Irwin,Kim, Stephen,Lombardi, Sabrina,Park, Kaapjoo,Mallon, Robert,Gilbert, Adam M.
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scheme or table
p. 2586 - 2590
(2010/06/19)
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- A versatile synthetic route to 11H-indolo[3,2-c]isoquinolines
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A wide variety of indoloisoquinoline derivatives are prepared from the acid-catalyzed cyclization of 3-amido-2-phenylindoles, which in turn were obtained from the Beckmann rearrangement of 2-phenylindole-3-oximes.
- Qu, Ji,Kumar, Naresh,Alamgir, Mahiuddin,Black, David StC.
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scheme or table
p. 5628 - 5630
(2011/02/22)
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- Creation of new promoters for plant's root growth: its application for the syntheses of vulcanine and borreline, and for combating desertification at gobi desert in inner mongolia 1#
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Abstract - Various new 2-substituted indole-3-carbaldehydes are prepared. Structurally related alkaloids, vulcanine and borreline, are synthesized as well. Among the compounds, 2-haloindole-3-carbaldehydes are found to be potent promoters of plant's root growth. Its successful preliminary application is reported for making Gobi desert in Inner Mongolia full of plant.
- Somei, Masanori,Sayama, Shinsuke,Naka, Katsumi,Shinmoto, Kotaro,Yamada, Fumio
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experimental part
p. 537 - 554
(2009/09/25)
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- Synthesis of benz[5,6]azepino[4,3-b]indoles by 1,7-electrocyclisation of azomethine ylides
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A new, general route to the benz[5,6]azepino[4,3-b]indole ring system has been developed via the 1,7-dipolar electrocyclisation reactions of azomethine ylides. A new, general route to the benz[5,6]azepino[4,3-b]indole ring system has been developed via the 1,7-dipolar electrocyclisation reactions of azomethine ylides derived from easily available 3-formyl indole derivatives. The intermediacy of azomethine ylides was shown by the trapping of the proposed α,β:γ,δ-conjugated dipole with N-phenylmaleimide.
- Nyerges, Miklós,Pintér, áron,Virányi, Andrea,Bitter, István,Toke, László
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p. 377 - 380
(2007/10/03)
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- Synthesis, spectral, and antimicrobial studies of 1-butyl-3-substituted-4-(2-aryl-1H-indol-3-yl)-2-azetidinones
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Ketene generated from acetyl chloride or chloroacetyl chloride adds on indolyl Schiff's base double bond to afford 1-butyl-3-substituted-4-(2-aryl-1H-indol-3-yl)-2-azetidinones in THF. The reaction proceeds stereospecifically via concerted trans cycloaddi
- Pathak, Vijai N.,Gupta, Ragini,Garg, Meenu
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p. 494 - 501
(2007/10/03)
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- 2-Substituted 3-aryl- and 3-heteroarylindoles by the palladium-catalyzed reaction of o-trifluoroacetanilides with aryl bromides and triflates
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The palladium-catalyzed reaction of aryl and heteroaryl bromides and triflates with o-alkynyltrifluoroacetanilides affords 2-substituted 3-aryl- and heteroarylindoles usually in excellent yield. The procedure can be applied to the synthesis of 2-substituted indole-3-carboxaldehydes.
- Cacchi, Sandro,Fabrizi, Giancarlo,Lamba, Doriano,Marinelli, Fabio,Parisi, Luca M.
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p. 728 - 734
(2007/10/03)
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- (1-Substituted-indol-3-yl) alkylidenehydrazinecarboximidamide derivatives as 5-hydroxytryptamine-6 ligands
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The present invention provides a compound of formula I and the use thereof for the therapeutic treatment of a disorder relating to or affected by the 5-HT6 receptor.
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- An unusual oxidation of gramine methiodides under NaNO2/DMF conditions
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Gramine methiodides of a few indoles undergo an unusual oxidation under NaNO2/DMF conditions to produce the corresponding indole-3-aldehydes.
