75822-54-7Relevant academic research and scientific papers
Isatin derivatives as a new class of aldose reductase inhibitors with antioxidant activity
Liu, Wenchao,Chen, Huan,Zhang, Xiaonan,Zhang, Xin,Xu, Long,Lei, Yanqi,Zhu, Changjin,Ma, Bing
, p. 1588 - 1602 (2021)
In this work, isatin was employed as the scaffold to design aldose reductase inhibitors with antioxidant activity. Most of the isatin derivatives were proved to be excellent in the inhibition of aldose reductase (ALR2) with IC50 values at submi
Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction
Burke, Anthony J.,Erxleben, Andrea,Marques, Carolina S.,McArdle, Patrick
supporting information, (2020/06/30)
A one-step, three-component Petasis reaction of isatin derived 5-arylboronate-3-substituted oxindole derivatives with salicylaldehydes and secondary amines affords new enantiomerically pure structurally diverse 5-α-(3-substituted-oxindole)-benzylamine derivatives. The reaction shows good substrate and reagent scope affording the products with good to excellent yields (up to >99 % yield) and enantioselectivities (up to 99 % ee) using cheap and readily available (R)-BINOL as the organocatalyst. A diastereoselective version of the reaction was also developed where moderate yields (37 to 55 % yield), excellent enantioselectivities (up to 99 % ee) and good diastereoselectivities (up to 86 % de) were obtained for new 5-α-(3-hydroxy-oxindole)-benzylamine derivatives, having two stereocenters. The reaction is also feasible on gram-scale.
Triarylethylene-indolin-2,3-dione molecular conjugates: Design, synthesis, docking studies and anti-proliferation evaluation
Kumar, Sumit,Palma, Gabriella,Perumal, Shanen,Kaur, Mandeep,Singh-Pillay, Ashona,Raj, Raghu,Singh, Parvesh,Kumar, Vipan
, p. 42409 - 42414 (2020/01/08)
A series of 1H-1,2,3-triazole-linked ospemifene-isatin and O-methylated ospemifene-isatin conjugates were synthesized and assayed for their anti-proliferative activities against estrogen-responsive as well as estrogen-non-responsive cells. The non-cytotoxic conjugate 14e, with an optimal combination of bromo substituents at the C-5/C-7 positions of isatin, proved to be a promising hit with an IC50 value of 31.62 μM against MCF-7 and 19.23 μM against MDA-MB-231. The observed anti-proliferative activities of active conjugates were further corroborated via docking studies carried out on estrogen receptor subtypes α and β.
Cu(ii)-: TBu-PHOX catalyzed enantioselective malonate addition onto 3-hydroxy 2-oxindoles: Application in the synthesis of dimeric pyrroloindoline alkaloids
Babu, K. Naresh,Kinthada, Lakshmana K.,Pratim Das, Partha,Bisai, Alakesh
supporting information, p. 7963 - 7966 (2018/07/25)
An efficient Cu(ii)-PHOX-catalyzed malonate addition onto 3-hydroxy 3-indolyl-2-oxindoles is envisioned to afford excellent enantioselectivities (up to >99% ee) in high chemical yields. Detailed characterization techniques including X-ray, NMR, CV and EPR experiments suggest that a Cu(ii)-complex is involved as an active species in this process. Applying this strategy, an advanced intermediate of cyclotryptamine alkaloids has been synthesized in few steps for a general approach to bis-cyclotryptamine alkaloids.
N-{[2-(PIPERIDIN-1-YL)PHENYL](PHENYL)METHYL}-2-(3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXA ZIN-7-YL)ACETAMIDE DERIVATIVES AND RELATED COMPOUNDS AS ROR-GAMMA MODULATORS FOR TREATING AUTOIMMUNE DISEASES
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Page/Page column 68; 111; 112, (2018/08/20)
The present invention provides e.g. N-{[2-(piperidin-1-yl)phenyl] (phenyl)methyl}-2-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)acetamide derivatives and related compounds as ROR-gamma modulators for treating e.g. autoimmune diseases, autoimmune-related diseases, inflammatory diseases, metabolic diseases, fibrotic diseases or cholestatic diseases, such as e.g. arthitis and asthma.
Design, synthesis and anti-tumor activity study of novel histone deacetylase inhibitors containing isatin-based caps and o-phenylenediamine-based zinc binding groups
Gao, Shuai,Zang, Jie,Gao, Qianwen,Liang, Xuewu,Ding, Qinge,Li, Xiaoyang,Xu, Wenfang,Chou, C. James,Zhang, Yingjie
, p. 2981 - 2994 (2017/05/25)
As a hot topic of epigenetic studies, histone deacetylases (HDACs) are related to lots of diseases, especially cancer. Further researches indicated that different HDAC isoforms played various roles in a wide range of tumor types. Herein a novel series of HDAC inhibitors with isatin-based caps and o-phenylenediamine-based zinc binding groups have been designed and synthesized through scaffold hopping strategy. Among these compounds, the most potent compound 9n exhibited similar if not better HDAC inhibition and antiproliferative activities against multiple tumor cell lines compared with the positive control entinostat (MS-275). Additionally, compared with MS-275 (IC50 values for HDAC1, 2 and 3 were 0.163, 0.396 and 0.605?μM, respectively), compound 9n with IC50 values of 0.032, 0.256 and 0.311?μM for HDAC1, 2 and 3 respectively, showed a moderate HDAC1 selectivity.
