- Anticonvulsant and sedative-hypnotic activities of N-substituted isatin semicarbazones
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A series of N-methyl/acetyl, 5-(un)-substituted isatin-3-semicarbazones were screened for anticonvulsant and sedative-hypnotic activities. The results revealed that protection was obtained in all the screens i.e., MES, scPTZ, and scSTY. Compounds 2, 4, 6, 10 but not 1 and 3 showed low neurotoxicity when compared to clinically used drugs. Compounds 5, 7, 8 and 9 were completely non-toxic. Compound 6 showed good activity in the rat oral MES screen. Among all the compounds, 3 and 6 emerged as the most active compounds as indicated by the protection they exhibit in MES, scSTY, and scPTZ screens. All the compounds showed significant sedativehypnotic activity.
- Pandeya, Surendra N.,Smitha, Sivakumar,Stables, James P.
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- Design, synthesis and biological evaluation of novel semicarbazone-selenochroman-4-ones hybrids as potent antifungal agents
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A series of novel 2,3-dihydro-4H-1-benzoselenin-4-one (thio)semicarbazone derivatives were designed and synthesized by using molecular hybridization approach. All the target compounds were characterized by HRMS and NMR and evaluated in vitro antifungal activity against five pathogenic strains. In comparison with precursor selenochroman-4-ones, the hybrid molecules in this study showed significant improvement in antifungal activities. Notably, compound B8 showed significant antifungal activity against other strains excluding Aspergillus fumigatus (0.25 μg/mL on Candida albicans, 2 μg/mL on Cryptococcus neoformans, 8 μg/mL on Candida zeylanoides and 2 μg/mL on fluconazole-sensitive strains of Candida albicans). Moreover, compounds B8, B9 and C2 also displayed most potent activities against four fluconazole-resistance strains. Especially the MIC values of the hybrid molecule B8 against fluconazole-resistant strains were in the range of 0.5–2 μg/mL. Therefore, the molecular hybridization approach in this study provided new ideas for the development of antifungal drug.
- Xu, Hang,Su, Xin,Liu, Xiao-qian,Zhang, Kai-peng,Hou, Zhuang,Guo, Chun
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- Gold-Catalyzed Functionalization of Semicarbazides with Terminal Alkynes to Achieve Substituted Semicarbazones
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Gold-catalyzed functionalization of semicarbazides (ArNHCONHNH2) with various terminal alkynes R2C≡CH (R2 = Alk or Ar) in the presence of Ph3PAuNTf2 (3 mol-%) grants a range of substituted semicarbazo
- Zimin, Dmitry P.,Dar'in, Dmitry V.,Eliseeva, Anastasiya A.,Novikov, Alexander S.,Rassadin, Valentin A.,Kukushkin, Vadim Yu.
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supporting information
p. 6094 - 6100
(2019/08/22)
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- Discovery and structure activity relationships of 2-pyrazolines derived from chalcones from a pest management perspective
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Synthesis of chalcones and 2-pyrazoline derivatives has been an active field of research due to the established pharmacological effects of these compounds. In this study, a series of chalcone (1a-i), 2-pyrazoline-1-carbothioamides (2a-i), and 2-pyrazoline
- Kocyigit-Kaymakcloglu, Bedia,Beyhan, Nagihan,Tabanca, Nurhayat,Ali, Abbas,Wedge, David E.,Duke, Stephen O.,Bernier, Ulrich R.,Khan, Ikhlas A.
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p. 3632 - 3644
(2015/09/07)
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- Facile one-pot synthesis of 4-substituted semicarbazides
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A diverse library of twenty-five 4-mono- and disubstituted semicarbazides was prepared in a one-pot two-step approach. The method includes formation of a carbamate from bis(2,2,2-trifluoroethyl)carbonate or 2,2,2-trifluoroethylchloroformate and a primary or secondary amine and subsequent interaction of the carbamate with hydrazine to result in a semicarbazide. The approach allowed to obtain 4-substituted semicarbazides on a large scale in good yield and high purity. This journal is
- Bogolubsky, Andrey V.,Moroz, Yurii S.,Mykhailiuk, Pavel K.,Dmytriv, Yurii V.,Pipko, Sergey E.,Babichenko, Liudmyla N.,Konovets, Anzhelika I.,Tolmachev, Andrey
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p. 1063 - 1069
(2015/02/18)
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- Design and synthesis of novel triazole antifungal derivatives by structure-based bioisosterism
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The incidence of life-threatening fungal infections is increasing dramatically. In an attempt to develop novel antifungal agents, our previously synthesized phenoxyalkylpiperazine triazole derivatives were used as lead structures for further optimization. By means of structure-based bioisosterism, triazolone was used as a new bioisostere of oxygen atom. This type of bioisosteric replacement can improve the water solubility without loss of hydrogen-bonding interaction with the target enzyme. A series of triazolone-containing triazoles were rationally designed and synthesized. As compared with fluconazole, several compounds showed higher antifungal activity with broader spectrum, suggesting their potential for further evaluations.
- Sheng, Chunquan,Che, Xiaoying,Wang, Wenya,Wang, Shengzheng,Cao, Yongbing,Miao, Zhenyuan,Yao, Jianzhong,Zhang, Wannian
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p. 5276 - 5282
(2011/12/03)
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- N6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA), a very selective agonist with high affinity for the human adenosine A1 receptor
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Four subtypes of adenosine receptors are currently known, that is, A1, A2A, A2B, and A3 receptors. Interestingly, quite substantial species differences exist especially between human and rat A3 receptors. As a result, ligands such as CCPA, which are very selective for the rat A1 receptor versus the human A3 receptor, are substantially less selective when the human A1 and A3 receptors are compared. New 2-substituted and 2,N6-disubstituted adenosines were synthesized, and their affinities for the human adenosine A1, A2A, A2B, and A3 receptors were determined. Although large substituents on the C2-position are generally thought to yield adenosine A2A receptor selective ligands, the reported series of 2-triazeno-substituted adenosines had a very high affinity for the A1 receptor. For example, 2-(3-phenylaminocarbonyltriazene-1-yl)adenosine had an affinity of 6.1 ± 1.3 nM for the human adenosine A1 receptor. Introduction of a diphenethyl substituent at the N6-position of this compound resulted in a high-affinity agonist, 3.1 ± 0.9 nM, for the human adenosine A1 receptor with 316- and 45-fold selectivity versus the human A2A and human A3 receptors, respectively. The most selective, high-affinity human adenosine A1 receptor agonist was the disubstituted compound N6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA). TCPA had an affinity of 2.8 ± 0.8 nM for the human adenosine A1 receptor and was 75-fold and 214-fold selective versus the human A2A and human A3 receptors, respectively. In addition, TCPA was a full agonist and inhibited the forskolin-induced cAMP production of CHO cells stably transfected with the human adenosine A1 receptor with an IC50 of 1.5 ± 0.5 nM.
- Beukers, Margot W.,Wanner, Martin J.,Von Frijtag Drabbe Künzel, Jacobien K.,Klaasse, Elisabeth C.,IJzerman, Adriaan P.,Koomen, Gerrit-Jan
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p. 1492 - 1503
(2007/10/03)
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