149990-27-2

Usage

Uses

As the provided materials do not specify the exact uses of Carbamic acid, 3-butynyl-, 1,1-dimethylethyl ester (9CI), it is not possible to list its applications in different industries or as an application type for a specific reason. However, given that it is a carbamate ester, it may have potential applications in various fields such as pharmaceuticals, agrochemicals, or as an intermediate in the synthesis of other organic compounds. Further research and information would be required to determine its specific uses.

InChI:InChI=1/C9H15NO2/c1-5-6-7-10-8(11)12-9(2,3)4/h1H,6-7H2,2-4H3,(H,10,11)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 6089-09-4 4-pentynoic acid 
• 75-65-0 tert-butyl alcohol 
• 338463-00-6 N-(tert-butoxycarbonyl)-N-but-3-ynyl-4-methylbenzenesulfonamide 
• 14044-63-4 but-3-yn-1-amine 
• 10451-00-0 4-azido-1-butyne 
• 88211-50-1 4-amino-1-butyne hydrochloride 
• 14396-90-8 N-(3-butynyl)phthalimide 
• 142-71-2 copper diacetate 
• 146-75-8 sodium L-ascorbate 
• 622-79-7 benzyl azide 
• 1538-75-6 2,2-dimethylpropanoic anhydride 

Downstream Products

• 742102-25-6 [4-(4-Nitrophenyl)but-3-ynyl]carbamic acid tert-butyl ester 
• 1026516-37-9 [4-(2-hydroxy-phenyl)-but-3-ynyl]-carbamic acid tert-butyl ester 
• 905293-03-0 [4-(3-methoxy-phenyl)-but-3-ynyl]-carbamic acid tert-butyl ester 
• 905293-06-3 [4-(2-methoxy-phenyl)-but-3-ynyl]-carbamic acid tert-butyl ester 
• 363599-38-6 N-(tert-Butoxycarbonyl)penta-3,4-dienylamine 
• 1507378-99-5 N-Boc-(E)-3,4-diiodobut-3-en-1-amine 
• 1445985-80-7 (R)-tert-butyl 4-(2,5-dicbloro-4-((4-(4-cyclopropyl-1,2,3,4-tetrahydroquinoxaline-1-carbonyl)thiazolidin-3-yl)methyl)phenyl)butylcarbamate 
• 1445985-79-4 tert-butyl N-[4-[2,5-dichloro-4-(hydroxymethyl)phenyl]butyl]carbamate 
• 1445985-78-3 tert-butyl 4-(2,5-dichloro-4-formylphenyl)butylcarbamate 

Relevant academic research and scientific papers

A Domino 10-Step Total Synthesis of FR252921 and Its Analogues, Complex Macrocyclic Immunosuppressants

FR252921, FR252922, and FR256523 are a family of potent macrocyclic polyene immunosuppressive agents with a novel mode of action. However, the lack of an efficient and flexible synthesis has hindered further biological studies, mostly due to the fact that the natural products appear to be kinetic isomers regarding the triene moiety. Herein, we report the development and application of an unprecedented, unique domino Suzuki-Miyaura/4π-electrocyclic ring-opening macrocyclization, resulting in a concise, unified, and stereoselective synthetic route to these complex targets in only 10 steps. This in turn enables ready access to a range of unnatural analogues, among which several compounds showed inhibition of T-lymphocyte proliferation at levels equal or superior to those of the natural products themselves.

68Ga/DOTA- and 64Cu/NOTA-phthalocyanine conjugates as fluorescent/PET bimodal imaging probes

In this paper, we describe the synthesis and characterization of a series of new bimodal probes combining water-soluble sulfonated zinc phthalocyanine (ZnPc) as a fluorescence imaging unit and either 68Ga/1,4,7,10- tetraazocyclododecane-N,N′N″,N′″-tetraacetic acid (DOTA) or 64Cu/1,4,7-triazacyclononane-1,4,7-triacetic acid (NOTA) for PET imaging. The two moieties were linked through aliphatic chains of different lengths to modulate amphiphilicity. Labeling of DOTA- or NOTA-ZnPc conjugates with 68Ga (t1/2 = 68 min) and 64Cu (t 1/2 = 12.7 h) was performed at 100 C for 15 min with >90% efficiency for all conjugates. In vitro plasma stability assays demonstrated high stability of the 64Cu/NOTA-ZnPc conjugate, which remained intact over a 24 h time period, and reasonably high stability of the 68Ga/DOTA-ZnPc conjugate, which released up to 7% of free 68Ga over a 3 h period. Based on in vitro plasma stability results, we performed biodistribution studies on two 64Cu-labeled derivatives, which allowed us to select a single candidate for preliminary in vivo experiments. Fluorescence and PET imaging confirmed the potential of these novel conjugates to act as bimodal probes.

