27640-33-1

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-(+)-2-Indolinemethanol is used as a key intermediate in the synthesis of various pharmaceuticals for its unique reactivity and potential medicinal properties.
Used in Cancer Treatment Research:
(S)-(+)-2-Indolinemethanol is used as a therapeutic agent in cancer treatment research, as it has shown promise in targeting and treating cancer cells.
Used as a Chiral Auxiliary in Organic Chemistry:
(S)-(+)-2-Indolinemethanol is used as a chiral auxiliary in the synthesis of complex molecules in organic chemistry, facilitating the creation of enantiomerically pure compounds for various applications.
Used in Scientific Research:
(S)-(+)-2-Indolinemethanol is utilized in scientific research to explore its unique chemical properties and potential biological activity, contributing to the advancement of knowledge in the field of chemistry and medicine.

InChI:InChI=1/C9H11NO/c11-6-8-5-7-3-1-2-4-9(7)10-8/h1-4,8,10-11H,5-6H2/t8-/m0/s1

Upstream product

• 59040-84-5 indoline-2-carboxylic acid methyl ester 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 76182-48-4 methyl 1-methyl-2,3-dihydro-1H-indole-2-carboxylate 
• 50501-07-0 (S)-2,3-dihydro-1H-indole-2-carboxylic acid,ethyl ester 
• 24621-70-3 2-(hydroxymethyl)indole 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 111457-18-2 N-(2-allyl-phenyl)-benzamide 
• 32704-22-6 2-allyl-phenylamine 
• 589-09-3 N-allyl-N-phenylamine 
• 62-53-3 aniline 
• 79815-20-6 (S)-indoline-2-carboxylic acid 
• 321744-15-4 (±)-2-(((tert-butyldimethylsilyl)oxy)methyl)indoline 
• 6872-06-6 2-methyl indoline 

Downstream Products

• 135829-04-8 benzyl 2-(Hydroxymethyl)-1-indolinecarboxylate 
• 1031238-94-4 (3aS)-1-(4-nitrophenoxy)-3a,4-dihydro-3H-[1,3,2]oxazaphospholo[3,4-a]indole 1-oxide 
• 1031238-96-6 C₁₅H₁₃BrNO₃P 
• 1031238-92-2 C₁₅H₁₄NO₃P 
• 1031238-93-3 C₁₅H₁₃ClNO₃P 
• 1094359-58-6 (S)-(1-tosylindolin-2-yl)methanol 
• 1186240-95-8 (S)-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methanol 
• 1226884-79-2 (S)-1-(4-(2-(hydroxymethyl)indolin-1-yl)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone 
• 1226888-86-3 (S)-tert-butyl 4-(2-(hydroxymethyl)indolin-1-yl)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate 
• 1226884-39-4 (S)-(1-(6-methyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol 
• 1307801-02-0 3-(2-allylphenyl)-1,3-benzothiazol-2-one 
• 1186240-97-0 (S)-2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methoxy)acetic acid 
• 1186240-96-9 (S)-tert-butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methoxy)acetate 
• 313234-76-3 1-[(2S)-2-(hydroxymethyl)indolinyl]-2-{4-[(4-chlorophenyl)methyl]piperazinyl}ethan-1-one 

Relevant academic research and scientific papers

SYNTHESIS OF PYRROLIZIDINES AND RELATED COMPOUNDS BY ALDOL CYCLIZATION OF N--α-AMINOALDEHYDES

Treatment of 1--2-pyrrolidinecarbaldehyde with sodium hydride in tetrahydrofuran (THF) gave the aldol condensation product, 5,6,7,7a-tetrahydro-2-methylthio-3H-pyrrolizin-3-one.However, when the same aldehyde was treated with sodium hydroxide in aqueous THF, 5,6,7,7a-tetrahydro-7a-hydroxy-3-methylthio-3H-pyrrolizin-3-one was obtained.These reactions were applied to the synthesis of indolizidine and pyrroloindole derivatives.

