622-73-1Relevant academic research and scientific papers
Colorimetric quantification of α-tocopherol (vitamin E) in pure form and different comestible samples by using newly synthesized tetrazolium salts
Kumar, Ashwani,Kamboj, Mamta
, p. 429 - 443 (2020/09/01)
A quick, susceptible, and viable spectrophotometric procedure for the assay of α-tocopherol by newly synthesized tetrazolium reagents 2-phenyl-3-(2-thiazolyl)-5-(4-methoxyphenyl)tetrazolium bromide (PTMPT) and 2-phenyl-3-(2-thiazolyl)-5-(4-nitrophenyl)tet
Synthesis of and characterization of some Heterocyclic Compounds derived from Thiophenol
AL-Khazraji, Shaima Ibraheem Chyad
, p. 5655 - 5662 (2021/09/11)
This research work involved preparation of heterogeneous pent lateral cyclic compounds (thiazolidine -4- one, benzothiazole, triazole, 4-oxothiazolidin) using thiophenol as raw materials: Thiophenol was reacted with mono chloroacetic acid in the presence of potassium hydroxide to prepare (sh1) followed by ortho amino aniline results the (sh2). The reaction of thiophenol with ethylchloroacetate afforded (sh3) and the reaction of (sh3) with thiosemicarbazide and 4% NaOH leads to ring closure giving 1,2,4- triazole (sh5). A treatment of thiophenol with hydrazine hydrate to obtain the intermediate (sh6) with aromatic aldehyde synthesized azomethines (sh7- sh9) then treated with mercaptoacetic acid to obtained (sh10-sh12). A treatment of thiophenol with chloroacetyl chloride produced (sh13) compound then treated with hydrazine hydrate to obtain (sh14) compound followed by bromobenzaldehyde synthesized azomethine (sh15) compound then treated with mercaptoacetic acid to obtained (sh16) compound. Characterization results for the prepared compounds using IR spectroscopy, NMR and melting points confirmed their chemical structures.
Identification of novel 1,3-diaryl-1,2,4-triazole-capped histone deacetylase 6 inhibitors with potential anti-gastric cancer activity
Zhang, Xin-Hui,Kang, Hui-Qin,Tao, Yuan-Yuan,Li, Yi-Han,Zhao, Jun-Ru,Ya-Gao,Ma, Li-Ying,Liu, Hong-Min
, (2021/04/12)
Histone deacetylase 6 (HDAC6) has emerged as a critical regulator of many cellular pathways in tumors due to its unique structure basis and abundant substrate types. Over the past few decades, the role played by HDAC6 inhibitors as anticancer agents has sparked great interest of biochemists worldwide. However, they were less reported for gastric cancer therapy. In this paper, with the help of bioisosteric replacement, in-house library screening, and lead optimization strategies, we designed, synthesized and verified a series of 1,3-diaryl-1,2,4-triazole-capped HDAC6 inhibitors with promising anti-gastric cancer activities. Amongst, compound 9r displayed the best inhibitory activity towards HDAC6 (IC50 = 30.6 nM), with 128-fold selectivity over HDAC1. Further BLI and CETSA assay proved the high affinity of 9r to HDAC6. In addition, 9r could dose-dependently upregulate the levels of acetylated α-tubulin, without significant effect on acetylated histone H3 in MGC803 cells. Besides, 9r exhibited potent antiproliferative effect on MGC803 cells, and promoted apoptosis and suppressed the metastasis without obvious toxicity, suggesting 9r would serve as a potential lead compound for the development of novel therapeutic agents of gastric cancer.
Sequential [3+2] annulation reaction of prop-2-ynylsulfonium salts and hydrazonyl chlorides: Synthesis of pyrazoles containing functional motifs
Jia, Tingting,Liu, Shourong,Shao, Jiaan,Shi, Tao,Wu, Zhaoxiao,Zeng, Linghui,Zhang, Chong,Zhang, Jiankang,Zhu, Huajian,Zhuang, Rangxiao
supporting information, p. 8460 - 8463 (2021/09/08)
A novel sequential [3+2] annulation reaction has been developed using prop-2-ynylsulfonium salts and hydrazonyl chlorides, affording a series of pyrazoles with functional motifs that can be post modified in the preparation of various drugs or drug candidates. Further transformation and gram-scale operations could also be achieved efficiently. This journal is
1,3-dipolar cycloaddition reactions of the compound obtaining from cyclopentadiene-PTAD and biological activities of adducts formed selectively
Bayrak, Cetin,Menzek, Abdullah,Taskin-Tok, Tugba,Taslimi, Parham,Yavari, Mirali Akbar
, (2022/01/04)
After known adduct (4) was synthesized by cycloaddition reaction of cyclopentadiene with 4-phenyl-1,2,4-triazoline-3,5-dione, seven new isoxazoline derivatives were synthesized from reactions of 4 with corresponding oximes prepared from benzaldehyde derivatives in the existence of the aqueous NaOCl in CH2Cl2 at 0°C—RT via nitrile oxides. Four new pyrazoline derivatives were also synthesized from reactions of 4 with corresponding prepared reagents via nitrile imines. Selectively, each of all isoxazole and pyrazoline derivatives was synthesized by 1,3-dipolar cycloaddition reactions of compound 4 with the corresponding reagents. Based on the results of their biological activity analyses, Ki values for acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and alpha-glucosidase (α-Gly) enzymes were obtained in this range 32.15 ± 5.73–107.44 ± 19.52 22.57 ± 4.30–186.07 ± 23.51, and 69.08 ± 8.54–528.07 ± 38.46 nM, respectively. Besides that, these compounds were subjected to molecular docking to describe the interaction against AChE, BChE, and α-Gly enzymes in which important interactions were visualized and evaluated with residues of the binding region in each target enzyme.
