- Rationalizing Distinct Mechanical Properties of Three Polymorphs of a Drug Adduct by Nanoindentation and Energy Frameworks Analysis: Role of Slip Layer Topology and Weak Interactions
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Three concomitant polymorphs of 3-((4-chlorophenyl)imino)indolin-2-one, a Schiff's base, are identified and sorted based on morphology and mechanical response of their crystals. Form I grows as blocks and shows brittle fracture, Form II has long needles and shows plastic bending, and Form III also has long needles and shows elastic bending under similar qualitative mechanical deformation tests. Furthermore, the brittle Form I was found to exhibit thermosalient behavior (jumping) when heated on a hot plate. The distinct mechanical behavior of the three forms is rationalized by analyzing intermolecular interaction energies from energy frameworks analysis, slip layer topology, Hirshfeld surface analysis, and nanoindentation. The quantitative nanoindentation studies unveiled that Form III has higher elastic modulus and stiffness than Forms I and II, while the hardness was lowest for the plastic Form II. Despite high structural similarity in Forms II (plastic) and III (elastic), the E of elastic Form III was found to be 3 orders of magnitude higher than that of plastic Form II crystals, which is attributed to the subtle differences in interaction energies and slip layer topology in the two cases. Consideration of slip layer topology and interaction energies from the structures are very useful for rationalizing mechanical properties, but may not be always sufficient, and one may also need to know the topology of the potential energy surface of the slip layers for understanding the distinct mechanical behavior.
- Raju, K. Bal,Ranjan, Subham,Vishnu,Bhattacharya, Manjima,Bhattacharya, Biswajit,Mukhopadhyay, Anoop K.,Reddy, C. Malla
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Read Online
- Synthesis of 1,3-diaryl-spiro[azetidine-2,3′-indoline]-2′,4-diones: Via the Staudinger reaction: Cis - Or trans -diastereoselectivity with different addition modes
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A new synthetic approach for realizing biologically relevant bis-aryl spiro[azetidine-2,3′-indoline]-2′,4-diones was developed based on Staudinger ketene-imine cycloaddition through the one-pot reaction of substituted acetic acids and Schiff bases in the presence of oxalyl chloride and an organic base. A series of [azetidine-2,3′-indoline]-2′,4-diones were synthesized using this method. For comparison, the same compounds were obtained using a known technique, where ketene is generated from pre-synthesized acyl chloride. It was shown that the use of oxalyl chloride for ketene generation in the one-pot reaction at room temperature allows for the reversal of the diastereoselectivity of spiro-lactam formation, unlike previously described procedures.
- Beloglazkina, Elena,Filatov, Vadim,Kukushkin, Maksim,Kuznetsova, Juliana,Majouga, Alexander,Skvortsov, Dmitry,Tafeenko, Viktor,Zyk, Nikolay
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p. 14122 - 14133
(2020/04/23)
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- Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds
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The design of a series of styrene and spiroisatin hybrids was based on the structure of combretastatin A-4 1. This library of 20 compounds were synthesized with the pharmacophoric units: 3,4,5-trimethoxy or/and 4-hydroxy-3-methoxy phenyl moities in their structure. Thereby, the libraries of β-nitrostyrenes 10a-10c, spiroisatin-dihydroquinolines 14a-14c, spiroisatinthiazolidinones 17a-17c and spiroisatin-nitropyrrolizidines 20a-20k were evaluated for their in vitro cytotoxic, anti-proliferative, antifungal and antiviral activities. Biological results revealed that among these compounds, β-nitrostyrenes 10a-10c exhibited significant cytotoxicity (HeLa and Jurkat tumor cells) and antifungal (T. mentagrophytes) activities. Moreover, the spiroisatin-dihydroquinoline 14a and 14c showed promising cytotoxicity (U937 cells). 14a-14c molecules were active against human herpesviruses serotypes 1 and 2 (HHV-1 and HHV-2), but only 14a and 14b were effective against dengue virus serotype 2 (DENV-2). The spiroisatin-nitropyrrolizidine 20c exhibited moderate anti-herpetic activity, while 17c spiroisatin-thiazolidinone derivative also reduced the infection of HHV-1 and DENV-2. Finally, the molecular docking showed that these kind of molecules interact with the subunit α/β-tubulin.
