- Synthesis of Novel 1-(5-(Benzylsulfinyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-thiourea/urea Derivatives and Evaluation of Their Antimicrobial Activities
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A new series of 1-(5-(benzylsulfinyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-thiourea/urea derivatives (1a–j) were designed and synthesized. For the first time, (i) a new process was developed for N-methylation of 1,3,4-thiadiazole moiety using dimethyl carbonate an environmentally benign reagent in presence of N,N,N′,N′-tetramethylethylenediamine and (ii) the sulfide was selectively oxidized to sulfoxide in higher yield by using chlorine (g) in aqueous acetic acid media under mild reaction condition. The synthesized compounds (1a–j) were investigated for their antimicrobial activities. The tested compounds (1a–j) were exhibited moderate to excellent antibacterial activities against both Gram-positive and Gram-negative bacterial strains. The same compounds exhibited good antifungal activities against selected fungal strains. Particularly, the compounds 1b, 1d, 1h, and 1i were proved to be promising leads exhibiting both antibacterial and antifungal activities compared with standard drugs, ciprofloxacin, and fluconazole. The presence of 1,3,4-thiadiazole moiety has a significant role in the display of antimicrobial activity. In addition, the presence of both sulfinyl and thiourea or urea functionalities has enhanced the activity as per obtained antimicrobial activity data.
- Mannam, Madhava Rao,Srimurugan,Kumar, Pramod,R. S. Prasad
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Read Online
- Synthesis and Bioactivity Evaluation of Novel Thiochroman-4-One Derivatives Incorporating Carboxamide and 1, 3, 4-Thiadiazole Thioether Moieties
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A series of novel thiochroman-4-one derivatives incorporating carboxamide and 1, 3, 4-thiadiazole thioether moieties were synthesized. Bioassay results indicated that the EC50 values of compound 6-chloro-N-(5-(methylthio)-1, 3, 4-thiadiazol-2-yl)-4-oxothiochromane-2-carboxamide (5a) against Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv. Citri (Xac) were 24 and 30 μg/mL, respectively, which were even better than those of bismerthiazol and thiadiazole copper. Meanwhile, compound 6-methyl-4-oxo-N-(5-(propylthio)-1, 3, 4-thiadiazol-2-yl)thiochromane-2-carboxamide (5m) showed a better antifungal activity against Botrytis cinerea (B. cinerea), with an inhibition rate of 69%, than carbendazim. As far as we know, this is the first report on the antibacterial and antifungal activities of this series of novel thiochroman-4-one derivatives incorporating carboxamide and 1, 3, 4-thiadiazole thioether moieties.
- Chi, Jiyan,Li, Jie,Li, Pei,Tan, Shuming,Xiao, Lingling,Yu, Lu
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- Synthesis, characterization and biological evaluation of thiadiazole amide derivatives as nucleoside triphosphate diphosphohydrolases (NTPDases) inhibitors
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Importance of extracellular nucleotides is widely understood. These nucleotides act as ligand for P2X and P2Y receptors and modulate a variety of biological functions. However, their extracellular concentration is maintained by a chain of enzymes termed as ecto-nucleotidases. Amongst them, nucleoside triphosphate diphosphohydrolases (NTPDases) is an important enzyme family responsible for the dephosphorylation of these nucleotides. Overexpression of NTPDases leads to many pathological conditions such as cancer and thrombosis. So far, only a few NTPDase inhibitors have been reported. Considering this scarcity of (NTPDase) inhibitors, a number of thiadiazole amide derivatives were synthesized and screened against human (h)-NTPDases. Several compounds showed promising inhibitory activity; compound 5a (IC50 (μM); 0.05 ± 0.008) and 5g (IC50 (μM); 0.04 ± 0.006) appeared to be the most distinguished molecules corresponding to h-NTPDase1 and -2. However, h-NTPDase3 was the least susceptible isozyme and only three compounds (5d, 5e, 5j) strongly inhibited h-NTPDase3. Interestingly, compound 5e was recognized as the most active compound that showed dual inhibition against h-NTPDase3 as well as against h-NTPDase8. For better comprehension of binding mode of these inhibitors, most potent inhibitors were docked with their respective isozyme.