CHIRAL PHOSPHORAMIDITE AUXILIARIES AND METHODS OF THEIR USE

Disclosed are P-stereogenic groups that may be used in the synthesis of compounds including stereochemically enriched P-stereogenic phosphorothioates. P-stereogenic groups may be provided in nucleoside phosphoramidites including a sugar bonded to a nucleobase and to a stereochemically enriched phosphoramidite as well as methods of their use and methods of making them.

Design and synthesis of novel indoline-(thio)urea hybrids

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.

FUSED THIAZOLOPYRIMIDINE DERIVATIVES AS MNKS INHIBITORS

The present invention relates to compounds of formulae I and H, or pharmaceutically acceptable salts or esters thereof. Further aspects of the invention relate to pharmaceutical compositions and therapeutic uses of said compounds in the treatment of diseases of uncontrolled cell growth, proliferation and/or survival, inappropriate cellular immune responses, inappropriate cellular inflammatory responses, or neurodegenerative disorders, preferably tauopathies, even more preferably, Alzheimer's disease.

Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst

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.

Enantioselective Synthesis of 2-Bromomethyl Indolines via BINAP(S)-Catalyzed Bromoaminocyclization of Allyl Aniline

An enantioselective bromoamination of allyl aniline with N-bromosuccinimide (NBS) catalyzed by BINAP(S) (BINAP monosulfide) is described. This protocol could provide a range of chiral 2-bromomethyl indolines in good to excellent yields with up to 87% ee.

Green Organocatalytic Synthesis of Indolines and Pyrrolidines from Alkenes

Employing a green and efficient 2,2,2-trifluoroacetophenone-catalyzed oxidation of alkenes, which utilizes H2O2 as the green oxidant, a novel and sustainable synthesis of indolines and pyrrolidines was developed. This constitutes a cheap, general and environmentally-friendly protocol for the synthesis of substituted nitrogen-containing heterocycles. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated leading to the desired nitrogen heterocycles in good to excellent yields. (Figure presented.).

Asymmetric Hydrogenation of Unprotected Indoles Catalyzed by η6-Arene/N-Me-sulfonyldiamine-Ru(II) Complexes

Protecting-group-free transformation is a challenging and important issue in atom-economical organic synthesis. The η6-arene/N-Me-sulfonyldiamine-Ru(II)-BF4 complex-catalyzed asymmetric hydrogenation of 2-substituted unprotected indoles in weakly acidic hexafluoroisopropanol gives optically active indoline compounds with up to >99% ee. Under mild reaction media, halogen atoms and synthetically important protecting groups (e.g., silyl ether, acetal, benzyl ether, and ester) on indoles are maintained, which is advantageous for the synthesis of further complex indoline molecules.

MORPHOLINO COMPOUNDS, USES AND METHODS

The invention relates to morpholino-derivatives according to Formula (I) or stereoisomers or pharmaceutically acceptable salts or solvate thereof, wherein R1, R2, R3, R4, R5, R6, R7/s

Design, synthesis, and biological activities of novel hexahydropyrazino[1, 2-a]indole derivatives as potent inhibitors of apoptosis (IAP) proteins antagonists with improved membrane permeability across MDR1 expressing cells

We previously reported octahydropyrrolo[1,2-a]pyrazine derivative 2 (T-3256336) as a potent antagonist for inhibitors of apoptosis (IAP) proteins. Because compound 2 was susceptible to MDR1 mediated efflux, we developed another scaffold, hexahydropyrazino[1,2-a]indole, using structure-based drug design. The fused benzene ring of this scaffold was aimed at increasing the lipophilicity and decreasing the basicity of the scaffold to improve the membrane permeability across MDR1 expressing cells. We established a chiral pool synthetic route to yield the desired tricyclic chiral isomers. Chemical modification of the core scaffold led to a representative compound 50, which showed strong inhibition of IAP binding (X chromosome-linked IAP [XIAP]: IC 50 23 nM and cellular IAP [cIAP]: IC50 1.1 nM) and cell growth inhibition (MDA-MB-231 cells: GI50 2.8 nM) with high permeability and low potential of MDR1 substrate.