Synthesis and investigation of antimicrobial properties of pyrrolidine appended calix[4]arene

Abstract

Background: Calixarenes are widely used macromolecules in supramolecular chemistry synthesized by simple phenol formaldehyde condensation reaction in the presence of base. This article describes the synthesis, antibacterial, and antifungal properties of calix[4]arene appended with pyrrolidine at the upper rim (CAP3). Methods: Antimicrobial activity of CAP3 was determined by Kirby-Bauer well agar diffusion method in Mueller-Hinton agar (MHA) medium of growth against Escherichia coli (ATCC 8739), Staphylococcus aureus (ATCC 10231) and Streptococcus viridans (ATCC 12392), Candida albicans (ATCC 32333), Aspergillus niger (ATCC 16404), and Aspergillus flavus (ATCC 90906). Structure-activity relationship was also used to evaluate the active site of CAP3.

Preparation andin vitrobioactivity evaluation of N-heterocyclic-linked dihomooxacalix[4]arene derivatives

“…Such synthetic dihomooxacalix [4]arene N-heterocyclic derivatives 4a-4n have not been reported before; their structures were conrmed from their 1 H NMR, 13 C NMR, and HRMS spectra. As expected, the 1 H NMR spectra of 4a exhibited three single signals at 8.86, 8.49, and 7.80 ppm for protons of the unreacted free phenolic hydroxyl groups.…”

“…Upon the completion of the reaction (TLC monitoring; typically, 4 h), water was added to the reaction mixture and then ltered, leaving a pale-yellow solid that was later puried by ash chromatography (silica gel/ dichloromethane/methanol) to yield the product in a quantitative yield. 7,13,19,29,-aminocarbonylmethoxyl)-2,3-dihomo-3oxacalix [4]arene (4a). White solid, yield 90.1%, mp 155.9-157.2 C; IR (KBr, cm À1 ) n 3333, 2961, 2868, 1690, 1603, 1487, 1362, 1209, 1074, 876; 1 H NMR (CDCl 3 , 400 MHz) d 9.31 (t, 1H, J ¼ 5.…”

“…White solid, yield 90.1%, mp 155.9-157.2 C; IR (KBr, cm À1 ) n 3333, 2961, 2868, 1690, 1603, 1487, 1362, 1209, 1074, 876; 1 H NMR (CDCl 3 , 400 MHz) d 9.31 (t, 1H, J ¼ 5. 6 Hz),8.86 (s,1H),8.53 (dd,2H,J ¼ 4.4,1.6 Hz),8.49 (s,1H),7.80 (s,1H),7.39 (d,2H,J ¼ 5.6 Hz),7.28 (t,2H,J ¼ 2.4 Hz),7.16 (d,1H,J ¼ 2.4 Hz),2H) 2, 151.7, 150.8, 150.1, 149.0, 148.5, 147.2, 146.8, 144.2, 143.0, 142.9, 132.1, 131.6, 128.2, 127.7, 127.3, 127.2, 127.1, 126.8, 126.4, 126.1, 125.8, 125.5, 124.5, 122.9, 122.2, 74.4, 71.7, 71.5, 42.4, 34.3, 34.0, 33.9, 33.8, 32.3, 31.5, 31.4, 31.1, 31 7,13,19,29,-(N-(2pyridin-3-ylmethyl)-aminocarbonylmethoxyl)-2,3-dihomo-3oxacalix [4]arene (4b). White solid, yield 82.9%, mp 154.1-156.9 C; IR (KBr, cm À1 ) n 3331, 2959, 2868, 1686, 1605, 1535, 1487, 1364, 1202, 1076, A mixture of carboxylic acid 3a or 3b (0.22 g or 0.25 g, 0.3 mmol) and oxalyl chloride (0.75 g, 5.9 mmol) was dissolved in dry dichloromethane (2 mL) and stirred at room temperature.…”

Structural Design, Synthesis, and Preliminary Biological Evaluation of Novel Dihomooxacalix[4]arene-Based Anti-tumor Agents

“…In this regard, calixarenes and their derivatives are currently being studied and used in a variety of medicinal applications beyond their traditional place in chemistry. They could be served as chemotherapy agent (Yousaf et al, 2015;Naseer et al, 2017;Zhou et al, 2017), including antibacterials (Soares et al, 2014;Muneer et al, 2017;Ali et al, 2018;Consoli et al, 2018), antivirals (Motornaya et al, 2006;Mourer et al, 2010), antimalarials (Shah et al, 2016), and anti-inflammatory (Granata et al, 2017) enzymatic inhibitors (Läppchen et al, 2015). Moreover, they especially can be used as anti-tumor drugs (Consoli et al, 2004;Hulíková et al, 2010;Neagu et al, 2010;Nasuhi Pur and Dilmaghani, 2014); which have gained considerable attention from us.…”

Structure investigation, spectral characterization, electronic properties, and antimicrobial and molecular docking studies of 3′‐(1‐benzyl‐5‐methyl‐1H‐1,2,3‐triazole‐4‐carbonyl)‐1′‐methyl‐4′‐phenyl‐2H‐spiro[acenaphthylene‐1,2′‐pyrrolidine]‐2‐one

“…Due to the numerous bioactive and medicinal features of pyrrolidines and associated heterocyclic compounds, the compound has received significant interest in the medical field because of widespread medical needs . The remarkable biological properties of these molecules are instigated by the heterocyclic center, which includes pyrrolidine‐2,4‐dione (natural tetrameric acids) …”