- Novel panaxadiol triazole derivatives induce apoptosis in HepG-2 cells through the mitochondrial pathway
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In this study, we introduced 1, 2, 4-triazole groups into panaxadiol (PD) to obtain 18 panaxadiol triazole derivatives. Five cancer cells and one normal cell were evaluated for cytotoxicity by MTT assay. The results showed that most of the derivatives could inhibit cancer cell proliferation, and the anti-proliferative activity of compound A1 was the most significant. For HepG-2 cells, the IC50 value was 4.21 ± 0.54 μM, which was nearly 15 times higher than the activity of PD. Further studies showed that compound A1 could induce apoptosis in HepG-2 cells, and could enhance the expression of Cl-caspase-3, Cl-caspase-9 and Cl-PARP. Moreover, Western blot analysis showed that after treating HepG-2 cells with compound A1, the expression of p53 protein was increased and the ratio of Bax/Bcl-2 was gradually increased. The cytoplasmic Bax is then translocated to the mitochondria, causing the release of Cyt c protein. Therefore, the results indicate that compound A1 induces apoptosis through the mitochondrial pathway and can be used the potential to develop new anti-proliferative agents.
- Xiao, Shengnan,Wang, Xude,Xu, Lei,Li, Tao,Cao, Jiaqing,Zhao, Yuqing
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- Dammarane sapogenin derivative and preparation method and application thereof
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The invention belongs to the technical field of medicines, and relates to a dammarane sapogenin derivative and a preparation method and application thereof. A series of dammarane sapogenin derivativesare obtained by combining dammarane sapogenins from plants with different groups. Anticancer activity evaluation and anticancer activity mechanism research are carried out on the derivative, and results show that the prepared dammarane sapogenin derivative has a remarkable anticancer effect, has no toxic effect on normal cells and can be used for preparing drugs for treating cancers.
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- Discovery of [1,2,4]triazole derivatives as new metallo-β-lactamase inhibitors
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The emergence and spread of metallo-β-lactamase (MBL)-mediated resistance to β-lactam antibacterials has already threatened the global public health. A clinically useful MBL inhibitor that can reverse β-lactam resistance has not been established yet. We here report a series of [1,2,4]triazole derivatives and analogs, which displayed inhibition to the clinically relevant subclass B1 (Verona integron-encoded MBL-2) VIM-2. 3-(4-Bromophenyl)-6,7-dihydro-5H-[1,2,4]triazolo [3,4-b][1,3]thiazine (5l) manifested the most potent inhibition with an IC50 (half-maximal inhibitory concentration) value of 38.36 μM. Investigations of 5l against other B1 MBLs and the serine β-lactamases (SBLs) revealed the selectivity to VIM-2. Molecular docking analyses suggested that 5l bound to the VIM-2 active site via the triazole involving zinc coordination and made hydrophobic interactions with the residues Phe61 and Tyr67 on the flexible L1 loop. This work provided new triazole-based MBL inhibitors and may aid efforts to develop new types of inhibitors combating MBL-mediated resistance.
- Yuan, Chen,Yan, Jie,Song, Chen,Yang, Fan,Li, Chao,Wang, Cheng,Su, Huiling,Chen, Wei,Wang, Lijiao,Wang, Zhouyu,Qian, Shan,Yang, Lingling
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- Click 1,4-regioselective synthesis, characterization, and antimicrobial screening of novel 1,2,3-triazoles tethering fluorinated 1,2,4-triazole and lipophilic side chain
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Base-catalyzed alkylation of 5-(4-fluorophenyl)-2,4-dihydro-1,2,4-triazole-3-thione (3) with one or two equivalents of propargyl bromide in presence of triethylamine as catalyst selectively produced the thiopropargylated 1,2,4-triazole 7 in 90?% yield. Un
- Rezki, Nadjet,Mayaba, Mariem Mohammed,Al-blewi, Fawzia Faleh,Aouad, Mohamed Reda,El Ashry, El Sayed Helmi
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p. 995 - 1011
(2017/02/10)
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- Synthesis and biological evaluation of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione as antimycobacterial agents
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Resistance among dormant mycobacteria leading to multidrug-resistant and extremely drug-resistant tuberculosis is one of the major threats. Hence, a series of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione derivatives (4a–5c) have been synthesized and screened for their antitubercular activity against Mycobacterium tuberculosis H37Ra (H37Ra). The triazolethiones 4b and 4v showed high antitubercular activity (both MIC and IC50) against the dormant H37Ra by in vitro and ex vivo. They were shown to have more specificity toward mycobacteria than other Gram-negative and Gram-positive pathogenic bacteria. The cytotoxicity was almost insignificant up to 100?μg/ml against THP-1, A549, and PANC-1 human cancer cell lines, and solubility was high in aqueous solution, indicating the potential of developing these compounds further as novel therapeutics against tuberculosis infection.
