14396-90-8

Usage

Uses

Used in Organic Synthesis:
N-(3-Butynyl)phthalimide is used as a reagent for introducing the butynyl group into various organic molecules, which is crucial for the synthesis of a range of organic compounds.
Used as a Ligand in Catalysis:
In the field of catalysis, N-(3-Butynyl)phthalimide is utilized as a ligand for transition metal complexes, enhancing the efficiency and selectivity of catalytic reactions.
Used in Antimicrobial and Antifungal Applications:
N-(3-Butynyl)phthalimide has been studied for its potential antimicrobial and antifungal properties, indicating its possible use in pharmaceuticals and other industries where such properties are beneficial.
While the provided materials do not specify different industries for the applications, the general uses listed above can be applicable across various chemical and pharmaceutical industries where organic synthesis, catalysis, and antimicrobial/antifungal agents are required.

InChI:InChI=1/C12H9NO2/c1-2-3-8-13-11(14)9-6-4-5-7-10(9)12(13)15/h1,4-7H,3,8H2

Upstream product

• 16156-58-4 prop-2-yn-1-ol methanesulfonate 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 1074-82-4 potassium phtalimide 
• 484673-75-8 C₂₂H₂₀N₂O₂ 
• 927-74-2 3-Butyn-1-ol 
• 136918-14-4 phthalimide 
• 38771-21-0 4-bromobut-1-yne 
• 2436-29-5 3-(N-phthaloyl)propionaldehyde 
• 85-44-9 phthalic anhydride 
• 14044-63-4 but-3-yn-1-amine 
• 51908-64-6 4-chlorobut-1-yne 
• 72486-09-0 methanesulfonic acid but-3-ynyl ester 

Downstream Products

• 141019-38-7 diethyl N-<4-(4-phthalimidobut-1-ynyl)benzoyl>-L-glutamate 
• 125030-48-0 2-[4-[6-(2-Fluorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-8-yl]-3-butynyl]-1H-isoindole-1,3(2H)-dione 
• 1229971-44-1 (E)-2-(4-(dimethyl(perfluorophenyl)silyl)but-3-enyl)isoindoline-1,3-dione 
• 1229971-47-4 2-(3-(dimethyl(perfluorophenyl)silyl)but-3-enyl)isoindoline-1,3-dione 
• 1875-48-5 N-aminophthalamide 
• 88211-50-1 4-amino-1-butyne hydrochloride 
• 14044-63-4 but-3-yn-1-amine 
• 1262028-98-7 2-[4-(2-phenoxythiazol-4-yl)-3-butynyl]isoindole-1,3-dione 
• 1262028-96-5 2-[4-(2-benzylthiazol-4-yl)-3-butynyl]isoindole-1,3-dione 
• 1262028-93-2 2-[4-(2-phenylthiazol-4-yl)-3-butynyl]isoindole-1,3-dione 
• 1285573-16-1 2-(2-(3-(perfluorophenyl)isoxazol-5-yl)ethyl)isoindoline-1,3-dione 
• 1060671-67-1 2-{2-[1-(toluene-4-sulphonyl)-1H-indol-2-yl]ethyl}isoindole-1,3-dione 
• 1003001-06-6 2-(2-(1-phenyl-1H-[1,2,3]-triazol-5-yl)ethyl)isoindoline-1,3-dione 
• 587880-44-2 N-{4-[4-(2-Hydroxyethyloxy)phenyl]but-3-yn-1-yl}phthalimide 

Relevant academic research and scientific papers

Synthesis of the analogs of plocabulin and their preliminary structure-activity relationship study

Plocabulin, a marine natural polyketide isolated from the sponge Lithoplocamia lithistoides, is a novel and potent microtubule-destabilizing agent. Guided by the reported binding mode, several new analogs of plocabulin have been designed through removing

Facile preparation of 2-aryl-3-iodopyrroles with N-tosyl 4-aryl-3-butyn-1-ylamines, I2, andtBuOK

Treatment of N-tosyl 4-aryl-3-butyn-1-ylamines with I2 and K2CO3, followed by the reaction withtBuOK under mild conditions gave 2-aryl-3-iodopyrroles in good yields. The present approach is a one-pot method for the preparation of 2-aryl-3-iodopyrroles from N-tosyl 4-aryl-3-butyn-1-ylamines, which could be easily prepared from aryl iodides, N-(3-butyn-1-yl)phthalimides, and p-toluenesulfonyl chloride.

