99984-61-9Relevant academic research and scientific papers
Enantioseletive Fluorination of 3-Functionalized Oxindoles Using Electron-rich Amino Urea Catalyst
Jiang, Xiaojian,Wang, Haitao,He, Haoquan,Wang, Wei,Wang, Yuqiang,Ke, Zhihai,Yeung, Ying-Yeung
supporting information, p. 4710 - 4714 (2018/11/10)
An enantioselective fluorination of 3-functionalized oxindoles using electron-rich amino urea catalyst is described. Various 3-functionalized 3-fluoro-2-oxindoles were obtained in good yields and enantio-selectivity. The resulting enantioenriched 3-methylene nitrile 3-fluoro-2-oxindole product was found to inhibit indoleamine 2,3-dioxygenase considerably. (Figure presented.).
Spirooxindoles as novel 3D-fragment scaffolds: Synthesis and screening against CYP121 from M. tuberculosis
Davis, Holly J.,Kavanagh, Madeline E.,Balan, Tudor,Abell, Chris,Coyne, Anthony G.
supporting information, p. 3735 - 3740 (2016/07/22)
The search for new scaffolds to complement current HTS and fragment libraries is an active area of research. The development of novel strategies to synthesise compounds with 3D character in order to expand the diversity of a fragment library was explored. A range of substituted bicyclo[2,2,1]spirooxindoles were synthesised using a Diels–Alder [4+2] cycloaddition reaction. Both diastereoisomers were isolated from the reactions and these 3D fragment scaffolds were screened against the cytochrome P450 enzyme CYP121 from Mycobacterium tuberculosis. A number of hits were identified to bind to CYP121 and were shown to exhibit Type I binding interactions with the heme group.
Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: Reaction development and applications
Trost, Barry M.,Zhang, Yong
supporting information; experimental part, p. 2916 - 2922 (2011/05/02)
We report a full account of our work towards the development of Mo-catalyzed asymmetric allylic alkylation reactions with 3-alkyloxindoles as nucleophiles. The reaction is complementary to the Pd-catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3-alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good-to-excellent enantioselectivities. Applications of this method to the preparation of indoline alkaloids such as (-)-physostigmine, ent-(-)-debromoflustramine B, and the indolinoquinoline rings of communesin B are reported.
Synthesis and biological evaluation of (-)- and (+)-debromoflustramine B and its analogues as selective butyrylcholinesterase inhibitors
Rivera-Becerril, Ernesto,Joseph-Nathan, Pedro,Pérez-álvarez, Víctor M.,Morales-Ríos, Martha S.
scheme or table, p. 5271 - 5284 (2009/07/01)
A series of pyrrolidinoindolines have been synthesized as debromoflustramine B (4a) analogues for their evaluation as cholinesterase inhibitors. Structure-activity studies of this series revealed the optimum pharmacophore elements required for activity and resulted in the discovery of selective butyrylcholinesterase inhibitors with micromolar potency. Biological testing demonstrated that (-)-4a was 7500 times more potent than its enantiomer (+)-4b. The most active inhibitor against BChE in the series was demethyldebromoflustramine B (5a), with an IC50 value of 0.26 μM. X-ray crystallography of 15 and docking studies of selected compounds into human BChE (PDB 1POI) are presented. Molecular modeling studies showed that π-hydrogen bond, classical hydrogen bond, and cation-π interactions are critical for optimum potency.
Synthesis of isotope labeled Me(3a)-13C-physostigmine and debromoflustramine B
Morales-Ríos, Martha S.,Santos-Sánchez, Norma F.,Mora-Pérez, Yolanda,Joseph-Nathan, Pedro
, p. 1131 - 1142 (2007/10/03)
A versatile and concise synthetic route for the synthesis of selectively functionalized pyrrolo[2,3-b]indole alkaloid analogues has been developed starting from 3-indolylacetonitriles. Employing this route, physostigmine with 13C-enrichment at Me(3a) (99 atom% 13C) and debromoflustramine B have been prepared.
