4290-87-3

Usage

Uses

Since the provided materials do not specify any particular applications for 1-(2-Propynyl)-1H-indole-2,3-dione, it is not possible to list its uses according to the given information. However, based on its classification as a chemical compound with potential applications in organic synthesis and medicinal chemistry, it can be inferred that it may be used in the following general ways:
Used in Organic Synthesis:
1-(2-Propynyl)-1H-indole-2,3-dione is used as a building block or intermediate in the synthesis of more complex organic compounds for various purposes, such as pharmaceuticals, agrochemicals, or materials science.
Used in Medicinal Chemistry:
1-(2-Propynyl)-1H-indole-2,3-dione is used as a potential active pharmaceutical ingredient or a precursor in the development of new drugs, due to its unique chemical structure and properties.

InChI:InChI=1/C11H7NO2/c1-2-7-12-9-6-4-3-5-8(9)10(13)11(12)14/h1,3-6H,7H2

Upstream product

• 91-56-5 indole-2,3-dione 
• 106-96-7 propargyl bromide 
• 85670-80-0 1-(prop-2-yn-1-yl)indoline 
• 62-53-3 aniline 

Downstream Products

• 125030-39-9 1-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo [-4,3-a][1,4]diazepin-2-yl]-2-propynyl]-1H-indole2,3-dione 
• 945736-73-2 1-[3-(3,4-dichlorophenyl)prop-2-yn-1-yl]-1H-indole-2,3-dione 
• 1171982-54-9 C₂₂H₁₆N₄O₂ 
• 1258795-79-7 C₂₄H₁₄N₄O₃S 
• 1310453-11-2 3-(4-methoxyphenyl)-6-prop-2-ynylspiro[1,4,2-dioxazoline-5,3'-indoline]-7-one 
• 1310453-12-3 3-(4-methoxyphenyl)-6-{[3-(4-methoxyphenyl)isoxazol-5-yl]methyl}spiro[1,4,2-dioxazoline-5,3'-indoline]-7-one 
• 1372552-31-2 C₁₈H₁₄N₄O₃ 
• 1372552-30-1 C₁₇H₁₂N₄O₂ 
• 1420904-38-6 1-(prop-2-yn-1-yl)-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)-dione 
• 1383565-80-7 2-(2,4,5-trichlorophenoxy)-N-(2,4'-dioxo-1-(prop-2-ynyl)-1,2-dihydro-3'H-spiro[indole-3,2'-[1,3]thiazolidin]-3'-yl)propanamide 

Relevant academic research and scientific papers

Design, Synthesis and Antitumor Activities of 1,2,3-triazole-diethylene Glycol Tethered Isatin Dimers

A series of novel 1,2,3-triazole-diethylene glycol tethered isatin dimers were designed, synthesized, and screened for their in vitro antitumor activities in this paper. All dimers showed promising activities against the tested HepG2, Hela, A549, DU145, S

Click-chemistry-based multicomponent condensation approach for design and synthesis of spirochromene-tethered 1,2,3-triazoles as potential antitubercular agents

A series of spirochromene-tethered 1,2,3-triazoles (1,2,3-triazolylspirochromenes) were designed and synthesized via click-chemistry-based one-pot five-component reaction between N-propargyl isatins, malononitrile, dimedone (or 4-hydroxyl-6-methyl-2H-pyran-2-one), arylalkyl halides, and sodium azide using cellulose-supported CuI nanoparticles (Cell-CuI NPs) as heterogeneous catalyst. All synthesized compounds were screened for inhibitory activity against Mycobacterium tuberculosis H37Ra (ATCC 25177) and Mycobacterium bovis BCG (ATCC 35743), in active as well as dormant state. During screening, compounds 6h, j, l were found to exhibit promising antimycobacterial activity against M.?bovis BCG, while compounds 7d, h, l showed promising antimycobacterial activity against M.?tuberculosis H37Ra as well as M.?bovis BCG. The active compounds were found to be noncytotoxic to three human cancer cell lines (MCF-7, HCT116, and A549). The active compounds exhibited selectivity index >10, indicating potential as antitubercular agents. The active compounds were also evaluated for in?vitro antibacterial activity, with five (6h, l, 7b, f, l) showing good antibacterial activity against Gram-positive as well as Gram-negative bacteria. Compounds 6h, j, l exhibiting promising activity against M.?bovis BCG can serve as good leads for further modification and optimization.

Ugi Reaction Synthesis of Oxindole-Lactam Hybrids as Selective Butyrylcholinesterase Inhibitors

Molecular hybridization is a valuable approach in drug discovery. Combining it with multicomponent reactions is highly desirable, since structurally diverse libraries can be attained efficiently in an eco-friendly manner. In this work, isatin is used as the key building block for the Ugi 4-center 3-component reaction synthesis of oxindole-lactam hybrids, under catalyst-free conditions. The resulting oxindole-β-lactam and oxindole-γ-lactam hybrids were evaluated for their potential to inhibit relevant central nervous system targets, namely cholinesterases and monoamine oxidases. Druglikeness evaluation was also performed, and compounds 4eca and 5dab exhibited great potential as selective butyrylcholinesterase inhibitors, at the low micromolar range, with an interesting predictive pharmacokinetic profile. Our findings herein reported suggest oxindole-lactam hybrids as new potential agents for the treatment of Alzheimer's disease.

