- Synthesis, Structural and Spectroscopic Characterization of CrIII, FeIII, CoIII, NiII and CuII Complexes with an Asymmetric 1,3,4-Thiadiazole Ligand
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The reaction of the new asymmetric 1,3,4-thiadiazole-based ligand 2-[(5-ethylthio-1,3,4-thiadiazol-2-yl)hydrazonomethyl]phenol (H1ETHP) with various third-row transition metal salts resulted in the formation of six new mononuclear complexes [Cr(ETHP)2]ClO4 (1), [Fe(ETHP)2][FeCl4] (2), [Co(ETHP)(ETHP-H)] (3), [Ni(ETHP)(H1ETHP)]Cl (4), [Ni(ETHP)(H1ETHP)](ClO4) (5), [Ni(ETHP)(H1ETHP)]Br (6), and one tetranuclear complex [Cu2Cl3(ETHP)(H1ETHP)]2 (7). H1ETHP and all complexes have been analyzed by single crystal X-ray diffraction. Structural analysis of 1-6 reveals complexes of the [ML2]n+-type (n = 0,1), in which the mono anionic ligand ETHP coordinates in a tridentate NNO fashion via its imine, thiadiazole and phenolate functional groups. Complex 7 has also been investigated by variable-temperature magnetic susceptibility measurements and shows weak antiferromagnetic exchange interactions between the copper centers. The g values for the copper ions in the tetramer were obtained by EPR spectroscopy. All compounds were found to display an extended hydrogen bond network via their N-H or O-H ligand functional groups towards the corresponding counterions, solvent molecules or neighboring complex cations. The connectivity of the complexes results in the formation of supramolecular chains or, in the case of 4, a 3D-network including large solvent accessible cavities.
- Deckert, Christoph,Bittner, Denis,Carrella, Luca M.,Schollmeyer, Dieter,Rentschler, Eva
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- COMPOUNDS HAVING PDE9A INHIBITORY ACTIVITY, AND PHARMACEUTICAL USES THEREOF
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The present invention provides a compound having a specific chemical structure and having PDE9A inhibitory activity, or a pharmaceutically acceptable salt thereof. The present invention provides a composition containing the compound or a pharmaceutically acceptable salt thereof. The present invention provides a pharmaceutical use, for treating or preventing PDE9A-related diseases, of the compound according to the present invention, a salt thereof, and a composition containing the compound or salt. The present invention also provides a method for treating or preventing PDE9A-related diseases, the method comprising administering an effective amount of the compound according to the present invention, a salt thereof, or a composition containing the compound or salt to a subject in need of treatment.
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Paragraph 0144-0147
(2021/10/15)
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- Design and development of 1,3,4-thiadiazole based potent new nano-fungicides
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Being the important organic reaction intermediates and biological scaffolds, a series of 2-alkyl/aralkyl/heterocyclyl sulfanyl-5-amino/methyl-1,3,4-thiadiazoles have been synthesized by suitable synthetic route and characterized by analytical and spectral data. The evaluation of these compounds for their bioefficacy against two phyto-pathogenic fungi revealed their fungicidal potency against Rhizoctonia bataticola (ED50 values, 3.9–300.4 μg/mL) and Rhizoctonia solani (ED50 values, 4.2–228.5 μg/mL). To further augment their fungicidal efficacy, the potent five fungicidal compounds were nano-sized. The protocol for preparing 1,3,4-thiadiazole based nano-fungicide employing polyethylene glycol was developed and standardized. Characterization of nano-forms of 1,3,4-thiadiazole derivatives by particle size analyzer and electron microscopy (TEM) techniques confirmed the 100 nm average particle sizes of all nano-fungicides. The 2–4 times higher fungicidal activity was observed with nano-forms than the corresponding conventional sized 1,3,4-thiadiazole derivatives against phytopathogenic fungi, namely, Rhizoctonia solani and R. bataticola.