- Betancur-Galvis, Liliana,Brand, Yaneth M.,Casta?o, Verónica T.,Kouznetsov, Vladimir V.,Linares, Vicky C. R.,Puerto, Carlos E.
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p. 999 - 1010
(2020/10/14)
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- Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines]
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A novel stereocontrolled assembly of spiro[oxindole-3,2′-pyrrolidines] via [3+2]-cycloaddition of donor-acceptor cyclopropanes to electron-poor ketimines, iminooxindoles, was developed. The method allows for efficient employment of common readily available donor-acceptor cyclopropanes, functionalized with ester, keto, nitro, cyano etc. groups, and N-unprotected iminooxindoles. The stereospecificity of the initial SN2-like imine attack on a cyclopropane molecule together with a high diastereoselectivity of further C-C bond formation facilitate a rapid access to spiro[oxindole-3,2′-pyrrolidines] in their optically active forms. Preliminary in vitro testing of the synthesized compounds against LNCaP (p53+) and PC-3 (p53-) cells revealed good antiproliferative activities and p53-selectivity indices for several compounds that are intriguing in terms of their further investigation as inhibitors of MDM2-p53 interaction.
- Akaev, Andrey A.,Bezzubov, Stanislav I.,Desyatkin, Victor G.,Vorobyeva, Nataliya S.,Majouga, Alexander G.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.
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p. 3340 - 3356
(2019/03/11)
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- Preparation and antiplasmodial activity of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones
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A series of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones were prepared by the inverse-electron-demand aza-Diels–Alder reaction (Povarov reaction) of imines derived from isatin and substituted anilines, and the electron-rich alkenes trans-isoeuge
- Mathebula, Bakolise,Butsi, Kamogelo Rosinah,van Zyl, Robyn Lynne,Jansen van Vuuren, Natasha Colleen,Hoppe, Heinrich Carl,Michael, Joseph Philip,de Koning, Charles Bernard,Rousseau, Amanda Louise
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p. 1849 - 1858
(2019/08/30)
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- Anti-leishmanial effect of spiro dihydroquinoline-oxindoles on volume regulation decrease and sterol biosynthesis of Leishmania braziliensis
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Diverse spiro dihydroquinoline-oxindoles (JS series) were prepared using the BF3?OEt2-catalyzed imino Diels-Alder reaction between ketimine-isatin derivatives and trans-isoeugenol. Ten spiro-oxiindole derivatives were selected and ev
- Lea?ez, Jacques,Nu?ez, Jorge,García-Marchan, Yael,Sojo, Felipe,Arvelo, Francisco,Rodriguez, Daniel,Buscema, Ignacio,Alvarez-Aular, Alvaro,Serrano-Martín, Xenón
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- Design, synthesis and biological activity of novel tacrine-isatin Schiff base hybrid derivatives
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A series of novel tacrine-isatin Schiff base hybrid derivatives (7a-p)were designed, synthesized and evaluated as multi-target candidates against Alzheimer's disease (AD). The biological assays indicated that most of these compounds displayed potent inhibitory activity toward acetylcholinesterase (AChE)and butyrylcholinesterase (BuChE)and specific selectivity for AChE over BuChE. It was also found that they act as excellent metal chelators. The compounds 7k and 7m were found to be good inhibitors of AChE-induced amyloid-beta (Aβ)aggregation. Most of the compounds inhibited AChE with the IC50 values, ranging from 0.42 nM to 79.66 nM. Amongst them, 7k, 7m and 7p, all with a 6 carbon linker between tacrine and isatin Schiff base exhibited the strongest inhibitory activity against AChE with IC50 values of 0.42 nM, 0.62 nM and 0.95 nM, respectively. They were 92-, 62- and 41-fold more active than tacrine (IC50 = 38.72 nM)toward AChE. Most of the compounds also showed a potent BuChE inhibition among which 7d with an IC50 value of 0.11 nM for BuChE is the most potent one (56-fold more potent than that of tacrine (IC50 = 6.21 nM)). In addition, most compounds exhibited the highest metal chelating property. Kinetic and molecular modeling studies revealed that 7k is a mixed-type inhibitor, capable of binding to catalytic and peripheral site of AChE. Our findings make this hybrid scaffold an excellent candidate to modify current drugs in treating Alzheimer's disease (AD).
