34880-79-0Relevant academic research and scientific papers
Eco-friendly Polyethylene Glycol-400 as a Rapid and Efficient Recyclable Reaction Medium for the Synthesis of Anticancer Isatin-linked Chalcones and Their 3-Hydroxy Precursor
Gupta, Alpana K.,Bharadwaj, Mausumi,Mehrotra, Ravi
, p. 703 - 709 (2019)
Isatin chalcones and their 3-hydroxy precursors are shown to possess potential anticancer activity and are also versatile substrates and key intermediates for the synthesis of a large variety of bioactive spiro-oxindoles. An environmental friendly tandem
Lewis acid-promoted synthesis of highly substituted pyrrole-fused benzoxazinones and quinoxalinones
Selvendran, Suresh,Rajendran, Saravanakumar
supporting information, p. 437 - 445 (2020/10/22)
A synthesis of a series of novel fused tricyclic heterocyclic compounds has been achieved in one-pot reaction set up starting from (E)-3-(2-oxo-2-phenylethylidene)indolin-2-one and 1,4-benzoxazinone/quinoxalinone derivatives promoted by tin(IV) chloride.
Diastereoselective trans Cyclopropanation of 3-Alkylidene Oxindoles with in Situ Generated α-Diazo Carbonyls or α,β-Unsaturated Diazo Compounds
Pramanik, Sayan,Ray, Suman,Maity, Suvendu,Ghosh, Prasanta,Mukhopadhyay, Chhanda
supporting information, p. 2240 - 2252 (2021/03/18)
An efficient diastereoselective trans cyclopropanation of 3-alkylidene oxindoles with in situ generated α-diazo carbonyl compounds or α,β-unsaturated diazo compounds under metal-free conditions has been developed to synthesize 3-spirocyclopropyl-2-oxindol
Asymmetric Synthesis of Spirooxindoles with Seven Stereocenters via Organocatalyzed One-pot Three-component Sequential Cascade Reactions
Zhao, Bo-Liang,Du, Da-Ming
supporting information, p. 3412 - 3419 (2019/05/10)
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.).
Regioselective hydrodehalogenation of aromatic α-and β-halo carbonyl compounds by cui in isopropanol
Parveen, Iram,Khan, Danish,Ahmed, Naseem
, p. 759 - 764 (2019/01/09)
An operationally efficient and regioselective hydrodehalogenation methodology of aromatic α-and β-halo carbonyl compounds has been developed using CuI in isopropanol at 90 °C under basic condition. The catalytic system effectively dehalogenates chloride, bromide, and iodide groups and af-forded high yield (up to 97 %) as carbonyl compounds. The methodology is environmentally friendly and demonstrates excellent tolerance to a broad range of electronically rich and poor substituents.
Application of isatin analogues in preparing antineoplastic drugs
-
Paragraph 0035; 0036; 0040; 0056, (2018/07/30)
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.
Design, synthesis and QSAR study of novel isatin analogues inspired Michael acceptor as potential anticancer compounds
Wang, Jiabing,Yun, Di,Yao, Jiali,Fu, Weitao,Huang, Fangyan,Chen, Liping,Wei, Tao,Yu, Cuijuan,Xu, Haineng,Zhou, Xiaoou,Huang, Yanqing,Wu, Jianzhang,Qiu, Peihong,Li, Wulan
, p. 493 - 503 (2018/01/01)
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.
Synthesis of (E)-3-(2-Oxo-2-arylethylidene)indolin-2-ones through Alkyne Carbonyl Metathesis and Their Stereospecific Application towards Spiro-oxindolopyrrolizidine Scaffolds
Basu, Soumyadip,Mukhopadhyay, Chhanda
, p. 1496 - 1506 (2018/04/06)
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.
Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast
Rossetti, Arianna,Sacchetti, Alessandro,Bonfanti, Marta,Roda, Gabriella,Rainoldi, Giulia,Silvani, Alessandra
, p. 4584 - 4590 (2017/07/11)
3-Substituted oxindoles are very interesting molecules both for their potential biological activity and for their role as starting materials toward more complex oxindole-based structures. These molecules can be prepared by the reduction of a 3-ylidene oxi
Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents
Reddy, Chada Narsimha,Nayak, V. Lakshma,Mani, Geeta Sai,Kapure, Jeevak Sopanrao,Adiyala, Praveen Reddy,Maurya, Ram Awatar,Kamal, Ahmed
, p. 4580 - 4586 (2015/10/12)
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),