- Gogoi, Robin,Kumar, Rajesh,Pal, Suprabhat,Singh, Vikrant
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- Containing 1, 3, 4 - thiadiazole thioether (sulfone) of 2 - (trifluoromethyl) benzamide derivatives, their preparation and use
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The invention discloses a containing 1, 3, 4 - thiadiazole thioether (sulfone) of 2 - (trifluoromethyl) benzamide derivatives, their preparation and application, its general formula as follows, wherein: R1 Is methyl, ethyl, 2 - chloroethyl, 2 - fluoro ethyl, 2 - bromo ethyl, propyl, butyl, pentyl, 4 - cyano-benzyl, 4 - benzylic, 2 - fluorobenzyl, cyanomethyl, 2 - cyanoethyl, 3 - cyano-propyl, ; X is S or - S (O)2 -. The invention can control the south-knot nematode and rice [...], tobacco bacterial wilt and citrus canker composite infection.
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Paragraph 0065; 0067
(2019/03/28)
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- Design, synthesis, and biological activity of novel myricetin derivatives containing amide, thioether, and 1,3,4-thiadiazole moieties
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A series of myricetin derivatives containing amide, thioether, and 1,3,4-thiadiazole moieties were designed and synthesized, and their antiviral and antibacterial activities were assessed. The bioassays showed that all the title compounds exhibited potent in vitro antibacterial activities against Xanthomonas citri (Xac), Ralstonia solanacearum (Rs), and Xanthomonas oryzae pv. Oryzae (Xoo). In particular, the compounds 5a, 5f, 5g, 5h, 5i, and 5l, with EC50 values of 11.5–27.3 μg/mL, showed potent antibacterial activity against Xac that was better than the commercial bactericides Bismerthiazol (34.7 μg/mL) and Thiodiazole copper (41.1% μg/mL). Moreover, the in vivo antiviral activities against tobacco mosaic virus (TMV) of the target compounds were also tested. Among these compounds, the curative, protection, and inactivation activities of 5g were 49.9, 52.9, and 73.3%, respectively, which were better than that of the commercial antiviral Ribavirin (40.6, 51.1, and 71.1%, respectively). This study demonstrates that myricetin derivatives bearing amide, thioether, and 1,3,4-thiadiazole moieties can serve as potential alternative templates for the development of novel, highly efficient inhibitors against plant pathogenic bacteria and viruses.
- Ruan, Xianghui,Zhang, Cheng,Jiang, Shichun,Guo, Tao,Xia, Rongjiao,Chen, Ying,Tang, Xu,Xue, Wei
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- Myricetin derivative containing amide thioether thiadiazole, and preparation method and application of same
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The invention discloses a myricetin derivative containing amide thioether thiadiazole, of which a general formula is represented as follows, wherein R is hydrocarbyl groups, phenyl groups, substituted phenyl groups, heteroaromatic ring groups or substituted heteroaromatic ring groups. The compound has high treatment and prevention effect against tobacco mosaic virus (TMV), has high anti-plant virus activity and can be used for preparing anti-plant virus pesticides. The compound has high inhibition activity on Xanthomonas axonopodis and Xanthomonas oryzae and can be used for preparing agricultural bactericides.
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Paragraph 0051; 0052
(2018/03/28)
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- Design, synthesis and anti-bacterial evaluation of novel 1,3,4-thiadiazole derivatives bearing a semicarbazone moiety
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Novel 1,3,4-thiadiazole derivatives bearing a semicarbazone moiety were prepared and evaluated for their anti-bacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac) by performing a turbidimetre test. The products were structurally characterised by IR, 1H NMR, 13C NMR, 19F NMR and HRMS. Anti-bacterial testing showed that most of the evaluated compounds (6a-6s) exhibited excellent activity (≥74.19%) against Xoo at a concentration of 200?μg/mL, with 50% effective concentration (EC50) values ranging from 12.21 to 67.20?μg/mL, which were superior to the commercial antibacterial agent bismerthiazol (92.23?μg/mL). Among them, compound 2-((2-chloro-1H-indol-3-yl)methylene)-N-(5-((2-chlorobenzyl)thio)-1,3,4-thiadiazol-2-yl)hydrazine-1-carboxamide (6b) demonstrated good inhibitory activity against Xac (89.46% at 200?μg/mL) and Xoo (EC50 = 18.28?μg/mL); compound 2-((2-chloro-1H-indol-3-yl)methylene)-N-(5-((4-methoxybenzyl)thio)-1,3,4-thiadiazol-2-yl)hydrazine-1-carboxamide (6g) displayed excellent activity against Xoo with EC50 value of 12.21?μg/mL.
