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Bao-Qu Wang, Cong-Hai Zhang, Xiao-Xue Tian, Jun Lin, Sheng-Jiao Yan
A one-step methodology for the synthesis of multisubstituted quinoline-4-carboxamides was developed by simply refluxing a mixture of isatins 1 and various kinds of 1,1-enediamines 2-4 in a reaction catalyzed by NH2SO3H. As a result, a series of quinolone-4-carboxamides were produced through a novel cascade reaction mechanism. This reaction involved the formation of the quinoline ring accompanied by the formation of an amide bond in one step. Accordingly, this protocol is suitable for combinatorial and parallel syntheses of quinolone-4-carboxamide drugs or natural products...
January 11, 2018: Organic Letters
Hamid Reza Safaei, Mohsen Shekouhy
γ-Spiroiminolactone derivatives can be synthesized through an one-pot three-component reaction of cyclic carbonyl compounds (isatin, acenaphthoquinone, ninhydrin), activated α-methylene carbonyl groups and isocyanides in water using sodium dodecyl sulfate (SDS) as a commercially available and cheap surfactant compound. All products were obtained in good to excellent yields without formation of any by-products in water as a green and benign reaction medium. Moreover, presented method was successfully applied for the synthesis of some novel bis(spiroiminolactone) derivatives...
December 2017: Acta Chimica Slovenica
Max Moskowitz, Kaluvu Balaraman, Christian Wolf
A highly diastereoselective organocatalytic method that produces 3-fluoro-3'-hydroxy-3,3'-bisoxindoles and the corresponding 3-fluoro-3'-amino derivatives having two adjacent chirality centers from fluorooxindoles and isatins in high yields is described. The reaction occurs in protic solvents at room temperature, it can be upscaled without compromising yield and stereoselectivity, and chromatographic product purification is not required.
January 9, 2018: Journal of Organic Chemistry
Mahshid Hamzehloueian, Zakieh Davari
The molecular mechanism of the [3+2] cycloaddition (32CA) reaction of an azomethine ylide, generated in situ from isatin and sarcosine, with benzo-imidazol-2-yl-3-phenylacrylonitrile have been theoretically studied by using DFT at the B3LYP and M06-2X levels of theory. This reaction takes place through an asynchronous one-step mechanism. Analysis of the global electron density transfer (GEDT) indicates that this 32CA has a polar character. The regiochemistry of this reaction was investigated using Parr functions analysis, as well as HSAB principle and potential energy surface analysis, where the results are in agreement with the experimental observations...
December 29, 2017: Journal of Molecular Graphics & Modelling
Quangang Chen, Lihua Xie, Zhaojing Li, Yu Tang, Peng Zhao, Lili Lin, Xiaoming Feng, Xiaohua Liu
Isatin-derived ketimines undergo enantioselective alkynylation reactions in the presence of copper iodide and easily accessible guanidine-amides. The corresponding 3-alkynyl-3-aminooxyindoles are obtained in up to 95% yield and 96% ee. The guanidine plays a role in the formation of copper acetylide and the enantiodetermining step and the basic additive is excluded.
January 5, 2018: Chemical Communications: Chem Comm
Mary Ensch, Vanessa Y Maldonado, Greg M Swain, Robert Rechenberg, Michael F Becker, Thomas Schuelke, Cory A Rusinek
Boron-doped diamond (BDD) is a promising electrochemical tool that exhibits excellent chemical sensitivity and stability. These intrinsic advantages coupled with the material's vast microfabrication flexibility make BDD an attractive sensing device. In this study, two different 3-in-1 BDD electrode sensors were fabricated, characterized, and investigated for their capability to detect isatin, an anxiogenic indole that possesses anticonvulsant activity. Each device is comprised of a working, reference, and auxiliary electrode, all made of BDD...
January 3, 2018: Analytical Chemistry
Jiabing Wang, Di Yun, Jiali Yao, Weitao Fu, Fangyan Huang, Liping Chen, Tao Wei, Cuijuan Yu, Haineng Xu, Xiaoou Zhou, Yanqing Huang, Jianzhang Wu, Peihong Qiu, Wulan Li
Molecular hybridization is considered as an effective tactic to develop drugs for the treatment of cancer. A series of novel hybrid compounds of isatin and Michael acceptor were designed and synthesized on the basis of association principle. These hybrid compounds were tested for cytotoxic potential against human cancer cell lines namely, BGC-823, SGC-7901 and NCI-H460 by MTT assay. Most compounds showed good anti-growth activities in all tested human cancer cells. SAR and QSAR analysis may provide vital information for the future development of novel anti-cancer inhibitors...
