Synthesis of 5‐substituted 2‐(2,4‐dihydroxyphenyl)‐1,3,4‐thiadiazoles

Matysiak, Joanna

doi:10.1002/jhet.5570430108

Cited by 12 publications

(5 citation statements)

References 24 publications

(21 reference statements)

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“…The 5-substituted-(1,3,4-thiadiazol-2-yl)benzene-1,3-diol derivatives ( I–V ) were synthesized by the reaction of commercially available hydrazides with sulphinylobis [(2,4-dihydroxyphenyl)methanethion (STB) in methanol at reflux (2.5–3 h) as described elsewhere. ,− Molecular formulas and the simplified reaction scheme are presented in Scheme . STB was obtained from the combination of 2,4-dihydroxybenzenecarbodithioic acid and SOCl 2 in diethyl ether to give the 1,3,4-thiadiazole ring.…”

Section: Methodsmentioning

confidence: 99%

Interplay of Inter- and Intramolecular Interactions in Crystal Structures of 1,3,4-Thiadiazole Resorcinol Derivatives

Hoser

Kamiński

Skrzypek

et al. 2018

Crystal Growth & Design

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Five new 1,3,4-thiadiazole derivatives have been synthesized, and their crystal structures have been determined by single crystal X-ray diffraction. The influence of substituents on molecular geometry and the three-dimensional arrangement of molecules has been studied by means of single crystal X-ray diffraction, fluorescence, UV–vis spectroscopy, and computational methods. The 1,3,4-thiadiazole derivatives occur in two possible conformations in their crystal lattices: with the ortho-hydroxyl group of the resorcyl ring pointing toward the S or the N atoms from the 1,3,4-thiadiazole ring. In the latter conformation, an intramolecular hydrogen bond is created which is energetically favorable for the isolated molecule as confirmed by theoretical calculations. However, for the molecules in the crystal structures in the former conformation, some intermolecular interactions between the neighboring molecules are strong enough to overrule the intramolecular OH···N hydrogen bond. In the case of one of the 1,3,4-thiadiazole derivatives, a significant disorder was observed, and both conformations were present in one crystal lattice in the ratio 80% to 20% for the two conformers, respectively. On the basis of resonance light scattering results, we explain why crystals of 1,3,4-thiadiazole derivatives can be grown from DMSO and are difficult to be grown from methanol solution.

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Section: Methodsmentioning

confidence: 99%

Interplay of Inter- and Intramolecular Interactions in Crystal Structures of 1,3,4-Thiadiazole Resorcinol Derivatives

Hoser

Kamiński

Skrzypek

et al. 2018

Crystal Growth & Design

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“…The 1,3,4-thiadiazole derivatives exemplified in this paper were prepared according to the route described in Figure 1 [27,28]. Treatment of sulfinyl-bis ((2,4-dihydroxyphenyl)methanethione) (STB) with appropriate 4-substituted-3-thiosemicarbazides in methanol afforded N-substituted 4-(5-amino-1,3,4thiadiazol-2-yl)benzene-1,3-diols (1-5).…”

Section: Chemistrymentioning

confidence: 99%

“…The removed product was crystallized from methanol (2 × 30 mL). 1 (19), 136 (7), 135 (22), 108 (6), 107 (5), 106 (2), 103 (3), 102 (26), 97 (8), 88 (28), 87 (13), 80 (4), 79 (3), 73 (4), 71 (4), 69 (9), 65 (4), 63 (4), 57 (5), 56 (5), 53 (5), 52 (8), 51 (7), 44 (14), 43 (17), 42 (17), 39 (8), 38 (5), 36 (14). Heptyl-1,3,4-thiadiazol-2-yl)benzene-1,3-diol (6).…”

Section: -(5-(naphthalen-1-ylamino)-134-thiadiazol-2yl)benzene-13unclassified

Synthesis and antifungal activity of novel 5‐substituted 4‐(1,3,4‐thiadiazol‐2‐yl)benzene‐1,3‐diols

Matysiak¹,

Skrzypek²,

Niewiadomy³

2010

Heteroatom Chemistry

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“…The synthesis of compounds belonging to the group of 5-substituted 4-(1,3,4-thiadiazol-2-yl) benzene-1,3-diols has already been described in different publications [13–16]. The antifungal activity of these compounds was previously referred to as the average values of MICs against several species of Candida only, for which they range from a few dozen to several hundred μg/ml [14], and in relation to phytopathogenic fungi [16].…”

Section: Introductionmentioning

confidence: 99%

Antifungal effects of a 1,3,4-thiadiazole derivative determined by cytochemical and vibrational spectroscopic studies

et al. 2019

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Compounds belonging to the group of 5-substituted 4-(1,3,4-thiadiazol-2-yl) benzene-1,3-diols exhibit a broad spectrum of biological activity, including antibacterial, antifungal, and anticancer properties. The mechanism of the antifungal activity of compounds from this group has not been described to date. Among the large group of 5-substituted 4-(1,3,4-thiadiazol-2-yl) benzene-1,3-diol derivatives, the compound 4-(5-methyl-1,3,4-thiadiazole-2-yl) benzene-1,3-diol, abbreviated as C1, was revealed to be one of the most active agents against pathogenic fungi, simultaneously with the lowest toxicity to human cells. The C1 compound is a potent antifungal agent against different Candida species, including isolates resistant to azoles, and molds, with MIC100 values ranging from 8 to 96 μg/ml. The antifungal activity of the C1 compound involves disruption of the cell wall biogenesis, as evidenced by the inability of cells treated with C1 to maintain their characteristic cell shape, increase in size, form giant cells and flocculate. C1-treated cells were also unable to withstand internal turgor pressure causing protoplast material to leak out, exhibited reduced osmotic resistance and formed buds that were not covered with chitin. Disturbances in the chitin septum in the neck region of budding cells was observed, as well as an uneven distribution of chitin and β(1→3) glucan, and increased sensitivity to substances interacting with wall polymerization. The ATR-FTIR spectral shifts in cell walls extracted from C. albicans cells treated with the C1 compound suggested weakened interactions between the molecules of β(1→3) glucans and β(1→6) glucans, which may be the cause of impaired cell wall integrity. Significant spectral changes in the C1-treated cells were also observed in bands characteristic for chitin. The C1 compound did not affect the ergosterol content in Candida cells. Given the low cytotoxicity of the C1 compound to normal human dermal fibroblasts (NHDF), it is possible to use this compound as a therapeutic agent in the treatment of surface and gastrointestinal tract mycoses.

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Synthesis of 5‐substituted 2‐(2,4‐dihydroxyphenyl)‐1,3,4‐thiadiazoles

Cited by 12 publications

References 24 publications

Interplay of Inter- and Intramolecular Interactions in Crystal Structures of 1,3,4-Thiadiazole Resorcinol Derivatives

Interplay of Inter- and Intramolecular Interactions in Crystal Structures of 1,3,4-Thiadiazole Resorcinol Derivatives

Synthesis and antifungal activity of novel 5‐substituted 4‐(1,3,4‐thiadiazol‐2‐yl)benzene‐1,3‐diols

Antifungal effects of a 1,3,4-thiadiazole derivative determined by cytochemical and vibrational spectroscopic studies

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