56680-33-2

Upstream product

• 70452-26-5 3-hydroxy-3-(2-(4-methoxyphenyl)-2-oxoethyl)indolin-2-one 
• 62-53-3 aniline 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 91-56-5 indole-2,3-dione 
• 768-60-5 4-methoxyphenylacetylen 
• 1777-55-5 (4-methoxyphenacylidene)triphenyl phosphorane 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 159862-03-0 (Z)-3-(2-(4-methoxyphenyl)-2-oxoethylidene)indolin-2-one 
• 56680-31-0 1-acetyl-3-[(E)-2-(4-methoxy-phenyl)-2-oxo-ethylidene]-1,3-dihydro-indol-2-one 
• 56680-49-0 (2c-ethoxy-2,3,4,9-tetrahydro-pyrano[2,3-b]indol-4r-yl)-(4-methoxy-phenyl)-methanone 
• 56680-50-3 3-[5-ethoxy-2-(4-methoxy-phenyl)-4,5-dihydro-furan-3-yl]-1,3-dihydro-indol-2-one 

Relevant academic research and scientific papers

Asymmetric Synthesis of Spirooxindoles with Seven Stereocenters via Organocatalyzed One-pot Three-component Sequential Cascade Reactions

A bifunctional squaramide-catalyzed one-pot three-component Michael/Mannich-Michael/cyclization sequential cascade reaction for the construction of bispirooxindole-spirooxindoles was developed in good yields with excellent stereoselectivities (up to >20:1 dr, 99% ee). A series of original cinnamoyl-3-ylideneoxindoles have been applied to this sequential cascade strategy for the first time. This new strategy provides a process for the enantioselective construction of bispirooxindole-spirooxindoles with seven stereocenters, of which three are quaternary spiro-stereocenters. (Figure presented.).

Synthesis of (E)-3-(2-Oxo-2-arylethylidene)indolin-2-ones through Alkyne Carbonyl Metathesis and Their Stereospecific Application towards Spiro-oxindolopyrrolizidine Scaffolds

An iron-salt catalyzed, atom economic, unfamiliar type of alkyne carbonyl metathesis strategy has been developed by using isatins and acetylenes for the regioselective synthesis of (E)-3-(2-oxo-2-arylethylidene)indolin-2-one derivatives, which has been further utilized to develop a catalyst-free methodology for the synthesis of biologically active spiro-oxindolopyrrolizidine scaffolds in a highly regio- and stereospecific manner by reacting with l-proline and aldehydes. Both methods are acceptable towards various functionalities that include electron-donating and electron-accepting groups at the ortho-, meta- and para-positions. This protocol provides an environmentally friendly reaction methodology for the synthesis of a series of (1′S,2′R,3′R,7a′R)-1′,3′,5′,6′,7′,7a′-hexahydrospiro[indoline-3,2′-pyrrolizin]-2-ones.

Design, synthesis and QSAR study of novel isatin analogues inspired Michael acceptor as potential anticancer compounds

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. Notably, compound 6a showed potent growth inhibition on BGC-823, SGC-7901 and NCI-H460 with the IC50 values of 3.6 ± 0.6, 5.7 ± 1.2, 3.2 ± 0.7 μM, respectively. Besides, colony formation assays, wound healing assays and flow cytometry analysis indicated 6a exhibited a potent anti-growth and anti-migration ability in a concentration-dependence manner through arrested cells in the G2/M phase of cell cycle. Moreover, 6a significantly repressed tumor growth in a NCI-H460 xenograft mouse model. Overall, our findings suggested isatin analogues inspired Michael acceptor may provide promising lead compounds for the development of cancer chemotherapeutics.

Application of isatin analogues in preparing antineoplastic drugs

The invention belongs to the field of medicinal chemistry, and in particular relates to an application of isatin analogues in preparing antineoplastic drugs. A series of isatin analogues can be synthesized by splicing isatin and [alpha],[beta]-unsaturated ketone via a medicinal chemistry splicing principle. The compounds (the isatin analogues) are relatively good in inhibitory activity on three tumor cells, and an antineoplastic effect can be achieved by inhibiting growth and migration of tumor cells and by blocking cell cycle G2/M period; and based upon in vivo experimental results, it is also indicated that the compounds can inhibit tumor growth.

Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents

Libraries of spiro[cyclopropane-1,3′-indolin]-2′-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer),

Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

The designation of E/Z-geometrical isomers in 3-acylidene 2-oxindoles by NMR spectroscopy can lead to erroneous assignment of alkene stereochemistry because of the narrow chemical shift range observed over a large series of analogues. In contrast, UV-Vis spectroscopy offers a convenient and more reliable method for alkene stereochemical assignment. A combination of X-ray crystallography and theoretical studies shows that the observed differences in UV-Vis spectroscopic behaviour relate to the twisted conformation of the Z-isomers that provides reduced conjugation and weaker hypsochromic (blue-shifted) absorbances relative to those of the E-isomers.

Facile synthesis of β-lactam-grafted spirooxindolopyrrolidine through regioselective 1,3-dipolar cycloaddition reaction

One-pot synthesis of novel β-lactam-grafted spiropyrrolidines has been accomplished in good yield via a facile [3+2] cycloaddition reaction of azomethine ylides, derived from β-lactam aldehyde and sarcosine, with various p-substituted (E)-2-oxoindoline-3-