Synthesis and antifungal activity of 3-(1,3,4-oxadiazol-5-yl)-indoles and 3-(1,3,4-oxadiazol-5-yl)methyl-indoles

Zhang, Ming-Zhi; Mulholland, Nick; Beattie, David T.; Irwin, Dianne; Gu, Yu‐Cheng; Chen, Qiong; Yang, Guang‐Fu; Clough, James R.

doi:10.1016/j.ejmech.2013.01.038

Cited by 135 publications

(64 citation statements)

References 30 publications

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“…Discussion 1,3,4-Oxadiazole nucleus represents the key pharmacophore of several biologically-active agents. Thus, several 1,3,4-oxadiazole derivatives were reported to possess marked chemotherapeutic activities as antibacterial, antifungal, anti-HIV and anticancer activities [1][2][3][4]. In addition, potent anti-inflammatory activity was observed for several 1,3,4-oxadiazole derivatives [4,5].…”

Section: Methodsmentioning

confidence: 99%

Crystal structure of 3-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-5-(thiophen- 2-yl)-2,3-dihydro-1,3,4-oxadiazole-2-thione, C17H17FN4OS2

Al-Omary

AlRabiah

Ghabbour

et al. 2015

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of material 1-(4-Fluorophenyl)piperazine (360 mg, 2 mmol) and a formaldehyde solution (0.5 mL, 37%) were added to a solution of 5-(thiophen-2-yl)-1,3,4-oxadiazole-2-thiol (369 mg, 2 mmol) in ethanol (8 mL). The mixture was stirred at room temperature for two hours and allowed to stand overnight. Experimental detailsThere is a 2:1 disorder in the thiophen-2-yl moiety (cf. fig.). All hydrogen atoms are attached to the parent atoms using riding models (AFIX 23 and AFIX 43 [10]). The measured crystal was a non-merohedral twin. Discussion 1,3,4-Oxadiazole nucleus represents the key pharmacophore of several biologically-active agents. Thus, several 1,3,4-oxadiazole derivatives were reported to possess marked chemotherapeutic activities as antibacterial, antifungal, anti-HIV and anticancer activities [1][2][3][4]. In addition, potent anti-inflammatory activity was observed for several 1,3,4-oxadiazole derivatives [4,5]. The title compound was synthesized among a series of 2-thienyl-1,3,4-oxadiazoles and related derivatives as potential antimicrobial agents [6]. In continuation to our previous studies on the molecular structures of 3-aminomethyl-5-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thiones [7-9], we report herein the crystal structure of the title compound. In the title compound, C 17 H 17 FN 4 OS 2 , the piperazine ring adopts a chair conformation. The oxadiazole ring forms dihedral angles of 4.03(4)°, 68.87(8)°a nd 87.68(9)°with the thiophene, piperazine and benzene rings, respectively, resulting in an approximate V-shaped conformation for the molecule. The molecule is twisted about the C7, with a N1-N2-C7-N3 torsion angle of 69.4(4)°. The molecules packing in the crystal structure is stabilized by two intermolecular hydrogen bonds, of which F1 and S2 work as hydrogen bond acceptors and C1 and C7 work as hydrogen bond donors. The distance of the interactions between C1-H1A×××F1 is 2.54(1) Å and C7-H7B×××S2 is 2.75(1) Å and the angles are 139°and 152°, respectively.

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Section: Methodsmentioning

confidence: 99%

Crystal structure of 3-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-5-(thiophen- 2-yl)-2,3-dihydro-1,3,4-oxadiazole-2-thione, C17H17FN4OS2

Al-Omary

AlRabiah

Ghabbour

et al. 2015

Zeitschrift Für Kristallographie - New Crystal Structures

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“…It is a plant hormone of the auxin class [22] Tryptophan An essential amino acid that participates in many essential biological processes [23] Serotonin or 5-hydroxyl tryptamine It is a compound biochemically derived from tryptophan. It is a neurotransmitter that can be found in all bilateral animals [24] Melatonin…”

Section: Compoundmentioning

confidence: 99%

Electrosprayed poly(butylene succinate) microspheres loaded with indole derivatives: A system with anticancer activity

Murase

Aymat

Calvet

et al. 2015

European Polymer Journal

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Electrospraying of poly(butylene succinate) and its mixture with different indole derivatives was successfully performed using chloroform as solvent and relatively low flow rates and concentrations. Morphology of particles (size, diameter distribution and surface texture) and encapsulation efficiency were dependent on the loaded drug and specifically on the type of substituent (methyl or phenyl) and its position in the indole core. In general, particles showed a raisin-like morphology caused by the shell collapsing of the resulting structurally weak microspheres. Accumulation of electrosprayed particles gave rise to consistent mats and they had a more hydrophobic surface than that determined for smooth films. The increase of hydrophobicity was mainly dependent on the porosity and the hydrophobic nature of the incorporated drugs. Indole derivatives were hardly delivered in a standard phosphate saline buffer due to their scarce solubility in aqueous media but the addition of ethanol caused a drastic change in the release behavior. This was generally characterized by a fast burst effect and followed by the establishment of an equilibrium condition that was dependent on the indole derivative. However, a clearly different behavior was found when the indole was unable to form hydrogen bonds (e.g. 1-methylindole) since in this case a slow and sustained release was characteristic. Microspheres loaded with indole derivatives showed a high antiproliferative activity that was dependent on encapsulation efficiency and the type of loaded drug. The best results were specifically attained for the indole with an aromatic substituent. Interestingly significant differences were found between cancer and immortalized cells, a feature that points out the potential use of such systems for cancer prevention and treatment. (C) 2015 Elsevier Ltd. All rights reserved.Postprint (author's final draft

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“…1 H NMR spectra were recorded on a VARIAN Mercury-Plus 600 spectrometer in CDCl 3 or DMSO-d 6 with TMS as the internal reference. 13 C NMR spectra were recorded in CDCl 3 or DMSO-d 6 …”

Section: Chemicals and Instrumentsmentioning

confidence: 99%

“…In our previous work, we have described various structural modifications to streptochlorin, including the introduction of different substituents at the nitrogen of the indole ring, replacement of Cl on the oxazole ring by Br or H [12], and replacement of the oxazole ring by oxadiazole [13]. In a continuation of our studies aimed at the discovery of novel analogues with improved antifungal activity, we now describe work which has focused on the optimization of the substituents on the indole ring of streptochlorin (shown in Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antifungal activity of novel streptochlorin analogues

Zhang

Chen

Xie

et al. 2015

European Journal of Medicinal Chemistry

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Synthesis and antifungal activity of 3-(1,3,4-oxadiazol-5-yl)-indoles and 3-(1,3,4-oxadiazol-5-yl)methyl-indoles

Cited by 135 publications

References 30 publications

Crystal structure of 3-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-5-(thiophen- 2-yl)-2,3-dihydro-1,3,4-oxadiazole-2-thione, C17H17FN4OS2

Crystal structure of 3-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-5-(thiophen- 2-yl)-2,3-dihydro-1,3,4-oxadiazole-2-thione, C17H17FN4OS2

Electrosprayed poly(butylene succinate) microspheres loaded with indole derivatives: A system with anticancer activity

Synthesis and antifungal activity of novel streptochlorin analogues

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