- Synthesis, in vitro thymidine phosphorylase activity and molecular docking study of thiadiazole bearing isatin analogs
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A series of seventeen analogs (1─17) were synthesized and characterized through different spectroscopic techniques such as 1H, 13CNMR, HR-EI-MS and were evaluated for in vitro thymidine phosphorylase inhibition. All compounds showed excellent to good thymidine phosphorylase activity having IC50 value ranging between 4.10 ± 0.20 and 54.60 ± 1.40?μM when compared with standard drug 7-deazaxanthine (IC50 = 38.68 ± 1.12?μM). Among the series, compounds 1 (IC50 = 8.30 ± 0.30?μM), 6 (IC50 = 6.30 ± 0.10?μM), 11 (IC50 = 8.40 ± 0.30?μM) and 16 (IC50 = 4.10 ± 0.20?μM) were found more potent. Potent compounds were further subjected to molecular docking study to identify their interactions with the active site of amino acid. Structure activity relationship was done for all analogs mostly based on substitution pattern on phenyl and isatin rings. Graphic abstract: [Figure not available: see fulltext.]
- Ullah, Hayat,Liaqat, Anjum,Khan, Qudrat Ullah,Taha, Muhammad,Khan, Fahad,Rahim, Fazal,Uddin, Imad,Rehman, Zia Ur
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p. 213 - 224
(2021/09/09)
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- New biologically dynamic hybrid pharmacophore triazinoindole-based-thiadiazole as potent α-glucosidase inhibitors: In vitro and in silico study
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Triazinoindole bearing thiadiazole derivatives (1–25) have been synthesized and characterized through different spectroscopic techniques such as 1H, 13C-NMR and HREI-MS. The purpose of the study was to investigate the anti-diabetic activity of the synthesized triazinoindole bearing thiadiazole derivatives by inhibition of α-glucosidase. All synthesized analogues showed outstanding inhibition of α-glucosidase enzyme with IC50 values ranging from 2.5 ± 0.10 to 38.10 ± 0.10 μM as compared to the standard drug acarbose (IC50 = 38.45 ± 0.80 μM). Analogue 4 (IC50 = 2.5 ± 0.10 μM) was identifies as the most potent analogue in the series with fifteen folds more active than standard acarbose. Structure activity relationship (SAR) studies suggested that α-glucosidase activities of triazinoindole bearing thiadiazole are primarily dependent upon on number and position of different substitutions present on phenyl parts. Molecular docking study were conducted of the optimized compounds (i.e., compound 4, 6, and 3 etc. using MOE default parameters), the results revealed that compound 4, 6, and 3 showed numerous key interactions with the target protein, which indicate the high potential of these compounds against the target compound. All these compounds were screened for cytotoxic activity against normal normal Vero cell line and found non-toxic.
- Ahmad, Nisar,Alshehri, Sultan,Ghoneim, Mohammed M.,Iqbal, Naveed,Khan, Aftab Ahmad,Khan, Khalid Mohammed,Rahim, Fazal,Rehman, Wajid,Salahuddin, Mohammed,Shah, Syed Adnan Ali,Taha, Muhammad,Wadood, Abdul
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- N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound
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The invention belongs to the technical field of medicines, relates to a compound with antitumor activity and a specific chemical structure, and in particular relates to an N-((6, 7-dimethoxyquinoline-4-yl) oxy) methyl)-N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound and a preparation method and an application thereof. The structural general formula of the compound is shown in the specification, wherein an R group is mono-substituted or double-substituted phenyl, fluorophenyl, chlorphenyl, bromophenyl, benzyl, benzyloxy, benzene nitro or trifluoromethyl substituted at 2-position, 3-position or 4-position. Pharmacological studies show that the compound provided by the invention has a relatively remarkable proliferation inhibition effect on HER-2 positive breast cancer cells SK-Br-3, the effect is obviously superior to that of HER-2 negative breast cancer cells MCF-7, the compound can be used for preparing antitumor drugs, and a new way is opened up for deep research and development of tumor drugs in the future. The preparation method provided by the invention is simple and feasible, relatively high in yield and easy for large-scale production.
