- Azo dyes containing 1,3,4-thiadiazole fragment: Synthesis and properties
-
New 1,3,4-thiadiazole derivatives containing a diazenyl group, as well as both a diazenyl and an imino group, were synthesized and their optical and thermal properties were investigated. Initially, new azo compounds containing an azo group directly in the thiadiazole block were obtained by the coupling of diazonium bisulfates based on the previously known 5-derivatives of 2-amino-1,3,4-thiadiazoles with N,N-dialkyl anilines (N(n-Bu)2, NEt2, and NEt(EtOH)). Schiff bases were obtained by the interaction of p-toluidine, p-phenylenediamine and p-aminophenol with azo compounds containing an aldehyde group in the 1,3,4-thiadiazole ring. The new dyes were characterized by spectral (IR, UV, 1H NMR, 13C NMR and mass spectra) and X-ray analyses. This journal is
- Amosov, Evgeny,Bagryanskaya, Irina,Karpova, Elena,Selivanova, Galina,Shundrina, Inna,Skolyapova, Alexandrina,Wang, Jiaying
-
p. 1929 - 1942
(2022/01/31)
-
- Diazole heterocyclic compound and preparation method and application thereof
-
The invention relates to the technical field of pesticides, in particular to a diazole heterocyclic compound and a preparation method and application thereof. The diazole heterocyclic compound has anexcellent prevention and treatment effect on plant diseases such as plutella xylostella, myzus persicae and tetranychus urticae, and particularly has a remarkable prevention and treatment effect on plutella xylostella. The compound can be used for preparing insecticides in the fields of agriculture, horticulture and the like and developing novel insecticides without cross resistance, and has goodresearch value and market development prospect.
- -
-
Paragraph 0050-0051; 0103-0106
(2021/02/10)
-
- Synthesis of Emodin Amide Derivatives Containing 1,3,4-Thiadiazole and Their Inhibitory Activity on Vibrio harveyi
-
A series of new 1,3,4-thiadiazole Emodin amide derivatives were synthesized through the connection of 5-substituted-1,3,4-thiadiazole-2-amine and Emodin carboxylic acids which were obtained by a two-step procedure starting from Emodin. Vibrio harveyi inhibition activities of the newly prepared compounds were evaluated. Results revealed that all compounds showed different degrees of inhibition on V. harveyi. Among them, compound 7a showed the best V. harveyi inhibition effect and the minimum inhibitory concentration (MIC) was 0.0625 mg/mL.
- Cao, Lian-Gong,Cao, Zhi-Ling,Chen, Chao,Jiang, Kai-Jun,Liu, Shu-Hao,Liu, Wei-Wei,Ruan, Xin-Chi,Shao, Zhong-Bai,Shi, Da-Hua,Su, Zi-Qin,Wang, You-Xian,Wu, Yu-Ran,Wu, Yu-Yu
-
p. 281 - 286
(2021/08/05)
-
- Discovery of novel nonpeptide small-molecule NRP1 antagonists: Virtual screening, molecular simulation and structural modification
-
Multifaceted roles of vascular endothelial growth factor (VEGF)-neuropilin-1 (NRP1) interaction have been implicated in cancer, but reports on small-molecule inhibitors of VEGF-NRP1 interaction are scarce. Herein, we describe the identification of 1, a novel nonpeptide small-molecule NRP1 antagonist with moderate activity via structure-based virtual screening. Ensemble docking and molecular dynamics (MD) simulations of 1 were carried out and an interesting binding model was obtained. We found that the “aromatic box” enclosed by Tyr297, Trp301 and Tyr353 of NRP1 is critical for NRP1-1 binding. Further structure modification of 1 based on the binding model derived from MD simulations resulted in the identification of 12a with significantly improved activity.
