112663-43-1

Usage

Uses

Used in Organic Synthesis:
Methanesulfonic acid 3-tert-butoxycarbonylamino-propyl ester is used as a protecting group for amino groups in organic synthesis. The protective group allows for selective reactions to occur at other functional groups, preventing unwanted side reactions with the amino group.
Used in Pharmaceutical Research and Development:
In the pharmaceutical industry, Methanesulfonic acid 3-tert-butoxycarbonylamino-propyl ester is used for the synthesis of new drugs and pharmaceutical intermediates. Its ability to protect amino groups during chemical reactions enables the development of complex drug molecules with specific functionalities and improved therapeutic properties.
Used in Peptide Synthesis:
Methanesulfonic acid 3-tert-butoxycarbonylamino-propyl ester is particularly useful in peptide synthesis, where it serves as a protecting group for amino groups. This allows for the stepwise assembly of peptide chains without premature reactions between amino groups, facilitating the synthesis of longer and more complex peptides with desired sequences and properties.

Upstream product

• 58885-58-8 N-tert-butoxycarbonyl-3-aminopropanol 
• 7143-01-3 Methanesulfonic anhydride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 129392-84-3 tert-butyl N-(3-azidopropyl)carbamate 
• 425644-03-7 N⁸-benzyloxycarbonyl-N¹-tert-butyloxycarbonyl-N⁴-(2-nitrobenzenesulfonyl)-spermidine 
• 1202760-18-6 tert-butyl 3-(3-(5-methyl-4-(3-nitrophenylamino)pyrimidin-2-ylamino)phenoxy)propylcarbamate 
• 1202760-19-7 tert-butyl 3-(3-(4-(3-aminophenylamino)-5-methylpyrimidin-2-ylamino)phenoxy)propylcarbamate 
• 1202756-32-8 tert-butyl 3-(3-(4-(3-acrylamidophenylamino)-5-methylpyrimidin-2-ylamino)phenoxy)propylcarbamate 
• 1175649-60-1 [3-(3-aminophenoxy)propyl]carbamic acid tert-butyl ester 
• 1426687-03-7 tert-butyl (3-(((4S)-6-(4-chlorophenyl)-4-(2-(ethylamino)-2-oxoethyl)-1-methyl-4H-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepin-8-yl)oxy)propyl)carbamate 
• 849473-02-5 [3-(benzylmethylamino)propyl]carbamic acid tert-butyl ester 
• 1202757-90-1 tert-butyl 3-(3-(4-(3-acrylamidophenylamino)-5-fluoropyrimidin-2-ylamino)phenoxy)propylcarbamate 
• 1202760-20-0 C₂₄H₂₇FN₆O₅ 
• 1202760-21-1 C₂₄H₂₉FN₆O₃ 

Relevant academic research and scientific papers

Synthesis and biological evaluation of dihydromotuporamine derivatives in cells containing active polyamine transporters

Dihydromotuporamine C (4) and its 4,4-triamine analogue (5) were synthesized in good yield using ring-closing metathesis (RCM) methods. Comparison of their biological activities (Ki determinations in L1210 cells and IC50 determinations in L1210, CHO, and CHO-MG cells) revealed that the motuporamine derivatives do not use the polyamine transporter (PAT) for cellular entry. Bioevaluation of a N1-(anthracen-9- ylmethyl)-n1-(ethyl)homospermidine control (7) revealed that the presence of a N1 tertiary amine center imparted a significant reduction in the PAT affinity of the polyamine conjugate and abolished its PAT-targeting selectivity.

Novel bifunctional [16]anes4-derived chelators for soft radiometals

The field of targeted radionuclide therapy is rapidly growing, highlighting the need for wider radionuclide availability. Soft Lewis acid ions, such as radioisotopes of platinum, rhodium and palladium, are particularly underdeveloped. This is due in part to a lack of compatible bifunctional chelators. These allow for the practical bioconjugation to targeting vectors, in turn enabling radiolabeling. The [16]andS4 macrocycle has been reported to chelate a number of relevant soft metal ions. In this work, we present a procedure for synthesizing [16]andS4 in 45% yield (five steps, 12% overall yield), together with a selection of strategies for preparing bifunctional derivatives. An ester-linked N-hydroxysuccimide ester (NHS, seven steps, 4% overall yield), an ether-linked isothiocyanate (NCS, eight steps, 5% overall yield) and an azide derivative were prepared. In addition, a new route to a carbon-carbon linked carboxylic acid functionalized derivative is presented. Finally, a general method for conjugating the NHS and NCS derivatives to a polar peptide (octreotide) is presented, by dissolution in water:acetonitrile (1:1), buffered to pH 9.4 using borate. The reported compounds will be readily applicable in radiopharmaceutical chemistry, by facilitating the labeling of a range of molecules, including peptides, with relevant soft radiometal ions.

Mono-Protected Diamines. Nα-tert-Butoxycarbonyl α,ω-Alkanediamine Hydrochlorides from Amino alcohols.

