387342-89-4

Upstream product

• 100-52-7 benzaldehyde 
• 928782-97-2 4-chloro-2-(phenylethynyl)aniline 
• 201230-82-2 carbon monoxide 
• 53691-91-1 N-(4-chlorophenyl)-3-phenylacrylamide 
• 17630-76-1 5-chloroindole 2,3-dione 
• 17630-75-0 5-chloro-indolin-2-one 
• 100-46-9 benzylamine 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part 2

A series of heterocycle-containing oxindoles was synthesized and their HIV antiviral activities were assessed. Some of these analogs exhibited potent inhibitory activities against both wild-type virus and a number of drug-resistant mutant viruses. In addi

Oxidative electro-organic synthesis of dimeric hexahydropyrrolo-[2,3-: B] indole alkaloids involving PCET: Total synthesis of (±)-folicanthine

An efficient electrochemical oxidation strategy for the total synthesis of a dimeric hexahydropyrrolo[2,3-b]indole alkaloid, (±)-folicanthine (1b), has been envisioned. Control experiments suggest that a PCET pathway involving stepwise electron transfer f

Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators

An enantioselective hetero-Diels-Alder reaction of alkylidene oxindoles and 2-aza-3-silyloxy-1,3-butadienes, catalyzed by divalent transition metal complexes with N, N ′-dioxide ligands offered an efficient access to natural-product-based 3,3′-piperidinoyl spirooxindole class of small molecules. exo -Cycloadducts formed via stereospecific cycloaddition with Z -olefin displayed potent activity in modulation of hedgehog pathway.

Synthesis of (E)-3-Alkylideneindolin-2-ones by an Iron-Catalyzed Aerobic Oxidative Condensation of Csp3–H Bonds of Oxindoles and Benzylamines

A novel synthetic route for the construction of (E)-3-alkylideneindolin-2-ones through iron-catalyzed aerobic oxidative condensation of oxindoles with benzylamines has been developed. This oxidative reaction involves a sequence of C–H activation, amine self-condensation, nucleophilic addition, and C–C double bond formation. The synthetic importance of this protocol has been demonstrated by preparing tyrosine kinase inhibitors, anticonvulsant and antitumor agents, and other valuable 3-alkylideneindolin-2-one derivatives. Key intermediates are isolated and a plausible mechanistic pathway for the reaction has been discussed.

(E)-3-(Aryl(arylamino)methylene)indolin-2-one derivatives: An efficient synthetic approach and evaluation of their cancer inhibitory activity

A series of (E)-3-(aryl(arylamino)methylene)indolin-2-one derivatives were synthesised using an efficient synthetic approach. The method involved reaction of 3-bromo-3-(bromo(aryl)methyl)indolin-2-one with substituted anilines through nucleophilic substitution and a simultaneous elimination using NaHCO3 in DMF. The anticancer activity of the products against four cell lines, HCT-116, A549, SKOV3 and MDA-MB-231, was also evaluated, and several compounds showed moderate inhibitory activity.

In?vitro targeting of colon cancer cells using spiropyrazoline oxindoles

We report on the synthesis and biological evaluation of a library of twenty-three spiropyrazoline oxindoles. The antiproliferative activity of the chemical library was evaluated in HCT-116 p53(+/+) human colon cancer cell line with eight deriva

3-substituted arylcarbonylindol-2-ketone and preparation method thereof

The invention relates to 3-substituted arylcarbonylindol-2-ketone and a preparation method thereof. According to the preparation method, indole-2-ketone and aromatic aldehyde are taken as raw materials, and a 3-substituted arylcarbonylindol-2-ketone compound with moderate-good yield is obtained through catalytic synthesis of inorganic salt under a mild condition. The preparation method has the characteristics of being quick in reaction speed, mild in reaction conditions, simple and convenient to operate and the like.

N'-Alkylaminosulfonyl Analogues of 6-Fluorobenzylideneindolinones with Desirable Physicochemical Profiles and Potent Growth Inhibitory Activities on Hepatocellular Carcinoma

The benzylideneindolinone 6-chloro-3-(3′-trifluoromethylbenzylidene)-1,3-dihydroindol-2-one (4) was reported to exhibit potent and selective growth inhibitory effects on hepatocellular carcinoma (HCC). Corroborative evidence supported multi-receptor tyrosine kinase (RTK) inhibition as a possible mode of action. However, the poor physicochemical properties of 4 limited its furtherance as a lead compound. In this study, the modification of 4 was investigated with the aim of improving its potency and physicochemical profile. The 6-fluorobenzylideneindolinone 3-12 bearing a 3′-N-propylaminosulfonyl substituent was found to be a promising substitute. Compound 3-12 [6-fluoro-3-(3′-N-propylaminosulfonylbenzylidene)-1,3-dihydroindol-2-one] was found to be tenfold more soluble than 4 and to have sub-micromolar growth inhibitory activities on HCC cells. It is apoptogenic and inhibits the phosphorylation of several RTKs in HuH7, of which the inhibition of FGFR4 and HER3 are prominent. Compound 3-12 decreased the tumor load in a physiologically relevant orthotopic HCC xenograft murine model. Structure-activity relationships support pivotal roles for the fluoro and N′-propylaminosulfonyl moieties in enhancing cell-based activity and moderating the physicochemical profile (solubility, permeability) of 3-12.

Synthesis of novel spiropyrazoline oxindoles and evaluation of cytotoxicity in cancer cell lines

A series of novel spiropyrazoline oxindole derivatives was synthesized by 1,3-dipolar cycloaddition reaction. The compounds were screened for their in vitro cytotoxic activity against MCF-7 breast cancer cell line (estrogen receptor positive (ER+) and hum

Indolinone based LRRK2 kinase inhibitors with a key hydrogen bond

The most prevalent leucine-rich repeat kinase 2 (LRRK2) mutation G2019S is associated with Parkinson's disease (PD). It enhances kinase activity and has been identified in both familial and sporadic cases. Kinase activity was reported to be required for LRRK2 mutants to exert their toxic effects. Hence LRRK2 kinase inhibition may be a promising therapeutic target for PD. Here we report on the discovery and characterization of indolinone based LRRK2 inhibitors. Indolinone 15b, the most potent and selective inhibitor of the present series, is characterized by an IC50of 15 nM against wild-type LRRK2 and 10 nM against the LRRK2 G2019S mutant, respectively. Compound 15b was further evaluated in a kinase panel including 46 human protein kinases and in a zebrafish embryo phenotype assay, which enabled toxicity determination in whole organisms.