208943-24-2

Upstream product

• 98-91-9 thiobenzoic acid 
• 54060-30-9 3-acetylenephenylamine 
• 65-85-0 benzoic acid 
• 455-32-3 benzoyl fluoride 
• 14235-81-5 4-Ethynylaniline 
• 98-88-4 benzoyl chloride 
• 591-50-4 iodobenzene 
• 67-66-3 chloroform 

Downstream Products

• 1428318-68-6 C₂₂H₁₇FN₄O 
• 1443138-63-3 C₂₂H₁₇IN₄O 

Relevant academic research and scientific papers

ANTIBACTERIAL AND ANTIFUNGAL PLEUROMUTILIN CONJUGATES

Compounds of formula (1) comprising a pleuromutilin backbone with a triazole based side-group at C22 are provided. The compounds can be used for treatment of bacterial infections and fungal infections. Importantly, infections caused by multidrug-resistant

PdCl2-catalyzed synthesis of a new class of isocoumarin derivatives containing aminosulfonyl / aminocarboxamide moiety: First identification of a isocoumarin based PDE4 inhibitor

While anti-inflammatory properties of isocoumarins are known their PDE4 inhibitory potential was not explored previously. In our effort the non-PDE4 inhibitor isocoumarins were transformed into the promising inhibitors via introducing an aminosulfonyl/aminocarboxamide moiety to the C-3 benzene ring attached to the isocoumarin framework. This new class of isocoumarins were synthesized via a PdCl2-catalyzed construction of the 4-allyl substituted 3-aryl isocoumarin ring starting from the appropriate 2-alkynyl benzamide derivative. Several compounds showed good inhibition of PDE4B in vitro and the SAR indicated superiority of aminosulfonamide moiety over aminocarboxamide in terms of PDE4B inhibition. Two compounds 3q and 3u with PDE4B IC50 = 0.43 ± 0.11 and 0.54 ± 0.19 μM and ≥ 2-fold selectivity over PDE4D emerged as initial hits. The participation of aminosulfonamide moiety in PDE4B inhibition and the reason for selectivity though moderate shown by 3q and 3u was revealed by the in silico docking studies. In view of potential usefulness of moderately selective PDE4B inhibitors the compound 3u (that showed PDE4 selectivity over other PDEs) was further evaluated in adjuvant induced arthritic rats. At an intraperitoneal dose of 30 mg/kg the compound showed a significant reduction in paw swelling (in a dose dependent manner), inflammation and pannus formation (in the knee joints) as well as pro-inflammatory gene expression/mRNA levels and increase in body weight. Moreover, besides its TNF-α inhibition and no significant toxicity in an MTT assay the compound did not show any adverse effects in a thorough toxicity studies e.g. teratogenicity, hepatotoxicity, cardiotoxicity and apoptosis in zebrafish. Thus, the isocoumarin 3u emerged as a new, safe and moderately selective PDE4B inhibitor could be useful for inflammatory diseases possibly including COVID-19.

Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages

The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.

Copper-Catalyzed Cross-Coupling of Secondary α-Haloamides with Terminal Alkynes: Access to Diverse 2,3-Allenamides

A copper-catalyzed C(sp)?C(sp3) cross-coupling of terminal alkynes with readily available secondary α-haloamides for the efficient synthesis of 2,3-allenamides is realized. The methodology is characterized by its wide substrate scope, which makes it an important complement to traditional methods for synthesizing allenes. A mechanism involving an alkynylcopper species is proposed. (Figure presented.).

Cu-Catalyzed Aminodifluoroalkylation of Alkynes and α-Bromodifluoroacetamides

The copper-catalyzed highly regioselective aminodifluoroalkylation of alkynes and α-bromodifluoroacetamides was realized for the first time. With this method, 3,3-difluoro-1H-pyrrol-2(3H)-ones were constructed in a single step from various alkynes and α-b

Sulfur–Fluoride Exchange (SuFEx)-Mediated Synthesis of Sterically Hindered and Electron-Deficient Secondary and Tertiary Amides via Acyl Fluoride Intermediates

Amide bond formation is one of the most executed reactions in chemistry and biology. This is largely due to the ubiquity of the amide functional group in biological molecules, natural products and pharmaceutically important drugs. We report here the development of “SuFExAmide”: a new sulfur–fluoride exchange (SuFEx) click chemistry based protocol for the efficient amidation of carboxylic acids via acyl fluoride intermediates. We have developed benzene-1,3-disulfonyl fluoride as a cost effective, powerful and versatile coupling agent, which delivers challenging secondary and tertiary amides in excellent yields from sterically hindered and electron-deficient amines. The straightforward method offers significant benefits over existing protocols in terms of substrate scope, efficiency and ease of operation and is demonstrated by the synthesis of 44 amides, including GNF6702, an antiprotozoal drug candidate. In the majority of cases, the amide products are obtained in high yield without the need for excess reagents or chromatographic purification.

A facile and efficient method for the synthesis of alkynone by carbonylative Sonogashira coupling using CHCl3 as the CO source

A facile and efficient method for the synthesis of alkynones by a Pd-catalyzed carbonylative Sonogashira coupling reaction starting from aryl iodide, terminal alkyne and chloroform (CHCl3) as the CO source is described. This procedure proves th

PYRROLO[2,3-D]PYRIMIDINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS KINASE INHIBITORS

The present invention relates to 6-amino-7-deaza-purine derivatives which modulate the activity of protein kinases and are therefore useful in treating diseases caused by dysregulated protein kinase activity, in particular RET family kinases. The present

Continuous flow synthesis of secondary amides by tandem azidation-amidation of anilines

The continuous flow synthesis of a variety of secondary amides by tandem azidation-amidation of anilines is described. This new procedure benefits from the improved safety feature of generating aromatic azides in flow, thus ensuring low concentrations of any potentially hazardous intermediates. The protocol was amenable to the production of multi-gram quantities of the amide product. Georg Thieme Verlag Stuttgart · New York.