In vitro and in vivo Candicidal Activities of 2-(<i>p</i>-n-Hexylphenylamino)-1,3-Thiazoline

Abstract

The 2-amino-1,3-thiazoline, 2-(p-n-hexylphenylamino)-1,3-thiazoline (MDL 20,245) killed 105 logarithmic or stationary phase Candida albicans/ml in less than 1 h. Miconazole killed logarithmic phase cells at that rate, but miconazole, clotrimazole or econazole killed stationary phase cells at a slower rate of 10²–10⁴ cells/ml in 24 h. MDL 20,245 induced efflux of K⁺ and L[U-¹⁴C] lysine from C. albicans, indicating that the candicidal mechanism is to exert direct damage upon the cytoplasmic membrane. The activity of MDL 20,245 in vitro was antagonized by fatty acids, triglycerides and phospholipids. Topical application of MDL 20,245 ointment (10% w/v) twice per day for 4 days to rats suppressed C. albicans-induced vaginitis 100%. Single-dose regimens of MDL 20,245, miconazole or clotrimazole correlated with 97, 90 and 73% suppression, respectively. These data suggest that MDL 20,245 may be effective in the treatment of C. albicans-induced vaginitis in humans.

Evaluation of the metal binding properties of the histidine-rich antimicrobial peptides histatin 3 and 5 by electrospray ionization mass spectrometry

“…Histatins are a family of histidine‐rich human salivary peptides secreted by the parotid and submandibular glands 1. These peptides possess several diverse biological properties.…”

Straightforward Approach Toward Dihydrothiazoles via Intramolecular Bromocyclization

“…[4] In this protocol, different nucleophiles such as carbon, nitrogen, and oxygen are applicable and make this method more attractive for the construction of halogenated natural products. [5] 2-Aminothiazolines have been regarded as privileged scaffolds possessing a wide range of biological activities, including neuronal acetylcholine receptor modulators, [6] antimicotic agents, [7] antimicrobial agents, [8] and nitric oxide synthase inhibitors. [9] Thiazolines were also investigated as an alternative substituent to find new riluzol-like drugs.…”

Computer prediction and synthesis of new azoles based on N-benzoyl-N'-(9,10-dioxo-9,10-dihydroanthracen-1-yl)thioureas

“…2-Iminothiazolines are characterized by a wide range of biological properties [9][10][11][12]. The thiazolidene-2-imine [13] or thiazol-2-imine [14] or 2iminothiazoline [15][16][17][18] ring system, as it has been named by different groups, is present in several drug candidates possessing interesting biological activities such as muscarinomimetic, antimycotic, hypolipemic, antidiabetic, thrombopoietinagonism, cell adhesion antagonists, platelet GPIIb/IIIa receptorantagonists, anti-inflammatory, analgesic and kinase (CDK1, CDK5 and GSK3) inhibition, schistosomicides, cadiotonicsand trichomonides [19][20][21][22][23]. Thiazoline derivatives have been found to exhibit promising applications in agriculture, such as acaricides, insecticides, and plant growth regulators [24,25].…”