41568-27-8Relevant academic research and scientific papers
Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst
Murray, James I.,Flodén, Nils J.,Bauer, Adriano,Fessner, Nico D.,Dunklemann, Daniel L.,Bob-Egbe, Opetoritse,Rzepa, Henry S.,Bürgi, Thomas,Richardson, Jeffery,Spivey, Alan C.
supporting information, p. 5760 - 5764 (2017/05/12)
The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
METHOD FOR PRODUCING OPTICALLY ACTIVE COMPOUND, AND NOVEL METAL-DIAMINE COMPLEX
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Paragraph 0300; 0301; 0302; 0303, (2016/12/22)
The present invention pertains to a method for producing an optically active compound which includes a step for reducing an imino group of an imine compound or a step for reducing an unsaturated bond of a heterocyclic compound, while in the presence of hydrogen gas as a hydrogen donor and one or more types of complexes selected from a group consisting of a complex represented by general formula (1), a complex represented by general formula (2), a complex represented by general formula (3), and a complex represented by general formula (4) (the general formulas (1)-(4) are as stipulated by claim 1).
Synthesis of indoles through Rh(III)-catalyzed C-H cross-coupling with allyl carbonates
Gong, Tian-Jun,Cheng, Wan-Min,Su, Wei,Xiao, Bin,Fu, Yao
, p. 1859 - 1862 (2014/03/21)
A practical Rh-catalyzed reaction was developed to achieve 2-alkyl-substituted indole synthesis. The reaction can tolerate a variety of synthetically important functional groups. The indole products can also be transformed into other important skeletons. Two bioactive compounds, that is indomethacin and pravadoline were prepared using the new method.
Discovery of 4-amino and 4-hydroxy-1-aroylindoles as potent tubulin polymerization inhibitors
Liou, Jing-Ping,Wu, Zi-Yi,Kuo, Ching-Chuan,Chang, Chi-Yen,Lu, Pei-Yi,Chen, Chi-Ming,Hsieh, Hsing-Pang,Chang, Jang-Yang
scheme or table, p. 4351 - 4355 (2009/05/26)
1-Aroylindoline, 1-aroyl-1,2,3,4-tetrahydroquinoline, and 1-aroylindole derivatives were synthesized and evaluated for anticancer activity. The 4-amino and 4-hydroxy-1-aroylindoles 26 and 27 with IC50 of 0.9 and 0.6 μM, respectively, exhibited
Kinetic resolutions of lndolines by a nonenzymatic acylation catalyst
Arp, Forrest O.,Fu, Gregory C.
, p. 14264 - 14265 (2008/03/13)
The first method for the kinetic resolution of indolines through catalytic N-acylation is described. To improve the selectivity factor, new planar-chiral PPY-derived catalysts were synthesized, wherein the chiral environment was systematically modified. This work provides a rare example of a nonenzyme-based acylation catalyst for the kinetic resolution of amines. Copyright
Chemoenzymatic preparation of optically active secondary amines: a new efficient route to enantiomerically pure indolines
Gotor-Fernandez, Vicente,Fernandez-Torres, Pedro,Gotor, Vicente
, p. 2558 - 2564 (2007/10/03)
An efficient chemoenzymatic route for the synthesis of optically active substituted indolines has been developed. Different lipases have been tested in the alkoxycarbonylation of these secondary amines, Candida antarctica lipase A (CAL-A) was found to be the best biocatalyst for 2-substituted-indolines, and C. antarctica lipase B (CAL-B) for 3-methylindoline. The combination of lipases with a variety of allyl carbonates and tert-butyl methyl ether (TBME) as solvent has allowed the isolation of the carbamate and amine derivatives with a high level of enantiopurity.
Zn2+ montmorillonite catalyzed 3-aza-Cope rearrangement under microwave irradiation
Yadav,Reddy, B.V. Subba,Rasheed, M. Abdul,Kumar, H. M. Sampath
, p. 487 - 488 (2007/10/03)
N-Allylanilines undergo 3-aza-Cope rearrangement in the presence of Zn2+ montmorillonite under microwave irradiation in the absence of solvent to afford indoline derivatives in high yields. Similarly arylallyl thioethers are rearranged to dihydrobenzothiophenes.
Indole inhibitors of human nonpancreatic secretory phospholipase A2. 2. Indole-3-acetamides with additional functionality
Dillard, Robert D.,Bach, Nicholas J.,Draheim, Susan E.,Berry, Dennis R.,Carlson, Donald G.,Chirgadze, Nickolay Y.,Clawson, David K.,Hartley, Lawrence W.,Johnson, Lea M.,Jones, Noel D.,McKinney, Emma R.,Mihelich, Edward D.,Olkowski, Jennifer L.,Schevitz, Richard W.,Smith, Amy C.,Snyder, David W.,Sommers, Cynthia D.,Wery, Jean-Pierre
, p. 5137 - 5158 (2007/10/03)
As reported in our previous paper, a series of indole-3-acetamides which possessed potency and selectivity as inhibitors of human nonpancreatic secretory phospholipase A2(hnps-PLA2) was developed. The design of these compounds was based on information derived from x-ray crystal structures determined for complexes between the enzyme and its inhibitors. We describe here the further implementation of this structure-based design strategy and continued SAR development to produce indole-3-acetamides with additional functionalities which provide increased interaction with important residues within the enzyme active site. These efforts led to inhibitors with substantially enhanced potency and selectivity.
