Synthesis and antibacterial evaluation of macrocyclic diarylheptanoid derivatives

Abstract

Bacterial infections, caused by M. tuberculosis and other problematic bacterial pathogens, continue to pose a significant threat to global public health. As such, new chemotype antibacterial agents are desperately needed to fuel and strengthen the antibacterial drug discovery and development pipeline. As part of our antibacterial research program to develop natural product-inspired new antibacterial agents, here we report synthesis, antibacterial evaluation, and structure-activity relationship studies of an extended chemical library of macrocyclic diarylheptanoids with diverse amine, amide, urea, and sulfonamide functionalities. Results of this study have produced macrocyclic geranylamine and 4-fluorophenethylamine substituted derivatives, exhibiting moderate to good activity against M. tuberculosis and selected Gram-positive bacterial pathogens.

Coordination Engineering of Single‐Atom Catalysts for the Oxygen Reduction Reaction: A Review

“…synthesized Cu–N 2 by leaching Cu–N/C in different acidic solutions, where Cu–N 2 and Cu–N 4 were obtained by leaching in H 2 SO 4 and HNO 3 , respectively. [ 51 ] This might be caused by different corrosive abilities between these acids. XANES shows that the valence state of Cu in Cu–N/C–H 2 SO 4 is between 0 and +1 by comparison with the reference spectra of Cu foil and Cu 2 O.…”

“…Another problem of ORR in energy conversion devices is the production of H 2 O 2 via the two‐electron pathway, which is harmful to energy efficiency and durability of the device. [ 48–50 ] Many methods have been developed to address this problem, [ 51–55 ] such as pore engineering, construction of heterostructures, and etc. Besides, the electrochemical H 2 O 2 synthesis via the two‐electron pathway has become a new research direction over recent years because of the great role of H 2 O 2 in environmental remediation [ 56–59 ] and as a promising clean fuel (for jet car and rockets, 60 wt% H 2 O 2 has an energy density of 3.0 MJ L −1 , higher than compressed H 2 gas at 35 MPa, 2.8 MJ L −1 ).…”

Selective Oxidation of Activated Alcohols by Supported Gold Nanoparticles under an Atmospheric Pressure of O2: Batch and Continuous‐Flow Studies

“…3‐(4‐(Benzyloxy)‐3‐methoxyphenyl)‐prop‐2‐enal (11 b) : 1 H NMR (200 MHz, CDCl 3 ): δ =9.58 (d, J= 6 Hz, 1 H), 7.38–7.19 (m, 6 H), 7.04–6.99 (m, 2 H), 6.83 (d, J= 8 Hz, 1 H), 6.58–6.47 (m, 1 H), 5.14 (s, 2 H), 3.85 ppm (s, 3 H); 13 C NMR (50 MHz, CDCl 3 ): δ =193.5, 152.7, 151.1, 149.9, 136.3, 128.6, 128.1, 127.3, 127.2, 126.8, 123.2, 113.4, 110.4, 70.8, 56.0 ppm; MS (EI, 70 eV): m / z =268.1 (6), 91.1 (100), 65.0 (9); HRMS calcd for C 17 H 16 O 3 : 268.1099; found: 268.1097 (Δ=0.7).…”

Recent Advancement of Ullmann Condensation Coupling Reaction in the Formation of Aryl-Oxygen (C-O) Bonding by Copper-Mediated Catalyst

“…Hao Lin's research group reported the structure-activity, route of synthesis, and antibacterial study of macrocyclic diarylheptanoids compound with the various amine, amide, urea, and sulfonamide functionalities in the extended pharmaceutical library. The outcome of their study produced macrocyclic geranylamine and 4-fluorophenethylamine substituted derivatives, which can be performed reasonable activity against M. tuberculosis and picked Gram-positive bacterial pathogens (Scheme 52) [129]. Bacterial contagion triggered by Mycobacterium tuberculosis (TB) and various problematic bacterial germ keep posing a vital threat to world public health.…”