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Journal articles on the topic 'Indolinoren'

Author: Grafiati

Published: 4 June 2025

Last updated: 23 June 2025

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1

Anna, Markina, and Mishсhenko Oksana. "The influence of indolinoren on kidney function in conditions of water and salt load." ScienceRise: Pharmaceutical Science, no. 4(14) (August 31, 2018): 20–23. https://doi.org/10.15587/2519-4852.2018.141304.

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Diuretics are widely used to correct kidney disorders. In turn, the ionic composition of food, mostly sodium ions, which directly affect the excretory function of the kidneys, can act as modulators of the action of diuretics. The aim of the study was to investigate the effects of the new 2-oxoindoline derivative with the conventional name "Indolinoren" on the state of the excretory function of the kidneys under the conditions of water and salt load. Materials and methods. Studies were performed on white non-linear rats. The water load was modelled by introducing distilled water (5 ml per 100 g of body weight of the animal); salt load - intragastric administration of 0.45 % sodium chloride solution in an amount of 3 % of body weight. Indolinoren and comparison drug furosemide were administered intragastrically at a dose of 29.5 mg / kg and 5 mg / kg, respectively. Results and discussion. It has been established that indolinoren has a saluretic effect in conditions of water load, accompanied by an increase in sodium excretion by 132 % and potassium by 2.4 %. Against the background of the introduction of indolinoren, a significant increase in the sodium-potassium coefficient of urine was established 2.3-fold (p <0.05), which indicates a more pronounced natriuresis than kaliuresis. Under conditions of salt load, indolinoren promotes a significant increase in urine output by 381 % (p <0.05), increases sodium excretion by 127 % (p <0.05), potassium by 7 %. There were no significant differences in creatinine excretion. The expression of diuretic activity in conditions of salt load indolinoren exceeds furosemide and does not have a significant difference under conditions of water load. Conclusion: The increase in natriuresis and, to a lesser extent, the kaliuresis, as well as the absence of significant changes in the excretion of creatinine, a glomerular filtration marker, on the background of the introduction of indolinoren indicates that its diuretic effect is realized due to oppression of tubular reabsorption. In the mechanism of indolinoren action involved inhibition of mineralocorticoid control of the excretory function of the kidney, as evidenced by the increase in the sodium-potassium coefficient of urine. The obtained data justify the need for further in-depth study of indolinoren as a perspective diuretic

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2

Markina, A. Yu, and O. Ya Mishchenko. "The experimental study of antihypoxic and antioxidant indolinoren activity." Ukraïns’kij bìofarmacevtičnij žurnal, no. 3(50) (June 16, 2017): 22–25. http://dx.doi.org/10.24959/ubphj.17.112.

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3

Chakrabarty, Manas, Sandipan Sarkar, and Yoshihiro Harigaya. "A Facile Clay-Mediated Synthesis of 3,3-diindolyl-2-indolinones from Isatins." Journal of Chemical Research 2005, no. 8 (2005): 540–42. http://dx.doi.org/10.3184/030823405774663264.

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Dry reaction of isatins (3a, 3b) with indoles (4a–e) on montmorillonite K10 clay at room temperature furnished within minutes 3,3-bis(3′-indolyl)-2-indolinones (1a–f) in high yields. 5-Nitroisatin (3c) furnished, in addition to the expected indolinone 1h, 3-hydroxy-3-(3′-indolyl)-5-nitro-2-indolinone (6), a likely intermediate to 1h.

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4

Markina, Anna, and Oksana Mishсhenko. "The influence of indolinoren on kidney function in conditions of water and salt load." ScienceRise: Pharmaceutical Science, no. 4 (14) (August 31, 2018): 20–23. http://dx.doi.org/10.15587/2519-4852.2018.141304.

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5

Markina, Anna, Oksana Mishсhenko, and Julia Laryanovska. "The impact of indolinoren on histrotructure of kidney on the glixerroid acute renal failure model." ScienceRise: Pharmaceutical Science, no. 5 (9) (October 31, 2017): 10–14. http://dx.doi.org/10.15587/2519-4852.2017.113361.

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6

B., Raja Sekhara Reddy, Reddy P. Malleswara, Babu G. Surendra, Narayana V. Venkata, and Babu K. Sudhakar. "Organo catalytic construction of novel Pyrazol-2-Indolinone derivatives." Research Journal of Chemistry and Environment 26, no. 2 (2022): 9–13. http://dx.doi.org/10.25303/2602rjce0913.

