56911-81-0

Upstream product

• 768-94-5 1-Adamantanamine 
• 874-60-2 4-methyl-benzoyl chloride 
• 51-67-2 tyrosamine 
• 117-34-0 2,2-diphenylacetic acid 
• 3261-62-9 2-(p-tolyl)ethylamine 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 64-04-0 phenethylamine 
• 99-94-5 p-Toluic acid 
• 55-81-2 4-Methoxyphenethylamine 
• 24313-88-0 3,4,5-Trimethoxyaniline 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 2045-79-6 o-methoxy-2-phenylethylamine 
• 299-42-3 2-methylamino-1-phenylpropanol 
• 768-90-1 1-Adamantyl bromide 

Downstream Products

• 1596377-24-0 N-adamantyl-4-methyl-2-[4-(trifluoromethyl)phenylamino]benzamide 

Relevant academic research and scientific papers

Environmentally sustainable production and application of acyl phosphates

A versatile and environmentally friendly synthetic method for the formation of acyl phosphates is reported. By employing electrochemical oxidative dehydrogenative coupling, this transformation features a broad range of substrates, as well as metal-free, o

Ionic liquid catalyzed Ritter reaction/Pd-catalyzed directed Ortho-arylation; facile access to diverse libraries of biaryl-amides from Aryl-nitriles

Diverse libraries of biaryl-amides bearing N-t-butyl and N-adamantyl groups were synthesized in two steps by the Ritter reaction of aryl-nitriles, using tBuOH and AdaOH as carbocation precursors, and employing [BMIM(SO3H)][OTf] (neat or with [B

Practical Synthesis of N -(Diphenylmethyl)- and N -(1-Adamantyl)amides Directly from Aldehydes via a One-Pot Schmidt and Ritter Reaction Sequence

Nonoxidative and noncoupling reaction conditions have been developed for the synthesis of N-(diphenylmethyl)- and N-(1-adamantyl)amide derivatives directly from aldehydes by employing the concept of a Schmidt and Ritter reaction sequence in a one-pot operation. The reagent mixture consisting of sodium azide and HBF4·OEt2 in acetic acid converts the aldehydes into their respective nitrile analogues which in situ undergo the Ritter reaction with diphenylmethanol or 1-adamantanol to afford the corresponding N-(diphenylmethyl)- or N-(1-adamantyl)amide derivatives in very good yields. The method does not require column chromatographic purification for isolation of the products. With its simple reaction procedure and easy product purification technique, this method outshines earlier conventional two-step methods.

Iridium-catalyzed C-H amination with anilines at room temperature: Compatibility of iridacycles with external oxidants

Described herein is the development of an iridium-catalyzed direct C-H amination of benzamides with anilines at room temperature, representing a unique example of an Ir catalyst system that is compatible with external oxidants. Mechanistic details, such as the isolation and characterization of key iridacycle intermediates, are also discussed.

Microwave assisted, Ca(II)-catalyzed Ritter reaction for the green synthesis of amides

An efficient solvent-free synthesis of amides by Ca(II) catalyzed Ritter reaction has been reported under microwave irradiation. This green protocol tolerates the substrate diversity and delivers the high yielding amides with minimal loading of inexpensive and more abundant Ca(II) catalyst.

Ritter reaction of organic nitriles with 1-bromo- and 1-hydroxyadamantanes catalyzed by manganese compounds and complexes

Manganese compounds and complexes [MnCl2, MnBr2, Mn(OAc)2, Mn(acac)2, Mn(acac)3, Mn 2(CO)10] catalyze Ritter reaction of organic nitriles with 1-bromo- and 1-hydroxyadamantanes. The reaction proceeds in water environment in the absence of acids at 100-130°C over 3-5 h and affords N-(adamantan-1-yl)amides in 75-100% yields.

Synthesis and identification of small molecules that potently induce apoptosis in melanoma cells through G1 cell cycle arrest

Late-stage malignant melanoma is a cancer that is refractory to current chemotherapeutic treatments. The average survival time for patients with such a diagnosis is 6 months. In general, the vast majority of anticancer drugs operate through induction of cell cycle arrest and cell death in either the DNA synthesis (S) or mitosis (M) phase of the cell cycle. Unfortunately, the same mechanisms that melanocytes possess to protect cells from DNA damage often confer resistance to drugs that derive their toxicity from S or M phase arrest. Described herein is the synthesis of a combinatorial library of potential proapoptotic agents and the subsequent identification of a class of small molecules (triphenylmethylamides, TPMAs) that arrest the growth of melanoma cells in the G1 phase of the cell cycle. Several of these TPMAs are quite potent inducers of apoptotic death in melanoma cell lines (IC50 ～ 0.5 μM), and importantly, some TPMAs are comparatively nontoxic to normal cells isolated from the bone marrow of healthy donors. Furthermore, the TPMAs were found to dramatically reduce the level of active nuclear factor κ-B (NFκB) in the cell; NFκB is known to be constitutively active in melanoma, and this activity is critical for the proliferation of melanoma cells and their evasion of apoptosis. Compounds that reduce the level of NFκB and arrest cells in the G1 phase of the cell cycle can provide insights into the biology of melanoma and may be effective antimelanoma agents.

COMPOUNDS AND METHODS FOR TREATMENT OF CANCER AND MODULATION OF PROGRAMMED CELL DEATH FOR MELANOMA AND OTHER CANCER CELLS

Compounds and related methods for synthesis, and the use of compounds and combination therapies for the treatment of cancer and modulation of apoptosis in cells are disclosed. The generation of synthetic combinatorial libraries and the evaluation of library member compounds regarding induction of apoptosis selectively in cancer cells are disclosed. Compounds, methods of making the compounds, and therapeutic methods with application against breast cancer cells, melanoma cancer cells, colon cancer cells, and other cancer cells are described.

Self-folding cavitands

A novel class of resorcinarene-based cavitands 2a-e that fold into a deep (8 x 10 ? dimensions) open-ended cavity by means of intramolecular hydrogen bonds has been synthesized. As follows from the FTIR and 1H NMR spectral data in apolar solvent, a seam of eight intramolecular hydrogen bonds is stitched along the upper rim of the structure 2a-e; the amide C=O···H-N interactions bridge adjacent rings-interannular binding-and are held in place by the seven-membered intraannular hydrogen bonds. The self- folding in 2a-e is reversibly controlled by solvent and temperature. Complexation of self-folding cavitands 2a-e with organic molecules such as (1-substituted) adamantanes, lactams, and cyclohexane derivatives was demonstrated by 1H NMR spectroscopy in CDCl3, benzene-d6 and p-xylene- d10; the binding energy -ΔG°values of 2-4 kcal mol-1 in p-xylene- d10 at 295 K were calculated. The exchange between complexed and free guest species is slow on the NMR time-scale, and it is proposed that hydrogen bonds are responsible for these unique features. Employing the pronounced upfield 1H NMR shifts of the complexed guest molecules, attempts were made to study the structure of the caviplexes 'from inside', and the orientation of the encapsulated adamantanes 12, 13, as well as noncovalent interactions of complexed ε-caprolactam 9b with the host walls were deduced. Even though the guest-exchange process in 2a-e is slow on the NMR time scale (k = 2 ± 1 s- 1), it is still faster than that observed for the completely closed hydrogen-bonded calixarene-based capsules or for covalently sealed hemicarceplexes. This places them in an unusual position in the scale of cavity-containing receptors and opens new perspectives to use 2a-e in catalysis and as 1H NMR supramolecular shift reagents.