Synthesis of 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenylformazans) and 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenyl-5,6-dihydro-1,2,4,5-tetrazin-1-ium) Perchlorates
Alalwan, D. H. K.,Jassim, T.,Kostryukov, S. G.,Kozlov, A. Sh.,Masterova, Yu. Yu.,Tezikova, V. S.
, p. 1600 - 1607 (2021/12/13)
Abstract: New bis-formazans and bis(5,6-dihydro-1,2,4,5-tetrazin-1-ium) perchlorates were synthesized with high yields under mild conditions. 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenylformazans) were obtained by diazo coupling of para-substituted benzaldehyde phenylhydrazones with [1,1′-biphenyl]-4,4′-bis(diazonium chloride). Treatment of the obtained bis-formazans with formaldehyde in the presence of perchloric acid in dioxane afforded 1,1′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-5-phenyl-5,6-dihydro-1,2,4,5-tetrazin-1-ium) diper-chlorates. The structure of the synthesized compounds was confirmed by elemental analyses and UV, IR, and 1H and 13C NMR spectra.
Broad-Spectrum Antifungal Agents: Fluorinated Aryl- and Heteroaryl-Substituted Hydrazones
Thamban Chandrika, Nishad,Dennis, Emily K.,Brubaker, Katelyn R.,Kwiatkowski, Stefan,Watt, David S.,Garneau-Tsodikova, Sylvie
supporting information, p. 124 - 133 (2020/10/20)
Fluorinated aryl- and heteroaryl-substituted monohydrazones displayed excellent broad-spectrum activity against various fungal strains, including a panel of clinically relevant Candida auris strains relative to a control antifungal agent, voriconazole (VRC). These monohydrazones displayed less hemolysis of murine red blood cells than that of VRC at the same concentrations, possessed fungicidal activity in a time-kill study, and exhibited no mammalian cell cytotoxicity. In addition, these monohydrazones prevented the formation of biofilms that otherwise block antibiotic effectiveness and did not trigger the development of resistance when exposed to C. auris AR Bank # 0390 over 15 passages.
From Phenylhydrazone to 1H-1,2,4-Triazoles via Nitrification, Reduction and Cyclization
Hao, Liqiang,Wang, Guodong,Sun, Jian,Xu, Jun,Li, Hongshuang,Duan, Guiyun,Xia, Chengcai,Zhang, Pengfei
supporting information, p. 1657 - 1662 (2020/03/19)
Herein we report an annulation of phenylhydrazone via a tandem nitrification, reduction, cyclization protocol employing cobalt nitrate and 1,2-dichloroethane to produce substituted 1H-1,2,4-triazoles. Notably, 1,2-dichloroethane serves both the solvent and a hydrogen source for transfer hydrogenation. This methodology works under mild conditions, providing a direct approach for the synthesis of 1H-1,2,4-triazoles. (Figure presented.).
Acid-Mediated Three Component Assembly of 4-Fluoropyrazoles from α-Fluoronitroalkenes, Hydrazines, and Aldehydes
Ioffe, Sema L.,Motornov, Vladimir A.,Nelyubina, Yulia V.,Nenajdenko, Valentine G.,Tabolin, Andrey A.
, (2020/08/06)
A new approach for the synthesis of highly pharmaceutically relevant 4-fluoropyrazoles via oxidative annulation of α-fluoronitroalkenes with in situ prepared hydrazones was developed. The reaction is efficiently promoted by trifluoroacetic acid while atmo
Transition-Metal-Free Coupling of 1,3-Dipoles and Boronic Acids as a Sustainable Approach to C?C Bond Formation
Livingstone, Keith,Bertrand, Sophie,Kennedy, Alan R.,Jamieson, Craig
supporting information, p. 10591 - 10597 (2020/07/25)
The need for alternative, complementary approaches to enable C?C bond formation within organic chemistry is an on-going challenge in the area. Of particular relevance are transformations that proceed in the absence of transition-metal reagents. In the current study, we report a comprehensive investigation of the coupling of nitrile imines and aryl boronic acids as an approach towards sustainable C?C bond formation. In situ generation of the highly reactive 1,3-dipole facilitates a Petasis–Mannich-type coupling via a nucleophilic boronate complex. The introduction of hydrazonyl chlorides as a complementary nitrile imine source to the 2,5-tetrazoles previously reported by our laboratory further broadens the scope of the approach. Additionally, we exemplify for the first time the extension of this protocol into another 1,3-dipole, through the synthesis of aryl ketone oximes from aryl boronic acids and nitrile N-oxides.