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Paragraph 0051; 0057; 0105-0107
(2021/06/09)
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- Synthesis and antiviral activity of novel 1,3,4-thiadiazole inhibitors of DDX3x
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The human ATPase/RNA helicase X-linked DEAD-box polypeptide 3 (DDX3X) emerged as a novel therapeutic target in the fight against both infectious diseases and cancer. Herein, a new family of DDX3X inhibitors was designed, synthesized, and tested for its inhibitory action on the ATPase activity of the enzyme. The potential use of the most promising derivatives it has been investigated by evaluating their anti-HIV-1 effects, revealing inhibitory activities in the low micromolar range. A preliminary ADME analysis demonstrated high metabolic stability and good aqueous solubility. The promising biological profile, together with the suitable in vitro pharmacokinetic properties, make these novel compounds a very good starting point for further development.
- Brai, Annalaura,Ronzini, Stefania,Riva, Valentina,Botta, Lorenzo,Zamperini, Claudio,Borgini, Matteo,Trivisani, Claudia Immacolata,Garbelli, Anna,Pennisi, Carla,Boccuto, Adele,Saladini, Francesco,Zazzi, Maurizio,Maga, Giovanni,Botta, Maurizio
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- Synthesis, in vitro and in silico Anti-Proliferative Studies of Novel Piperiene-Oxadiazole and Thiadiazole Analogs
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Piperine is a component of pepper which has earlier been reported as anticancer active compound. This work is emphasized on the design and synthesis of new hybrid piperine analogs by coupling piperine with the amine group of oxadiazoles and thiadiazoles.
- Amperayani,Parimi
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p. 2301 - 2307
(2020/01/08)
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- Synthesis, in vitro α-glucosidase inhibitory potential and molecular docking study of thiadiazole analogs
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α-Glucosidase is a catabolic enzyme that regulates the body's plasma glucose levels by providing energy sources to maintain healthy functioning. 2-Amino-thiadiazole (1–13) and 2-amino-thiadiazole based Schiff bases (14–22) were synthesized, characterized by 1H NMR and HREI-MS and screened for α-glucosidase inhibitory activity. All twenty-two (22) analogs exhibit varied degree of α-glucosidase inhibitory potential with IC50 values ranging between 2.30 ± 0.1 to 38.30 ± 0.7 μM, when compare with standard drug acarbose having IC50 value of 39.60 ± 0.70 μM. Among the series eight derivatives 1, 2, 6, 7, 14, 17, 19 and 20 showed outstanding α-glucosidase inhibitory potential with IC50 values of 3.30 ± 0.1, 5.80 ± 0.2, 2.30 ± 0.1, 2.70 ± 0.1, 2.30 ± 0.1, 5.50 ± 0.1, 4.70 ± 0.2, and 5.50 ± 0.2 μM respectively, which is many fold better than the standard drug acarbose. The remaining analogs showed good to excellent α-glucosidase inhibition. Structure activity relationship has been established for all compounds. The binding interactions of these compounds were confirmed through molecular docking.
- Javid, Muhammad Tariq,Rahim, Fazal,Taha, Muhammad,Rehman, Haseeb Ur,Nawaz, Mohsan,wadood, Abdul,Imran, Syahrul,Uddin, Imad,Mosaddik, Ashik,Khan, Khalid Mohammed
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p. 201 - 209
(2018/04/02)
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- Metal-free synthesis of 2-aminothiadiazoles via TBHP-Mediated oxidative C-S bond formation
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An efficient one-pot synthesis of 2-amino-1,3,4-thiadiazoles from easily available aldehydes and thiosemicarbazide using TBHP as an oxidant has been described. Notably, these reactions were carried out at room temperature using ethanol as solvent. This is the first example for one-pot synthesis of 2-amino-1,3,4-thiadiazole derivatives from aldehydes. This new synthetic methodology provides a simple procedure utilizing a safer oxidizing system that affords the target products in mild reaction condition with satisfactory yields and wide substrate scope.