- Sridar,Maheswari,Reddy
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p. 1253 - 1254
(2007/10/03)
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- Vilsmeier reagent for formylation in solvent-free conditions using microwaves
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POCl3-DMF over silica gel has been used for the synthesis of β-chlorovinylaldehydes (1-5), 2-aryl-3-formylindoles (6-8), 2-chloro-3-formylquinolines (9-13) and other aromatic aldehydes (14-20) using solvent-free conditions and microwave irradiation.
- Paul,Gupta,Gupta
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p. 1115 - 1118
(2007/10/03)
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- Methoxy-substituted 3-formyl-2-phenylindoles inhibit tubulin polymerization
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The aim of this study was the identification of the essential structural elements in the 12-formyl-5,6-dihydroindolo[2,1-a]isoquinoline system required for the inhibition of tubulin polymerization which is understood to be the predominant mode of action o
- Gastpar, Robert,Goldbrunner, Michael,Marko, Doris,Von Angerer, Erwin
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p. 4965 - 4972
(2007/10/03)
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- Synthesis and biological activities of some 2-substituted phenyl-3-(3-alkyl/aryl-5,6-dihydro-s-triazolo[3,4-b][1,3,4]thiadiazol-6-yl)indoles
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Some 2-substituted phenyl-3-(3-alkyl/aryl-5,6-dihydro-s-triazolo[3,4-b][1,3,4]thiadiazol-6-yl)indoles 3 have been synthesised by the condensation of 2-arylindole-3-aldehydes 1 with 3-substituted-4-amino-5-mercapto-1,2,4-triazoles 2 in DMF containing p-TsO
- Gupta, Rajive,Paul, Satya,Gupta, Avinash K.,Kachroo, P. L.,Bani, S.
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p. 707 - 710
(2007/10/03)
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- ADENOSINE DERIVATIVES, PREPARATION METHODS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
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The present invention relates to the derivatives of the formula STR1 and their addition salts, and to their use in therapeutics, especially as analgesics and as antihypertensives.
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- STUDIES ON THE SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF 5-(3'-INDOLAL)-2-THIOHYDANTOIN DERIVATIVES AS ALDOSE REDUCTASE ENZYME INHIBITORS
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A new series of 5-(3'-indolal)-2-thiohydantoin derivatives was synthesized and tested for the ability to inhibit bovine lens aldose reductase (AR) enzyme.The compounds were prepared by condensation of substituted indole-3-aldehyde derivatives with 2-thiohydantoin.The capacity of inhibiting the semi-purified bovine lens enzyme in vitro was observed for several of the compounds tested.One of them was found to be effective in reducing the enzyme activity compared with a corresponding well-known AR inhibitor.
- Bueyuekbingoel, Erdem,Suezen, Sibel,Klopman, Gilles
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p. 443 - 448
(2007/10/02)
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- New Evidence on the Formation of 3-Acylindoles by Reaction of N-Phenylnitrones with α,β-Acetylenic Sulfones
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N-Phenylnitrones react with α,β-acetylenic sulfones to give ultimately 3-acylindoles via unstable 4-sulfonyl-substituted 2,3-dihydroisoxazoles.In one case, a minor pathway is also operative leading to a different kind of indole derivative.Mechanistic possibilities are discussed.
- Broggini, Gianluigi,Diliddo, Dario,Zecchi, Gaetano
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- Fused Indoles. Synthesis of β-Carbolines and Azerinoindoles from 3-(2-Alkylindol-3-yl)-2-azidoacrylates
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Decomposition of the azidoacrylates (6) derived from 2-substituted indole-3-carbaldehydes gives pharmacologically important β-carbolines , azepinoindoles (13), or enamines (14) depending on the conditions.The formation of azepinoindoles, shown to proceed by cyclisation of the initially formed enamines, represents a new reaction of vinyl azides which is particularly favoured in the indole series.
- Moody, Christopher J.,Ward, John G.
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p. 2895 - 2901
(2007/10/02)
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