120539-91-5

Usage

Uses

Used in Organic Synthesis:
N-Cbz-propargylamine is used as a building block for the preparation of complex organic molecules, particularly in the synthesis of natural products and pharmaceutical compounds. Its unique structure allows for selective reactions and the formation of diverse molecular frameworks.
Used in Asymmetric Gold Catalysis:
N-Cbz-propargylamine is used as a one-point binding ligand for asymmetric gold catalysis, enabling efficient and selective organic synthesis reactions. This application is particularly valuable in the development of enantioselective catalysts, which are essential for producing chiral molecules with a single handedness, often required in the pharmaceutical industry.
Used as a Protective Group:
In organic synthesis, N-Cbz-propargylamine serves as a protective group for amines, preventing unwanted side reactions and ensuring the selective formation of the desired product. The Cbz group can be easily removed when no longer needed, allowing for further functionalization of the molecule.

Upstream product

• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 2450-71-7 Propargylamine 
• 501-53-1 benzyl chloroformate 
• 15430-52-1 prop-2-yn-1-amine hydrochloride 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 1885-14-9 phenyl chloroformate 

Downstream Products

• 610796-32-2 5-(benzyloxycarbonylamino-methyl)-isoxazole-3-carboxylic acid ethyl ester 
• 144734-57-6 benzyl allyl(prop-2-yn-1-yl)carbamate 
• 479400-97-0 benzyl 3-(6-{3-[(tert-butoxycarbonyl)amino]prop-1-ynyl}pyridin-3-yl)prop-2-ynylcarbamate 
• 210115-35-8 5-(3-benzyloxycarbonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid tert-butyl ester 
• 916770-76-8 3-(4-[3-(3-benzyloxycarbonylamino-prop-1-ynyl)-phenyl]-4-methyl-2,5-dioxo-imidazolidin-1-ylmethyl)-benzoic acid methyl ester 
• 1129528-30-8 C₃₃H₄₉N₉O₆Si₂ 
• 214982-22-6 benzyl (3-phenylprop-2-yn-1-yl)carbamate 
• 1041464-81-6 (1-benzyl-1H-indole-2-carbonyl)prop-2-ynylcarbamic acid benzyl ester 
• 1052676-87-5 benzyl ((4S,5R,6R)-4-tert-butoxy-7-oxo-1-azabicyclo[3.2.0]heptan-6-yl)methylcarbamate 
• 1160112-81-1 7'-aza-5'-(N-benzyloxycarbonyl-3-aminoprop-1-ynyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)isoindigo 
• 1160112-82-2 7'-aza-5'-(N-benzyloxycarbonyl-3-aminoprop-1-ynyl)-5-bromo-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)isoindigo 
• 1160112-72-0 5'-(N-benzyloxycarbonyl-3-aminoprop-1-ynyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)isoindigo 
• 1160112-73-1 5'-(N-benzyloxycarbonyl-3-aminoprop-1-ynyl)-5-bromo-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)isoindigo 
• 1159604-62-2 tert-butyl 5-(benzyloxycarbonylamino)pent-3-ynoate 

Relevant academic research and scientific papers

A strategic approach to [6,6]-bicyclic lactones: Application towards the CD fragment of DHβE

We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of t

Synthesis and structure-bactericidal activity relationships of non-ketolides: 9-Oxime clarithromycin 11,12-cyclic carbonate featured with three-to eight-atom-length spacers at 3-OH

In general, potent non-ketolide versions of erythromycin possessed conformationally constricted two- or three-atom-length sidechains at 3-OH. Novel 14-membered non-ketolides possessing long spacers beyond three-atom length were evaluated for antibacterial

An Alkynylpyrimidine-Based Covalent Inhibitor That Targets a Unique Cysteine in NF-κB-Inducing Kinase

NF-κB-inducing kinase (NIK) is a key enzyme in the noncanonical NF-κB pathway, of interest in the treatment of a variety of diseases including cancer. Validation of NIK as a drug target requires potent and selective inhibitors. The protein contains a cysteine residue at position 444 in the back pocket of the active site, unique within the kinome. Analysis of existing inhibitor scaffolds and early structure-activity relationships (SARs) led to the design of C444-targeting covalent inhibitors based on alkynyl heterocycle warheads. Mass spectrometry provided proof of the covalent mechanism, and the SAR was rationalized by computational modeling. Profiling of more potent analogues in tumor cell lines with constitutively activated NIK signaling induced a weak antiproliferative effect, suggesting that kinase inhibition may have limited impact on cancer cell growth. This study shows that alkynyl heterocycles are potential cysteine traps, which may be employed where common Michael acceptors, such as acrylamides, are not tolerated.

Design and synthesis of a peptide derivative of ametantrone targeting the major groove of the d(GGCGCC)2 palindromic sequence

In oncology, some DNA intercalating agents have been used in chemotherapy for years to eradicate cancer cells, but these drugs generally suffer from a lack of selectivity for malignant tissues and consequently induce major side-effects. We report herein the design and synthesis of an antitumor intercalating agent ametantrone complemented with two identical peptide arms including a central Lys residue in order to selectively target palindromic sequences of DNA of malignant cells. The peptide arms are linked to the ametantrone core through 1,2,3-triazole. According to our docking prediction, this compound should be double-stranded β-sheet structured, and it has been designed to interact with two guanine residues upstream from a central d(CpG)2 intercalation site on each DNA strand, owing to the H-bonds involving the Lys terminal side chain ammonium group of the peptide arms. This new ametantrone derivative has been obtained thanks to a convergent synthetic pathway, whose key steps were double nucleophilic substitution performed on the ametantrone core, followed by "double-site" 1,3-dipolar cycloaddition affording the 1,4-disubstituted triazole linker almost quantitatively. Preliminary binding assays performed by mass spectrometry proved its accuracy for DNA palindromic sequences. The cytotoxicity of this compound was evaluated on three cancer cell lines and one healthy cell line, and compared to that of mitoxantone, a dihydroxylated analog of ametantrone. Such a peptide derivative was about ten-fold less cytotoxic than mitoxantrone on these cancer cell lines, but about fifty times less cytotoxic on healthy cells. This study could open new avenues towards the design of targeted intercalating agents.