- Hatvate, Navnath T.,Ghodse, Shrikant M.,Telvekar, Vikas N.
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supporting information
p. 285 - 290
(2018/02/09)
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- Thiadiazolodiazepine analogues as a new class of neuromuscular blocking agents: Synthesis, biological evaluation and molecular modeling study
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The synthesis, biological evaluation and molecular modeling study of 6,7-dihydro-[1,3,4] thiadiazolo[3,2-a][1,3]diazepine analogues as new class of neuromuscular blocking agents are described. The new compounds act via competitive mechanism with ACh which
- El-Subbagh, Hussein I.,El-Azab, Adel S.,Hassan, Ghada S.,El-Messery, Shahenda M.,Abdel-Aziz, Alaa A.-M.,El-Taher, Kamal E.H.
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- Synthesis and evaluation of the trypanocidal activity of a series of 1,3,4-thiadiazoles derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones
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In this study, we synthesized a series of 1,3,4-thiadiazole derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones (2a–k). We also determined the cytotoxicity in LLCMK2 cells and the activity against epimastigote and trypomastigote forms
- Martins, Solange C.,Desoti, Vania C.,Lazarin-Bidóia, Danielle,Vandresen, Fábio,da Silva, Cleuza C.,Ueda-Nakamura, Tania,Silva, Sueli de O.,Nakamura, Celso V.
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p. 1193 - 1203
(2016/07/06)
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- Synthesis, bioevaluation and docking study of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents
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Since the first histone deacetylase (HDAC) inhibitor (Zolinza, widely known as suberoylanilide hydroxamic acid; SAHA) was approved by the Food and Drug Administration for the treatment of T-cell lymphoma in 2006, the search for newer HDAC inhibitors has attracted a great deal of interest of medicinal chemists worldwide. As a continuity of our ongoing research in this area, we designed and synthesized a series of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as analogues of SAHA and evaluated their biological activities. A number of compounds in this series, for example, N1-hydroxy-N8-(5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5b), N1-hydroxy-N8-(5-(3-chlorophenyl-1,3,4-thiadiazol-2-yl)octandiamide (5c) and N1-hydroxy-N8-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5d), were found to possess potent anticancer cytotoxicity and HDAC inhibition effects. Compounds 5b-d were generally two- to five-fold more potent in terms of cytotoxicity compared to SAHA against five cancer cell lines tested. Docking studies revealed that these hydroxamic acid displayed higher affinities than SAHA toward HDAC8.
- Nam, Nguyen-Hai,Huong, Tran Lan,Dung, Do Thi Mai,Dung, Phan Thi Phuong,Oanh, Dao Thi Kim,Park, Sang Ho,Kim, Kyungrok,Han, Byung Woo,Yun, Jieun,Kang, Jong Soon,Kim, Youngsoo,Han, Sang-Bae
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p. 611 - 618
(2015/02/18)
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- Mild and convenient one-pot synthesis of 2-amino-1,3,4-thiadiazoles using trimethylsilyl isothiocyanate (TMSNCS)
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A novel and efficient one-pot method has been developed for the synthesis of 2-amino-1,3,4-thiadiazoles using various carboxylic acid hydrazides with trimethylsilyl isothiocyanate (TMSNCS). In situ preparation of various thiosemicarbazides by the reaction
- Guda, Dinneswara Reddy,Cho, Hyeon Mo,Lee, Myong Euy
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p. 6813 - 6816
(2013/05/22)
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- New thiazolidinedione-5-acetic acid amide derivatives: Synthesis, characterization and investigation of antimicrobial and cytotoxic properties
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The present work describes the synthesis, antimicrobial and cytotoxic activity of 2,4-thiazolidinedione- 5-acetic acid amides 3a-n. The structures of the compounds were confirmed by IR, 1H, 13C NMR and elemental analysis. All compounds were tested for antimicrobial activity by twofold serial dilution technique. The preliminary results revealed that the compound 3d exhibits promising antibacterial and antifungal activity. The cytotoxic (MTT) activity of 2,4-thiazolidinedione-5-acetic acid amides were tested in four tumour cell lines. We found that compound 3j inhibited proliferation of HeLa, HT29, A549 and MCF-7 cell lines with IC50 values of 33, 35, 30 and 36 μM, respectively. Springer Science+Business Media, LLC 2011.