- Riazimontazer,Sadeghpour,Nadri,Sakhteman,Tüylü Kü?ükk?l?n?,Miri,Edraki
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- Microwave-assisted synthesis and evaluation of indole derivatives as potential anthelmintic agents
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An efficient method is developed and exploited for the synthesis of indole derivatives via microwave-assisted technology. By considering the advantage microwave synthesis in terms of high efficient energy, indole derivatives are prepared. In the current study, the Schiff's bases are first synthesized by reaction of 1H-indole-2,3-dione (isatin) with various substituted anilines in presence of acetic acid under microwave irradiation. Then the Mannich bases are produced by condensation of Schiff bases with different secondary amines in the presence of formaldehyde. The newly synthesized compounds are characterized by TLC report and spectral data followed by evaluation for anthelmintic activity against Pheretima posthuma. Albendazole is used as standard drug for comparative study. The titled compounds are screened for anthelmintic activity at the concentration of 10, 20 and 50 mg/ml. The anthelmintic effect of standard drug Albendazole is also evaluated at 10 mg/ml. The results of present study indicate that some of the tested compounds exhibit significant anthelmintic activity in dose dependent manner.
- Panda, Jnyanaranjan,Kumar, Anjan,Sahoo, Biswa Mohan,Banik, Bimal Krishna
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p. 1283 - 1288
(2020/06/27)
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- Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1
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Indoleamine 2,3-dioxygenase 1 (IDO1) is considered as an important therapeutic target for the treatment of cancer, chronic infections and other diseases that are associated with immune suppression. Recent developments in understanding the catalytic mechanism of the IDO1 enzyme revealed that conversion of l-tryptophan (l-Trp) to N-formylkynurenine proceeded through an epoxide intermediate state. Accordingly, we synthesized a series of 3-substituted oxindoles from l-Trp, tryptamine and isatin. Compounds with C3-substituted oxindole moieties showed moderate inhibitory activity against the purified human IDO1 enzyme. Their optimization led to the identification of potent compounds, 6, 22, 23 and 25 (IC50 = 0.19 to 0.62 μM), which are competitive inhibitors of IDO1 with respect to l-Trp. These potent compounds also showed IDO1 inhibition potencies in the low-micromolar range (IC50 = 0.33-0.49 μM) in MDA-MB-231 cells. The cytotoxicity of these potent compounds was trivial in different model cancer (MDA-MB-231, A549 and HeLa) cells and macrophage (J774A.1) cells. Stronger selectivity for the IDO1 enzyme (124 to 210-fold) over the tryptophan 2,3-dioxygenase (TDO) enzyme was also observed for these compounds. These results suggest that the oxindole moiety of the compounds could mimic the epoxide intermediate state of l-Trp. Therefore, the structural simplicity and low-micromolar inhibition potencies of these 3-substituted oxindoles make them quite attractive for further investigation of IDO1 function and immunotherapeutic applications.