- Abbas, Sadia,Afzal, Saira,Nadeem, Humaira,Hussain, Dilawar,Langer, Peter,Sévigny, Jean,Ashraf, Zaman,Iqbal, Jamshed
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- Synthesis, carbonic anhydrase enzyme inhibition evaluations, and anticancer studies of sulfonamide based thiadiazole derivatives
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The sulfonamide-based thiadiazole derivatives (STDs) with different hydrophobic/hydrophilic substitutions were synthesized to investigate their potentials in carbonic anhydrase inhibition (CAI). The CAI activity of the STDs (4a-4h) and the mechanism of the inhibition kinetics were determined. STD 4f contained both methoxy and Cl groups at benzene ring in STD 4f showed the lowest IC50 value. The molecular docking study confirmed that STDs bind strongly with the active sites of the target protein PDBID 1V9E. With the help of Lineweaver-Burk plots, inhibition kinetics of PDBIR 1V9E protein with STDs were determined. Cytotoxicity was checked against human keratinocyte cell lines and the anticancer properties were determined against MCF-7 cell lines. The electrochemical method was used to investigate the binding study with DNA and CA enzymes. Anticancer studies showed that STDs have weak bonding ability to DNA and strong binding ability with CA. It is concluded that anticancer activity is through CAI rather than by DNA binding.
- Bahadur, Ali,Iqbal, Shahid,Muneer, Saiqa,Alsaab, Hashem O.,Awwad, Nasser S.,Ibrahium, Hala A.
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supporting information
(2022/01/03)
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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 0164-0168
(2021/10/15)
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- Synthesis and radioligand-binding assay of 2,5-disubstituted thiadiazoles and evaluation of their anticonvulsant activities
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In this study, a number of 2,5-disubstituted 1,3,4-thiadiazoles were synthesized using an appropriate synthetic route, and their anticonvulsant activity was determined by the maximal electroshock seizure (MES) test and their neurotoxicity was evaluated by the rotarod test. Additionally, their hypnotic activity was tested using the pentobarbital-induced sleep test. Compounds 7 (ED50 = 1.14 and 2.72 μmol/kg in the MES and sleep tests, respectively) and 11 (ED50 = 0.65 and 2.70 μmol/kg in the MES and sleep tests, respectively) were the most potent ones in the sleep test and anticonvulsant test, showing a comparable activity with diazepam as the reference drug. The results of in vivo studies, especially the antagonistic effects of flumazenil, and also the radioligand-binding assay confirmed the involvement of benzodiazepine (BZD) receptors in the anticonvulsant and hypnotic activity of compounds 7 and 11. Finally, the docking study of compound 11 in the BZD-binding site of the GABAA (gamma-aminobutyric acid) receptor confirmed the possible binding of the compound to the BZD receptors. We concluded that the novel 1,3,4-thiadiazole derivatives with appropriate substitution at positions 2 and 5 of the heterocyclic ring had a good affinity to BZD receptors and showed significant efficacy in the pharmacological tests.
- Toolabi, Mahsa,Khoramjouy, Mona,Aghcheli, Ayoub,Ayati, Adileh,Moghimi, Setareh,Firoozpour, Loghman,Shahhosseini, Soraya,Shojaei, Rouhallah,Asadipour, Ali,Divsalar, Kouros,Faizi, Mehrdad,Foroumadi, Alireza
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- Design, synthesis, and biological evaluation of 1-(5-(benzylthio)-1,3,4-thiadiazol-2-yl)-3-phenylurea derivatives as anticancer agents
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A novel series of 1-(5-(benzylthio)-1,3,4-thiadiazol-2-yl)-3-phenylurea derivatives (5a–l) were designed and synthesized as sorafenib analogs. The in vitro cytotoxicity effects of synthesized compounds were evaluated against four different human cancer cells including MCF-7, HepG2, A549, and HeLa cell lines. The biological results showed that most of the compounds significantly prevented the proliferation of tested cancer cells. In particular, 2-F, 4-Cl, and 2,6-diF substituted derivatives (5d, 5g, and 5k) showed promising activities, especially against Hela cancer cells (IC50 = 0.37, 0.73 and 0.95 μM, respectively) which were significantly more potent than sorafenib as the reference drug (IC50 = 7.91 μM). Flow cytometry analysis revealed that the prototype compounds (5d, 5g, and 5k) significantly induced apoptotic cell death in HeLa cancer cells and blocked the cell cycle at the sub-G1 phase. Moreover, in silico docking study confirmed the binding of the prototype compound to the active site of VEGFR-2.
