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4290-87-3

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4290-87-3 Usage

Description

1-(2-Propynyl)-1H-indole-2,3-dione, a derivative of indole with the molecular formula C11H7NO2, is a yellow to orange-colored solid that is insoluble in water. As a monomeric dione, it has been studied for its potential applications in organic synthesis and medicinal chemistry, although its specific properties and uses have not been extensively reported in the literature.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 4290-87-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,2,9 and 0 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 4290-87:
(6*4)+(5*2)+(4*9)+(3*0)+(2*8)+(1*7)=93
93 % 10 = 3
So 4290-87-3 is a valid CAS Registry Number.
InChI:InChI=1/C11H7NO2/c1-2-7-12-9-6-4-3-5-8(9)10(13)11(12)14/h1,3-6H,7H2

4290-87-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(2-Propynyl)-1H-indole-2,3-dione

1.2 Other means of identification

Product number -
Other names 1-prop-2-ynylindole-2,3-dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4290-87-3 SDS

4290-87-3Relevant articles and documents

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

Fan, Yi-Lei,Huang, Zhong-Ping,Liu, Min

, p. 2990 - 2995 (2018)

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

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

Brand?o, Pedro,López, óscar,Leitzbach, Luisa,Stark, Holger,Fernández-Bola?os, José G.,Burke, Anthony J.,Pineiro, Marta

, p. 1718 - 1725 (2021)

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

Anh, Duong Tien,Dung, Do Thi Mai,Hai, Pham-The,Han, Sang-Bae,Huong, Le Thi Thu,Jeon, Hye Won,Kang, Jong Soon,Lan, Ta Thu,Nam, Nguyen-Hai,Park, Eun Jae,Thuan, Nguyen Thi

, (2019)

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

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

Dung, Do Thi Mai,Hai, Pham-The,Anh, Duong Tien,Huong, Le-Thi-Thu,Yen, Nguyen Thi Kim,Han, Byung Woo,Park, Eun Jae,Choi, Yeo Jin,Kang, Jong Soon,Hue, Van-Thi-My,Han, Sang-Bae,Nam, Nguyen-Hai

, (2018)

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.

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

Tavari, Mohsen,Malan, Sarel F.,Joubert, Jacques

, p. 1628 - 1639 (2016)

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

7-chloroquinoline-isatin conjugates: Antimalarial, antitubercular, and cytotoxic evaluation

Raj, Raghu,Biot, Christophe,Carrère-Kremer, Séverine,Kremer, Laurent,Guérardel, Yann,Gut, Jiri,Rosenthal, Philip J.,Forge, Delphine,Kumar, Vipan

, p. 622 - 629 (2014)

A series of twenty piperazine-tethered 7-chloroquinoline-isatin hybrids have been synthesized via either direct nucleophilic substitution or Cu(Ι)Cl-mediated Mannich reaction. These new conjugates were evaluated for their antimalarial and antitubercular efficacy against a chloroquine-resistant strain of Plasmodium falciparum and Mycobacterium tuberculosis, respectively, while the cytotoxic profiles were evaluated against 3T6 cell line, a permanent mouse embryonic fibroblast cell line. The most potent of the test compound with IC50 of 0.22 μm against W2 strain of P. falciparum and 31.62 μm against the embryonic fibroblast cell line (cytotoxicity) displayed a high selective index of 143.73. Synthesis, antimalarial, anti-TB, and cytotoxic evaluation of piperazine-tethered 7-chloroquinoline-isatin conjugates.

Synthesis of 1H-1,2,3-triazole linked β-lactam-isatin bi-functional hybrids and preliminary analysis of in vitro activity against the protozoal parasite Trichomonas vaginalis

Raj, Raghu,Singh, Pardeep,Haberkern, Nathan T.,Faucher, Ryan M.,Patel, Neal,Land, Kirkwood M.,Kumar, Vipan

, p. 897 - 906 (2013)

Twenty-two different triazoles were prepared to examine the anti-Trichomonas vaginalis structure-activity relationships (SAR) within the β-lactam-isatin-triazole conjugate family. The compounds were synthesized by copper-catalyzed 'click chemistry.' In vi

Organosilanes and their magnetic nanoparticles as naked eye red emissive sensors for Ag+ions and potent anti-oxidants

Singh, Gurjaspreet,Diksha,Singh, Akshpreet,Satija, Pinky,Pawan,Mohit,González-Silvera,Espinosa-Ruíz, Cristóbal,Esteban, María Angeles

, p. 5517 - 5525 (2021)

