157869-14-2

Usage

Functional Groups

Phenethylamine derivative
Contains a triple bond (alkyne)
Hydroxyl group (alcohol)

Medical Applications

Studied as a potential antipsychotic
Investigated for anxiolytic properties

Drug Development Potential

Investigated as a potential drug target

Chemical Research and Synthesis

Unique structure suggests applications in organic synthesis
Potential for use in chemical research due to its distinctive properties

Upstream product

• 615-43-0 2-iodophenylamine 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 615-36-1 2-bromoaniline 
• 1111-97-3 3-chloro-3-methylbut-1-yne 

Downstream Products

• 139927-26-7 3,3-dimethyl-3,4-dihydro-1H-furo[3,4-b]indol-1-one 
• 78133-83-2 2-(propylene-1-en-2-yl)-1H-indole 

Relevant academic research and scientific papers

Cyclodiphosphazanes as synthetic probes: P-C/P-N bond formation from the reaction with functionalized propargyl alcohols and N-hydroxy substrates

Phosphano-indoles were synthesized in a fairly straightforward route from the reaction of simple cyclodiphosphazanes [XP(μ-N-t-Bu)2PY] [X = Y = NH-t-Bu (1a); X = Y = NH-i-Pr (1b)] with o-aminophenyl functionalized propargyl alcohols. The reaction occurs via an allene intermediate formed by P III-O-C → P V(O)-C rearrangement, followed by cyclization utilizing the central allenic carbon and the -NH2 functionality. In a similar way, cyclodiphosphazanes [XP(μ-N-t-Bu)2PY] [X = Y = Cl (1c); X = Cl, Y = NH-t-Bu (1d)] have been treated with N-hydroxy substrates to obtain novel P III-O-N → P V(O)-N rearranged products. X-ray structures of the four products, 2-(1-phenyl-ethyl)-3-[(t-Bu)NH)P(μ-N-t-Bu)2P(O)]-indole [14], cis-{[-C(=O)-C6 H 4-C(=O)-]-N-P(=O)-N-t-Bu}2 [cis-18], trans-{[-C(=O)-C6 H 4-C(=O)-]-N-P(=O)-N-t-Bu}2 [trans-18] and cis-[(t-BuNH)P(μ-N- t-Bu)2P(=O)-N{ -C(=O)-CH2-CH2-C(=O)-}] [cis- 19] are also reported.

SUBSTITUTED, SATURATED AND UNSATURATED N-HETEROCYCLIC CARBOXAMIDES AND RELATED COMPOUNDS FOR THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted, saturated and unsaturated N-heterocyclic carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.

PYRANOPYRAZOLE AND PYRAZOLOPYRIDINE IMMUNOMODULATORS FOR TREATMENT OF AUTOIMMUNE DISEASES

Pyranoyrazoles and pyrazolopyridines of formula I or formula II are disclosed: (I), (II) These compounds inhibit Coagulation Factor Xlla in the presence of thrombin and other coagulation factors. They are useful to treat autoimmune diseases.

An efficient synthesis of indoles via a CuMgAl-LDH-catalyzed cyclization of 2-alkynylsulfonanilides

A highly efficient method for the synthesis of indoles has been successfully developed via a CuMgAl-LDH-catalyzed intramolecular annulation reaction of 2-alkynylsulfonanilides. This CuMgAl-LDH catalyst features facile preparation, recovery, and reuse at l

Photophysical and theoretical studies of diphenylacetylene derivatives with restricted rotation

Diphenylacetylene derivatives containing electron-donor (amino) and electron-acceptor (ester) groups in 2,2′ or 3,2′ positions in phenyl rings were synthesized to study the effects of intramolecular charge transfer and stiffening of the conformation by in

A simple synthesis of the debrominated analogue of veranamine

A facile synthesis of 4,5,5-trimethyl-5,6-dihydrobenzo[c][2,7]naphthyridine, the debrominated analogue of the marine alkaloid veranamine, has been achieved in three steps with a 38% overall yield. from the commercially available 2-bromoaniline. The key be

Palladium-catalyzed oxidative deacetonative coupling of 4-aryl-2-methyl-3-butyn-2-ols with H-phosphonates

An efficient and generally applicable protocol for palladium-catalyzed oxidative deacetonative coupling of 4-aryl-2-methyl-3-butyn-2-ols with dialkyl H-phosphonates has been developed. This methodology provides a new and practical route to alkynylphosphonates using the inexpensive 4-aryl-2-methyl-3-butyn-2-ols as the alkyne sources. This reaction could also be performed with aryl bromides, 2-methyl-3-butyne-2-ol and dialkyl H-phosphonates using the cheap 2-methyl-3-butyne-2-ol as an alkyne source. This journal is

An effective two-step synthesis, fluorescent properties, antioxidant activity and cytotoxicity evaluation of benzene-fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones

Abstract This study describes a simple and efficient procedure to synthesize a series of benzene-fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones by the PTSA-catalyzed cyclocondensation reaction of the corresponding ortho-alkynylanilines prepared by the Sonogashira reaction of fluoro-substituted 2-iodanilines with 2-methylbut-3-yn-2-ol. The photofluorescent properties (shape of bands, λex, λem, Stokes shift) of the new compounds were investigated. It has been revealed that the 2,3-dihydroquinolinones with different number of fluoro-substituents have almost the same fluorescence properties. The cytotoxicity evaluation of the 2,3-dihydroquinolinones against human myeloma, human mammary adenocarcinoma, human hepatocellular carcinoma HepG2 epithelial tumor cells, normal mouse fibroblasts and Chinese hamster Ag 17 cells was performed. It has been found that the benzo-perfluorinated derivatives of 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones show enhanced cytotoxic effect against the tumor RPMI (human myeloma) cells line compared with the normal cells. Mutagenic and antioxidant properties of the compounds using Salmonella tester strain were studied. It has been shown, that the compounds are well antioxidants.

Merging synthesis and enantioselective functionalization of indoles by a gold-catalyzed asymmetric cascade reaction

All at once: The simultaneous synthesis and enantioselective functionalization of an indole core is achieved with the assistance of chiral cationic AuI complexes. A range of vinyloxazino-[4,3-a]indoles is obtained by a cascade process in a highly enantioselective manner (see scheme; L=chiral diphosphine). Copyright

Au-catalyzed formation of functionalized quinolines from 2-alkynyl arylazide derivatives

A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.