- Paul, Saurav,Roy, Ashalata,Deka, Suman Jyoti,Panda, Subhankar,Srivastava, Gopal Narayan,Trivedi, Vishal,Manna, Debasis
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p. 1640 - 1654
(2017/08/22)
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- Spirotriazoline oxindoles: A novel chemical scaffold with in vitro anticancer properties
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The design and synthesis of a library of twenty-six spirotriazoline oxindoles and their in vitro evaluation as potential anticancer agents is reported. The antiproliferative activity of the synthesized compounds was assessed against four different cancer cell lines (HCT-116 p53 (+/+), HCT-116 p53 (?/?), MCF-7, and MDA-MB-231). Four spirotriazoline oxindoles showed selectivity against the four cancer cell lines tested over the non-cancer derived HEK 293T cell line. To characterize the molecular mechanisms involved in compound antitumoral activity, two spirotriazoline oxindoles were selected for further studies. Both compounds were able to induce apoptosis and cell cycle arrest at G0/G1 phase and upregulated p53 steady-state levels, while decreasing its main inhibitor MDM2, in HCT-116 cells. Importantly, cytotoxic effects induced by spirotriazoline oxindoles occurred in cancer cells without eliciting cell death in non-malignant CCD-18Co human colon fibroblasts. In addition, four spirotriazoline oxindoles showed selectivity against the triple-negative breast cancer cell line MDA-MB-231 with IC50 values of 3.5–6.7 μM. These results highlight the anticancer potential of spirotriazoline oxindoles, especially when dealing with aggressive and challenging triple-negative breast cancer.
- Ribeiro, Carlos J.A.,Nunes, Rute C.,Amaral, Joana D.,Gon?alves, Lídia M.,Rodrigues, Cecília M.P.,Moreira, Rui,Santos, Maria M.M.
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p. 494 - 509
(2017/10/10)
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- Practical Synthesis, Antidepressant, and Anticonvulsant Activity of 3-Phenyliminoindolin-2-one Derivatives
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Herein, a series of 3-phenyliminoindolin-2-one derivatives were designed, synthesized, and screened for their antidepressant and anticonvulsant activities. The IR spectra of the compounds afforded NH stretching (3340-3346 cm-1) bands and C=O stretching (1731-1746 cm-1). In the 1H-NMR spectra of the compounds, N-H protons of indoline ring were observed at 10.65-10.89 ppm generally as broad bands, and 13C-NMR spectra of the compounds C=O were seen at 161.72-169.27 ppm. Interestingly, compounds 3o, 3p and 3r significantly shortened immobility time in the The forced swimming test (FST) and The tail suspension test (TST) at 50 mg/kg dose levels. In addition, compound 3r exhibited higher levels of efficacy than the reference standard fluoxetine but had no effect on locomotor activity in the open-field test. Compound 3r significantly increased serotonin and norepinephrine and the metabolite 5-hydroxyindoleacetic acid in mouse brain, suggesting that the effects of compound 3r may be mediated through these neurotransmitters. In the seizure screen, 15 compounds showed some degree against PTZ-induced seizure at a dose of 100 mg/kg, and the tested compounds did not show any neurotoxicity at a dose of 300 mg/kg in the rotarod test.
- Ma, Jian-Yin,Quan, Ying-Chun,Jin, Hong-Guo,Zhen, Xing-Hua,Zhang, Xue-Wu,Guan, Li-Ping
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p. 342 - 351
(2016/03/12)
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- Synthesis, biological evaluation, in silico docking, and virtual ADME studies of 2-[2-Oxo-3-(arylimino)indolin-1-yl]-N-arylacetamides as potent anti-breast cancer agents
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A series of ten novel isatin analogs have been synthesized and screened for their in vitro anti-breast cancer activity against MCF-7 cell line using sulforhodamine-B assay method. All the tested compounds showed highly potent activity against MCF-7 cell line with especially four compounds exhibited demonstrative antiproliferative effects on MCF-7 breast cancer cell line compared to reference adramycin (doxorubicin) and GI 50 0.02 μM. Docking the synthesized compounds into the epidermal growth factor receptor, which is highly expressed in breast cancer, was employed to explore the possible interactions of these compounds with the receptor. Structure activity relationship as well as virtual ADME studies were carried out and a connection between activities, electronic and physicochemical properties of the target compounds was determined.