PURINE INHIBITORS OF HUMAN PHOSPHATIDYLINOSITOL 3-KINASE DELTA
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Page/Page column 111-112, (2017/11/01)
The instant invention provides compounds of formula (I) which are PI3K-delta inhibitors, and as such are useful for the treatment of PI3K-delta-mediated diseases such as inflamation, asthma, COPD and cancer.
Design, synthesis and preliminary biological evaluation of indoline-2,3-dione derivatives as novel HDAC inhibitors
Jin, Kang,Li, Shanshan,Li, Xiaoguang,Zhang, Jian,Xu, Wenfang,Li, Xuechen
, p. 4728 - 4736 (2015/08/03)
Histone deacetylases (HDACs) are zinc-dependent or NAD+ dependent enzymes and play a critical role in the process of tumor development. Herein a series of indoline-2,3-dione derivatives have been designed and synthesized as potential HDACs inhibitors. The preliminary biological evaluation showed that most compounds synthesized have exhibited moderate Hela cell nuclear extract inhibitory activities, among which compound 25a (IC50 = 10.13 nM) has shown the best efficacy. The anti-proliferative activities of some of these compounds were also discussed.
Identification of the First Highly Subtype-Selective Inhibitor of Human GABA Transporter GAT3
Damgaard, Maria,Al-Khawaja, Anas,Vogensen, Stine B.,Jurik, Andreas,Sijm, Maarten,Lie, Maria E. K.,B?k, Mathias I.,Rosenthal, Emil,Jensen, Anders A.,Ecker, Gerhard F.,Fr?lund, Bente,Wellendorph, Petrine,Clausen, Rasmus P.
, p. 1591 - 1599 (2015/09/28)
Screening a library of small-molecule compounds using a cell line expressing human GABA transporter 3 (hGAT3) in a [3H]GABA uptake assay identified isatin derivatives as a new class of hGAT3 inhibitors. A subsequent structure-activity relationship (SAR) study led to the identification of hGAT3-selective inhibitors (i.e., compounds 20 and 34) that were superior to the reference hGAT3 inhibitor, (S)-SNAP-5114, in terms of potency (low micromolar IC50 values) and selectivity (>30-fold selective for hGAT3 over hGAT1/hGAT2/hBGT1). Further pharmacological characterization of compound 20 (5-(thiophen-2-yl)indoline-2,3-dione) revealed a noncompetitive mode of inhibition at hGAT3. This suggests that this compound class, which has no structural resemblance to GABA, has a binding site different from the substrate, GABA. This was supported by a molecular modeling study that suggested a unique binding site that matched the observed selectivity, inhibition kinetics, and SAR of the compound series. These compounds are the most potent GAT3 inhibitors reported to date that provide selectivity for GAT3 over other GABA transporter subtypes.
Novel 2-oxoindoline-based hydroxamic acids: Synthesis, cytotoxicity, and inhibition of histone deacetylation
Huong, Tran Thi Lan,Dung, Do Thi Mai,Dung, Phan Thi Phuong,Huong, Phung Thanh,Vu, Tran Khac,Hahn, Hyunggu,Han, Byung Woo,Kim, Jisung,Pyo, Minji,Han, Sang-Bae,Nam, Nguyen-Hai
supporting information, p. 6425 - 6429 (2015/11/16)
In a continuation of a research program to discover novel small molecules targeting histone deacetylases, a series of 2′-oxospiro[1,3]dioxolane/dithiolane-2,3′-indoline-based hydroxamic acids have been designed and synthesized. These 2-oxoindoline-based hydroxamic acids displayed potent cytotoxicity against three human cancer cell lines, including SW620 (colon cancer), PC-3 (prostate cancer) and AsPC-1 (pancreatic cancer), with IC50 values as low as 0.05-0.07 μM, 74-fold lower than that of SAHA (1.64-3.70 μM). Additionally, compounds in this series exhibited good inhibition against histone-H3 and histone-H4 deacetylation, as evaluated by Western blot assay. These compounds also strongly inhibited HDAC2 with IC50 values as low as 0.03 μM. Docking studies performed using Autodock Vina showed all compounds bound to HDAC2 with relatively higher affinities (from -7.7 to -8.0 kcal/mol) compared to SAHA (-7.4 kcal/mol).