December 18, 2017: European Journal of Medicinal Chemistry
Jun Yan, Kuangxi Shi, Chengtao Zhao, Liyuan Ding, Shengsheng Jiang, Limin Yang, Guofu Zhong
A chiral NHC-catalyzed cycloaddition of γ-fluoroenals is developed. The nucleophilic γ-carbon generated via C-F bond cleavage undergoes highly enantioselective cycloaddition (up to >99% ee) to isatins and provides 3'-spirocyclic oxindoles in good yields (up to 91%).
December 18, 2017: Chemical Communications: Chem Comm
Muhammad Farooq, Zainab M Almarhoon, Nael Abu Taha, Almohannad A R Baabbad, Mohammed A Al-Wadaan, Ayman El-Faham
Isatin (1H-indole-2,3-dione) and many of its derivatives are reported to have pharmacological properties. In this study, we report the synthesis and biological activity of a new class of N-alkyl-isatin-3-iminobenzoic acid derivatives prepared via the condensation of N-alkyl isatin with 4-aminobenzoic acid by conventional, microwave, and ultrasonic methods. Microwave irradiation yielded the products in a shorter reaction time with higher yields and purities. The compounds were screened in zebrafish embryos, and also in three human cancer cell lines (MCF7, HepG2, and Jurkat) and one normal human cell line i...
December 16, 2017: Biological & Pharmaceutical Bulletin
Lalita Uribe, Gregor Diezemann, Jürgen Gauss, Jens Preben Morth, Michele Cascella
We performed quantum-chemical calculations, ab initio molecular dynamics, hybrid QM/MM and enhanced sampling metadynamics simulations to investigate the origin of metal specificity in isatin hydrolase from Labrenzia aggregata. The peculiar octahedral binding geometry of the Mn2+ ion in the Michaelis complex includes both the isatin substrate and the catalytic water within the first coordination shell of the cation. Our calculations show that the same arrangement of the ligands cannot be efficiently achieved in the presence of other small divalent cations such as Zn2+ or Cu2+...
December 15, 2017: Chemistry: a European Journal
Xiaohong Jin, Yan Xu, Xuhong Yang, Xiuling Chen, Minghu Wu, Jianguo Guan, Lianshun Feng
A new class of ethylene/propylene-1H-1,2,3-triazole-4-methylene-tethered isatin-coumarin hybrids 8a-j, integrate three anti-tuberculosis pharmacophores coumarin, isatin and 1,2,3-triazole was designed and synthesized. These hybrids were assessed for their in vitro anti-TB activity against MTB H37Rv and MDR-TB, as well as anti-bacterial activity against Gram-positive and Gram-negative strains, and cytotoxicity in VERO cell line. The results showed that all hybrids with acceptable cytotoxicity (CC50: 64-512 μg/mL) exhibited weak to moderate anti-microbial activity...
December 14, 2017: Current Topics in Medicinal Chemistry
Xinjia Yan, Zaosheng Lv, Jing Wen, Shijia Zhao, Zhi Xu
Twelve novel substituted isatin-propylene-1H-1,2,3-triazole-4-methylene-moxifloxacin hybrids 5a-l were designed, synthesized and screened for their in vitro anti-mycobacterial activities against drug-sensitive and multidrug-resistant Mycobacterium tuberculosis as well as cytotoxicity in VERO cell line. All hybrids exhibited excellent activities against two Mycobacterium tuberculosis strains with minimum inhibitory concentration in the range from 0.05 to 2.0 μg/mL. The most active hybrid 5i was 2-8 times more potent than the reference agents (moxifloxacin and rifampicin) in vitro against Mycobacterium tuberculosis H37Rv, while 2->2048 times more potent than the reference agents (moxifloxacin, rifampicin and isoniazid) in vitro against multidrug-resistant Mycobacterium tuberculosis...
December 2, 2017: European Journal of Medicinal Chemistry
Guangcheng Wang, Ming Chen, Jie Qiu, Zhenzhen Xie, Anbai Cao
A novel series of chromone-isatin derivatives 6a-6p were designed, synthesized and characterized by 1H NMR, 13C NMR and HRMS. These novel synthetic compounds were evaluated for inhibitory activity against yeast α-glucosidase enzyme. The results of biological test have shown that all tested compounds exhibited excellent to potent inhibitory activity in the range of IC50 = 3.18 ± 0.12-16.59 ± 0.17 μM as compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM). Compound 6j (IC50 = 3...