- Alegaon, Shankar G.,Alagawadi, Kallanagouda R.
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experimental part
p. 816 - 824
(2012/10/07)
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- An efficient synthesis of novel bis-1,3,4-thiadiazolyl-carbamate derivatives based on deoxycholic acid under microwave irradiation
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An easy and efficient method for the synthesis of novel deoxycholic acid bis-1,3,4-thiadiazol-carbamate derivatives under microwave irradiation has been developed. Twelve new methyl 3α,12α-bis-[(5-aryl-1,3,4-thiadiazol-2- yl) carbamoyloxy]-cholan-24-oates
- Zhao, Zhigang,Li, Lin,Liu, Min,Mei, Qinggang
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experimental part
p. 218 - 221
(2012/10/08)
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- Synthesis, insecticidal evaluation of novel 1,3,4-thiadiazole chrysanthemamide derivatives formed by an EDCI/HOBt condensation
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A series of novel pesticides with two components derived from a 1,3,4-thiadiazole and chrysanthemic acid were synthesised via an EDCI/HOBt condensation. These 1,3,4-thiadiazole chrysanthemamides were identified by IR, 1H NMR and elemental analyses. Their insecticidal activity was also evaluated.
- Yu, Peng,Hu, Jun,Zhou, Tao-Yu,Wang, Peng,Xu, Yan-Hua
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experimental part
p. 703 - 706
(2012/03/10)
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- AMIDE DERIVATIVES AS SIRTUIN MODULATORS
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Provided herein are novel sirtuin-modulating compounds represented by Structural Formula (I) and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benfit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin- modulating compound in combination with another therapeutic agent.
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Page/Page column 81-82
(2009/06/27)
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- Synthesis and anti-Helicobacter pylori activity of 5-(nitroaryl)-1,3,4-thiadiazoles with certain sulfur containing alkyl side chain
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A series of 5-(nitroaryl)-1,3,4-thiadiazoles bearing certain sulfur containing alkyl side chain similar to pendent residue in tinidazole molecule were synthesized and evaluated against Helicobacter pylori using disk diffusion method. The synthesized compounds were also evaluated for their antibacterial, antifungal and cytotoxic effects. Study of the structure-activity relationships of this series of compounds indicated that both the structure of the nitroaryl unit and the pendent group on 2-position of 1,3,4-thiadiazole ring dramatically impact the anti-H. pylori activity. While compound 7a containing 2-[2-(ethylsulfonyl)ethylthio]-side chain from nitrothiophene series was the most potent compound tested against clinical isolates of H. pylori, however, nitroimidazoles 6c and 7c were found to be more promising compounds because of their respectable anti-H. pylori activity besides less cytotoxic effects.
- Foroumadi, Alireza,Rineh, Ardeshir,Emami, Saeed,Siavoshi, Farideh,Massarrat, Sadegh,Safari, Fatemeh,Rajabalian, Saeed,Falahati, Mehraban,Lotfali, Ensieh,Shafiee, Abbas
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scheme or table
p. 3315 - 3320
(2009/04/11)
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- Synthesis and in vitro antibacterial activity of some N-(5-aryl-1,3,4-thiadiazole-2-yl)piperazinyl quinolone derivatives
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A series of N-[5-(1-methyl-5-nitro-2-imidazolyl)-1,3,4-thiadiazole-2-yl] and N-[5-(nitrophenyl)-1,3,4-thiadiazole-2-yl] piperazinyl quinolone derivatives (5a-c and 5d-l) were synthesized and evaluated for in vitro antibacterial activity against some Gram-positive and Gram-negative bacteria. The antibacterial data revealed that all nitroimidazole derivatives (5a-c) showed interesting activity against tested Gram-positive bacteria (minimum inhibitory concentration, MIC=0.008-0.03 μg/ml) while they did not show good activity against Gram-negative organisms. Despite the significant activity of nitroimidazole series, all nitrophenyl analogues (5d-l) were inactive against both Gram-positive and Gram-negative bacteria. Among all of the tested compounds, 5a (ciprofloxacin derivative in nitroimidazole series) exhibited excellent activity against Staphylococcus aureus and Staphylococcus epidermidis (MIC=0.008 μg/ml).