Regio- And stereoselective electrochemical synthesis of sulfonylated enethers from alkynes and sulfonyl hydrazides

An electrooxidative direct difunctionalization of internal alkynes with sulfonyl hydrazides has been developed for the construction of sulfonated enethers. In this transformation, metal catalysts or stoichiometric amount of oxidants are not required and molecular nitrogen and hydrogen are the sole byproducts, providing a simple and green approach for preparing various sulfonyl tetrasubstituted alkenes. Notably, the protocol could be efficiently scaled up and the follow-up procedures of the corresponding functionalized alkenes demonstrate the practicality of the electrochemical synthesis.

Radical Carbonyl Propargylation by Dual Catalysis

Carbonyl propargylation has been established as a valuable tool in the realm of carbon–carbon bond forming reactions. The 1,3-enyne moiety has been recognized as an alternative pronucleophile in the above transformation through an ionic mechanism. Herein, we report for the first time, the radical carbonyl propargylation through dual chromium/photoredox catalysis. A library of valuable homopropargylic alcohols bearing all-carbon quaternary centers could be obtained by a catalytic radical three-component coupling of 1,3-enynes, aldehydes and suitable radical precursors (41 examples). This redox-neutral multi-component reaction occurs under very mild conditions and shows high functional group tolerance. Remarkably, bench-stable, non-toxic, and inexpensive CrCl3 could be employed as a chromium source. Preliminary mechanistic investigations suggest a radical-polar crossover mechanism, which offers a complementary and novel approach towards the preparation of valuable synthetic architectures from simple chemicals.

Synthesis of Exo- and Endocyclic Enamides Through Copper-Catalyzed Regioselective Intramolecular N-Halovinylation

Cross-couplings between amides and 1,2-dihaloalkenes are an efficient and straightforward way to access β-haloenamides which, in turn, can be functionalized into complex, stereodefined enamide motifs. However, the intramolecular version of these cross-couplings, leading to cyclic β-haloenamides, has not been formally studied. In this paper, we report an investigation of factors affecting the efficiency of the reaction and its selectivity between potential exo and endo cyclization products. We demonstrate that exo/endo selectivity is largely determined by ring strain, whether it arises from the size of the resulting ring or from the structure of the starting compound, but that selectivity can also be modulated by varying reaction conditions. Finally, we show that resulting β-haloenamides readily undergo transition metal-catalyzed reactions, making this sequence a viable way to access highly functionalized cyclic enamides.

Design, synthesis and structure-activity relationships of novel 15-membered macrolides: Quinolone/quinoline-containing sidechains tethered to the C-6 position of azithromycin acylides

In the search for novel hybrid molecules by fusing two biologically active scaffolds into one heteromeric chemotype, we found that hybrids of azithromycin and ciprofloxacin/gatifloxacin 26j and 26l can inhibit the supercoiling activity of E. coli gyrase by poisoning it in a way similar to fluoroquinolones. This may modestly contribute to their potencies, which are equal to ciprofloxacin against constitutively resistant Staphylococcus aureus, whose growth is not inhibited by the presence of macrolides. In contrast, introduction of quinolines (the 3-quinoline 26b and the 6-quinoline 26o) with an optimized rigid spacer at the 6-OH of azithromycin acylides did not exert significant potency against constitutively resistant S. aureus, despite the fact that the quinoline-containing compounds, exemplified by 26o, were as active as telithromycin against susceptible, inducibly- and efflux-resistant pathogens. The novel dual modes of action involving protein synthesis inhibition and poisoning DNA replication may pave the way for restoration of antibacterial activities of the current macrolides against constitutively resistant clinical isolates.

