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Keywords = carbothioimidate

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14 pages, 1485 KiB  
Article
Synthesis, Antimicrobial, and Anti-Proliferative Activities of Novel 4-(Adamantan-1-yl)-1-arylidene-3-thiosemicarbazides, 4-Arylmethyl N′-(Adamantan-1-yl)piperidine-1-carbothioimidates, and Related Derivatives
by Aamal A. Al-Mutairi, Monirah A. Al-Alshaikh, Fatmah A. M. Al-Omary, Hanan M. Hassan, Areej M. El-Mahdy and Ali A. El-Emam
Molecules 2019, 24(23), 4308; https://doi.org/10.3390/molecules24234308 - 26 Nov 2019
Cited by 20 | Viewed by 4243
Abstract
The reaction of 4-(adamantan-1-yl)-3-thiosemicarbazide 3 with various aromatic aldehydes yielded the corresponding thiosemicarbazones 4a–g. 1-Adamantyl isothiocyanate 2 was reacted with 1-methylpiperazine or piperidine to yield the corresponding N-(adamantan-1-yl)carbothioamides 5 and 6, respectively. The latter was reacted with benzyl or substituted [...] Read more.
The reaction of 4-(adamantan-1-yl)-3-thiosemicarbazide 3 with various aromatic aldehydes yielded the corresponding thiosemicarbazones 4a–g. 1-Adamantyl isothiocyanate 2 was reacted with 1-methylpiperazine or piperidine to yield the corresponding N-(adamantan-1-yl)carbothioamides 5 and 6, respectively. The latter was reacted with benzyl or substituted benzyl bromides to yield the S-arylmethyl derivatives 7a–c. Attempted cyclization of 1,3-bis(adamantan-1-yl)thiourea 8 with chloroacetic acid via prolonged heating to the corresponding thiazolidin-4-one 9 resulted in desulfurization of 8 to yield its urea analogue 10. The thiazolidin-4-one 9 and its 5-arylidene derivatives 11a,b were obtained via microwave-assisted synthesis. The in vitro antimicrobial activity of the synthesized compounds was evaluated against a panel of Gram-positive and Gram-negative bacteria and yeast-like pathogenic fungus Candida albicans. Compounds 7a–c displayed marked broad spectrum antibacterial activities (minimal inhibitory concentration (MIC), 0.5–32 μg/mL) and compounds 4a and 4g showed good activity against Candida albicans. Nine representative compounds were evaluated for anti-proliferative activity towards three human tumor cell lines. Compounds 7a–c displayed significant generalized anti-proliferative activity against all the tested cell lines with IC50 < 10 μM. Full article
(This article belongs to the Section Medicinal Chemistry)
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12 pages, 837 KiB  
Article
Adamantane-Isothiourea Hybrid Derivatives: Synthesis, Characterization, In Vitro Antimicrobial, and In Vivo Hypoglycemic Activities
by Lamya H. Al-Wahaibi, Hanan M. Hassan, Amal M. Abo-Kamar, Hazem A. Ghabbour and Ali A. El-Emam
Molecules 2017, 22(5), 710; https://doi.org/10.3390/molecules22050710 - 29 Apr 2017
Cited by 39 | Viewed by 5950
Abstract
A new series of adamantane-isothiourea hybrid derivatives, namely 4-arylmethyl (Z)-N′-(adamantan-1-yl)-morpholine-4-carbothioimidates 7a–e and 4-arylmethyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidates 8a–e were prepared via the reaction of N-(adamantan-1-yl)morpholine-4-carbothioamide 5 and N-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioamide 6 with benzyl or [...] Read more.
A new series of adamantane-isothiourea hybrid derivatives, namely 4-arylmethyl (Z)-N′-(adamantan-1-yl)-morpholine-4-carbothioimidates 7a–e and 4-arylmethyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidates 8a–e were prepared via the reaction of N-(adamantan-1-yl)morpholine-4-carbothioamide 5 and N-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioamide 6 with benzyl or substituted benzyl bromides, in acetone, in the presence of anhydrous potassium carbonate. The structures of the synthesized compounds were confirmed by 1H-NMR, 13C-NMR, electrospray ionization mass spectral (ESI-MS) data, and X-ray crystallographic data. The in vitro antimicrobial activity of the new compounds was determined against certain standard strains of pathogenic bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 7b, 7d and 7e displayed potent broad-spectrum antibacterial activity, while compounds 7a, 7c, 8b, 8d and 8e were active against the tested Gram-positive bacteria. The in vivo oral hypoglycemic activity of the new compounds was carried on streptozotocin (STZ)-induced diabetic rats. Compounds 7a, 8ab, and 8b produced potent dose-independent reduction of serum glucose levels, compared to the potent hypoglycemic drug gliclazide. Full article
(This article belongs to the Section Medicinal Chemistry)
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13 pages, 776 KiB  
Article
Crystal Structures and Antifungal Activities of Fluorine-Containing Thioureido Complexes with Nickel(II)
by Chun Li, Wen Yang, Huanhuan Liu, Mengying Li, Weiqun Zhou and Juan Xie
Molecules 2013, 18(12), 15737-15749; https://doi.org/10.3390/molecules181215737 - 17 Dec 2013
Cited by 14 | Viewed by 5860
Abstract
Ni(II) complexes with N-2-fluorobenzoylpiperidine-1-carbothioimidate (L2−), N-4-fluorobenzoylpiperidine-1-carbothioimidate (L3−), N-2-fluorobenzoylmorpholine- 1-carbothioimidate (L5−) and N-4-fluorobenzoylmorpholine-1-carbothioimidate (L6−) have been synthesized and characterized by elemental analysis, FTIR and 1H-NMR. The crystal structures of three ligands (HL2, HL3 [...] Read more.
Ni(II) complexes with N-2-fluorobenzoylpiperidine-1-carbothioimidate (L2−), N-4-fluorobenzoylpiperidine-1-carbothioimidate (L3−), N-2-fluorobenzoylmorpholine- 1-carbothioimidate (L5−) and N-4-fluorobenzoylmorpholine-1-carbothioimidate (L6−) have been synthesized and characterized by elemental analysis, FTIR and 1H-NMR. The crystal structures of three ligands (HL2, HL3 and HL6) and the corresponding Ni(II) complexes ([Ni(L2)2], [Ni(L3)2] and [Ni(L6)2]) have been determined by X-ray diffraction. The antifungal activities of the Ni(II) complexes together and the corresponding ligands against the fungi Botrytis cinerea, Trichoderma spp., Myrothecium and Verticillium spp. have been investigated. The experimental results showed that the ligands and their complexes have antifungal abilities. When the fluorine was substituted on the para-benzoyl moiety, the antifungal activity of the ligands was obviously increased. Moreover, the ligands were stronger than their complexes in inhibiting fungal activities. The antifungal ability of HL6 is especially strong, and similar to that of the commercial fungicide fluconazole. Full article
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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