89332-53-6

Upstream product

• 64-18-6 formic acid 
• 2038-57-5 3-Phenylpropan-1-amine 
• 75-87-6 chloral 
• 75822-14-9 N-nitroso-N-(3-phenylpropyl)glycine 
• 68-12-2 N,N-dimethyl-formamide 
• 104-53-0 3-phenyl-propionaldehyde 
• 77287-34-4 formamide 
• 50-00-0 formaldehyd 
• 124-38-9 carbon dioxide 
• 67-56-1 methanol 
• 645-59-0 dihydrocinnamonitrile 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 23580-89-4 methyl-(3-phenyl-propyl)-amine 
• 870103-24-5 5-[[4-[3-[[(2R)-2-(3-chloro-phenyl)-2-hydroxyethyl]amino]propyl]phenyl]sulfonyl]-2-hydroxybenzamide hydrochloride 
• 870103-71-2 2-hydroxy-5-[[4-[3-[[(2R)-2-hydroxy-2-phenylethyl]amino]propyl]-phenyl]sulfonyl]benzamide hydrochloride 

Relevant academic research and scientific papers

Design, synthesis and in vitro evaluation of novel SARS-CoV-2 3CLpro covalent inhibitors

Severe diseases such as the ongoing COVID-19 pandemic, as well as the previous SARS and MERS outbreaks, are the result of coronavirus infections and have demonstrated the urgent need for antiviral drugs to combat these deadly viruses. Due to its essential role in viral replication and function, 3CLpro (main coronaviruses cysteine-protease) has been identified as a promising target for the development of antiviral drugs. Previously reported SARS-CoV 3CLpro non-covalent inhibitors were used as a starting point for the development of covalent inhibitors of SARS-CoV-2 3CLpro. We report herein our efforts in the design and synthesis of submicromolar covalent inhibitors when the enzymatic activity of the viral protease was used as a screening platform.

PHYTOSPHINGOSINE DERIVATIVES AS ADJUVANTS IN IMMUNE STIMULATION

The invention relates to phytosphingosine derivatives, suitable as adjuvants in immune stimulation. The invention further relates to pharmaceutical compositions comprising such compounds and the medical use of said compounds and/or compositions in therapeutic or prophylactic methods of immune stimulation in a subject, and for use in the treatment of a disease, for which stimulation of an immune response in a subject produces a therapeutic benefit. The invention further relates to the phytosphingosine derivative as described herein for use as an adjuvant in a method of vaccinating a subject. The invention further relates to the phytosphingosine derivative as described herein for use in stimulating antibody production, stimulating an immune response against infection, stimulating an immune response against a cancer, or preventing and/or treating septic shock. The invention further relates to a method for the manufacture of said derivatives comprising an Ugi-4-component reaction (Ugi-4CR).

A substituent- And temperature-controllable NHC-derived zwitterionic catalyst enables CO2upgrading for high-efficiency construction of formamides and benzimidazoles

Chemocatalytic upgrading of the greenhouse gas CO2 to valuable chemicals and biofuels has attracted broad attention in recent years. Among the reported approaches, N-formylation of CO2 with an amine is of great significance due to its versatility in the construction of N-containing linear and cyclic skeletons. Herein, a stable N-heterocyclic carbene-carboxyl adduct (NHC-CO2) was facilely prepared and could be used as a recyclable zwitterionic catalyst for efficient CO2 reductive upgrading via either N-formylation or further coupling with cyclization under mild conditions (25 °C, 1 atm CO2) using hydrosilane as a hydrogen source. More than 30 different alkyl and aromatic amines could be transformed into the corresponding formamides or benzimidazoles with remarkable yields (74%-98%). The electronic effect of the introduced substituent on NHC-CO2 was found to evidently affect the thermostability and nucleophilicity of the zwitterionic catalyst, which is directly correlated with its catalytic activity. Moreover, NHC-CO2 could supply CO2 by in situ decarboxylation at a specific temperature that is dependent on the introduced substituent type. Experimental and computational studies showed that the carboxyl species on NHC-CO2 was not only a nucleophilic center, but also a C1 source which rapidly captures or substitutes ambient CO2 during hydrosilylation. In addition, a simple and green conceptual process was designed for the product purification and catalyst recycling, with a good feasibility for small-scale production.