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A few novel series of pyrazol-2-indolinone entities have been designed and synthesized using pyrazalone and α, β-unsaturated oxindole esters as starting materials (5a–j). The chemical structures of the new synthesized compounds were characterized by 1H NMR, 13C NMR, MS spectroscopy and elemental analysis. This procedure provides a highly efficient and facile route to functionalized pyrazol-2-indolinones from readily available substrates under mild reaction conditions.

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7

Smallheer, J. M., M. J. Otto, C. A. Amaral-Ly, et al. "Synthesis and anti-HIV Activity of a Series of 2-Indolinones and Related Analogues." Antiviral Chemistry and Chemotherapy 4, no. 1 (1993): 27–39. http://dx.doi.org/10.1177/095632029300400104.

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A novel series of 2-indolinones with in vitro anti-HIV (human immunodeficiency virus) activity is described. Two structurally related compounds, 1, 3,3-(4- N-methyl-1,2,5,6-tetrahydropyridylmethyl)-1- phenyl-2-indolinone, and 2, its 4- N-methylpiperidinylmethyl analogue (Fig. 1), formed the basis of a structure-activity study. The synthesis of approximately 50 analogues and their respective activities vs. HIV are presented. Both 1 and 2 were effective inhibitors of HIV(IIIb) in cell protection assays with IC90 values of 4.4 and 14.9μM (2.2 and 7.9μg ml−1), respectively. In the same concentration range, 1 and 2 also inhibit syncytia formation. These compounds represent a novel class of anti-HIV agents which appear to act by inhibiting virus-dependent cell fusion.

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8

Liao, Albert T., May B. Chien, Narmada Shenoy, et al. "Inhibition of constitutively active forms of mutant kit by multitargeted indolinone tyrosine kinase inhibitors." Blood 100, no. 2 (2002): 585–93. http://dx.doi.org/10.1182/blood-2001-12-0350.

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Abstract Mutations in the proto-oncogene c-kit, including point mutations, deletions, or duplications in the negative regulatory juxtamembrane (JM) domain or point mutations in the catalytic domain, have been observed in human and canine cancers and often result in constitutive activation of Kit in the absence of ligand binding. To identify a receptor tyrosine kinase (RTK) inhibitor capable of blocking the function of mutant Kit, we evaluated 3 indolinones (SU11652, SU11654, and SU11655) that act as competitive inhibitors of adenosine triphosphate binding to several members of the split kinase family of RTKs, including VEGFR, FGFR, PDGFR, and Kit. Mast cell lines expressing either wild-type (WT) Kit, a point mutation in the JM domain, a tandem duplication in the JM domain, or a point mutation in the catalytic domain were used for these studies. All 3 indolinones inhibited phosphorylation of WT Kit in the presence of stem cell factor at concentrations as low as 0.01 μM. Autophosphorylation of both JM mutants was inhibited at 0.01 to 0.1 μM, resulting in cell cycle arrest within 24 hours, whereas autophosphorylation of the catalytic domain mutant was inhibited at 0.25 to 0.5 μM, resulting in cell death within 24 hours. poly(ADP-ribose) polymerase (PARP) cleavage was noted in all Kit mutant lines after indolinone treatment. In summary, SU11652, SU11654, and SU11655 are effective RTK inhibitors capable of disrupting the function of all forms of mutant Kit. Because the concentrations of drug necessary for receptor inhibition are readily achievable and nontoxic in vivo, these compounds may be useful in the treatment of spontaneous cancers expressing Kit mutations.

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9

Somogyi, László, and Attila Csaba Bényei. "Contributions to the chemistry of 3-cyanoacetylhydrazono-2-indolinones and X-ray structure ofZ-3-cyanoacetylhydrazono-2-indolinone monohydrate." Heteroatom Chemistry 20, no. 4 (2009): 183–93. http://dx.doi.org/10.1002/hc.20531.

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10

Ivanenkov, Yan A., Maxim E. Kukushkin, Anastasia A. Beloglazkina, et al. "Synthesis and Biological Evaluation of Novel Dispiro-Indolinones with Anticancer Activity." Molecules 28, no. 3 (2023): 1325. http://dx.doi.org/10.3390/molecules28031325.

