Synthesis and in vivo biological activity of large-ringed calixarenes against Mycobacterium tuberculosis

Goodworth, Kerry J.; Hervé, Anne-Cécile; Stavropoulos, Evangelos; Hervé, Gwénaëlle; Casades, Isabel; Hill, Alison M.; Weingarten, Gordon G.; Tascon, Ricardo E.; Colston, M. Joseph; Hailes, Helen C.

doi:10.1016/j.tet.2010.11.034

Cited by 19 publications

(9 citation statements)

References 26 publications

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“…[16] In addition, a class of large-ringed calixarene analogues such as compound 106 was evaluated for their antimycobacterial activity. [55] The results demonstrated that the introduction of a cyanopropoxyl substituent increases antimycobacterial activity, while the introduction of an acetate substituent exhibited pro-TB (profound tuberculosis) effects. In contrast, the absence of p-phenylcalixarene and tert-butylcalixarene functionalities at the lower rim showed weak activity against M. tuberculosis H37Rv.…”

Section: Macrocyclic Compoundsmentioning

confidence: 96%

“…Among them, compound 95 characterized by 1H-benzo [2,3]benzofuro[4,5e] [1,3]oxazin-3(2H)-one, demonstrated high activity against M. tuberculosis H37Rv with a MIC value of 1.56 mg mL À1 . [55] Similarly, phenothiazine derivatives also showed in vitro antimycobacterial activity and inhibited the growth of M. tuberculosis H37Rv in a mouse model of acute infection. Compound 96, which contained a quaternary amine side chain linked to the nitrogen atom of the phenothiazine ring, displayed a MIC value of 3.4 mg mL À1 .…”

Section: Tetracyclic Compoundsmentioning

confidence: 97%

“…In contrast, the absence of p-phenylcalixarene and tert-butylcalixarene functionalities at the lower rim showed weak activity against M. tuberculosis H37Rv. [55]…”

Section: Macrocyclic Compoundsmentioning

confidence: 99%

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Recent Advances in the Research of Heterocyclic Compounds as Antitubercular Agents

Yan¹,

Ma²

2012

ChemMedChem

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Tuberculosis (TB) is a major health problem, with approximately one-third of the world's population infected with Mycobacterium tuberculosis, eight million people in the active disease state, and two million dying annually. Furthermore, the prevalence of TB/HIV co-infection, and the emergence of multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) have further aggravated the spread of this disease and thus mortality by it. There is an urgent need for novel antitubercular agents with improved properties, such as lower toxicity, shortened duration of therapy, rapid bactericidal action, and enhanced activity against MDR strains. Fortunately, a number of new potential antitubercular candidate drugs with heterocyclic rings, which are most likely to be effective against resistant strains, have entered clinical trials in recent years. This review highlights recent advances in the research of novel heterocyclic compounds, with particular focus on their antimycobacterial activity, mechanisms of action, toxicity, and structure-activity relationships (SARs).

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Section: Macrocyclic Compoundsmentioning

confidence: 96%

Section: Tetracyclic Compoundsmentioning

confidence: 97%

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Recent Advances in the Research of Heterocyclic Compounds as Antitubercular Agents

Yan¹,

Ma²

2012

ChemMedChem

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“…One such macrocyclic scaffold is calixarene. [11][12][13][14][15][16][17][18][19][20] Calix [n]arenes are one of the most exciting synthetic macrocycles known to date besides cyclodextrins, crown ethers, cryptands, and cucurbiturils having diverse applications in supramolecular chemistry. [21][22][23] They can easily be synthesized by the reaction of p-tert-butyl phenol and formaldehyde in the presence of a base.…”

Section: S P E C I a L I S S U E A R T I C L E Functionalized Calix[4mentioning

confidence: 99%

Functionalized calix[4]arenes as potential therapeutic agents

2017

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Calixarenes, composed of phenolic units linked by methylene bridges at the 2,6-positions, represent a versatile class of macrocyclic compounds in supramolecular chemistry that can host small molecules or ions in their well-defined hydrophobic cavities. In recent years, it has been recognized that this class of compounds has the potential to serve as platform for the design of biological active compounds. Therefore, the calixarenes functionalized with different pharmacophoric groups have been synthesized as target structure by many researchers and were further evaluated for their biological activities. Owing to their promising biological activities such as antiviral, antibacterial, antifungal, and anticancer, the functionalized calixarenes are recently receiving increased attention from pharmaceutical/medicinal chemistry community. In this review, we summarize and discuss the synthetic approaches and the biological potential of functionalized calixarenes, mainly focusing on the selected recent studies for a comprehensive and target-oriented information, which could help in the design and synthesis of new therapeutic agents leading to the development of clinically viable drugs based on these macrocyles. K E Y W O R D Sbiological activity, calixarenes, cone conformation, functionalization, upper/lower rim/annulus

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“…[1][2][3][4] Among various applications of calixarenes one should point out that they may serve as fluorescent sensors 5,6 and form complexes with metal ions, [7][8][9] allowing detection of metals; also they find applications in chromatography, 2,10 and some calixarene derivatives show biological activity. 11 Calixarenes can be functionalized at their wide [12][13][14] and narrow [15][16][17] rims, and the present review deals with functionalization of the meso positions of calixarenes. It is noteworthy that functionalization of the meso positions of calixarenes has not been as intensively studied as that of the wide and narrow rims.…”

Section: Introductionmentioning

confidence: 99%