The present article reports the synthesis and structural characterization of a triazole appended isatin linked silane-based sensor using a highly efficient click chemistry approach. The yellow-coloured solution of the highly selective chemosensor turned red in the presence of Ag+ions and a red shift in the absorption spectra was also observed during the addition of these ions. IR spectroscopic studies support the metal ion binding with organosilanes in the cavity created by the carbonyl group of isatin, the nitrogen atom of the triazole ring and the Si-O bond of silane. Furthermore, the sensing application was enhanced by the immobilization of the ligand on the surface of iron oxide silica nanoparticles and the resulting silica surfaced nanocomposites were characterized using various techniques. B-H plots and calibration curves were employed to measure the association constants and limits of detection, respectively, of the synthesized ligands and their magnetic nanoparticles. The nanohybrids demonstrate a greater binding potential to Ag+ions. In addition, the synthesized organosilanes were investigated for cytotoxicity using the MTT assay, and the antioxidant activity was measured by decolouration of ABTS˙+

New Imatinib Derivatives with Antiproliferative Activity against A549 and K562 Cancer Cells

Bastos, Monica,Boechat, Nubia,Dantas, Rafael,Moura, Stefany,Neto, Jo?o,Oliveira, Andressa,Pimentel, Luiz,Silva, Floriano

, (2022/01/31)

Tyrosine kinase enzymes are among the primary molecular targets for the treatment of some human neoplasms, such as those in lung cancer and chronic myeloid leukemia. Mutations in the enzyme domain can cause resistance and new inhibitors capable of circumventing these mutations are highly desired. The objective of this work was to synthesize and evaluate the antiproliferative ability of ten new analogs that contain isatins and the phenylamino-pyrimidine pyridine (PAPP) skeleton, the main pharmacophore group of imatinib. The 1,2,3-triazole core was used as a spacer in the derivatives through a click chemistry reaction and gave good yields. All the analogs were tested against A549 and K562 cells, lung cancer and chronic myeloid leukemia (CML) cell lines, respectively. In A549 cells, the 3,3-difluorinated compound (3a), the 5-chloro-3,3-difluorinated compound (3c) and the 5-bromo-3,3-difluorinated compound (3d) showed IC50 values of 7.2, 6.4, and 7.3 μM, respectively, and were all more potent than imatinib (IC50 of 65.4 μM). In K562 cells, the 3,3-difluoro-5-methylated compound (3b) decreased cell viability to 57.5% and, at 10 μM, showed an IC50 value of 35.8 μM (imatinib, IC50 = 0.08 μM). The results suggest that 3a, 3c, and 3d can be used as prototypes for the development of more potent and selective derivatives against lung cancer.

Discovery of Isatin-Based Carbohydrazones as Potential Dual Inhibitors of Fatty Acid Amide Hydrolase and Monoacylglycerol Lipase

Jaiswal, Shivani,Ayyannan, Senthil Raja

, (2021/11/09)

Using ligand-based design strategy, a set of isatin-3-carbohydrazones was designed, synthesized and evaluated for dual fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL) inhibition properties. Compound 5-chloro-N′-(5-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 b) emerged as a potent MAGL inhibitor with nanomolar activity (IC50=3.33 nM), while compound 5-chloro-N′-(1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 j) was the most potent selective FAAH inhibitor (IC50=37 nM). Compound 5-chloro-N′-(6-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 c) showed dual FAAH-MAGL inhibitory activity with an IC50 of 31 and 29 nM respectively. Enzyme kinetics studies revealed that the isatin-based carbohydrazones are reversible inhibitors for both FAAH and MAGL. Further, blood-brain permeability assay confirmed that the lead compounds (13 b, 13 c, 13 g, 13 m and 13 q) are suitable as CNS candidates. Molecular dynamics simulation studies revealed the putative binding modes and key interactions of lead inhibitors within the enzyme active sites. The lead dual FAAH-MAGL inhibitor 13 c showed significant antioxidant activity and neuroprotection in the cell-based cytotoxicity assay. In summary, the study yielded three potent FAAH/MAGL inhibitor compounds (13 b, 13 c and 13 j) with acceptable pharmacokinetic profile and thus can be considered as promising candidates for treating neurological and mood disorders.

Dynamic Kinetic Asymmetric Transformation of Racemic Diastereomers: Diastereo- and Enantioconvergent Michael–Henry Reactions to Afford Spirooxindoles Bearing Furan-Fused Rings

Sohail, Muhammad,Tanaka, Fujie

supporting information, p. 21256 - 21260 (2021/08/23)

Dynamic kinetic asymmetric transformation (DYKAT) reactions of racemic diastereomer mixtures that afford the products as essentially single diastereomers with high enantioselectivities are described. We demonstrated the DYKAT in the diastereo- and enantio

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