- Aghcheli, Ayoub,Toolabi, Mahsa,Ayati, Adileh,Moghimi, Setareh,Firoozpour, Loghman,Bakhshaiesh, Tayebeh Oghabi,Nazeri, Elahe,Norouzbahari, Maryam,Esmaeili, Rezvan,Foroumadi, Alireza
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p. 2000 - 2010
(2020/08/26)
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- Synthesis and biological assessment of ciprofloxacin-derived 1,3,4-thiadiazoles as anticancer agents
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The quinolone-3-carboxylic acid scaffold is essential structure for antibacterial activity of fluoroquinolones such as ciprofloxacin. Modification of 3-carboxylic functionality in this structure can be used for switching its activity from antibacterial to anticancer. Accordingly, a series of C-3 modified ciprofloxacin derivatives containing N-(5-(benzylthio)-1,3,4-thiadiazol-2-yl)-carboxamide moiety was synthesized as novel anticancer agents. Most of compounds showed significant activity against MCF-7, A549 and SKOV-3 cancer cells in the MTT assay. In particular, compounds 13a-e and 13g were found to be as potent as standard drug doxorubicin against MCF-7 cell line (IC50s = 3.26–3.90 μM). Furthermore, the 4-fluorobenzyl derivatives 13h and 14b with IC50 values of 3.58 and 2.79 μM exhibited the highest activity against SKOV-3 and A549 cells, being as potent as doxorubicin. Two promising compounds 13e and 13g were further tested for their apoptosis inducing activity and cell cycle arrest. Both compounds could significantly induce apoptosis in MCF-7 cells, while compound 13e was more potent apoptosis inducer resulting in an 18-fold increase in the proportion of apoptotic cells at the IC50 concentration in MCF-7 cells. The cell cycle analysis revealed that compounds 13e and 13g could increase cell portions in the sub-G1 phase, inducing oligonucleosomal DNA fragmentation and apoptosis confirmed by comet assay.
- Ahadi, Hamideh,Shokrzadeh, Mohammad,Hosseini-khah, Zahra,Ghassemi barghi, Nasrin,Ghasemian, Majid,Emadi, Elnaz,Zargari, Mehryar,Razzaghi-Asl, Nima,Emami, Saeed
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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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- Discovery and development of substituted thiadiazoles as inhibitors of Staphylococcus aureus Sortase A
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High-throughput screening of small-molecule libraries has led to the identification of thiadiazoles as a new class of inhibitors against Staphylococcus aureus sortase A (SrtA). N-(5-((4-nitrobenzyl)thio)-1,3,4-thiadiazol-2-yl)nicotinamide (IC50
- Wehrli, Patrick M.,Uzelac, Ivana,Olsson, Thomas,Jacso, Tomas,Tietze, Daniel,Gottfries, Johan
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- Ultrasound-assisted improved synthesis of 5-(benzylthio)-1,3,4-thiadiazol-2-amine derivatives: an experimental and computational study
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The main objects of this study are: (1) to propose alternative efficient methods for the synthesis of 5-amino-1,3,4-thiadiazole-2-thiol and 5-(benzylthio)-1,3,4-thiadiazol-2-amine derivatives, (2) to investigate the reactions and the chemical species which take place in the investigated reactions computationally via density functional theory (DFT) calculations, (3) to make a comparison between experimental and computationally obtained data, and (4) to make a comparison between the computational methods to find out the best computational technique to simulate the investigated molecules and reactions. The study consists of two parts. In the first part, synthesis of 5-amino-1,3,4-thiadiazole-2-thiol and 5-(benzylthio)-1,3,4-thiadiazol-2-amine derivatives have been carried out. For both syntheses, it has been proposed that the reactions can be carried out effectively with the use of ultrasound. To the best of our knowledge, this is the first use of ultrasound for both reactions. The results showed that ultrasound can increase the efficiency of the investigated reactions and can be a good alternative to conventional methods. In the second part of the study, some DFT calculations have been performed on the chemical species which take place in the investigated reactions. In computational studies, seven different basis sets have been used. In this second part, comparisons have been made (1) between experimental and computationally obtained data, and (2) between the computational techniques to reveal the best method for the investigated molecules.