- Sonawane, Amol D.,Rode, Navnath D.,Nawale, Laxman,Joshi, Rohini R.,Joshi, Ramesh A.,Likhite, Anjali P.,Sarkar, Dhiman
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p. 200 - 209
(2017/07/13)
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- 5H - [1, 2, 4] triazole [5, 1 - b] [1, 3] thiazine derivative and application thereof
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The invention discloses a 5H-[1, 2, 4] triazole [5, 1-b] [1, 3] thiazide derivative with a general formula I, or a pharmaceutically acceptable aquo-complex and salts of the derivative; the derivative comprises a stereisomer or a tautomer, wherein R1 and R2 in the formula I are respectively independent hydrogen, methyl, halogen, hydroxyl, methoxyl, acetyl, propiono, nitro or alkoxy. The 5H-[1, 2, 4] triazole [5, 1-b] [1, 3] thiazide derivative has an obvious inhibiting effect on acetylcholin esterase, and is used for improving the memory of a patient suffering from dementia and Alzheimer's disease. The invention also relates to a preparation method of the compound and an application in preparation of a drug for treating Senile Dementia.
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- 1,2,4-TRIAZOLE, 1,3,4-OXADIAZOLE, AND 1,3,4-THIADIAZOLE DERIVATIVES AND THEIR ANTIMYCOBACTERIAL ACTIVITY
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Disclosed herein are novel five membered heterocyclic compounds of Formula (I) wherein, X is S or SO2; n is 0, 1; m is1 or 2; Y is N, O or S; R2 independently represents H or alkyl or halo selected from -CI, -F; or -CF3, or -OH or-NH2 or - NO2; and R1 independently represents H or C1 to C5 straight or branched chain alkyl, alkenyl, alkynyl or a group -(CH2)5Br or pyrrolidine or - NHR' wherein R' is H or isopropyl or (II) or (III) which selectively act against dormant pathogenic tuberculi bacilli and exhibit antiproliferative activities and for treatment of a disease or disorder associated with GroEL1/GroEL2 activity. The invention relates to a process for preparation of novel five membered heterocyclic compounds of Formula I and to pharmaceutical compositions thereof.
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Paragraph 053
(2016/07/27)
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- Synthesis, characterization, and anticancer studies of S and N alkyl piperazine-substituted positional isomers of 1,2,4-triazole derivatives
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A series of 3-[3-[4-(substituted)-1-cyclicamine] propyl]thio-5- substituted[1,2,4]triazoles (8a-m) and 2-[3-[4-(substituted)-1-cyclicamine] propyl]-5-(substituted)-2,4-dihydro-3H[1,2,4]triazole-3-thiones (9a-h) were synthesized with good yields starting from corresponding carboxylic acids using two different methods. The cytotoxicity studies of these derivatives were studied against five different human cancer cell lines. Six compounds had shown good anticancer activity. The triazole derivatives, 9d, 8j, and 8i were most potent particularly against U937 and HL-60 cells. The cytotoxic potency of the compounds varied between the cell lines suggesting that a structural property of these compounds as possible determinant of their biological activity. Springer Science+Business Media 2013.
- Murty,Ram, Kesur R.,Rao, B. Ramalingeswara,Rao, Rayudu Venkateswara,Katiki, Mohana Rao,Rao, Janapala Venkateswara,Pamanji,Velatooru
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p. 1661 - 1671
(2014/05/06)
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- Synthesis of new S-alkylated-3-mercapto-1,2,4-triazole derivatives bearing cyclic amine moiety as potent anticancer agents
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A series of 3-[3-[4-(Substituted)-1-cyclicamine]propyl]thio-5- substituted[1,2,4]triazoles (8a-j) were synthesized with good yields starting from corresponding carboxylic acids. The cytotoxicity studies of these derivatives were studied against five different human cancer cell lines. Three compounds had shown good anticancer activity. The triazole derivatives, 8i and 8j were most potent particularly against U937 and HL-60 cells. The cytotoxic potency of the compounds varied between the cell lines suggesting that a structural property of these compounds as possible determinants of their biological activity.
- Murty,Ram, Kesur R.,Rao, Rayudu Venkateswara,Yadav,Rao, Janapala Venkateswara,Pamanji,Velatooru
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experimental part
p. 276 - 281
(2012/06/18)
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- THIAZOLTRIAZOLES AND THIAZOLIMIDAZOLES AS ANTAGONISTS OF THE MGLUR5 RECEPTOR
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This invention relates to novel thiazolotriazole and thiazoloimidazole derivatives of formula (I). The invention also relates to the use of the derivatives in treating diseases and conditions wherein antagonism of the mGluR5 receptor is beneficial, in particular substance related disorders. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.