Design, Synthesis, and In Vitro Anti-Tumor Activities of 1,2,3-triazole-tetraethylene Glycol Tethered Heteronuclear Bis-Schiff Base Derivatives of Isatin

We report herein the design, synthesis, and in vitro anti-tumor activities of a series of 1,2,3-triazole-tetraethylene glycol tethered heteronuclear bis-Schiff base derivatives of isatin. Our results indicated that all the synthesized bis-Schiff bases except 9e showed considerable in vitro anticancer activities against HepG2, Hela, HCT-116, A549, and MCF-7 human cancer cell lines with IC50 in a range of 9.79–48.75?μM and were more potent than etoposide against Hela, HCT-116, and A549 cell lines. In particular, the most potent bis-Schiff base 9g (IC50: 9.79–29.64?μg/mL) was highly active against the five cancer cell lines tested, could act as a lead for further optimization.

Design, synthesis, and bioevaluation of novel oxoindolin-2-one derivatives incorporating 1-benzyl-1H-1,2,3-triazole

In our search for novel bioactive molecules, three series of indolin-2-one derivatives incorporating 1-benzyl-1H-1,2,3-triazole moiety were synthesized. The compounds were initially designed as acetylcholine esterase (AChE) inhibitors based on the structu

Synthesis and antiplasmodial activity of glyco-conjugate hybrids of phenylhydrazono-indolinones and glycosylated 1,2,3-triazolyl-methyl-indoline-2,3-diones

A small library of 36 new glycohybrids of phenylhydrazono-indolinones was synthesized employing glycosylated 1,2,3-triazolyl-methyl-indoline-2,3-diones and different phenylhydrazines via acid catalyzed reaction. All the compounds were screened for their antiplasmodial activity in vitro. Compounds 6c, 7c, and 7b showed significant activity with the IC50 values 1.27, 1.64 and 1.96 μM, respectively against CQ sensitive Pf3D7 strain while compounds 7b and 6f showed good activity with IC50 1.61 and 1.93 μM, respectively against CQ resistant PfK1 strain.

Novel hydroxamic acids incorporating 1-((1H-1,2,3-Triazol-4-yl)methyl)-3-hydroxyimino-indolin-2-ones: synthesis, biological evaluation, and SAR analysis

Abstract: A series of seventeen novel hydroxamic acids incorporating 1-((1H-1,2,3-triazol-4-yl)methyl)-3-hydroxyimino-indolin-2-ones was designed and synthesized. Biological evaluation showed that these hydroxamic acids potently inhibited a class-I isoform of HDACs (HDAC2) with IC 50 values in low micromolar range. Several compounds also exhibited good cytotoxicity. Two compounds, 5e and 5f, emerged as the most potent HDAC2 inhibitors with cytotoxicity up to 8-fold more potent than SAHA in three human cancer cell lines, including SW620 (colon cancer), PC3 (prostate cancer) and AsPC-1 (pancreatic cancer). A molecular modeling approach has been carried out which revealed some structure-activity relationships. Further investigation on absorption, distribution, metabolism, excretion and toxicity (ADMET) suggested that compounds 5e and 5f, while showing potent HDAC2 inhibitory bioactivity, hold desirable characteristics for anticancer compounds. GRAPHICAL ABSTRACT: Three series of novel hydroxamic acids incorporating 1-((1H-1,2,3-triazol-4-yl)methyl)-3-hydroxyimino-indolin-2-ones (4a-c, 5a-g, 6a-g) were synthesized. Biological evaluation showed that these hydroxamic acids potently inhibited HDAC2 with IC 50 values in low micromolar range.

Click chemistry based multicomponent approach in the synthesis of spirochromenocarbazole tethered 1,2,3-triazoles as potential anticancer agents

A series of spirochromenocarbazole tethered 1,2,3-triazoles were synthesized via click chemistry based one-pot, five component reaction between N-propargyl isatins, malononitrile, 4-hydroxycarbazole, aralkyl halides and sodium azide using cellulose suppor

Design, synthesis, biological evaluation and docking studies of sulfonyl isatin derivatives as monoamine oxidase and caspase-3 inhibitors

The aim of this study was to design novel multifunctional neuroprotective agents that would slow down or halt neurodegeneration through inhibition of MAO-A, MAO-B and caspase-3. We focused on pharmacophoric groups of known MAO-inhibitors including selegil

Rapid cascade synthesis of poly-heterocyclic architectures from indigo

The base-induced propargylation of the dye indigo results in the rapid and unprecedented one-pot synthesis of highly functionalized representatives of the pyrazino[1,2-a:4,3-a′]diindole, pyrido[1,2-a:3,4-b′]diindole and benzo[b]indolo[1,2-h]naphthyridine heterocyclic systems, with the last two reflecting the core skeleton of the anticancer/antiplasmodial marine natural products fascaplysin and homofascaplysins and a ring B-homologue, respectively. The polycyclic compounds 6-8, whose structures were confirmed through single-crystal X-ray crystallographic analysis, arise from sequential inter/intramolecular substitution-addition reactions, and in some cases, ring rearrangement reactions. Preliminary studies on controlling the reaction path selectivity, and the potential reaction mechanisms, are also described. Initial biological activity studies with these new heterocyclic derivatives indicated promising in vitro antiplasmodial activity as well as good anticancer activity. The chemistry described is new for the indigo moiety and cascade reactions from this readily available and cheap starting material should be more broadly applicable in the synthesis of additional new heterocyclic systems difficult to access by other means. Published 2013 by the American Chemical Society.