- Erdogan, Taner
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p. 899 - 912
(2019/04/08)
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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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- 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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- Containing substituted 1, 3, 4-thiadiazole sulfide pyrazole amide and pyrazole imine derivatives and preparation method and application
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The invention discloses pyrazole amide and pyrazole imine derivatives containing substituted 1, 3, 4-thiadiazole thioether as well as a preparation method and an application of the derivatives. The compounds have the structures as shown in formulae (I) and (II). The preparation method comprises the following steps: by taking substituted hydrazine as an initial raw material, carrying out closed loop, chlorine formylation, oxidation and chloro reaction to obtain pyrazole acyl chloride; carrying out a reaction on 2-amino-5-mercapto-1, 3, 4-thiadiazole and substituted benzyl chloride to obtain 2-amino-5-substituted 1, 3, 4-thiadiazole thioether; and then, carrying out a substitution reaction on 2-amino-5-substituted 1, 3, 4-thiadiazole thioether and substituted pyrazole acyl chloride to obtain the pyrazole amide compound (I) containing substituted 1, 3, 4-thiadiazole thioether; by taking substituted hydrazine as an initial raw material, carrying out closed loop and chlorine formylation to obtain pyrazole aldehyde; carrying out an additive elimination reaction on pyrazole aldehyde and 2-amino-5-mercapto-1, 3, 4-thiadiazole under a backflow condition of anhydrous ethanol to obtain 2-substituted pyrazole imidogen-5-mercapto-1, 3, 4-thiadiazole; and then carrying out a reaction on 2-substituted pyrazole imidogen-5-mercapto-1, 3, 4-thiadiazole and substituted benzyl chloride to generate the pyrazole imine compound (II) containing substituted 1, 3, 4-thiadiazole thioether. The compounds disclosed by the invention have a good inhibiting effect on tobacco mosaic virus and can be used for preparing anti-plant virus drugs.
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Paragraph 0143; 0152; 0153
(2016/11/24)
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- Compositions and methods for the suppression of carbonic anhydrase activity
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The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for treating or preventing or modulating carbonic anhydrase activity in a disease may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of glaucoma, epileptic seizures, Idiopathic intracranial hypertension (pseudotumor cerebri), altitude sickness, cystinuria, periodic paralysis and dural ectasia, congestive heart failure, drug induced edema, diuretic, intermittent claudication resulting from obstructed arteries in the limbs, and vascular dementia.
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Page/Page column 27
(2016/04/05)
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- Molecular docking studies and biological evaluation of 1,3,4-thiadiazole derivatives bearing Schiff base moieties as tyrosinase inhibitors
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1,3,4-Thiadiazole derivatives bearing Schiff base moieties were designed, synthesized, and their tyrosinase inhibitory activities were evaluated. Some compounds displayed potent tyrosinase inhibitory activities, especially, 4-(((5-mercapto-1,3,4-thiadiazol-2-yl)-imino)methyl)-2-methoxy-phenol (14) exhibited superior inhibitory effect to the other compounds with an IC50 value of 0.036?μM. The structure–activity relationships (SARs) were preliminarily discussed and docking studies showed compound 14 had strong binding affinity to mushroom tyrosinase. Hydroxy might be the active groups. The inhibition kinetics study revealed that compounds (13 and 14) inhibited tyrosinase by acting as uncompetitive inhibitors. The LD50 value of the compound 14 was 5000?mg/kg.