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Novel variously substituted thiohydantoin-based dispiro-indolinones were prepared using a regio- and diastereoselective synthetic route from 5-arylidene-2-thiohydantoins, isatines, and sarcosine. The obtained molecules were subsequently evaluated in vitro against the cancer cell lines LNCaP, PC3, HCTwt, and HCT(−/−). Several compounds demonstrated a relatively high cytotoxic activity vs. LNCaP cells (IC50 = 1.2–3.5 µM) and a reasonable selectivity index (SI = 3–10). Confocal microscopy revealed that the conjugate of propargyl-substituted dispiro-indolinone with the fluorescent dye Sulfo-Cy5-azide was mainly localized in the cytoplasm of HEK293 cells. P388-inoculated mice and HCT116-xenograft BALB/c nude mice were used to evaluate the anticancer activity of compound 29 in vivo. Particularly, the TGRI value for the P388 model was 93% at the final control timepoint. No mortality was registered among the population up to day 31 of the study. In the HCT116 xenograft model, the compound (170 mg/kg, i.p., o.d., 10 days) provided a T/C ratio close to 60% on day 8 after the treatment was completed. The therapeutic index—estimated as LD50/ED50—for compound 29 in mice was ≥2.5. Molecular docking studies were carried out to predict the possible binding modes of the examined molecules towards MDM2 as the feasible biological target. However, such a mechanism was not confirmed by Western blot data and, apparently, the synthesized compounds have a different mechanism of cytotoxic action.

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11

Banik, Swarnayu, Tanmoy Sahoo, B. Sridhar, and B. V. Subba Reddy. "Enantioselective fluorination of 3-indolinone-2-carboxylates with NFSI catalyzed by chiral bisoxazolines." Organic & Biomolecular Chemistry 19, no. 27 (2021): 6085–91. http://dx.doi.org/10.1039/d1ob00144b.

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12

Enders, Dieter, V. Gajulapalli, Ehsan Jafari, et al. "Organocatalytic Asymmetric Synthesis of 2,3′-Connected Bis-Indolinones by Mannich Reactions of N-Acetylindolin-3-ones with Isatin N-Boc Ketimines." Synthesis 49, no. 22 (2017): 4986–95. http://dx.doi.org/10.1055/s-0036-1590823.

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A highly diastereo- and enantioselective Mannich reaction of N-acetylindolin-3-ones with isatin N-Boc ketimines to form 2,3′-connected bis-indolinones is developed employing a low loading of a readily available bifunctional thiourea catalyst. The asymmetric synthesis connects two indolinones via a vic-diamine unit and generates two neighboring stereocenters.

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13

Abu-Hashem, Ameen Ali, and Sami A. Al-Hussain. "Design, Synthesis of New 1,2,4-Triazole/1,3,4-Thiadiazole with Spiroindoline, Imidazo[4,5-b]quinoxaline and Thieno[2,3-d]pyrimidine from Isatin Derivatives as Anticancer Agents." Molecules 27, no. 3 (2022): 835. http://dx.doi.org/10.3390/molecules27030835.

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The current work aims to design and synthesis a new series of isatin derivatives and greatly enhances their cytotoxic activity. The derivatives 3-((bromophenyl) imino)-1-(morpholino (pyridine) methyl) indolin-2-one, 2-((oxoindoline) amino) benzoic acid, 3-(thiazolo-imino) indolinone, ethyl-2-((oxoindolin-3-ylidene)amino)-benzothiophene-3-carboxylate, 1-(oxoindoline)-benzo[4,5] thieno [2,3-d]pyrimidin-4(1H)-one, ethyl-2-(2-oxoindoline) hydrazine-1-carboxylate, N-(mercapto-oxo-pyrimidine)-2-(oxoindoline) hydrazine-1-carboxamide, N-(oxo-thiazolo[3,2-a] pyrimidine)-2-(oxoindolin-ylidene) hydrazine-carboxamide, 3-((amino-phenyl) amino)-3-hydroxy- indolinone, 3-((amino-phenyl) imino)-indolinone, 2-(2-((oxoindoline) amino) phenyl) isoindolinone, 2-(oxoindoline) hydrazine-carbothioamide, 5′-thioxospiro[indoline-3,3′-[1,2,4]triazolidin]-one, 5′-amino-spiro[indoline-3,2′-[1,3,4]thiadiazol]-2-one and 3-((2-thioxo-imidazo[4,5-b]quinoxaline) imino) indolinone were synthesized from the starting material 1-(morpholino (pyridine) methyl) indoline-2,3-dione and evaluated for their in vitro cytotoxic activity against carcinogenic cells. The new chemical structures were evidenced using spectroscopy (IR, NMR and MS) and elemental analysis. The results show that compounds imidazo[4,5-b]quinoxaline-indolinone, thiazolopyrimidine-oxoindoline, pyrimidine-oxoindoline-hydrazine-carboxamide, spiro[indoline-3,2′-[1,3,4] thiadiazol]-one and spiro[indoline-3,3′-[1,2,4]triazolidin]-one have excellent anti-proliferative activities against different human cancer cell lines such as gastric carcinoma cells (MGC-803), breast adenocarcinoma cells (MCF-7), nasopharyngeal carcinoma cells (CNE2) and oral carcinoma cells (KB).

