- Microwave-assisted multicomponent reaction: An efficient synthesis of indolyl substituted and spiroxindole pyrido[2,3-d]pyrimidine derivatives
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An efficient and catalyst-free protocol for the synthesis of a series of indole substituted or spiroxindole-consisted dihydropyrido[2,3-d]pyrimidine derivatives by one-pot three-component reaction of 2,6-diaminopyrimidin-4-one, various aryl aldehydes or isatins, and 3-cyanoacetyl indoles under microwave irradiation was investigated. The advantages of this methodology include high yields of products, short reaction time, easy work-up procedure and broad substrate scope.
- Wang, Jing,Zhu, Shuang,Liu, Yanni,Zhu, Xiaotong,Shi, Kexin,Li, Xiang,Zhu, Songlei
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- A combination of experimental and TD-DFT investigations on the fluorescent detection of sulfite and bisulfite ions in aqueous solution via nucleophilic addition reaction
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The selective detection of sulfite and bisulfite ions with anthracene-based compounds (CN1 and CN2) as chemo-dosimeters is reported using fluorescence changes in DMSO:HEPES (70:30%), v/v buffer solution (pH 7.4). Upon treatment with sulfite and bisulfite ions, the fluorescence of the probes gets enhanced significantly at 424 nm. The detection of these ions occurs through the nucleophilic addition at the vinylic C-atom of the probes, which terminates the photo-induced electron transfer (PET) process and consequently enhances the fluorescence. This detection mechanism is well supported by 1H NMR titration, HR-MS and DFT/TD-DFT calculations. The pseudo-first-order rate constants for the addition sulfite (at pH 7.4) and bisulfite (at pH 5) to CN1 are determined to be 3.22×10?3 and 5.02×10?3 s?1, respectively. The limits of detection for sulfite and bisulfite are found to be 1.85×10?7 and 1.56×10?7 M, respectively. The probe CN1 was successfully applied to the detection of bisulfite ion in real samples.
- Al-Sehemi, Abdullah G.,Elango, Kuppanagounder P.,Nandhini, C.,Pannipara, Mehboobali,Saravana Kumar, P.,Shanmugapriya, R.,Vennila, K. N.
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- Synthesis and Biological Evaluation of Indolyl Bis-chalcones as Anti-Breast Cancer and Antioxidant Agents
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A series of novel α-cyano substituted indolyl bis-chalcones (3a-l) has been synthesized and evaluated for their in vitro antitumor activity against the human breast cancer MCF7 (estrogen receptor-positive) and normal Vero cell lines using sulforhodamine B (SRB) assay method. Compounds 3a, 3c and 3d showed potent activity (GI50 = 11.7, 15.3 and 17.9 μM respectively) against the human breast cancer MCF7 cell line, which was almost as good as that of adriamycin (GI50 = 0.1 μM) whereas, screening against the normal Vero Monkey cell line showed moderate selectivity. Furthermore, all the synthesized compounds screened for their antioxidant potential against DPPH, NO, SOR, and H2O2 radicals. Most of the bis-chalcones exhibited significant DPPH (51.09-12.72 %) and NO (64.11-34.43 %) radical scavenging activity and modest activity against SOR (88.08-43.14 %) and H2O2 (80.13-56.0 %) radicals compared to the reference standard ascorbic acid (40.78 %, 42.63 %, 87.05 %, and 79.42 % respectively). Current study provides impetus for the development of highly potent indolyl bis-chalcone derivatives as anticancer leads.
- Bhale, Pravin S.,Bopalkar, Rajesh J.,Chavan, Hemant V.,Endait, Rupali S.,Gaikwad, Mandar S.,Kadam, Ashok T.