- Debnath, Biplab,Ganguly, Swastika
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p. 565 - 574
(2016/03/19)
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- Imidazolylpyridine-In(OTf)3 catalyzed enantioselective allylation of ketimines derived from isatins
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An enantioselective In(OTf)3-catalyzed allylation of ketimines derived from isatins in the presence of an imidazolylpyridine ligand is described. The reaction proceeded smoothly under mild conditions and resulted in 3-allyl 3-aminooxindoles with good yields and moderate to excellent enantioselectivities (up to 97% ee).
- Chen, Tingting,Cai, Chun
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supporting information
p. 5019 - 5022
(2016/06/14)
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- Tin powder-promoted one-pot synthesis of 3-spiro-fused or 3,3′-disubstituted 2-oxindoles
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A convenient and efficient method for the constructions of 3-spirooxindole derivatives or 3,3′-disubstituted oxindoles has been developed from one-pot reactions of isatins, hydrazides or aromatic amines, 2-(bromomethyl)acrylic ester and tin powder in the
- Wang, Juanjuan,Huang, Danfeng,Wang, Ke-Hu,Peng, Xiansha,Su, Yingpeng,Hu, Yulai,Fu, Ying
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supporting information
p. 9533 - 9542
(2016/10/22)
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- Diastereoselective Construction of 3-Aminooxindoles with Adjacent Stereocenters: Stereocontrolled Addition of γ-Substituted Allylindiums to Isatin Ketimines
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The diastereoselective construction of 3-allyl-3-aminooxindoles that have two adjacent stereocenters has been achieved by the In-promoted Barbier-type addition of γ-substituted allylic halides to the C=N bond of isatin ketimines. The reactions of cinnamyl
- Aslam, Nayyar Ahmad,Babu, Srinivasarao Arulananda,Rani, Soniya,Mahajan, Shivam,Solanki, Jagmohan,Yasuda, Makoto,Baba, Akio
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p. 4168 - 4189
(2015/06/30)
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- METHOD OF USING AN INDOLINONE MOLECULE AND DERIVATIVES FOR INHIBITING LIVER FIBROSIS AND HEPATITIS
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This invention relates to methods of reversing and inhibiting liver fibrosis and hepatitis using a small indolinone molecule Hesperadin and related compounds. Methods of identifying such agents and using them to inhibit the expression of collagens and ECM
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Paragraph 0277-0278
(2015/02/25)
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- Synthesis and biological study of novel indole-3-imine-2-on derivatives as src kinase and glutathione S-transferase inhibitors
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The aim of this study is to design and synthesize novel dual inhibitors of Src protein tyrosine kinase (PTK) and Glutathione S-transferases (GSTs), as a potential drug lead with therapeutic efficacy on cancer and immune disorders. The biological activity
- Kurt, Z. Kilic,Aydin,Isgoer,Isgoer,Olgen
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- Facile and highly diastereoselective synthesis of 3-aminooxindoles via AgOAc-catalyzed vinylogous Mannich reaction
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A novel AgOAc-catalyzed vinylogous Mannich reaction between easily prepared imines 1 derived from isatins and trimethylsilyloxyfuran 2 (TMSOF) was developed. This method provided a facile synthetic route to get access to synthetically useful quaternary 3-aminooxindole in excellent yields (94-99%) and diastereoselectivities (>99:1).