- Foroumadi, Alireza,Soltani, Fatemeh,Moshafi, Mohammad Hasan,Ashraf-Askari, Rogheeyeh
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p. 1023 - 1028
(2007/10/03)
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- Studies on the synthesis and bioactivity of some thiadiazole derivatives
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Several 2-aryl-3-(4-aryl-1,3,4-thiadiazolyl)-4-thiazolidinones 3 and several other fused heterocycles 5 have been prepared. Most of the compounds 3 have been screened for their fungicidal activity against two fungi Aspergillus clavatus and Aspergillus fum
- Padhy, Arun Kumar,Nag,Panda
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p. 998 - 1001
(2007/10/03)
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- Synthesis and in vitro antifungal activity of 2-aryl-5-phenylsulfonyl- 1,3,4-thiadiazole derivatives
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The synthesis and antifungal activity of a series of 2-nitroaryl-5- phenylsulfonyl-1,3,4-thiadiazoles (5a-e) are described. The in vitro antifungal activity of the compounds was determined against a variety of fungal strains in comparison to miconazole (CAS 22916-47-8) and fluconazole (CAS 86386-73-4). Two derivatives (5d, 5e) showed high activity against Candida albicans and Candida spp. having MIC values ranging from 0.048-3.12 μg/ml, providing higher potencies than the reference drug fluconazole. Compound 5a also showed high activity against Cryptococcus neoformans (MIC 0.048 μg/ml). The activity of this compound against Aspergillus niger and Aspergillus fumigatus was moderate (MIC = 1.56-6.25 μg/ml), while fluconazole was inactive. Moreover, the nitroimidazole derivative 5d possessed good activity against most fungal strains in comparison to fluconazole.
- Foroumadi, Alireza,Daneshtalab, Mohsen,Shafiee, Abbas
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p. 1035 - 1038
(2007/10/03)
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- Synthesis and antifungal activity of 2-aryl-1,3,4-thiadiazole-5-sulphides, sulphoxides and sulphones
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2-Aryl-1,3,4-thiadiazole-5-sulphides, sulphoxides and sulphones were synthesized and tested against a variety of fungal strains, Miconazole and fluconazole were used as reference drugs. The most active compounds against Candida albicans, Candida spp., Cryptococcus neoformans and Aspergillus niger were 2-(1-methyl-5-nitro-2-imidazolyl)-5-methylsulphonyl-1 ,3,4-thiadiazole (8h) and 2-(5-nitro-2-furyl)-5-methylsulphonyl-1,3,4-thiadiazole (8f). Our results showed that compounds 8h and 8f were several times more active than fluconazole in most fungal strains.
- Foroumadi,Daneshtalab,Mahmoudian,Falahati,Nateghian,Shahsavarani,Shafiee
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- Antihypertensive Thiadiazoles. 1. Synthesis of Some 2-Aryl-5-hydrazino-1,3,4-thiadiazoles with Vasodilator Activity
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Some 2-Aryl-5-hydrazino-1,3,4-thiadiazoles have been synthesized and screened for antihypertensive activity.In general, compounds with a 2-substituted phenyl ring had higher activity than their 3- or 4-substituted counterparts or those containing heteroar
- Turner, Stephen,Myers, Malcolm,Gadie, Brian,Nelson, Anthony J.,Pape, Robin,et al.
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p. 902 - 906
(2007/10/02)
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