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14

R., K. Tiwari, Rastogi Nisheeth, Sethi Rakesh, and Shukla Sarveshwar. "Synthesis and antileishmanial activity of 1-aminomethyl-5-substituted-3-{ 4' -(3"- chlorobenzyloxy)-benzoylhydrazone }-2-indolinones." Journal of Indian Chemical Society Vol. 85, Jan 2008 (2008): 85–88. https://doi.org/10.5281/zenodo.5808566.

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Department of Chemistry, Lucknow University, Lucknow-226 007, Uttar Pradesh, India Department of Chemistry, Lucknow Christian Post-Graduate College, Lucknow-226 018, Uttar Pradesh, India <em>E-mail:</em> nisheethrastogi2003@yahoo.co.in Department of Chemistry, Sri Jai Narain Post-Graduate College, Lucknow-226 001, Uttar Pradesh, India <em>Manuscript received 4 June 2007, accepted 5 November 2007</em> 5-Substituted-3-{ 4' -(3" -chlorobenzyloxy)-benzoylhydrazono}-2-indolinones (3-6) were synthesised by the condensation of 4-(3' -chlorobenzyloxy)-benzoylhydrazine (2) and 5-substituted isatins. Mannich reaction in the presence of formaldehyde and heterocyclic secondary amines on indolinones (3-6) furnished 1-aminomethyl-5-substituted-3- { 4' -(3" -chlorobenzyloxy)-benzoylhydrazono }-2-indolinones (7-22). The structures of the compounds have been established by means of correct elemental analysis and spectral data (IR, PMR and Mass). The compounds have been screened for their antileishmanial potential against <em>Leishmania donovani</em>.

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15

Roth, Gerald J., Armin Heckel, Florian Colbatzky, et al. "Design, Synthesis, and Evaluation of Indolinones as Triple Angiokinase Inhibitors and the Discovery of a Highly Specific 6-Methoxycarbonyl-Substituted Indolinone (BIBF 1120)." Journal of Medicinal Chemistry 52, no. 14 (2009): 4466–80. http://dx.doi.org/10.1021/jm900431g.

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16

Cheng, Li-Ting, Sheng-Qi Luo, Bor-Cherng Hong, Chia-Ling Chen, Wen-Shan Li, and Gene-Hsiang Lee. "Oxidative trimerization of indoles via water-assisted visible-light photoredox catalysis and the study of their anti-cancer activities." Organic & Biomolecular Chemistry 18, no. 32 (2020): 6247–52. http://dx.doi.org/10.1039/d0ob01298j.

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17

Ruberte, Ana Carolina, Carlos Aydillo, Arun K. Sharma, Carmen Sanmartín, and Daniel Plano. "Vilsmeier reagent, NaHSe and diclofenac acid chloride: one-pot synthesis of a novel selenoindolinone with potent anticancer activity." RSC Advances 10, no. 63 (2020): 38404–8. http://dx.doi.org/10.1039/d0ra07332f.

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18

Ibrahim, Samy M., Ahmed S. Abdelkhalek, Shaban A. A. Abdel-Raheem, et al. "An overview on 2-indolinone derivatives as anticancer agents." Current Chemistry Letters 13, no. 1 (2024): 241–54. http://dx.doi.org/10.5267/j.ccl.2023.6.005.

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2-Indolinone nucleus is considered one of a promising heterocyclic core in medicinal chemistry that showed numerous range of activity among which antimicrobial, antioxidant, antiviral, antitubercular and anticancer activities. Cancer targeting is still an issue so there is a need for developing new agents that inhibit cancer growth without or low effect on normal body cells. Some derivatives of indolin-2-one are known to be a critical structure in some inhibitors of receptor tyrosine kinases (RTKs); a cancer target therapy, for example, Sunitinib. Herein in this review we focus on 2-indolinone derivatives as RTKs inhibitors as cancer targeting therapy.

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19

Opoku-Temeng, Clement, Neetu Dayal, Jacob Miller, and Herman O. Sintim. "Hydroxybenzylidene-indolinones, c-di-AMP synthase inhibitors, have antibacterial and anti-biofilm activities and also re-sensitize resistant bacteria to methicillin and vancomycin." RSC Advances 7, no. 14 (2017): 8288–94. http://dx.doi.org/10.1039/c6ra28443d.

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Hydroxybenzylidene-indolinones, newly identified inhibitors of c-di-AMP synthases, inhibit biofilm formation, Gram-positive bacterial growth and sensitize resistant bacteria to methicillin and vancomycin.