- Peng, Kewen,Li, Yu,Bai, Ying,Jiang, Teng,Sun, Huiyong,Zhu, Qihua,Xu, Yungen
-
-
- Preparation of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles via chemoselective сyclocondensation of electrophilically activated nitroalkanes to (thio)semicarbazides or thiohydrazides
-
[Figure not available: see fulltext.] Unusual reaction proceeding via the electrophilic activation of nitroalkanes in the presence of polyphosphoric acid has been discovered. Subsequent nucleophilic attack with semicarbazides or thiosemicarbazides allows
- Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Arutiunov, Nikolai A.,Kirillov, Nikita K.,Rubin, Michael
-
p. 1067 - 1072
(2020/10/02)
-
- Novel synthesized SLC-0111 thiazole and thiadiazole analogues: Determination of their carbonic anhydrase inhibitory activity and molecular modeling studies
-
In the presented work, we report the design and synthesis of novel SLC-0111 thiazole and thiadiazole analogues (11a–d, 12a–d, 16a–c and 17a–d). A bioisosteric replacement approach was adopted to replace the 4-fluorophenyl tail of SLC-0111 with thiazole and thiadiazole ones, which were thereafter extended with lipophilic un/substituted phenyl moieties. All the newly synthesized SLC-0111 analogues were evaluated in vitro for their inhibitory activity towards a panel of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms (hCA I, II, IX and XII), using a stopped-flow CO2 hydrase assay. All the examined isoforms were inhibited by the primary sulfonamide derivatives (11a–d and 12a–d) in variable degrees with the following KI ranges: 162.6–7136 nM for hCA I, 9.0–833.6 nM for hCA II, 7.9–153.0 nM for hCA IX, and 9.4–94.0 nM for hCA XII. In particular, compounds 12b and 12d displayed 5.5-fold more potent inhibitory activity (KIs = 8.3 and 7.9 nM, respectively) than SLC-0111 (KI = 45 nM) towards hCA IX. Molecular docking study was carried out for 12d within the hCA IX (PDB 3IAI) active site, to justify its inhibitory activity.
- Abo-Ashour, Mahmoud F.,Eldehna, Wagdy M.,Nocentini, Alessio,Ibrahim, Hany S.,Bua, Silvia,Abdel-Aziz, Hatem A.,Abou-Seri, Sahar M.,Supuran, Claudiu T.
-
p. 794 - 802
(2019/04/13)
-
- Thiadiazole thiazolinone compounds, and preparation method and application thereof
-
The invention discloses thiadiazole thiazolinone compounds. The thiadiazole thiazolinone compounds have a chemical structure as shown in a formula which is described in the specification. In the formula, R is selected from the group consisting of chemical groups which are described in the specification. The preparation method comprises the following steps: with thiosemicarbazide as a raw material,carrying out cyclodehydration with formic acid under the catalytic condition of concentrated sulfuric acid so as to synthesize a first intermediate product, then carrying out synthesizing with chloroacetyl chloride so as to obtain a second intermediate product, carrying out cyclization under the action of ammonium thiocyanate so as to synthesize a third intermediate product, and allowing a thirdcompound to react with R1 through a Knoevenagle condensation reaction so as to obtain the thiadiazole thiazolinone compounds. According to the invention, by utilization of an active structure splicingprinciple, bis-heterocyclic compounds with a thiazole ring and thiazolinone are synthesized through structure splicing of 1,3,4-thiadiazole and 4-thiazolinone, so bis-heterocyclic pesticide derivatives with excellent activity are obtained; a novel green pesticide variety with high activity, low toxicity and less pollution is selected; and the thiadiazole thiazolinone compounds can be applied to bactericides or pesticides.
- -
-
Paragraph 0049; 0086-0090; 0144
(2018/04/03)
-
- A novel Fer/FerT targeting compound selectively evokes metabolic stress and necrotic death in malignant cells
-
Disruption of the reprogrammed energy management system of malignant cells is a prioritized goal of targeted cancer therapy. Two regulators of this system are the Fer kinase, and its cancer cell specific variant, FerT, both residing in subcellular compartments including the mitochondrial electron transport chain. Here, we show that a newly developed inhibitor of Fer and FerT, E260, selectively evokes metabolic stress in cancer cells by imposing mitochondrial dysfunction and deformation, and onset of energy-consuming autophagy which decreases the cellular ATP level. Notably, Fer was also found to associate with PARP-1 and E260 disrupted this association thereby leading to PARP-1 activation. The cooperative intervention with these metabolic pathways leads to energy crisis and necrotic death in malignant, but not in normal human cells, and to the suppression of tumors growth in vivo. Thus, E260 is a new anti-cancer agent which imposes metabolic stress and cellular death in cancer cells.