17BETA-HETEROCYCLYL-DIGITALIS LIKE COMPOUNDS FOR THE TREATMENT OF HEART FAILURE

Disclosed are compounds of formula (I) wherein X, Y, Z are annular atoms comprised in a five-membered carbocyclic or heterocyclic ring, selected from the group consisting of CH, NH, N, O, S; said carbocyclic or heterocyclic ring being optionally substituted with amino (C1-C4) linear or branched alkyl or guanidine or guanidino (C1-C4) linear or branched alkyl; with the proviso that the heterocycle ring is not furyl; n is 0 or 1; R is H or OH; the dotted line represents an optional double bond C=C; the thick line represents a bond in the β configuration; the wavy line represents a bond both in the α and β configuration; their enantiomeric and/or diastereomeric mixtures, their pharmaceutically acceptable salts, their solvates, hydrates; their metabolite and metabolic precursors. The compounds of formula (I) are for use as medicaments, in particular for the treatment of acute or chronic heart failure. Oral administration is also possible.

MACROCYCLE CONTAINING AMINOPYRAZOLE AND PYRIMIDINE AND PHARMACEUTICAL COMPOSITION AND USE THEREOF

The present application relates to a macrocycle containing aminopyrazole and pyrimidine, which is represented by formula (I), a pharmaceutical composition thereof, and a use thereof in inhibiting tropomyosin receptor kinase (Trk) activity and in treating diseases in mammals that are mediated by Trk.

Discovery of a New Isoxazole-3-hydroxamate-Based Histone Deacetylase 6 Inhibitor SS-208 with Antitumor Activity in Syngeneic Melanoma Mouse Models

Isoxazole is a five-membered heterocycle that is widely used in drug discovery endeavors. Here, we report the design, synthesis, and structural and biological characterization of SS-208, a novel HDAC6-selective inhibitor containing the isoxazole-3-hydroxamate moiety as a zinc-binding group as well as a hydrophobic linker. A crystal structure of the Danio rerio HDAC6/SS-208 complex reveals a bidentate coordination of the active-site zinc ion that differs from the preferred monodentate coordination observed for HDAC6 complexes with phenylhydroxamate-based inhibitors. While SS-208 has minimal effects on the viability of murine SM1 melanoma cells in vitro, it significantly reduced in vivo tumor growth in a murine SM1 syngeneic melanoma mouse model. These findings suggest that the antitumor activity of SS-208 is mainly mediated by immune-related antitumor activity as evidenced by the increased infiltration of CD8+ and NK+ T cells and the enhanced ratio of M1 and M2 macrophages in the tumor microenvironment.

Method for synthesizing alkyne through catalytic asymmetric cross coupling (by machine translation)

The invention belongs to the field of, asymmetric synthesis, and discloses a method for catalyzing asymmetric cross- coupling to synthesize: an alkyne, and the L method comprises, the following steps, of A: preparing B a cuprous, salt and C a: ligand; preparing a catalyst; adding a base; reacting the compound with the compound with the compound; and reacting the compound with the compound. Of these, one of them, X is selected from the group consisting of, R halogens. 1 Optionally substituted heteroarylsulfonylcyanamide groups selected from the, group consisting, of optionally substituted, phenyl groups In-flight vehicle, R6 Trialkyl silyl groups or alkyl radicals, R2 Cycloalkyl radicals optionally substituted with an, optionally substituted alkyl, (CH radical2 )n R4 Multi,layer chain, n＝0-10,R saw blade4 A group selected, from, the group consisting of phenyl, alkenyl, aralkynyls, noonyloxy,and, noonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylphenyl disiloxy-radicals. R3 A ligand, selected from hydrogen or any of the functional groups, is selected from the group consisting of, hydrogen and any L other functional group. The method, R disclosed by the, A invention has the, advantages of good catalytic, R ’ effect, wide application range. and high catalytic efficiency, and the, method disclosed by the, invention has the. advantages of good catalytic effect, wide application range and high catalytic efficiency. (by machine translation)