- Wan, Jinlin,Gan, Yiyuan,Hu, Weinan,Meng, Jiao,Tian, Kun,Li, Xiaoqin,Wu, Shouqun,Xu, Yang,Ouyang, Guiping,Wang, Zhenchao
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p. 443 - 450
(2018/03/12)
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- Synthesis and in vitro evaluation of west nile virus protease inhibitors based on the 1,3,4,5-tetrasubstituted 1H-Pyrrol-2(5H)-one scaffold
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West Nile virus (WNV), a member of the Flaviviridae family, is a mosquito-borne pathogen that causes a large number of human infections each year. There are currently no vaccines or antiviral therapies available for human use against WNV. Therefore, efforts to develop new chemotherapeutics against this virus are highly desired. In this study, a WNV NS2B-NS3 protease inhibitor with a 1,3,4,5-tetrasubstituted 1H-pyrrol-2(5H)-one scaffold was identified by screening a small library of nonpeptidic compounds. Optimization of this initial hit by the synthesis and screening of a focused library of compounds with this scaffold led to the identification of a novel uncompetitive inhibitor ((-)-1a16, IC50=2.2±0.7μM) of the WNV NS2B-NS3 protease. Molecular docking of the chiral compound onto the WNV protease indicates that the Renantiomer of 1a16 interferes with the productive interactions between the NS2B cofactor and the NS3 protease domain and is thus the preferred isomer for inhibition of the WNV NS2B-NS3 protease.
- Gao, Yaojun,Samanta, Sanjay,Cui, Taian,Lam, Yulin
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supporting information
p. 1554 - 1560
(2013/09/12)
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- Synthesis and in vitro biological evaluation of farnesylthiosalicylic acid derivatives as anti-tumor carcinoma agents
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Novel farnesylthiosalicylic acid (FTA) derivatives 5a-m with different substituted 1,3,4-thiadiazoles were synthesized. Compounds 5b, 5c, 5e and 5f displayed anti-tumor activities superior to FTA in most cancer cells tested. Furthermore, 5e induced tumor cell apoptosis, which was accompanied by lower Bcl-2 expression, but with higher Bax and caspase 3 expression activities in cancer cells.
- Ling, Yong,Chen, Guang Tong,Wang, Dong Geng,Li, Yu Qin,Wang, Xin Yang,Xiao, You An,Zheng, Heng
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p. 1141 - 1144,4
(2020/07/31)
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- Synthesis and in vitro antitumor activity of 1,3,4-thiadiazole derivatives based on benzisoselenazolone
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A series of novel 1,3,4-thiadiazole derivatives based on benzisoselenazolone were synthesized and evaluated for their cytotoxicity in vitro against human liver cancer cell SSMC-7721, human breast cancer cell MCF-7 and human lung cancer cell A549 by CCK-8 assay. The results showed that compounds 7e, 7f, 7h, 7k, 7l and 7m displayed good cytotoxicity against MCF-7 cell lines. Compound 7l exhibited the most potent antitumor activities among the tested compounds.