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- Synthesis of indolyl pyrazole scaffolds as potential anti-cancer agents and their molecular modelling studies
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Background: Indole and pyrazoles are one of the prime structural units in the field of medicinal chemistry and have been reported to exhibit a variety of biological activities specifically anti-cancer. In view of their medicinal significance, we synthesized a conjugate of the two moieties to get access to newer and potential anti-cancer agents. Methods: Indolyl pyrazoles [3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-(1-methyl-1H-indole-3-carbon yl)acrylonitriles] (4a-l) were synthesized by adopting simple and greener protocol and all the synthesized derivatives were docked against Bcl-2 protein and the selected chemical moieties were screened for their cytotoxicity by using the MTT assay. Results: All the synthesized compounds were docked against BCL-2 protein in order to understand their binding pattern. Among the 12 compounds docked, 4d, 4f, 4h, 4j, and 4l compounds exhibited better protein binding interactions and the same were screened for their anti-cancer activity against A549 (lung) cancer cell lines at a concentration of 100 μM using Doxorubicin as standard. Substitutions such as N-benzyl, N-ethyl groups and halogen groups such as Br, Cl on indole ring showed moderate activity against A-549 cell lines. Conclusion: Among the 5 indolyl pyrazole derivatives screened, compounds 4h and 4j showed significantly better activity with an IC50 of 33.12 and 34.24 μM, respectively. Further, structural tweaking of the synthesized new chemical entities may lead to potential hit/lead-like molecules.
- Gaddam, Ganga Reddy,Dubey, Pramod Kumar,Chittireddy, Venkata Ramana Reddy
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p. 828 - 839
(2020/07/10)
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- Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence
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A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.
- Adepu, Raju,Dhanaji, Jadhav Rahul,Samatha, Polasani,Mainkar, Prathama S.,Chandrasekhar, Srivari
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supporting information
p. 8224 - 8228
(2020/11/18)
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- EPAC1 ACTIVATORS AS HIV LATENCY REVERSAL AGENTS (LRA)
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The invention relates generally to novel EPAC1 activators, such as Formula I and the preparation thereof as well as the use of EPAC1 activators as human immunodeficiency virus (HIV) latency reversal agents (LRAs).
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- Synthesis of α-Ketoamides from β-Ketonitriles and Primary Amines: A Catalyst-Free Oxidative Decyanation–Amidation Reaction
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AN oxidative decyanation–amidation of β-ketonitriles and primary amines readily occurs using hydrogen peroxide sodium carbonate adduct (Na2CO3·1.5H2O2), K2CO3, and 1,4-dioxane. This reactio
- Zhang, Ya-Kai,Wang, Bin
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supporting information
p. 5732 - 5735
(2019/08/27)
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- Base-Promoted Tandem Cyclization for the Synthesis of Polyfunctional 2-Hydroxy-2,3-dihydrofurans from Arylglyoxal Monohydrates and 3-(1 H -Indol-3-yl)-3-oxopropanenitrile
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An efficient base-promoted tandem cyclization for the synthesis of polyfunctional 2-hydroxy-2,3-dihydrofurans from arylglyoxal monohydrates and 3-(1 H -indol-3-yl)-3-oxopropanenitrile has been established. The investigation of the mechanism suggested that this reaction proceeds through a Knoevenagel condensation-Michael addition-oxidation-cyclization sequence. This method demonstrates the compatibility with a wide range of functional groups to produce the 2-hydroxy-2,3-dihydrofuran scaffolds in good to excellent yields in one pot.
- Cai, Qun,Sheng, Hui-Yang,Li, Deng-Kui,Liu, Yi,Wu, An-Xin
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supporting information
p. 1926 - 1932
(2018/08/28)
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- Rh(iii)-Catalyzed dual C-H functionalization of 3-(1: H -indol-3-yl)-3-oxopropanenitriles with sulfoxonium ylides or diazo compounds toward polysubstituted carbazoles
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A rhodium-catalyzed annulation of 3-(1H-indol-3-yl)-3-oxopropanenitriles with sulfoxonium ylides or diazo compounds has been developed, leading to a series of polysubstituted carbazoles in moderate to good yields. This procedure proceeded with formal Rh(iii)-catalyzed (4 + 2) cycloaddition, with the functionalization of 2-C-H bonds of indole in a step-economical procedure. Additionally, this reaction could also be conducted under acidic conditions when diazo compounds were employed as the reaction partners, which was a complement to the annulation of sulfoxonium ylides under weak basic conditions.