- Elkis, Yoav,Cohen, Moshe,Yaffe, Etai,Satmary-Tusk, Shirly,Feldman, Tal,Hikri, Elad,Nyska, Abraham,Feiglin, Ariel,Ofran, Yanay,Shpungin, Sally,Nir, Uri
-
-
- Sodium difluoromethanesulfinate—A difluoromethylating agent toward protonated heterocyclic bases
-
Free radical difluoromethylation of protonated heteroaromatic bases was accomplished using sodium difluoromethanesulfinate in combination with tert-butyl hydroperoxide in a two-phase system (methylene chloride–water) at room temperature. The difluoromethylation products of methyl pyridine-4-carboxylate, pyridine-4-carbonitrile, and 2-amino-1,3,4-thiadiazole were isolated on a preparative scale.
- Lytkina,Eliseenkov,Boyarskii,Petrov
-
p. 539 - 546
(2017/06/06)
-
- 6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method
-
The present invention discloses a 6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method, which comprises: carrying out stirring mixing on 2-amino-1,3,4-thiadiazole, alpha-bromo-acetylferrocene and ethanol; placing the mixed solution in a microwave oven, and carrying out microwave irradiation; after the alpha-bromo-acetylferrocene completely reacts, adding water to the reaction solution, and adjusting the pH value of the reaction solution to 7-8 with a saturated sodium carbonate solution; carrying out suction filtration, washing the filter cake with water, and drying to obtain a crude product; and re-crystallizing with DMF to obtain the target product. According to the present invention, the microwave-assisted synthesis reaction is used so as to substantially shorten the reaction time and improve the reaction efficiency.
- -
-
Paragraph 0029; 0039; 0049; 0059
(2018/01/12)
-
- Alpha-amino phosphonate compound with 2-amino-1, 3, 4-thiadiazole structure and preparation method and application of alpha-amino phosphonate compound
-
The invention discloses an alpha-amino phosphonate compound with a 2-amino-1, 3, 4-thiadiazole structure and a preparation method and application of alpha-amino phosphonate compound. The alpha-amino phosphonate compound has the sterilizing effect of alpha-amino phosphonate compounds and has a pesticide effect by introducing the 2-amino-1, 3, 4-thiadiazole group, and the alpha-amino phosphonate compound is wide in application range and good in sterilizing and pesticide effect by combining the alpha-amino phosphonate compound with the 2-amino-1, 3, 4-thiadiazole group. The preparation method is few in step, simple to operate, high in yield and productivity, capable of saving a large amount of time and cost in actual production and good in economic benefit. The 2-amino-1, 3, 4-thiadiazole has an inhibition effect on the growth and proliferation of alternaria solani and on the growth of mythimna separata and can be used as the pesticide intermediate to apply to the preparation of different agricultural fungicide.
- -
-
Paragraph 0030; 0031
(2016/12/26)
-
- Thiadiazole phosphamide compound, preparation method thereof, and applications of thiadiazole phosphamide compound as pesticide
-
The invention discloses a thiadiazole phosphamide compound, a preparation method thereof, and applications of the thiadiazole phosphamide compound as a pesticide. The thiadiazole phosphamide compound possesses high efficiency and low toxicity of O,O-diethyl phosphoramidothioate as an intermediate, high efficiency, broad spectrum, low residue, and low drug resistance of chlorpyrifos, short residual period, and excellent preventing and controlling effect on injurious insects of tea trees, mulberry, vegetables, and fruit trees, and soil insects and warehouse pest-insects. The preparation method comprises a few steps; operation is simple; yield and productivity are high; a large amount of time and cost are saved in practical production; and economic benefit is high. The thiadiazole phosphamide compound also possesses inhibition effects on growth of gloeosporium musarum, alternaria solani, fusarium oxysporum, and fusarium oxysporum f.sp.cubense, and can be used in preparation and applications of different agricultural fungicides as a pesticide intermediate.