- Zhao, Jie,Chen, Bao Quan,Shi, Yan Ping,Liu, Yu Ming,Zhao, Hai Chuan,Cheng, Ji
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scheme or table
p. 817 - 819
(2012/09/21)
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- Synthesis of 2-alkyl/arylalkyl/phenacylsul-fanyl-1 -thia-3,3, 10-triaza-pentaleno[ 1,2-b]naphthalene-4,9-dione
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2,3-Dichloronaphthoquinone is condensed with 5-(alkyl/arylalkyl/ phenacylthio)-1,3,4-thiadiazol-2-amine in acetic acid to furnish a novel and hitherto unknown 2-alkyl/aralkyl/phenacylsulfanyl-1-thia-3,3a,10-triaza- pentaleno[1,2-b]naphthalene-4,9-dione. The structure of the synthesized compound has been confirmed by converting it into the corresponding reductive acetate. The structures of newly prepared compounds have been confirmed by analytical and spectral data.
- Srinivas,Rajeswar Rao
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body text
p. 115 - 118
(2010/04/29)
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- Azo dye and azo compound
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An azo dye including a compound represented by formula (I): wherein R1 represents a hydroxyl group, an aliphatic sulfonyl amino group, an aryl sulfonyl amino group, an aliphatic oxy group, an aryloxy group, or -CH(R2)(R3); R2 and R3 each represent a substituent with a a value of the Hammett's rule in the range of 0.2 or more and less than 1.4, and may be identical to or different from each other; W represents a sulfur atom or -N-(-R4)-; R4 represents a substituent; R5 represents a substituent; X, Y, and Z each represent an atom required for forming a five-membered aromatic heterocycle, where at least one atom of X, Y, and Z represents a nitrogen atom but both X and Y do not represent a carbon atom when Z represents a nitrogen atom; and R6 represents a hydrogen atom or a substituent, n represents 1 or 2, and two R6s may be coupled together to form an aromatic ring or a heteroaromatic ring when n represents 2.
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Page/Page column 17
(2008/12/07)
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- SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS
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The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed
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- Azo dyes derived from 5-membered heterocyclic amines and aromatic amine couplers containing sulfo groups, or salts thereof
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Disclosed are mono azo dyes derived from diazotized 5-membered heterocyclic amines and certain aniline, 1,2,3,4-tetrahydroquinoline, and benzomorpholine couplers containing sulfoalkyl groups. These dyes impart fast violet to blue shades on polyamide fibers and have the general formula wherein D is a thiadiazol, isothiazol, pyrazol or thiophene type radical, and the Coupler is an aniline, tetrahydroquinoline, or benzomorpholine derivative wherein a --Z--SO3 M group is attached to the nitrogen thereof, the coupler ring may contain one or more substituents selected from lower alkyl, lower alkoxy, halogen, acylamido, alkylthio or aryloxy, the remaining hydrogen of the aniline coupler may be replaced by a substituent such as lower alkyl, substituted lower alkyl, lower alkenyl, aryl, or cycloalkyl, M is Na+, K+, NH4+ or H+, and Z is a linking group such as ethylene.
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- Azo dyes from five membered ring heterocyclic amines and aniline, tetrahydroquinoline and benzomorpholine couplers containing thiosulfate alkyl groups
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Disclosed are mono azo dyes derived from diazotized 5-membered heterocyclic amines and certain aniline, 1,2,3,4-tetrahydroquinoline, and benzomorpholine couplers containing thiosulfate alkyl groups. These dyes are useful for dyeing synthetic fibers, cellulose acetate and wool, and particularly impart fast violet to blue shades on polyamide fibers, and in general, exhibit improved properties such as fastness to light, sublimation, ozone, oxides of nitrogen, perspiration, crock, and wash, and exhibit excellent build, pH stability, bloom resistance, depth of shade, leveling, migration, and the like. The dyes have the general formula: wherein D is a thiadiazol, isothiazol, pyrazol or thiophene type radical, and the Coupler is an aniline, tetrahydroquinoline, or benzomorpholine derivative wherein a --ZSSO3 M group is attached to the nitrogen thereof, the coupler ring may contain substituents such as alkyl, alkoxy, halogen, acylamido, alkylthio or aryloxy, the remaining hydrogen of the aniline coupler may be replaced by a substituent such as alkyl, substituted alkyl, alkenyl, aryl, or cycloalkyl, M is Na+, K+, NH4+ or H+, and Z is a linking group such as ethylene.
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