- Xiao, Yan,Xiong, Hao,Sun, Song,Yu, Jintao,Cheng, Jiang
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supporting information
p. 8715 - 8718
(2018/11/30)
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- Design, synthesis and crystallographic study of novel indole-based cyano derivatives as key building blocks for heteropolycyclic compounds of major complexity
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A four-stage reaction sequence has been designed and developed for the synthesis of highly functionalized enolate esters as key building blocks for the synthesis of novel heteropolycyclic compounds of potential pharmaceutical value. The sequence starts with simple commercially available indoles and proceeds via 3-(indol-3-yl)-3-oxopropanenitriles, which react with 2-bromobenzaldehyde to form the corresponding chalcones; these are readily reduced to dihydrochalcones, which are in turn acylated to form the enolate esters. The compounds in this sequence have been characterized by IR and 1H and 13C NMR spectroscopy, by mass spectrometry and by elemental analysis. The molecular and supramolecular structures are reported for representative examples, namely (E)-3-(2-bromophenyl)-2-(1-methyl-1H-indole-3-carbonyl)acrylonitrile, C19H13BrN2O, (Ib), (2RS)-2-(2-bromobenzyl)-3-(1-methyl-1H-indol-3-yl)-3-oxopropanenitrile, C19H15BrN2O, (IIb), and (2RS)-3-(1-benzyl-1H-indol-3-yl)-2-(2-bromobenzyl)-3-oxopropanenitrile, C25H19BrN2O, (IIc), the latter two of which crystallize with Z′ = 2, and (E)-1-(1-acetyl-1H-indol-3-yl)-3-(2-bromophenyl)-2-cyanoprop-1-en-1-yl acetate, C22H17BrN2O, (III), and (E)-1-(1-benzyl-1H-indol-3-yl)-3-(2-bromophenyl)-2-cyanoprop-1-en-1-yl benzoate, C32H23BrN2O, (IV). The structure of the related chalcone (E)-2-benzoyl-3-(2-bromophenyl)prop-2-enenitrile, (V), has been redetermined at 100 K, where it is monoclinic, as opposed to the triclinic form reported at ambient temperature.Crystal structures have been determined for representative compounds along a four-stage synthetic sequence newly developed for the production from simple indoles of highly functionalized enolate esters as key building blocks for the synthesis of novel heteropolycyclic compounds.
- García, Andrés C.,Abonía, Rodrigo,Jaramillo-Gómez, Luz M.,Cobo, Justo,Glidewell, Christopher
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p. 1040 - 1049
(2017/12/12)
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- N-Bromosuccinimide (NBS)-Catalyzed C-H Bond Functionalization: An Annulation of Alkynes with Electron Withdrawing Group (EWG)-Substituted Acetyl Indoles for the Synthesis of Carbazoles
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An N-bromosuccinimide-catalyzed intermolecular annulation of acetyl indoles with alkynes was developed, allowing for regioselective formation of valuable carbazoles through direct C-H bond functionalization. The readily available catalyst, wide substrate scope, gram scale synthesis, and mild conditions make this method practical. Mechanistic investigations indicate that the bromination of acetyl indole takes place to generate a bromide intermediate, followed by coupling with an alkyne and intramolecular cycloaromatization to furnish carbazole products.
- Wang, Han,Wang, Zhen,Wang, Yi-Long,Zhou, Rui-Rui,Wu, Guang-Chuan,Yin, Si-Yao,Yan, Xu,Wang, Bin
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supporting information
p. 6140 - 6143
(2017/11/24)
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- Multisubstituted indole-acrylonitrile hybrids as potential cytotoxic agents
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A series of multisubstituted indole-acrylonitrile hybrids were designed, synthesized and evaluated for their potential cytotoxic activities. The bio-evaluation results indicated that some of the target compounds (such as 3a, 3f, 3k, 3n) exhibited good to moderate cytotoxic effect on HepG2, BCG-823, BEL-7402, and HL-7702 cell lines. Especially, the compounds 3a and 3k also exhibited high cytotoxic activities (3a, 19.38 ± 3.38 μM; 3k, 15.43 ± 3.54 μM) against the BEL-7402 cell line resistant to Taxol (>25 μM) and 5-FU (>500 μM), which might be developed as novel lead scaffold for potential anticancer agents.
- Ke, Shaoyong,Yang, Ziwen,Zhang, Zhigang,Liang, Ying,Wang, Kaimei,Liu, Manli,Shi, Liqiao
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p. 1907 - 1911
(2014/04/17)
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- Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride
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Cyanoacetic acid was activated with acetic anhydride and when heated this reagent reacted with a variety of both activated and deactivated pyrroles, indoles and aniline derivatives.
- Slaett, Johnny,Romero, Ivan,Bergman, Jan
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p. 2760 - 2765
(2007/10/03)
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