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Page/Page column 37
(2009/09/04)
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- Condensed heterocyclic systems containing bridgehead nitrogen atom: Synthesis and antimicrobial activity of s-triazolo[3, 4-b][1, 3, 4] thiadiazines, thiazolo[3, 2-b]-s-triazoles and isomeric thiazolo[2, 3-c]-s-triazoles
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The synthesis of 2-p-fluorophenyl-5-p-bromophenylthiazolo[3, 2-b-s-triazole 5 has been achieved starting from 3-p-fluorophenyl-5-mercapto-s-triazole 3. Compound 3 on condensation with p-bromophenacyl bromide gave the ketone 4 which on cyclization with PPA
- Mohan, Jag
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p. 403 - 406
(2007/10/03)
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- Fluorine containing heterocyclic compounds: Synthesis of 6-substituted-2-substituted-aryl-1,2,4-triazolo[5,1-b] 1,3,5-thiadiazin-7-one derivatives
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A group of heterocylic compounds of condensed triazole-thiadiazinone derivatives containing fluorine (IIIa-h) were obtained in good yields by the reactions of the corresponding 3-aryl-5-mercapto-1,2,4-triazole (IIa-d) with N-substituted-N-chloromethyl carbamoyl chloride (I) in the presence of potassium carbonate in N,N-dimethylformamide at room temperature. Cyclization of 3-(2,3,5-trifluoro-4-methoxyl)phenyl-5-mercapto-1,2,4-triazole (IIe) with I was difficult due to an intermolecular hydrogen bond of IIe. The structures of the compounds synthesized were confirmed by IR, MS, 1H NMR and elemental analyses. Fungicidal and insecticidal activities of these compounds were also studied.
- Liu, Suyou,Qian, Xuhong,Song, Gonghua,Chen, Jing,Chen, Weidong
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p. 111 - 115
(2007/10/03)
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- Evaluation of antimycobacterial and anticonvulsant activities of new 1- (4-fluorobenzoyl)-4-substituted-thiosemicarbazide and 5-(4-fluorophenyl)-4- substituted-2,4-dihydro-3H,1,2,4-triazole-3-thione derivatives
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Some new 1-(4-fluorobenzoyl)-4-alkyl/arylthiosemicarbazide (2a-g), 5- (4-fluorophenyl)4-alkyl/aryl-2,4-dihydr-3H-1,2,4-triazole-3-thione (3a-g) derivatives, 3-(benzylthio)-5-(4-fluorophenyl)-4-phenyl-4H-1,2,4-triazole (3h) and 2-acetyl-5-(4-fluorophenyl)-
- Gulerman,Rollas
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p. 691 - 695
(2007/10/03)
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- Synthesis and structure-activity relationship of C-3 substituted triazolylthiomethyl cephems
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A series of C-3 substituted triazolylthiomethyl cephems with an aminothiazolemethoxyiminoacetamido side chain at C-7 were synthesized and tested for antimicrobial activity against clinically-relevant isolates. The compound with 3-pyridyl at C-5 and methyl at N-4 of the triazole moiety exhibited good antibacterial activity against both Gram-positive and Gram-negative bacteria, with the exception of pseudomonas spp against which none of the derivatives exhibited favorable activity.
- Singh,Fiakpui,Galpin,Stewart,Singh,Micetich
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p. 301 - 309
(2007/10/03)
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- 5-Aryl-3-(alkylthio)-4H-1,2,4-triazoles as selective antagonists of strychnine-induced convulsions and potential antispastic agents
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Selected examples from three series of isomeric (alkylthio)-1,2,4- triazoles were prepared and examined for anticonvulsant activity versus strychnine-, maximal-electroshock-, pentylenetetrazole-, and 3- mercaptopropionic-acid-induced seizures in mice. A n
- Kane,Staeger,Dalton,Miller,Dudley,Ogden,Kehne,Ketteler,McCloskey,Senyah,Chmielewski,Miller
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p. 125 - 132
(2007/10/02)
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- 2,4-Dihydro-3H-1,2,4-triazole-3-thiones as Potential Antidepressant Agents
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A series of 5-aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones was prepared and evaluated for potential antidepressant activity.Members of this series were generally prepared by the alkaline ring closures of the corresponding 1-aroylthiosemicarbazides.Several
- Kane, John M.,Dudley, Mark W.,Sorensen, Stephen M.,Miller, Francis P.
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p. 1253 - 1258
(2007/10/02)
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