Nα-tert-Butoxycarbonyl α,ω-alkanediamine hydrochlorides 3a-e are prepared from the amino alcohols in yields of 66-87percent.Reaction of the free amine with di-tert-butyl dicarbonate gives the N-tert-Butoxycarbonylamino alcohol 1a-e.One-pot conversion to the azide 2a-e via the mesylate under phase-transfer conditions followed by hydrogenolysis in the presence of chloroform yields the title compounds.

NanoSOSG: A Nanostructured Fluorescent Probe for the Detection of Intracellular Singlet Oxygen

A biocompatible fluorescent nanoprobe for singlet oxygen (1O2) detection in biological systems was designed, synthesized, and characterized, that circumvents many of the limitations of the molecular probe Singlet Oxygen Sensor Green (SOSG). This widely used commercial singlet oxygen probe was covalently linked to a polyacrylamide nanoparticle core using different architectures to optimize the response to 1O2. In contrast to its molecular counterpart, the optimum SOSG-based nanoprobe, which we call NanoSOSG, is readily internalized by E. coli cells and does not interact with bovine serum albumin. Furthermore, the spectral characteristics do not change inside cells, and the probe responds to intracellularly generated 1O2 with an increase in fluorescence.

MACROCYCLIC KINASE INHIBITOR

Disclosed is a macrocyclic kinase inhibitor, wherein the compound, or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof is as shown in formula I. Experiments show that the new compound as shown in formula I disclosed in the present invention exhibits an excellent TRK inhibitory activity, has a significant inhibitory effect on TRKA-mutant cell growth, and exhibits an excellent inhibitory effect on in vivo tumor growth, thus providing a new choice for the clinical treatment of diseases associated with abnormal TRK activity.

Organic Ligands For Templatable Mesoscale Nanocapsules

Organic ligands and methods for preparing a variety of organic ligands are provided. The subject methods provide for the preparation of organic ligands in high yield and purity for use as ligands for attachment to nanoparticles to enable the formation of three dimensional nanocapsules of stably associated organic ligand-functionalized nanoparticles. Compositions that include these nanocapsules, as well as methods of making the nanocapsules are also provided.

Discovery of Potential Neuroprotective Agents against Paclitaxel-Induced Peripheral Neuropathy

Chemotherapy-induced neurotoxicity is a common adverse effect of cancer treatment. No medication has been shown to be effective in the prevention or treatment of chemotherapy-induced neurotoxicity. Using minoxidil as an initial template for structural modifications in conjunction with an in vitro neurite outgrowth assay, an image-based high-content screening platform, and mouse behavior models, an effective neuroprotective agent CN016 was discovered. Our results showed that CN016 could inhibit paclitaxel-induced inflammatory responses and infiltration of immune cells into sensory neurons significantly. Thus, the suppression of proinflammatory factors elucidates, in part, the mechanism of action of CN016 on alleviating paclitaxel-induced peripheral neuropathy. Based on excellent efficacy in improving behavioral functions, high safety profiles (MTD > 500 mg/kg), and a large therapeutic window (MTD/MED > 50) in mice, CN016 might have great potential to become a peripherally neuroprotective agent to prevent neurotoxicity caused by chemotherapeutics as typified by paclitaxel.

NURR1 RECEPTOR MODULATORS

Described herein, inter alia, are Nurr1 receptor modulators and uses thereof. In an aspect is provided a method for treating a disease associated with dysregulation and/or degeneration of dopaminergic neurons in the central nervous system of a subject in need thereof, the method including administering to the subject in need thereof a therapeutically effective amount of a compound described herein.

MERTK DEGRADERS AND USES THEREOF

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

Ligand Conformational Bias Drives Enantioselective Modification of a Surface-Exposed Lysine on Hsp90

Targeted covalent modification of surface-exposed lysines is challenging due to their low intrinsic reactivity and high prevalence throughout the proteome. Strategies for optimizing the rate of covalent bond formation by a reversibly bound inhibitor (kinact) typically involve increasing the reactivity of the electrophile, which increases the risk of off-target modification. Here, we employ an alternative approach for increasing kinact of a lysine-targeted covalent Hsp90 inhibitor, independent of the reversible binding affinity (Ki) or the intrinsic electrophilicity. Starting with a noncovalent ligand, we appended a chiral, conformationally constrained linker, which orients an arylsulfonyl fluoride to react rapidly and enantioselectively with Lys58 on the surface of Hsp90. Biochemical experiments and high-resolution crystal structures of covalent and noncovalent ligand/Hsp90 complexes provide mechanistic insights into the role of ligand conformation in the observed enantioselectivity. Finally, we demonstrate selective covalent targeting of cellular Hsp90, which results in a prolonged heat shock response despite concomitant degradation of the covalent ligand/Hsp90 complex. Our work highlights the potential of engineering ligand conformational constraints to dramatically accelerate covalent modification of a distal, poorly nucleophilic lysine on the surface of a protein target.