- Tang, Junyuan,Liu, Jinbing,Wu, Fengyan
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- Identification of novel thiadiazoloacrylamide analogues as inhibitors of dengue-2 virus NS2B/NS3 protease
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Dengue virus is endemic throughout tropical and subtropical regions, and cause severe epidemic diseases. The NS2B/NS3 protease is a promising drug target for dengue virus. Herein, we report the discovery and modification of a novel class of thiadiazoloacrylamide derivatives with potent inhibitory activity against the NS2B/NS3 protease. Thiadiazolopyrimidinone 1 was firstly determined as a new chemical structure against NS2B/NS3 from a commercial compound library. Then, we sought to identify similar compounds with the thiadiazoloacrylamide core that would exhibit better activity. A series of analogues were synthesized and fourteen of them were identified with strong inhibitory activities, in which the nitrile group in the linker part was discovered as an essential group for the inhibitory activity. The best of these (8b) demonstrated an IC50 at 2.24 μM based on in vitro DENV2 NS2B-NS3pro assays.
- Liu, Hailong,Wu, Ruoming,Sun, Yanyan,Ye, Yan,Chen, Jing,Luo, Xiaomin,Shen, Xu,Liu, Hong
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p. 6344 - 6352
(2014/12/11)
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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 cytotoxic evaluation of new colchicine derivatives bearing 1,3,4-thiadiazole moieties
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In search of novel anticancer agents, a series of N-methyl colchiceinamide derivatives (7a-7i) containing 1,3,4-thiadiazole moieties were synthesized, and their structures were confirmed by spectral analysis. Cytotoxicity of these compounds was evaluated by MTT assay in vitro against four human tumor cell lines, i.e. A2780, A549, BEL7402, and MCF-7. The results indicated that most of the derivatives showed significant anticancer activities, particularly, compounds 7h and 7i showed more potent cytotoxic activities of all screened cancer cells than colchicine.
- Shen, Li-Hong,Li, Hong-Yu,Shang, Hui-Xia,Tian, Shu-Ting,Lai, Yi-Sheng,Liu, Li-Jie
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p. 299 - 302
(2013/07/19)
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- COMPOSITIONS AND METHODS FOR SUPPRESSION OF CARBONIC ANHYDRASE ACTIVITY
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Provided are the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for treating or preventing or modulating carbonic anhydrase activity in a disease may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral admimstration, syrup, or injection. Such compositions may be used to treatment of glaucoma, epileptic seizures, Idiopathic intracranial hypertension (pseudotumor cerebri), altitude sickness, cystinuria, periodic paralysis and dural ectasia, congestive heart failure, drug induced edema, diuretic, intermittent claudication resulting from obstructed arteries in the limbs, and vascular dementia.
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Paragraph 0094; 0095
(2013/12/03)
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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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- Discovery and SAR of 1,3,4-thiadiazole derivatives as potent Abl tyrosine kinase inhibitors and cytodifferentiating agents
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A series of substituted benzoylamino-2-[(4-benzyl)thio]-1,3,4-thiadiazoles has been discovered as potent Abl tyrosine kinase inhibitors. Molecular docking simulations on the Abl tyrosine kinase were conducted in order to rationalize the SAR of the synthesized inhibitors. The most active compound identified from the enzymatic screening (6a) showed interesting inhibitory activity on Imatinib-sensitive murine myeloid 3B clone and Bcr-Abl-independent Imatinib-resistant leukemia cells. Surprisingly, 6a was also proved to act as differentiating inducers in human promyelocytic leukemia cells (HL-60).
- Radi, Marco,Crespan, Emmanuele,Botta, Giorgia,Falchi, Federico,Maga, Giovanni,Manetti, Fabrizio,Corradi, Valentina,Mancini, Manuela,Santucci, Maria Alessandra,Schenone, Silvia,Botta, Maurizio
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p. 1207 - 1211
(2008/09/20)
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- Synthesis and antibacterial activity of N-(5-benzylthio-1,3,4-thiadiazol-2- yl) and N-(5-benzylsulfonyl-1,3,4-thiadiazol-2-yl)piperazinyl quinolone derivatives
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A series of N-(5-benzylthio-1,3,4-thiadiazol-2-yl) and N-(5-benzylsulfonyl- 1,3,4-thiadiazol-2-yl) derivatives of piperazinyl quinolones was synthesized and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. Some of these derivatives exhibit high activity against Gram-positive bacteria; Staphylococcus aureus and Staphylococcus epidermidis, comparable or more potent than their parent N-piperazinyl quinolones norfloxacin and ciprofloxacin as reference drugs. The SAR of this series indicates that both the structure of the benzyl unit and the S or SO2 linker dramatically impact antibacterial activity.