November 28, 2017: Bioorganic & Medicinal Chemistry Letters
Jairo Quiroga, Pablo Romo, Justo Cobo, Christopher Glidewell
Two spiro[indoline-3,3'-pyrrolizine] derivatives have been synthesized in good yield with high regio- and stereospecificity using one-pot reactions between readily available starting materials, namely L-proline, substituted 1H-indole-2,3-diones and electron-deficient alkenes. The products have been fully characterized by elemental analysis, IR and NMR spectroscopy, mass spectrometry and crystal structure analysis. In (1'RS,2'RS,3SR,7a'SR)-2'-benzoyl-1-hexyl-2-oxo-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine]-1'-carboxylic acid, C28H32N2O4, (I), the unsubstituted pyrrole ring and the reduced spiro-fused pyrrole ring adopt half-chair and envelope conformations, respectively, while in (1'RS,2'RS,3SR,7a'SR)-1',2'-bis(4-chlorobenzoyl)-5,7-dichloro-2-oxo-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine], which crystallizes as a partial dichloromethane solvate, C28H20Cl4N2O3·0...
December 1, 2017: Acta Crystallographica. Section C, Structural Chemistry
Karunanidhi Murali, Hazel A Sparkes, Karnam Jayarampillai Rajendra Prasad
A library of novel dispiro compounds containing oxindole-pyrrolo-carbazole hybrid frame works has been synthesized in a fully regio- and stereoselective fashion by the three-component 1,3-dipolar cycloaddition of azomethineylides generated in situ from the condensation of isatins and benzylamine with 2-arylidene/heteroarylidene-2,3,4,9-tetrahydro-1H-carbazole-1-one. The structures of the compounds were established by FT-IR, 1H NMR, 13C NMR, X-ray diffraction and elemental analysis. The synthesized dispiro heterocycles have been screened for in vitro cytotoxic activity by MTT assay and displayed enviable growth inhibition on both the cancer cell lines i...
November 20, 2017: European Journal of Medicinal Chemistry
Thomas Wurm, Ben W H Turnbull, Brett R Ambler, Michael J Krische
Benzocyclobutenones 1a-1g undergo cycloreversion at 150 °C in m-xylene solvent to form transient α-oxo-ortho-quinodimethanes or "ortho-quinoid ketene methides", which engage in intermolecular [4+2] cycloadditions with isatins 2a-2f to form 2-oxindole spirolactones 3a-3l. This process tolerates an array of different functional groups and substitution patterns, and is applicable to unprotected isatins 2b-2f bearing free NH-functionalities. The superior performance of isatins compared to other carbonyl based dienophiles was demonstrated and rationalized with the aid of quantum chemical calculations...
November 22, 2017: Journal of Organic Chemistry
Giulia Rainoldi, Matteo Faltracco, Claudia Spatti, Alessandra Silvani, Giordano Lesma
This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived N-tert-butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an organocatalytic strategy, exploiting a bifunctional cinchona-type β-isocupridine-based catalyst. Some post-transformation products, including unexpected spiropyrroline and 3,3-disubstituted oxindole derivatives, are also presented...
November 21, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Sivakumar Prasanth Kumar, Chirag N Patel, Prakash C Jha, Himanshu A Pandya
The identification of isatin sulfonamide as a potent small molecule inhibitor of caspase-3 had fuelled the synthesis and characterization of the numerous sulfonamide class of inhibitors to optimize for potency. Recent works that relied on the ligand-based approaches have successfully shown the regions of optimizations for sulfonamide scaffold. We present here molecular dynamics-based pharmacophore modeling of caspase-3-isatin sulfonamide crystal structure, to elucidate the essential non-covalent contacts and its associated pharmacophore features necessary to ensure caspase-3 optimal binding...
August 9, 2017: Computational Biology and Chemistry
Michael Kisiela, Annette Faust, Bettina Ebert, Edmund Maser, Axel J Scheidig
The human dehydrogenase/reductase SDR family member 4 (DHRS4) is a tetrameric protein that is involved in the metabolism of several aromatic carbonyl compounds, steroids and bile acids. The only invertebrate DHRS4 that has been characterized to date is that from the model organism Caenorhabditis elegans. We have previously cloned and initially characterized this protein that was recently annotated as DHRS4_CAEEL in the UniProtKB database. Crystallization and X-ray diffraction studies of the full-length DHRS4_CAEEL protein in complex with diacetyl revealed its tetrameric structure and showed that two subunits are connected via an intermolecular disulfide bridge that is formed by N-terminal cysteine residues (Cys5) of each protein chain, which increases the enzymatic activity...
November 19, 2017: FEBS Journal
Dieter Enders, Xiang-Yu Chen, Jia-Wen Xiong, Qiang Liu, Sun Li, He Sheng, Carolina von Essen, Kari Rissanen
A strategy to control the switchable linear and cycloaddition reactions of enals through NHC catalyisis has been developed. The new scalable protocol leads to γ-amino acid esters bearing a tetrasubstituted stereocenter in good yields and high stereoselectivities via homo-Mannich reactions of enals and isatin-derived ketimines. By simply changing the N-ketimine substituent to an ortho-hydroxy phenyl group, the corresponding spirocyclic oxindolo-γ-lactams are obtained.
November 17, 2017: Angewandte Chemie
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