- Shi, Yu-Hua,Wang, Zheng,Shi, Ying,Deng, Wei-Ping
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experimental part
p. 3649 - 3653
(2012/06/18)
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- Synthesis, biological activity and docking study of some new isatin Schiff base derivatives
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A set of novel Schiff bases of isatin were synthesized and characterized by reaction of isatin with various aromatic or heterocyclic primary amines. Cytotoxic activities for some of the synthesized compounds were evaluated byMTTassay in three human cancer cell lines (HeLa, LS180 and Raji). Half of the tested compounds showed good cytotoxicity in HeLa cells. 3-(2-(4-nitrophenyl) hydrazono) indolin-2-one was found to be the most potent molecule among the studied isatin derivatives. Docking studies of 3-substituted indolin-2-one scaffolds on vascular endothelial growth factor receptor 2 (VEGFR-2) involved in cell proliferation and angiogenesis was performed. 3-(naphthalen-1-ylimino) indolin-2-one and 3-(2-(4-nitrophenyl) hydrazono) indolin-2-one exhibited higher docking binding energies with receptor. For 3-(2-(4-nitrophenyl) hydrazono) indolin-2-one, H-bond interaction with Cys917 residue of target active site was in common with reported crystallographic benzoimidazole derivative (PDB code: 2OH4). New key H-bonds involving Glu915, Asn921, and Arg1049 residues in VEGFR-2 active site could be detected for 3-(2-(4-nitrophenyl) hydrazono) indolin-2-one. Extended lipophilic rings containing H-bond acceptors on the 3 position of indoline scaffold seemed to be important factors in developing potent VEGFR-2 inhibitors virtually. Based on the ligand efficiency indices, some isoxazole or thiazole substituted isatin derivatives may be regarded as efficient candidates for further molecular developments of anticancer agents. Springer Science+Business Media, LLC 2011.
- Azizian, Javad,Mohammadi, Mohammad K.,Firuzi, Omidreza,Razzaghi-Asl, Nima,Miri, Ramin
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p. 3730 - 3740
(2013/02/23)
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- Synthesis of 1′-aryl-2′-(2-oxoindolin-3-yl)spiro[indoline-3, 5′-pyrroline]-2,3′-dione via one-pot reaction of arylamines, acetone, and isatins
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An efficient synthetic method for 1′-aryl-2′-(2-oxoindolin-3- yl)spiro[indoline-3,5′-pyrroline]-2,3′-diones was successfully developed via the one-pot domino reaction of arylamines, acetone, and isatins in acetic acid. The reaction mechanism involved the
- Sun, Yan,Sun, Jing,Yan, Chao-Guo
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supporting information; experimental part
p. 3647 - 3649
(2012/09/22)
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- Synthesis and screening for antibacterial, analgesic and anti-inflammatory activity of Mannich bases derived from 1H-indole-2,3-dione
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The reaction of 1H-indole-2,3-dione) with substituted anilines in presence of acetic acid produces Schiff bases. Reaction of the Schiff bases with different secondary amines in presence of formaldehyde yields Mannich bases. The synthesized Mannich bases w
- Patro,Panda,Sahoo,Mishra,Panda
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p. 913 - 918
(2012/10/29)
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- 4-hydroxy-3-methoxyphenyl substituted 3-methyl-tetrahydroquinoline derivatives obtained through imino diels-alder reactions as potential antitumoral agents
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Two series of 17 tetrahydroquinoline compounds (2,4-DAr-THQs and DSQs), in which the 4-methoxy-3- hydroxyphenyl (isovanillin) structural unit is incorporated, were tested for their potential human tumor cell growth inhibitory effect on MCF-7, SKBR-3, PC3,
- Kouznetsov, Vladimir V.,Arenas, Diego R. Merchan,Arvelo, Francisco,Forero, Josue S. Bello,Sojo, Felipe,Munoz, Arturo
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scheme or table
p. 632 - 639
(2011/11/29)
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- Schiff bases of isatin: Inhibitory potential towards acetylcholinesterase and butyrylcholinesterase
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A series of different Schiff bases of isatin 1-20 was synthesized by the condensation of isatin with primary aromatic amines. It was observed that some of these compounds have the potential to inhibit acetylcholinesterase, whereas some others showed speci
- Khan, Khalid Mohammed,Mughal, Uzma Rasool,Ambreen, Nida,Rama, Nasim Hasan,Naz, Farzana,Perveen, Shahnaz,Choudhary, Muhammad Iqbal
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p. 716 - 720
(2013/01/09)
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- A simple entry to novel spiro dihydroquinoline-oxindoles using Povarov reaction between 3-N-aryliminoisatins and isoeugenol
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An easy, fast, and cheap way for the synthesis of the new 4′-(4-hydroxy-3-methoxyphenyl)-3′-methyl-3′,4′-dihydro-1′H-spiro[indoline-3,2′-quinolin]-2-ones using BF3 OEt2-promoted imino Diels-Alder cycloaddition between ketimine-isatin
- Kouznetsov, Vladimir V.,Bello Forero, Josué S.,Amado Torres, Diego F.