- Foroumadi, Alireza,Emami, Saeed,Hassanzadeh, Abdolreza,Rajaee, Majid,Sokhanvar, Kazem,Moshafi, Mohammad Hassan,Shafiee, Abbas
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p. 4488 - 4492
(2007/10/03)
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- Synthesis of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives and evaluation of their antidepressant and anxiolytic activity
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Recently a series of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives bearing different substituents were synthesized and screened pharmacologically in order to evaluate their central nervous system activity. The purpose of this study was to evaluate the effects of the title compounds on CNS activity by varying the substituents in the thiadiazole moiety. It was found that some of these compounds possess marked antidepressant and anxiolytic properties comparable in efficiency to the reference drugs Imipramine and Diazepam. The most potent compound 3k was further investigated to complete its pharmacological profile with respect to undesired side effects. Behavioral results showed that 3k is a very promising compound, characterized by a mixed antidepressant-anxiolytic activity accompanied by a therapeutic dose range that is essentially 2 orders of magnitude less than that at which side effects such as sedation and amnesia are evident.
- Clerici,Pocar,Guido,Loche,Perlini,Brufani
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p. 931 - 936
(2007/10/03)
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- Thiadiazoleamide derivative and anti-ulcer drug
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A thiadiazoleamide derivative or a salt thereof expressed by the following Formula 1: STR1 wherein each of R1 and R2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylamino group or an alkenyloxy gro
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- Agricultural-horticultural fungicide employing 5H-1,3,4-thiadiazolo[3,2-a]py
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It is disclosed that a class of 5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one derivatives exhibit remarkable fungicidal activities for cucumber gray mold, cucumber downy mildew, Alternaria sooty spot of Chinese mustard, rice blast, etc.
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- Azo dyes from 2-amino-5-alkylthio-1,3,4-thiadiazoles and N-acyloxyalkyl-m-acylamidoanilines
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Disclosed are novel azo dyes from 2-amino-5-alkylthio-1,3,4-thiadiazoles and N-acyloxyalkyl-m-acylamidoanilines. These dyes are useful for dyeing synthetic hydrophobic fibers and particularly polyester. The dyes have the general formula: STR1 wherein R is alkyl; X is hydrogen, or alkyl; R1 is hydrogen, alkyl, aralkyl or STR2 R2 is alkyl, aryl, aralkyl, cycloalkyl, alkylamino, or arylamino; and Ac is formyl or alkanoyl; and wherein R and the alkyl, alkylene, aryl and cycloalkyl moieties of R2 and the alkanoyl moiety of Ac may be substituted with a large variety of groups such as --OH, OOC-alkyl, --COO--alkyl, succinimido, phthalimido, alkoxy, carbamoyl and the like.
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- Azo dyes from 2-amino-5-organothio-1,3,4-thiadiazoles and N-cyanoethyl-m-acylamidoanilines
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Disclosed are novel azo dyes from 2-amino-5-organothio-1,3,4-thiadiazoles and N-cyanoethyl-m-acylamidoanilines. These dyes are useful for dyeing synthetic hydrophobic fibers and particularly polyester. The dyes have the general formula: STR1 wherein R is alkyl, aryl or cycloalkyl; X is hydrogen, or alkyl; R1 is hydrogen, alkyl or aralkyl; and R2 is formyl or alkanoyl; and wherein the alkyl, aryl and cycloalkyl moieties of R and R2 may be substituted with a large variety of groups such as --OH, OOC-alkyl, --COO-alkyl, succinimido, phthalimido, alkoxy, carbamoyl and the like.
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