- -
-
Paragraph 0032; 0033
(2017/04/03)
-
- Synthesis and antibacterial activities of thiadiazole maneb
-
Summary: Four novel maneb derivatives containing 1, 3, 4-thiadiazole were successfully synthesized and characterized by FT-IR, electrochemical analysis and 1H-NMR and 13C-NMR. And their antibacterial activities were screened for Paddy fusarium, Borrytis cinerea, Cucumber fusarium, Tomato gibberella, Grape white rot in vitro by filter paper disc diffusion technique. The target compounds exhibited moderate to excellent activity in comparison to maneb.
- Yuting, Liu,Gangtao, Liang,Dawei, Yin
-
p. 115 - 121
(2015/05/20)
-
- Synthesis of new 2,5-disubstituted-1,3,4-thiadiazole derivatives and their in vivo anticonvulsant activity
-
A series of 2,5-disubstituted-1,3,4-thiadiazole derivatives were synthesized by the reaction of 3-(2-cyanopropan-2-yl)-N-(5-(piperazine-1-yl)-1, 3,4-thiadiazol-2-yl)benzamide with various sulfonyl chlorides and evaluated for their anticonvulsant activity in MES test. Rotorod method was employed to determine the neurotoxicity. The purity of the compounds is confirmed on the basis of their elemental analysis. The structures of all the new compounds are established on the basis of 1H NMR and mass spectral data. Out of fifteen compounds, three were found to be potent anticolvunstants. The same compounds showed no neurotoxicity at the maximum dose administered (100 mg/kg).
- Harish,Mohana,Mallesha
-
-
- Fe3+-selective naked-eye 'off-on' fluorescent probe: Its crystal structure and imaging in living cells
-
Four novel rhodamine-active probes L1-L4 have been proposed and characterized as fluorescent chemosensors for Fe3+. An 'off-on' type fluorescent enhancement was observed, which was induced by the interactions between Fe3+ and the probe, proven to adopt a 1:1 binding stoichiometry. The recognition properties of the target compounds with metal ions have been investigated in methanol-water (1:1, v/v) solution by the fluorescence and ultraviolet spectrum. In addition, a plausible application of probes in the imaging of HepG2 (liver cells) under the condition of reoxygenation (95% air, 5% CO2) exposed to Fe3+ ions was also demonstrated.
- Meng, Wen-Fei,Yang, Mei-Pan,Li, Bo,Cheng, Zhao,Yang, Bing-Qin
-
p. 8577 - 8581
(2014/12/10)
-
- Synthesis and antifungal activity of thiadiazole-functionalized chitosan derivatives
-
A groups of novel water soluble chitosan derivatives containing 1,3,4-thiadiazole group were synthesized including 1,3,4-thiadiazole (TPCTS), 2-methyl-1,3,4-thiadiazole (MTPCTS), and 2-phenyl-1,3,4-thiadiazole (PTPCTS). Their antifungal activity against three kinds of phytopathogens was estimated by hypha measurement in vitro, and the fungicidal assessment shows that the synthesized chitosan derivatives have excellent activity against tested fungi. Of all the synthesized chitosan derivatives, MTPCTS inhibited the growth of the tested phytopathogens most effectively with inhibitory indices of 75.3%, 82.5%, and 65.8% against Colletotrichum lagenarium (Pass) Ell.et halst, Phomopsis asparagi (Sacc.) Bubak, and Monilinia fructicola (Wint.) Honey respectively at 1.0 mg/mL. These indices are higher than those of chitosan. These data also demonstrate that the hydrophobic moiety (alkyl and phenyl) and the length of alkyl substituent in thiadiazole tend to affect the antifungal activity of chitosan derivatives. It is hypothesized that thiadiazole groups enable the synthesized chitosan to possess obviously better antifungal activity and good solubility in water.
- Li, Qing,Ren, Jianming,Dong, Fang,Feng, Yan,Gu, Guodong,Guo, Zhanyong
-
p. 103 - 107
(2013/06/27)
-
- NOVEL TRIAZINE COMPOUNDS
-
The present invention relates to novel triazine compounds of formula (1), methods of their preparation, pharmaceutical compositions containing these compounds and the use of these compounds to treat proliferative disorders such as tumors and cancers and also other conditions and disorders related to or associated with dysregulation of PI3 Kinases, PI3 Kinase pathway, mTOR and/ or the mTOR pathway.
