108157-23-9

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 1003-03-8 Cyclopentamine 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 435345-22-5 N-[(4-methoxyphenyl)methyl]cyclopentanamine hydrochloride 
• 713-82-6 1‐(cyclopentylmethyl)‐4‐methoxybenzene 

Relevant academic research and scientific papers

Polyoxometalate-Driven Ease Conversion of Valuable Furfural to trans- N, N-4,5-Diaminocyclopenten-2-ones

We investigated the catalytic efficacy of silicotungstic acid (H4SiW12O40) polyoxometalate (POM) toward the reaction between furfural and amines that selectively yields trans-N,N-4,5-substituted-diaminocyclopenten-2-ones (trans-DACPs). H4SiW12O40 facilita

CD73 INHIBITORS

Disclosed are compounds that are inhibitors of CD73 and are useful in treating CD73-associated diseases or conditions, and compositions containing the compounds.

Design, Synthesis, and Structure-Activity Relationship of Economical Triazole Sulfonamide Aryl Derivatives with High Fungicidal Activity

Plant fungal diseases have caused great decreases in crop quality and yield. As one of the considerable agricultural diseases, cucumber downy mildew (CDM) caused by pseudoperonospora cubensis seriously influences the production of cucumber. Amisulbrom is a commercial agricultural fungicide developed by Nissan Chemical, Ltd., for the control of oomycetes diseases that is highly effective against CDM. However, the synthesis of amisulbrom has a high cost because of the introduction of the bromoindole ring. In addition, the continuous use of amisulbrom might increase the risk of resistance development. Hence, there is an imperative to develop active fungicides with new scaffolds but low cost against CDM. In this study, a series of 1,2,4-triazole-1,3-disulfonamide derivatives were designed, synthesized, and screened. Compound 1j showed a comparable fungicidal activity with amisulbrom, but it was low cost and ecofriendly. It has the potential to be developed as a new fungicide candidate against CDM. Further investigations of structure-activity relationship exhibited the structural requirements of 1,2,4-triazole-1,3-disulfonamide and appropriate modification in N-alkyl benzylamine groups with high fungicidal activity. This research will provide powerful guidance for the design of highly active lead compounds with a novel skeleton and low cost.

Electrochemical Approach for Direct C-H Phosphonylation of Unprotected Secondary Amine

Direct α-phosphonylation of an unprotected secondary amine in a single step is of practical importance to amino phophophates. However, this protocol is limited due to the high redox barrier of unprotected amine. In this paper, we report C-H phosphonylation of an unprotected secondary amine via an electrochemical approach in the presence of catalytic carboxylate salt. This metal-free and exogenous oxidant-free method furnishes diverse target molecules with satisfactory yield under mild reaction conditions. Successful application of the protocol in a gram-scale experiment demonstrates the potential utility for further functionalization.

Inhibition of the Cysteine Protease Human Cathepsin L by Triazine Nitriles: Amide???Heteroarene π-Stacking Interactions and Chalcogen Bonding in the S3 Pocket

We report an extensive “heteroarene scan” of triazine nitrile ligands of the cysteine protease human cathepsin L (hCatL) to investigate π-stacking on the peptide amide bond Gly67–Gly68 at the entrance of the S3 pocket. This heteroarene???peptide bond stacking was supported by a co-crystal structure of an imidazopyridine ligand with hCatL. Inhibitory constants (Ki) are strongly influenced by the diverse nature of the heterocycles and specific interactions with the local environment of the S3 pocket. Binding affinities vary by three orders of magnitude. All heteroaromatic ligands feature enhanced binding by comparison with hydrocarbon analogues. Predicted energetic contributions from the orientation of the local dipole moments of heteroarene and peptide bond could not be confirmed. Binding of benzothienyl (Ki=4 nm) and benzothiazolyl (Ki=17 nm) ligands was enhanced by intermolecular C?S???O=C interactions (chalcogen bonding) with the backbone C=O of Asn66 in the S3 pocket. The ligands were also tested for the related enzyme rhodesain.

Rapid and efficient access to secondary arylmethylamines

Ammoniomethyl trifluoroborates are very powerful reagents that can be used to access biologically relevant aryl- and heteroaryl-methylamine motifs via Suzuki-Miyaura cross-couplings. Until now, this method was limited to the production of tertiary and primary amines. The synthesis of a large array of secondary ammoniomethyltrifluoroborates has been achieved through a one step nucleophilic substitution reaction on the potassium bromomethyltrifluoroborate. Smooth cross-coupling conditions have been designed, based on the use of an aminobiphenyl palladium precatalyst, to couple these trifluoroborates efficiently with aryl bromides. This strategy offers a new way to access biologically relevant motifs and allows, with the previously developed methods, access to all three classes of aminomethylarenes. Secondary ammoniomethyltrifluoroborates can be easily synthesized by nucleophilic substitution on potassium bromomethyltrifluoroborate. These reagents have then been used in Suzuki-Miyaura cross-couplings with aryl bromides, offering an effective access to the aminomethylarene structural motif. This new method provides an interesting alternative to the reductive amination procedure (see scheme). Copyright