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20

Zhang, Lei, Yin Wang, Yunhui Yang, Ping Zhang, and Congyang Wang. "Rhenium-catalyzed alkylarylation of alkenes with PhI(O2CR)2via decarboxylation to access indolinones and dihydroquinolinones." Organic Chemistry Frontiers 7, no. 20 (2020): 3234–41. http://dx.doi.org/10.1039/d0qo00953a.

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Rhenium-catalyzed alkylarylation of alkenes with hypervalent iodine(iii) reagents (HIRs) via decarboxylation to access various 3,3-disubstituted indolinones and trans-3,4-dihydroquinolinones is described.

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21

Filatov, Vadim, Maksim Kukushkin, Juliana Kuznetsova, et al. "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." RSC Advances 10, no. 24 (2020): 14122–33. http://dx.doi.org/10.1039/d0ra02374d.

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22

Zhang, Shumin, Qin Yang, Lin Guo, et al. "Isolation, structure elucidation and racemization of (+)- and (−)-pratensilins A–C: unprecedented spiro indolinone-naphthofuran alkaloids from a marine Streptomyces sp." Chemical Communications 53, no. 72 (2017): 10066–69. http://dx.doi.org/10.1039/c7cc04983h.

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23

Ghosh, Arun K., and Zhi-Hua Chen. "An intramolecular cascade cyclization of 2-aryl indoles: efficient methods for the construction of 2,3-functionalized indolines and 3-indolinones." Org. Biomol. Chem. 12, no. 22 (2014): 3567–71. http://dx.doi.org/10.1039/c4ob00511b.

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24

Nisheeth, Rastogi, Anil Harrison Darwin, Tripathi Diwakar, and Shukla Sarveshwar. "Synthesis and antimicrobial potential of Mannich bases of 4-chloro-3-{ 4-(chlorobenzyloxy)-benzoylhydrazono}-indolin-2-ones." Journal of Indian Chemical Society Vol. 86, Sep 2009 (2009): 991–95. https://doi.org/10.5281/zenodo.5820060.

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Department of Chemistry, Lucknow Christian Post-Graduate College, Lucknow-226 018, Uttar Pradesh, India <em>E-mail </em>: nisheethrastogi2003@yahoo.co.in Department of Chemistry, Sri Jai Narain Post-Graduate College, Lucknow-226 001, Uttar Pradesh, India <em>Manuscript received 3 March 2009, accepted 26 May 2009</em> 4-Chloro-3-{ 4-(chlorobenzyloxy)-benzoylhydrazono}-indolin-2-ones (1-4) were synthesised by the condensation of 4-(chlorobenzyloxy)-benzoylhydrazines and 4-chloroisatin. On being subjected to aminomethylation in the presence of formaldehyde and heterocyclic secondary amines, indolinones 1-4, furnished aminomethylated indolinones (Mannich bases) 5-20. The structures of the compounds have been established by means of elemental analysis and spectral data (IR, PMR and Mass). The compounds have been screened for their antimicrobial potential against human pathogenic bacteria and fungi.

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25

R., S. VARMA, and GUPTA PREETI. "Nucleophilic Addition-Elimination Reactions of 4- and 6-Chloroindolin-2, 3-diones with 6-Chloro-2- hydrazinobenzothiazole." Journal of Indian Chemical Society Vol. 66, May 1989 (1989): 325–26. https://doi.org/10.5281/zenodo.5995356.

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Department of Chemistry, Lucknow University. Lucknow-:126 007 <em>Manuscript received 12 December 1988, accepted 21 February 1989</em> 4-Chloroindolin•2,3-dione (Ia) and its 1-methyl analog (2a) undergo nucleophilic addition-elimination reaction with 6-chloro 2-hydrazinobenzothiazole to yield 4-chloro•3- (6' -chloro-2' -hydrazonobenzothiazolyl)-2-indolinone (3a) and 4-chloro-1-methyl·3-(6' -chloro-2-hydrazonobenzothiazolyl)-2-indolinone (4a) respectively. Similarly, 6-chloroindolin-2,3-dione (1b) and its 1-methyl analog (2b) yielded 3b and 4b respectively. 3a and 3b on treatment with morpholine/piperidine and formaldehyde furnished the corres- ponding 1-morpholino/piperidinomethyl analogs (5a, b). The compounds have been characterised by ir, pmr and mass spectral data.

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26

Pranc, Paul. "THE PREPARATION OF 5-CHLORO-2-INDOLINONE BY DIRECT CHLORINATION OF 2-INDOLINONE." Organic Preparations and Procedures International 22, no. 1 (1990): 104–5. http://dx.doi.org/10.1080/00304949009356676.