- -
-
Page/Page column 61
(2012/08/08)
-
- Aza crown ether appended hetarylazo dye - Single molecular dual analyte chemosensor for Hg2+ and Pb2+
-
A hetarylazo dye appended with an aza crown ether detects and discriminates Hg2+ and Pb2+ from each other by immediate visual observation, significant from an 'on-site' evaluation point of view. It is accompanied by absorption based changes and is convincingly established from 1H NMR, TD-DFT and electrochemical studies. The Royal Society of Chemistry 2012.
- Kaur, Paramjit,Sareen, Divya,Singh, Kamaljit
-
supporting information; experimental part
p. 8767 - 8769
(2012/09/22)
-
- The synthesis and development of a dual-analyte colorimetric sensor: Simultaneous estimation of Hg2+ and Fe3+
-
The selectivity and sensitivity of a pH stable hetarylazo dye equipped with binding sites consisting of N, S and N, O combinations, towards Hg2+ and Fe3+ over a large number of other cations including lanthanides, is described. Hg2+ and Fe3+ ions coordinate to the dye through N, S binding site forming 2:1 and 1:1 complexes, respectively. Distinct naked-eye color changes for both Hg2+ (yellow to purple) and Fe 3+ (yellow to red) were quantified for simultaneous estimation of these ions. To further establish the binding and sensing phenomenon, another analogous hetarylazo dye lacking N, O combination was evaluated and found to give similar results. For practical applicability in routine life, very handy and ready-to-use paper strips coated with the dye have been prepared for the detection of Hg2+, just like the pH paper strips.
- Kaur, Paramjit,Sareen, Divya
-
experimental part
p. 296 - 300
(2011/05/30)
-
- Synthesis, antifungal activities and 3D-QSAR study of N-(5-substituted-1,3,4-thiadiazol-2-yl)cyclopropanecarboxamides
-
A series of cyclopropanecarboxamide were prepared and tested for antifungal activity in vivo. The preliminary bioassays indicated that some compounds are comparable to the commercial fungicides. To further explore the comprehensive structure-activity relationship on the basis of fungicidal activity data, comparative molecular field analysis (CoMFA) was performed, and a statistically reliable model with good predictive power (r2 = 0.8, q2 = 0.516) was achieved. Based on the CoMFA, compound 7p was designed and synthesized, which was found to display a good antifungal activity (79.38%) as 7g and 7h.
- Liu, Xing-Hai,Shi, Yan-Xia,Ma, Yi,Zhang, Chuan-Yu,Dong, Wei-Li,Pan, Li,Wang, Bao-Lei,Li, Bao-Ju,Li, Zheng-Ming
-
scheme or table
p. 2782 - 2786
(2009/10/19)
-
- Phase transfer catalysts promoting the one-pot synthesis under ultrasonic irradiation and biological activity of n-(5-substituted-1,3,4-thiadiazole-2-yl)- N'-(5-methylisoxazoyl)-thiourea derivatives
-
Reaction of 2-amino-5-substitute-1,3,4-thiadiazoles with 5-methylisoxazoyl chloride and ammonium thiocyanate under the condition of solid-liquid phase-transfer catalysis using polyethylene glycol-600 (PEG-600) as the catalyst under ultrasonic irradiation yielded N-(5-substituted-1,3,4-thiadiazole-2-yl)- N'-(5-methylisoxazoyl)-thiourea derivatives 3a-1 in good-to-excellent yield. The chemical structure of all compounds was established by 1H NMR, FTIR, MS, and elemental analysis studies. Some of the compounds were investigated for fungicidal activity. The bioassay results indicated that some of these compounds exhibit moderate fungicidal activities.