Expedited Approach toward the Rational Design of Noncovalent SARS-CoV-2 Main Protease Inhibitors

The main protease (Mpro) of SARS-CoV-2 is a validated antiviral drug target. Several Mpro inhibitors have been reported with potent enzymatic inhibition and cellular antiviral activity, including GC376, boceprevir, calpain inhibitors II, and XII, with eac

Copper-Catalyzed Formylation of Amines by using Methanol as the C1 Source

Cu/TEMPO catalyst systems are known for the selective transformation of alcohols to aldehydes, as well as for the simultaneous coupling of alcohols and amines to imines under oxidative conditions. In this study, such a Cu/TEMPO catalyst system is found to catalyze the N-formylation of a variety of amines by initial oxidative activation of methanol as the carbonyl source via formaldehyde and formation of N,O-hemiacetals and oxidation of the latter under very mild conditions. A vast range of amines, including aromatic and aliphatic, primary and secondary, and linear and cyclic amines are formylated under these conditions with good to excellent yields. Moreover, paraformaldehyde can be used instead of methanol for the N-formylation.

Tetracoordinate borates as catalysts for reductive formylation of amines with carbon dioxide

We report sodium trihydroxyaryl borates as the first robust tetracoordinate organoboron catalysts for reductive functionalization of CO2. These catalysts, easily synthesized from condensing boronic acids with metal hydroxides, activate main group element-hydrogen (E-H) bonds efficiently. In contrast to BX3 type boranes, boronic acids and metal-BAr4 salts, under transition metal-free conditions, sodium trihydroxyaryl borates exhibit high reactivity of reductive N-formylation toward a variety of amines (106 examples), including those with functional groups such as ester, olefin, hydroxyl, cyano, nitro, halogen, MeS-, ether groups, etc. The over-performance to catalyze formylation of challenging pyridyl amines affords a promising alternative method to the use of traditional formylation reagents. Mechanistic investigation supports electrostatic interactions as the key for Si/B-H activation, enabling alkali metal borates as versatile catalysts for hydroborylation, hydrosilylation, and reductive formylation/methylation of CO2.

Catalyst-Free Transamidation of Aromatic Amines with Formamide Derivatives and Tertiary Amides with Aliphatic Amines

A simple catalyst- and promoter-free protocol has been developed for the transamidation of weakly nucleophilic aromatic amines with formamide derivatives and low-reactivity tertiary amides with aliphatic amines. This strategy is advantageous because no catalyst or promoters are needed, no additives are required, separation and purification is easy, and the reaction is scalable. Significantly, this strategy was further applied to synthesize several pharmaceutical molecules on a gram scale, and excellent yields were achieved.

Method for preparing formamide derivative by using catalyst-free transamination reaction

The invention discloses a method for synthesizing a formamide derivative by using a low-reactive catalyst-free and solvent-free tertiary amide and aliphatic amine transamination reaction, wherein thehigh-yield formamide derivative is obtained by directly using N,N-dimethylformamide (DMF) as a formyl source. According to the present invention, the method has advantages of inexpensive and easily available raw materials, inexpensive and easily available acylating reagent, high reaction yield, one-step reaction, low cost, high reaction selectivity, simple operation and the like, and can overcomethe defects of high toxicity of the reaction reagent, requirement of different types of catalysts, high cost, more reaction steps, more by-products and the like in the prior art.

Mn(II)-Catalyzed N -Acylation of Amines

A practical protocol has been developed here for the Mn(II)-catalyzed N -acylation of amines with high yields using N, N -dimethylformamide and other amides as the carbonyl source. The protocol is simple, does not require any acid, base, ligand, or other additives, and encompasses a broad substrate scope for primary, secondary, and heterocyclic amines.

TBSOTf-promoted versatile N-formylation using DMF at room temperature

Hydrazides and amines were N-formylated by DMF in the presence of tert-butyldimethylsilyl triflate (TBSOTf) at room temperature, in good to excellent yields.