HYDROXY-PYRIDINALDOXIME SCAFFOLDS

The present invention relates to a compound of formula (I). It also relates to a pharmaceutical composition comprising at least one compound of formula (I) and at least one pharmaceutically acceptable support. Finally, it relates to the use of such a compound as a medicine, preferably in the treatment of a nervous and/or respiratory failure due to intoxication with at least one organophosphorous nerve agent; in the treatment of neurological diseases such as Alzheimer's disease; and/or in the treatment of cancer.

Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin**

Streptazone A and abikoviromycin are alkaloids that both feature an unusual arrangement of reactive functionalities within a compact tricyclic ring system. Here, we report a highly concise asymmetric synthesis of both natural products. The route first constructs another family member, streptazone B1, using a rhodium-catalyzed distal selective allene-ynamide Pauson–Khand reaction. A regio- and enantioselective epoxidation under chiral phase-transfer catalytic conditions directly afforded streptazone A in 8 steps overall. In one additional step, a chemoselective, iridium-catalyzed reduction of the enaminone system then gave abikoviromycin. The reactivity of streptazone A towards a cysteine mimic, N-acetylcysteamine, was studied and revealed unanticipated transformations, including bis-thiol conjugation which may proceed via formation of a cyclopentadienone intermediate. With flexible access to these compounds, studies aimed to identify their direct biological targets are now possible.

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

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.

A Domino 10-Step Total Synthesis of FR252921 and Its Analogues, Complex Macrocyclic Immunosuppressants

FR252921, FR252922, and FR256523 are a family of potent macrocyclic polyene immunosuppressive agents with a novel mode of action. However, the lack of an efficient and flexible synthesis has hindered further biological studies, mostly due to the fact that the natural products appear to be kinetic isomers regarding the triene moiety. Herein, we report the development and application of an unprecedented, unique domino Suzuki-Miyaura/4?€-electrocyclic ring-opening macrocyclization, resulting in a concise, unified, and stereoselective synthetic route to these complex targets in only 10 steps. This in turn enables ready access to a range of unnatural analogues, among which several compounds showed inhibition of T-lymphocyte proliferation at levels equal or superior to those of the natural products themselves.

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Design of Gut-Restricted Thiazolidine Agonists of G Protein-Coupled Bile Acid Receptor 1 (GPBAR1, TGR5)

Bile acid signaling and metabolism in the gastrointestinal tract have wide-ranging influences on systemic disease. G protein-coupled bile acid receptor 1 (GPBAR1, TGR5) is one of the major effectors in bile acid sensing, with demonstrated influence on metabolic, inflammatory, and proliferative processes. The pharmacologic utility of TGR5 agonists has been limited by systemic target-related effects such as excessive gallbladder filling and blockade of gallbladder emptying. Gut-restricted TGR5 agonists, however, have the potential to avoid these side effects and consequently be developed into drugs with acceptable safety profiles. We describe the discovery and optimization of a series of gut-restricted TGR5 agonists that elicit a potent response in mice, with minimal gallbladder-related effects. The series includes 12 (TGR5 EC50: human, 143 nM; mouse, 1.2 nM), a compound with minimal systemic availability that may have therapeutic value to patients with type 2 diabetes mellitus, nonalcoholic steatohepatitis, or inflammatory bowel disease.

Structure–Activity Relationships of Antiplasmodial Pantothenamide Analogues Reveal a New Way by Which Triazoles Mimic Amide Bonds

Pantothenamides are potent growth inhibitors of the malaria parasite Plasmodium falciparum. Their clinical use is, however, hindered due to the ubiquitous presence of pantetheinases in human serum, which rapidly degrade pantothenamides into pantothenate and the corresponding amine. We previously reported that replacement of the labile amide bond with a triazole ring not only imparts stability toward pantetheinases, but also improves activity against P. falciparum. A small library of new triazole derivatives was synthesized, and their use in establishing structure–activity relationships relevant to antiplasmodial activity of this family of compounds is discussed herein. Overall it was observed that 1,4-substitution on the triazole ring and use of an unbranched, one-carbon linker between the pantoyl group and the triazole are optimal for inhibition of intraerythrocytic P. falciparum growth. Our results imply that the triazole ring may mimic the amide bond with an orientation different from what was previously suggested for this amide bioisostere.