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experimental part
p. 5855 - 5857
(2009/04/05)
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- Comparative voltammetric behaviour of isatin and some of its Schiff bases at a solid electrode
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The electrochemical behaviour of isatin (1) and its Schiff base, 3-arylimino-2H-indol-2-ones (2a-g), has been investigated and compared using cyclic (CV) and differential pulse voltammetry (DPV) techniques at glassy carbon electrode (GCE) in different sol
- Gupta, Alpana K.,Sindal, Rajendra S.
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experimental part
p. 417 - 424
(2009/07/24)
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- Microwave induced dry-media synthesis of spiro[indole-thiazolidinones/ thiazinones] as potential antifungal and antitubercular agents and study of their reactions
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A series of new spiro[3H-indole-3,2′-thiazolidine]-2,4′(1H.)- diones (IV) and spiro[3H-indole-3,2′-tetrahydro-1,3-thiazine]-2, 4′(1H)-diones (V) have been synthesized in 85-93% yield by the one-pot environmentally benign microwave induced technique involving the cyclocondensation of 3-arylimino-2H-indol-2-ones (III) with thioacids viz. mercapto aceticacid (a) / 3-mercapto propionicacid (b) using montmorillonite KSF as inorganic solid support. Intermediates (III) were synthesized in situ by the reaction of indole-2,3-diones (I) and substituted anilines (II). The spiro compounds have been further subjected to solvent-free acetylation, aminoalkylation and thiation under microwave irradiation using solid supports. The synthesized compounds have been screened in vitro for antifungal activity against Rhizoctonia solani, Fusarium oxysporum, and Collectotrichum capsici, and antitubercular acivity against Mycobacterium tuberculosis.
- Dandia, Anshu,Singh, Ruby,Arya, Kapil
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p. 551 - 564
(2007/10/03)
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- Microwave assisted green chemical synthesis of novel spiro[indole-pyrido thiazines]: A system reluctant to be formed under thermal conditions
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Spiro [3H-indole-3,2′-[4H] pyrido [3,2-e]-1,3-thiazine]-2,4′ (1H) diones, a class of previously unknown compound which does not form under conventional conditions, can be prepared by treatment of 'in situ' generated 3-indolylimine derivatives with 2-mercaptonicotinic acid under microwave irradiation in absence of any solvent or solid support in 85-92% yields in 3-8 min. The facile one pot reaction is generalized for a variety of ketones and amines to give pure pyrido [3,2-e] thiazine derivatives, which do not require further purification processes.
- Dandia, Anshu,Arya, Kapil,Sati, Meha,Gautam, Sangeeta
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p. 5253 - 5258
(2007/10/03)
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- Synthesis, characterization and pharmacological screening of some isatinoid compounds
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Schiff bases and hydrazones of substituted isatins have been prepared by reacting isatin and the appropriate aromatic primary amine l hydrazines and characterized by spectral and elementary analysis. The compounds have been screened for analgesic, antiinflammatory and antipyretic activity. 3[(4-Bromo phenylidene)-1-amino] isatin is the only compound to exhibit all the activities. 3[(4-Bromo phenylidene)-1-amino] isatin and 3[(4- Bromo phenylidene)-1-amino]-5-methyl isatin possesses analgesic activity equipotent to paracetamol. 3(4-Phenylhydrazino) isatin and 3(thiosemicarbazino) isatin exhibit marked reduction of acetic acid induced inflammation. 3[(4-Methyl phenylidene)-1-amino] isatin at 200 mg/kg exhibits pronounced antipyretic activity comparable to paracetamol.