- Xiaodong, Yang
-
p. 387 - 392
(2008/09/19)
-
- 2-Amino-5-trifluoromethyl-1,3,4-thiadiazole and a redetermination of 2-amino-1,3,4-thiadiazole, both at 120 K: Chains of edge-fused R 22(8) and R44(10) rings, and sheets of R22(8) and R66(20) rings
-
Molecules of 2-amino-5-trifluoromethyl-1,3,4-thiadiazole, C 3H2F3N3S, are linked by two independent N - H...N hydrogen bonds into sheets of alternating R 22(8) and R66(20) rings, while the molecules of the unsubstituted 2-amino-1,3,4-thiadiazole, C2H 3N3S, are linked, again by two independent N - H...N hydrogen bonds, but into chains of edge-fused R22(8) and R44(10) rings.
- Boechat, Nubia,Ferreira, Sabrina B.,Glidewell, Christopher,Low, John N.,Skakle, Janet M.S.,Wardell, Solange M.S.V.
-
-
- Polymer-supported dichlorophosphate: A recoverable new reagent for synthesis of 2-amino-1,3,4-thiadiazoles
-
Poly(ethylene glycol) (PEG) supported dichlorophosphate was efficiently used as a recoverable new dehydration reagent for rapid synthesis of 2-amino-5-substituted-1,3,4-thiadiazoles under microwave irradiation and solvent-free condition by reactions of thiosemicarbazide with aliphatic acids, benzoic acid, aryloxyacetic acids or furan-2-carboxylic acids.
- Li, Zheng,Yu, Jin-Lan,Yang, Jing-Ya,Shi, Sheng-Yi,Wang, Xi-Cun
-
p. 341 - 343
(2007/10/03)
-
- Synthesis and biological activity of some new benzophenothiazines
-
Condensation of carboxylic acids with thiosemicarbazide in presence of conc. H2SO4 gives 2-amino-5-aralkyl-1,3,4-thiadiazoles 1 which on diazotization afford 5-aralkyl-1,3,4-thiadiazolyl-2-diazonium chlorides 2. Reaction of 2 with cold solution of β-naphthol in dilute NaOH furnishes α-(2-diazo-5-aralkyl-1,3,4-thiadiazolyl)-β-sodionaphthoxides 3 which on acidification with conc. HCl gives α-(2-diazo-5-aralkyl-1,3,4-thiadiazolyl)-β-naphthols 4. Reaction of 4 with p-anisidine gives α-(2-diazo-5-aralkyl-1,3,4-thiadiazolyl)-β-(p-anisidino) naphthalenes 5. Fusion of 5 with sulphur in presence of iodine results in 1-(2′-diazo-5′-aralkyl-1′,3′,4′- thiadiazolyl)-6-methoxy benzophenothiazines 6 in yields varying from 48% to 59%. The new compounds 6 have been screened for their antiviral and antifungal activities.
- Pandey,Negi,Joshi,Bajpai
-
p. 206 - 210
(2007/10/03)
-
- Synthesis of [1,3,4]thiadiazolo[3,2-a]pyrimidines in the presence of formic acid
-
Formic acid-phosphorus pentoxide was effective for the preparation of 5,7-dimethyl[1,3,4]thiadiazolo- and -[1,3]thiazolo[3,2-a]pyrimidin-4-ium salts. Further, the pyrimidine ring transformation and the isocyanation of 5imino-6H-[1,3,4]thiadiazolo- and -[1,3]thiazolo[3,2-a]pyrimidin-7-ones were carried out in the presence of formic acid and triethyl orthoformate, respectively.
- Takenaka, Keiko,Tsuji, Tadakazu
-
p. 1367 - 1370
(2007/10/03)
-
- 2-(Thi)oxo-3-imidazolyl-(2)-tetrahydroimidazoles
-
Imidazoles of the formula I STR1 wherein one of the radicals R1 and R2 denotes hydrogen or lower alkyl and the other denotes the nitro group, R3 is lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, lower alkyl-sulphonyl-lower alkyl or amino-lower alkyl, R4 is oxo or thioxo, R5 - if R1 is the nitro group - is hydrogen, lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, amino-lower alkyl, acyl, aryl or a heterocyclic radical or R5 -- if R2 is the nitro group -- is aryl or a heterocyclic radical, with the exception of an optionally substituted 2-imidazolyl group, and alk is lower alkylene and their therapeutically usable salts, S-oxides, sulphones or N-oxides are useful as agents against amoebae, schistosomes, filariae, trichomonades and bacteria and as intermediates.
- -
-
-