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27

Dong, Yu, Jun-Hu Qian, Xiang-Long Chen, et al. "Metal-free synthesis of C2-quaternary indolinones by (NH₄)₂S₂O₈ mediated oxidative dearomatization of indoles." RSC Advances 12, no. 33 (2022): 21022–25. http://dx.doi.org/10.1039/d2ra04191j.

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An efficient metal-free, (NH4)2S2O8 mediated oxidative dearomatization of indoles for construction of C2-quaternary indolinones was disclosed which provides an approach for generation of all-carbon quaternary centers at the C2 position of indoles.

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28

Xu, Guangyu, Shaixiao Tian, Yu Mao та Yongjun Jiang. "The Application of Vinamidinium Salt to the Synthesis of 3-Chloro-α-carbolines". Synlett 29, № 07 (2018): 949–53. http://dx.doi.org/10.1055/s-0037-1609151.

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A convenient synthesis of 3-chloro-α-carbolines by the condensation of vinamidinium salt with 2-indolinones via two steps is reported. This protocol has the advantages of readily available starting materials, high yields and easy workup.

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29

Vachhani, Dipak D., Himanshu H. Butani, Nandini Sharma, Umed C. Bhoya, Anamik K. Shah та Erik V. Van der Eycken. "Domino Heck/borylation sequence towards indolinone-3-methyl boronic esters: trapping of the σ-alkylpalladium intermediate with boron". Chemical Communications 51, № 80 (2015): 14862–65. http://dx.doi.org/10.1039/c5cc05193b.

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30

Demir-Yazıcı, Kübra, Çağla Begüm Apaydın, Özge Soylu-Eter, Nurten Özsoy, and Nilgün Karalı. "Synthesis, molecular modeling and cholinesterase inhibitory effects of 2-indolinone-based hydrazinecarbothioamides." Future Medicinal Chemistry 13, no. 24 (2021): 2133–51. http://dx.doi.org/10.4155/fmc-2021-0018.

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Background: 2-Indolinone-based hydrazinecarbothioamides carrying a 3-phenylsulfonamide moiety (7–9) were designed by replacement of donepezil's pharmacophore group indanone with a 2-indolinone ring. Method: Compounds 7–9 were synthesized by reaction of N-(3-sulfamoylphenyl)hydrazinecarbothioamide (6) with 1 H-indolin-2,3-diones (1–3). Acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitory effects of compounds 7–9 were assayed. Molecular modeling studies of 5-chloro-1,7-dimethyl-substituted compound 8e were carried out to determine the possible binding interactions at the active site of AChE. Results: Compound 8e showed the strongest inhibition against AChE ( Ki = 0.52 ± 0.11 μM) as well as the highest selectivity (SI = 37.69). The selectivity for AChE over BuChE of compound 8e was approximately 17-times higher than donepezil and 26-times higher than galantamine. Conclusion: Further development of compounds 7–9 may present new promising agents for Alzheimer's treatment.

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31

Zhang, Lijun, Wenzhong Zhang, Haibo Mei, Jianlin Han, Vadim A. Soloshonok, and Yi Pan. "Catalytic asymmetric aldol addition reactions of 3-fluoro-indolinone derived enolates." Organic & Biomolecular Chemistry 15, no. 2 (2017): 311–15. http://dx.doi.org/10.1039/c6ob02454h.

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Cu(i)/bisoxazoline ligand catalyzed asymmetric aldol reactions of fluoro-indolinone derived new type tertiary enolates have been developed. This process allows the preparation of a wide range of α-fluoro-β-aryl/hetaryl/alkyl-β-hydroxy-indolin-2-one products containing C–F quaternary stereogenic centers.

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32

Gasparič, Jiří, Tomáš Vontor, Antonín Lyčka, and Dobroslav Šnobl. "Formation of acetals and cleavage of the five-membered ring in the bromination of isatin in alcohols." Collection of Czechoslovak Chemical Communications 55, no. 12 (1990): 2963–66. http://dx.doi.org/10.1135/cccc19902963.

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Bromination of isatin (I) in alcohols affords in good yield 5,7-dibromo-3,3-dialkoxy-2-indolinones (IIIa and IIIb) which arise by reaction catalysed with hydrogen bromide liberated in the bromination. The reaction affords also minor amounts of 2,4,6-tribromoaniline (IV) formed by splitting off of two carbon atoms from the isatin five-membered ring.

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33

Singh, S. P., and Krishna Jha. "Indolinone Derivatives as Potential Antimicrobial Agents." Zentralblatt für Mikrobiologie 144, no. 2 (1989): 105–9. http://dx.doi.org/10.1016/s0232-4393(89)80073-3.