Development of Stem-Cell-Mobilizing Agents Targeting CXCR4 Receptor for Peripheral Blood Stem Cell Transplantation and beyond

The function of the CXCR4/CXCL12 axis accounts for many disease indications, including tissue/nerve regeneration, cancer metastasis, and inflammation. Blocking CXCR4 signaling with its antagonists may lead to moving out CXCR4+ cell types from b

Discovery and synthesis of 6,7,8,9-tetrahydro-5H-pyrido[4,3-c]azepin-5-one-based novel chemotype CCR2 antagonists via scaffold hopping strategy

The chemokine CC receptor subtype 2 (CCR2) has attracted intensive interest for drug development in diverse therapeutic areas, including chronic inflammatory diseases, diabetes, neuropathic pain, atherogenesis and cancer. By employing a cut-and-sew scaffold hopping strategy, we identified an active scaffold of 3,4-dihydro-2,6-naphthyridin-1(2H)-one as the central pharmacophore to derive novel CCR2 antagonists. Systematic structure–activity relationship study with respect to the ring size and the substitution on the naphthyridinone ring gave birth to 1-arylamino-6-alkylheterocycle-6,7,8,9-tetrahydro-5H-pyrido[4,3-c]azepin-5-ones as a brand new chemotype of CCR2 antagonists with nanomolar inhibitory activity. The best antagonism activity in this series was exemplified by compound 13a, which combined the optimal substitutions of 3,4-dichlorophenylamino at C-1 and 3-(4-(N-methylmethylsulfonamido)piperidin-1-yl)propyl at N-6 position, leading to an IC50 value of 61 nM and 10-fold selectivity for CCR2 over CCR5. Efficient and general synthesis was established to construct the innovative core structure and derive the compound collections. This is the first report on our designed 6,7,8,9-tetrahydro-5H-pyrido[4,3-c]azepin-5-one as novel CCR2 antagonist scaffold and its synthesis.

HETEROCYCLIC COMPOUNDS AND USE THEREOF

Heterocyclic compounds of Formula (I) shown herein. Also disclosed are pharmaceutical compositions containing the heterocyclic compounds and methods of using the heterocyclic compounds to mobilize hematopoietic stem cells and endothelial progenitor cells into the peripheral circulation. Further provided are methods for treating tissue injury, cancer, inflammatory disease, and autoimmune disease with the heterocyclic compounds.

Pathways to Functionalized Heterocycles: Propargyl Rearrangement using B(C6F5)3

The reactions of propargyl amides, ureas, carbamates, and carbonates with B(C6F5)3 proceed via an intramolecular 5-exo-dig cyclization across the alkyne unit to yield the corresponding vinyl borate species. The generated sp2 carbocation is stabilized by the flanking heteroatoms, allowing for isolation of oxazoline intermediates. The fate of these intermediates is strongly dependent upon the propargyl-functionalized starting material, with the carbamates and carbonates undergoing a ring-opening mechanism (propargyl rearrangement) to give cyclic allylboron compounds, while prolonged heating of the urea derivatives shows evidence of oxazole formation. In a deviation away from the reactivity of carbamates stated previously, the benzyl carbamate substrate undergoes dealkylation at the benzylic position, liberating 5-methyloxazol-2-(3H)-one.

Stem cell mobilizers targeting chemokine receptor CXCR4: Renoprotective application in acute kidney injury

We have discovered a novel series of quinazoline-based CXCR4 antagonists. Of these, compound 19 mobilized CXCR4+ cell types, including hematopoietic stem cells and endothelial progenitor cells, more efficiently than the marketed 1 (AMD3100) with subcutaneous administration at the same dose (6 mg/kg) in mice. This series of compounds thus provides a set of valuable tools to study diseases mediated by the CXCR4/SDF-1 axis, including myocardial infarction, ischemic stroke, and cancer metastasis. More importantly, treatment with compound 19 significantly lowered levels of blood urea nitrogen and serum creatinine in rats with renal ischemia-reperfusion injury, providing evidence for its therapeutic potential in preventing ischemic acute kidney injury. CXCR4 antagonists such as 19 might also be useful to increase circulating levels of adult stem cells, thereby exerting beneficial effects on damaged and/or inflamed tissues in diseases that currently are not treated by standard approaches.

AMIDS SUBSTITUTED INDAZOLE DERIVATIVEES AS PLOY (ADP-RIBOSE) POLYMERASE INHIBITORS

The present invention relates to amide substituted indazoles and benzotriazoles which are inhibitors of the enzyme poly (ADP-ribose) polymerase (PARP), previously known as poly (ADP-ribose) synthase and poly (ADP-ribosyl) transferase. The compounds of the present invention are useful as mono-therapies in tumors with specific defects in DNA-repair pathways, as enhancers of certain DNA-damaging agents such as anticancer agents and radiotherapy, for reducing cell necrosis (in stroke and myocardial infarction), regulating inflammation and tissue injury, treating retroviral infections, and protecting against the toxicity of chemotherapy.