59040-84-5Relevant academic research and scientific papers
Promoting the Furan Ring-Opening Reaction to Access New Donor–Acceptor Stenhouse Adducts with Hexafluoroisopropanol
Clerc, Michèle,Stricker, Friedrich,Ulrich, Sebastian,Sroda, Miranda,Bruns, Nico,Boesel, Luciano F.,Read de Alaniz, Javier
supporting information, p. 10219 - 10227 (2021/03/22)
Donor–acceptor Stenhouse adducts (DASAs) are visible-light-responsive photoswitches with a variety of emerging applications in photoresponsive materials. Their two-step modular synthesis, centered on the nucleophilic ring opening of an activated furan, ma
N-ALKYLSULFONYL INDOLINE COMPOUND, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPRISING THE COMPOUND, AND METHOD FOR USING THE INSECTICIDE
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Paragraph 0172; 0173, (2020/04/09)
In crop production in the fields of agriculture, horticulture and the like, the damage caused by insect pests etc. is still immense, and insect pests resistant to existing insecticides have emerged. Under such circumstances, the development of novel agricultural and horticultural insecticides is desired. The present invention provides an agricultural and horticultural insecticide comprising the indoline compound represented by the general formula (1): (wherein R1 and R4 are hydrogen atoms, R2 and R3 are halogen atoms, R5 is a haloalkyl group, Ra, Rb and Rc are hydrogen atoms, A1 is a CH group, A2 is a nitrogen atom, A3 is N-Me, m is 2, and n is 1), or a salt thereof as an active ingredient; and a method for using the insecticide.
Design and synthesis of novel indoline-(thio)urea hybrids
Lafzi, Ferruh,Kilic, Haydar,Tanriver, Gamze,Avc?, ?yküm Naz,Catak, Saron,Saracoglu, Nurullah
supporting information, p. 3510 - 3527 (2019/11/14)
A series of novel indoline-(thio)urea were designed and prepared using indoline(s) as a new platform and tested as organocatalysts in the Michael and Morita–Baylis–Hillman reactions. Most of the compounds were found to be very active catalysts although they did not promote the enantioselectivity. As agents for the conversion of thiocarbonyl compounds into carbonyl compounds, potentials of PIFA and DDQ were also displayed. Furthermore, DFT calculations rationalized the experimentally observed non-enantioselectivity of the catalysts.
Synthesis and evaluation of spumigin analogues library with thrombin inhibitory activity
?ula, Ale?,B?dziak, Izabela,Kikelj, Danijel,Ila?, Janez
, (2018/11/23)
Spumigins are marine natural products derived from cyanobacteria Nodularia spumigena, which mimics the structure of the D-Phe-Pro-Arg sequence and is crucial for binding to the active site of serine proteases thrombin and factor Xa. Biological evaluation of spumigins showed that spumigins with a (2S,4S)-4-methylproline central core represent potential lead compounds for the development of a new structural type of direct thrombin inhibitors. Herein, we represent synthesis and thrombin inhibitory activity of a focused library of spumigins analogues with indoline ring or L-proline as a central core. Novel compounds show additional insight into the structure and biological effects of spumigins. The most active analogue was found to be a derivative containing L-proline central core with low micromolar thrombin inhibitory activity.
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.
Aldolase-catalyzed synthesis of conformationally constrained iminocyclitols: Preparation of polyhydroxylated benzopyrrolizidines and cyclohexapyrrolizidines
Laborda, Pedro,Sayago, Francisco J.,Cativiela, Carlos,Parella, Teodor,Joglar, Jesus,Clapes, Pere
supporting information, p. 1422 - 1425 (2014/04/03)
A straightforward chemo-enzymatic synthesis of new polyhydroxylated benzopyrrolizidines and cyclohexapyrrolizidines is developed. The two-step strategy consists of l-fuculose-1-phosphate aldolase variant F131A-catalyzed aldol addition of dihydroxyacetone phosphate to rac-N-benzyloxycarbonylindoline- 2-carbaldehyde as well as (2S*,3aS*,7aS*)- and (2S*,3aR*,7aR*)-N-benzyloxycarbonyloctahydroindole-2- carbaldehydes and a subsequent one-step catalytic deprotection-reductive amination.
Ring expansion of cyclic β-amino alcohols induced by diethylaminosulfur trifluoride: Synthesis of cyclic amines with a tertiary fluorine at C3
Anxionnat, Bruno,Robert, Benoit,George, Pascal,Ricci, Gino,Perrin, Marc-Antoine,Gomez Pardo, Domingo,Cossy, Janine
experimental part, p. 6087 - 6099 (2012/09/11)
As the replacement of a hydrogen atom by a fluorine atom in a compound can have an important impact on its biological properties, the development of methods allowing the introduction of a fluorine atom is of great importance. The scope and limitations of
Stereoselective synthesis of optically active cyclic α- And β-amino esters through lipase-catalyzed transesterification or interesterification processes
Alatorre-Santamaria, Sergio,Gotor-Fernandez, Vicente,Gotor, Vicente
experimental part, p. 2307 - 2313 (2010/11/05)
A series of cyclic α- and β-amino esters belonging to a family of indolines and quinolines have been efficiently synthesized to study their behavior in lipase-mediated kinetic resolution reactions. The influence of the fused ring structure to the benzene ring and the position of the ester functionality relative to the amino group have been demonstrated, finding excellent values of enantiodiscrimination in the transesterification reaction of methyl indoline-3-carboxylate with n-butanol catalyzed by Candida antarctica lipase B being observed. On the other hand, low to moderate selectivities have been found when using a wide panel of lipases toward methyl indoline-2- carboxylate or 1,2,3,4-tetrahydroquinoline derivatives in alkoxycarbonylation, transesterification or interesterification reactions.
Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution
Alatorre-Santamaria, Sergio,Rodriguez-Mata, Maria,Gotor-Fernandez, Vicente,de Mattos, Marcos Carlos,Sayago, Francisco J.,Jimenez, Ana I.,Cativiela, Carlos,Gotor, Vicente
, p. 1714 - 1719 (2008/12/20)
A series of α-amino acid derivatives containing the 2,3-dihydroindole or octahydroindole core have been chemoenzymatically synthesized in good overall yields and high enantiomeric purity under mild reaction conditions using lipases for the introduction of chirality. Candida antarctica lipase type A has shown excellent activity and high enantiodiscrimination ability toward the two cyclic amino esters used as substrates. The selectivity of the process proved to be greatly dependent on the alkoxycarbonylating agent. Thus, the enzymatic kinetic resolution of methyl indoline-2-carboxylate has been successfully achieved using 3-methoxyphenyl allyl carbonate, whereas (2R,3aR,7aR)-benzyl octahydroindole-2-carboxylate required the less reactive diallyl carbonate.
Synthesis and pharmacological evaluation of pentacyclic 6a,7-dihydrodiindole and 2,3-dihydrodiindole derivatives as novel melatoninergic ligands
Attia, Mohamed I.,Witt-Enderby, Paula A.,Julius, Justin
, p. 7654 - 7661 (2008/12/23)
The synthesis of novel melatonin analogues 3a and 4a-c designed as melatonin receptor ligands is described. Among the newly synthesized ligands, 2-((S)-2-hydroxymethylindolin-1-ylmethyl)-melatonin 4b displayed the highest affinity for MT1 recep