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Novotortsev, Vladimir K., Maxim E. Kukushkin, Viktor A. Tafeenko, Nikolai V. Zyk, and Elena K. Beloglazkina. "New spiro-linked indolinone pyrrolidine selenoxoimidazolones." Mendeleev Communications 30, no. 3 (2020): 320–21. http://dx.doi.org/10.1016/j.mencom.2020.05.020.

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Naidenov, V. E., Z. I. Kuvaeva, D. V. Lopatik, M. M. Markovich, and A. V. Mikulich. "Preparative synthesis of N-acetyl-3-indolinones." Proceedings of the National Academy of Sciences of Belarus, Chemical Series 55, no. 1 (2019): 58–63. http://dx.doi.org/10.29235/1561-8331-2019-55-1-58-63.

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Lipkowski, Janusz, Roman Luboradzki, Lech Stefaniak, and Jacek Wójcik. "X-ray diffraction study of some indolinones." Journal of Chemical Crystallography 25, no. 6 (1995): 299–308. http://dx.doi.org/10.1007/bf01796054.

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Velezheva, V. S., V. V. Dvorkin, and N. N. Suvorov. "Synthesis of 2-amino-3-aryl-4-quinolones and 2-(aminoarylmethylidene)-3-indolinones from 2-arylidene-3-indolinones." Chemistry of Heterocyclic Compounds 21, no. 2 (1985): 234. http://dx.doi.org/10.1007/bf00504219.

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Ibrahim, Mohamed N., Mohamed F. El-Messmary, and Mohamed G. A. Elarfi. "Synthesis of Spiro Heterocyclic Compounds." E-Journal of Chemistry 7, no. 1 (2010): 55–58. http://dx.doi.org/10.1155/2010/604549.

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Reaction of isatin with acetophenone derivatives gave 3-hydroxy-3-phenacyl oxindole derivatives(II), dehydration of(II)gave 3-phenacylidene-2-indolinone derivatives(III). Condensation of(III)with hydrazine hydrate, phenylhydrazine and phenylthiourea afforded new spiropyrazolines(IV & V)and spiropyrimidinethione(VI)respectively. The structures of the final products were established by physical and spectral means.

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39

Bykov, V. V., A. V. Bykova, O. I. Aliev, et al. "Influence of a new stimulator of soluble guanylate cyclase on platelet aggregation and vascular endothelial function in experimental ischemic stroke against the background of arterial hypertension." "Arterial’naya Gipertenziya" ("Arterial Hypertension") 28, no. 6 (2022): 710–17. http://dx.doi.org/10.18705/1607-419x-2022-28-6-710-717.

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Background. Correction of endothelial dysfunction during arterial hypertension (AH) is an important measure in preventing cerebrovascular stroke. Drugs activating soluble guanylate cyclase (sGC) and 3’,5’-guanosine monophosphate (cGMP) production independently of nitric oxide (NO) were shown to be therapeutically useful in reducing the risk of stroke. The present work aims to study the antiaggregant and endothelium-protective activity of a new sGC stimulator, an indolinone derivative (2-[2-[(5RS)-5-(hydroxymethyl)-3-methyl-1,3-oxazolidine-2- yliden]-2-cyanoethylidene]-1H-indole-3(2H)-one (codename — GRS) in a model of ischemic stroke with AH. Prior studies have shown that GRS compound inhibits platelet aggregation, lowers blood pressure (BP) in spontaneouslyhypertensive SHR rats, prevents vascular occlusion in models of arterial and venous thrombosis. Antiplatelet drug clopidogrel, a P2Y12 receptor inhibitor, included in the standard of care for secondary prevention of ischemic stroke, was used as the reference drug.Objective. To assess the antiaggregant and endothelium-protective activity of a new indolinone derivative GRS, an sGC stimulator, compared to clopidogrel in a model of ischemic stroke concomitant with high arterial BP in spontaneously-hypertensive SHR rats.Design and methods. Focal brain ischemia/reperfusion was modelled in spontaneously-hypertensive SHR rats (n = 78). GRS in 10 mg/kg dose and clopidogrel in 10 mg/kg dose were administered orally once daily 3 days before modelling ischemia/reperfusion and for 5 days afterwards. Platelet aggregation and functioning of vascular endothelium were monitored.Results. Focal brain ischemia/reperfusion in SHR rats resulted in increased platelet aggregation and the development of endothelial dysfunction and disruption of vasodilatory function of endothelium. GRS compound and clopidogrel in repeated administration have prevented an increase in platelet aggregation (p < 0,05), GRS compound also alleviated endothelial dysfunction (p < 0,05).Conclusions. The indolinone derivative GRS, an sGC stimulator, inhibits increased platelet aggregation and prevents endothelial dysfunction in rats after focal brain ischemia/ reperfusion; the endothelium-protective effects of GRS aren’t related to its antiaggregant activity.