- Sridhar,Ramesh
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p. 668 - 672
(2007/10/03)
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- Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives
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Schiff bases and hydrazones of substituted isatins (1-28) were prepared by reacting isatin and aromatic primary amines/hydrazines. A new series of the corresponding N-Mannich base (29-35) was synthesised by reacting them with formaldehyde and diphenyl ami
- Sridhar, Seshaiah Krishnan,Saravanan, Muniyandy,Ramesh, Atmakuru
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p. 615 - 625
(2007/10/03)
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- Montmorillonite catalysed synthesis of novel spiro[3H-indole-3,3'-[3H- 1,2,4] triazol]-2(1H) ones in dry media under microwave irradiation
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A new route for the one pot synthesis of novel spiro[3H-indole-3,3'-[3H- 1,2,4] triazol]-2 (1H) ones utilizing 3-arylimino-2H-indol-2-ones (3) and thiosemicarbazide (4) as starting material under microwave irradiation is reported. Complete conversion was
- Dandia, Anshu,Sachdeva, Harshita,Devi, Ruby
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p. 272 - 275
(2007/10/03)
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- Improved one-pot synthesis of 3-spiro indolines under microwave irradiation
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The potential of the domestic microwave oven has been utilized to accelerate the one-pot synthesis of spiro[indole-thiazolidine]diones and spiro[indole-benzothiazine]diones by condensation of substituted indole-2,3-diones (1) and appropriate anilines (2)
- Dandia, Anshu,Saha, Mitali,Taneja, Harshita
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- Some isatin Schiff bases as corrosion inhibitors for iron in sulphuric acid solution
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Six isatin Schiff bases have been prepared and treated as inhibitors for the corrosion of iron in 1 mol L-1 sulphuric acid.The inhibitor efficiencies calculated from weight loss and polarization methods are in good agreement.The Tafel slope is
- Mohamed, A. K.,Bekheit, M. M.,Fouda, A. S.
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p. 331 - 336
(2007/10/02)
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- Synthesis of 2,4'-Dioxospiro-5'-acetic Acids: X-Ray Structure of 1-Benzyl-3'-(4-chlorophenyl)-2,4'-dioxospiro-5'-acetic Acid
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The title compounds have been prepared by the cyclocondensation of mercaptosuccinic acid with isatin-3-imines.The 1-benzyl derivatives have been synthesized by simultaneously reacting 1-benzylisatin, substituted anilines and mercaptosuccinic acid.The stru
- Popp, Frank D.,Rajopadhye Miland,Brown, David S.,Waddington, David,Uff, Barrie C.
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p. 261 - 265
(2007/10/02)
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- Reactions of 3-Arylimino-2-Indolinones with p-Substituted Phenylthiosemicarbazides
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3-Arylimino-2-indolinones (II) have been prepared by the condensation of isatins (I) with anilines.Reactions of II with p-substituted phenylthiosemicarbazides have resulted (in every instance) in the displacement of arylimino groups by the phenylthiosemic
- Varma, Rajendra S.,Garg, Pradeep K.
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p. 980 - 981
(2007/10/02)
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- A CONVENIENT SYNTHESIS AND REACTION OF SPIRO -2,4'(1h)-DIONES
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Spiro-2,4'(1H)-diones have been obtained by the condensation of indole-2,3-dione, aromatic amine and mercaptoacetic acid without isolating the intermediates i.e., isatin-3-anils.The spiro compounds have further been subjected
- Joshi, Krishna C.,Patni, R.,Chand, Pooran
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p. 1555 - 1559
(2007/10/02)
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