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40

Coldham, Iain, Harry Adams, Neil J. Ashweek, Thomas A. Barker, Andrew T. Reeder, and Melanie C. Skilbeck. "Synthesis of 2-hydroxy-3-indolinones and 3-hydroxy-2-indolinones by anionic cyclization, in situ oxidation and rearrangement." Tetrahedron Letters 51, no. 18 (2010): 2457–60. http://dx.doi.org/10.1016/j.tetlet.2010.02.159.

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Granik, V. G., I. P. Graevskaya, and S. Yu Ryabova. "Heterocyclization of 2-indolinone derivatives (A review)." Pharmaceutical Chemistry Journal 31, no. 12 (1997): 646–62. http://dx.doi.org/10.1007/bf02464251.

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Khan, Momin, Muhammad Yousaf, Abdul Wadood, et al. "2-Indolinone Derivatives as Potent Urease Inhibitors." Letters in Drug Design & Discovery 15, no. 8 (2018): 814–21. http://dx.doi.org/10.2174/1570180814666171116154110.

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Bykov, V. V., K. A. Leonov, V. Yu Serebrov, et al. "Metabolism of a New Antiaggregant, Indolinone Derivative." Bulletin of Experimental Biology and Medicine 168, no. 6 (2020): 739–42. http://dx.doi.org/10.1007/s10517-020-04792-y.

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Mochalov, S. S., A. N. Fedotov, D. S. Yufit, Yu T. Struchkov, and Yu S. Shabarov. "New rearrangement in the 3-indolinone series." Chemistry of Heterocyclic Compounds 27, no. 7 (1991): 737–40. http://dx.doi.org/10.1007/bf00476204.

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GRANIK, V. G., I. P. GRAEVSKAYA, and S. YU RYABOVA. "ChemInform Abstract: Heterocyclization of Indolinone-2 Derivatives." ChemInform 29, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199816292.

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Motevalli, Somayeh, and Jeffrey Johnson. "Phosphite-Mediated Reductive Cross-Coupling of Isatins and Nitrostyrenes." Synthesis 49, no. 12 (2017): 2663–76. http://dx.doi.org/10.1055/s-0036-1588170.

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A new reductive coupling reaction between N-alkylisatins, dimethyl phosphite, and nitrostyrenes has been developed. The reaction relies on Pudovik addition, subsequent phosphonate–phosphate rearrangement, and Michael-type addition of a transient carbanion on the indolinone with β-nitrostyrenes. This protocol introduces a convenient and versatile method for the construction of polyfunctionalized tertiary phosphates under mild conditions. Chiral general bases catalyze the title reaction with promising levels of enantioselectivity.

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Leroi, Corinne, Denis Bertin, Pierre-Emmanuel Dufils, et al. "Alkoxyamine-Mediated Radical Synthesis of Indolinones and Indolines." Organic Letters 5, no. 26 (2003): 4943–45. http://dx.doi.org/10.1021/ol0358049.

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Legrel, P., M. Baudy-Floc'h та A. Robert. "N-amino indolinones a partir d'arylhydrazides α-halogenes". Tetrahedron Letters 27, № 46 (1986): 5609–10. http://dx.doi.org/10.1016/s0040-4039(00)85278-8.

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Andreani, A., M. Rambaldi, A. Locatelli, et al. "Synthesis and cardiotonic activity of pyridylmethylene-2-indolinones." European Journal of Medicinal Chemistry 27, no. 2 (1992): 167–70. http://dx.doi.org/10.1016/0223-5234(92)90106-b.

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50

Zhang, Man, Yu-Xiang Shen, Qi Fang, Lei Wang, and Da-Zhi Li. "Crystal structure of 1-ethyl-5-iodoindolin-2-one." Acta Crystallographica Section E Crystallographic Communications 71, no. 6 (2015): 712–15. http://dx.doi.org/10.1107/s2056989015009937.

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In the title indolinone derivative, C10H10INO, all the non-H atoms, except the terminal methyl C atom, are almost coplanar. The molecules are arranged into columns extending along thea-axis direction and interact with the molecules in adjacent columnsviaC—H...O hydrogen bonds [H...O distance = 2.57 (3) Å] and I...I short contacts of 3.8986 (3) Å. A one-dimensional zigzag iodine chain along theaaxis is apparent between two neighbouring columns.

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