833-47-6Relevant academic research and scientific papers
Synthesis, in vitro thymidine phosphorylase activity and molecular docking study of thiadiazole bearing isatin analogs
Ullah, Hayat,Liaqat, Anjum,Khan, Qudrat Ullah,Taha, Muhammad,Khan, Fahad,Rahim, Fazal,Uddin, Imad,Rehman, Zia Ur
, p. 213 - 224 (2021/09/09)
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.]
N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound
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Paragraph 0051; 0057; 0108-0110, (2021/06/09)
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.
Novel fatty acid-thiadiazole derivatives as potential antimycobacterial agents
Mali, Jaishree K.,Sutar, Yogesh B.,Pahelkar, Akshata R.,Verma, Preeti M.,Telvekar, Vikas N.
, p. 174 - 181 (2019/11/03)
The discovery of antibiotics around the middle twentieth century led to a decrease in the interest in antimycobacterial fatty acids. In order to re-establish the importance of naturally abundant fatty acid, a series of fatty acid-thiadiazole derivatives were designed and synthesized based on molecular hybridization approach. In vitro antimycobacterial potential was established by a screening of synthesized compounds against Mycobacterium tuberculosis H37Rv strain. Among them, compounds 5a, 5d, 5h, and 5j were the most active, with compound 5j exhibiting minimum inhibitory concentration of 2.34?μg/ml against M.tb H37Rv. Additionally, the compounds were docked to determine the probable binding interactions and understand the mechanism of action of most active molecules on enoyl-acyl carrier protein reductases (InhA), which is involved in the mycobacterium fatty acid biosynthetic pathway.
Pyridine and nitro-phenyl linked 1,3,4-thiadiazoles as MDR-TB inhibitors
Patel, Harun,Jadhav, Harsha,Ansari, Iqrar,Pawara, Rahul,Surana, Sanjay
, p. 1 - 9 (2019/02/14)
In the present study, a series of substituted 1,3,4-thiadiazole derivatives 4(a–o), 5(a–m) and 6(a–j) were synthesized and characterized by IR, 1H NMR, 13C NMR and mass spectroscopic technique. The synthesized compounds were evaluate
Synthesis of matrinic amide derivatives containing 1,3,4-thiadiazole scaffold as insecticidal/acaricidal agents
Lv, Min,Liu, Guangci,Jia, Minghong,Xu, Hui
, p. 88 - 92 (2018/08/21)
In continuation of our program aimed at the development of natural product-based pesticidal agents, a series of matrinic amide derivatives containing 1,3,4-thiadiazole scaffold were prepared, and their insecticidal and acaricidal activities were evaluated against Mythimna separata and Tetranychus cinnabarinus. Some compounds exhibited potent insecticidal and acaricidal activities. It suggested that R1 as a nitro group and R2 as a fluorine atom, were important for the insecticidal activity; R1 as the electron-donating groups and R2 as the methyl group, were necessary for the acaricidal activity.
Synthesis, in vitro α-glucosidase inhibitory potential and molecular docking study of thiadiazole analogs
Javid, Muhammad Tariq,Rahim, Fazal,Taha, Muhammad,Rehman, Haseeb Ur,Nawaz, Mohsan,wadood, Abdul,Imran, Syahrul,Uddin, Imad,Mosaddik, Ashik,Khan, Khalid Mohammed
, p. 201 - 209 (2018/04/02)
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.
PhI-Catalyzed Intramolecular Oxidative Coupling Toward Synthesis of 2-Amino-1,3,4-Thiadizoles
Han, Yingzhi,Sun, Yadong,Abdukader, Ablimit,Liu, Bifu,Wang, Duozhi
, p. 3486 - 3491 (2018/09/27)
A highly efficient method for the synthesis of thiadiazole derivatives via intramolecular oxidative coupling of thiosemicarbazide, using the in situ generated hypervalent iodine(III) reagents is developed. The protocol can be carried out smoothly and provides a variety of thiadiazole derivatives in moderate to excellent yields. Graphical Abstract: A highly efficient method for the synthesis of thiadiazole derivatives via PhI-catalyzed intramolecular oxidative coupling of thiosemicarbazide has been developed.
Cyclization–oxidation of Benzylidenehydrazinecarbothioamides by FeCl3.6H2O or ZnCl2.6H2O Catalysts and Synthesis of New 1,3,4-Thiadiazolo-[3,2- α]Pyrimidines
Darehkordi, Ali,Zarezadeh Abarqouei, Behnam,Rahmani, Fariba
, p. 1872 - 1879 (2017/05/29)
We report new method for preparation of 2-amino-5-aryl-1,3,4-thiadiazoles by reaction of arylaldehyde with thiosemicarbazide and in the next step via cyclization of 2-aryl hydrazinecarbothioamide in the presence of ZnCl2.6H2O or FeCl3.6H2O. Also, in this research, new substituted 1,3,4-thiadiazolo-[3,2-α]pyrimidines were synthesized by the reaction of 2-amino-5-aryl-1,3,4-thiadiazoles derivatives with DMAD or DEAD in the presence of K2CO3 under reflux conditions. The FT-IR, 1H-NMR, 13C-NMR, elemental analysis and single- crystal X-ray analysis confirm the structures of the products.
Synthesis, characterization and biological evaluation of some novel fluoroquinolones
Pandit, Neelanjana,Shah, Kamal,Agrawal, Neetu,Upmanyu, Neeraj,Shrivastava, Sushant K.,Mishra, Pradeep
, p. 843 - 851 (2016/04/20)
Different derivatives of fluoroquinolones were synthesized by combining it with different thiadiazoles. The synthesized compounds were characterized by infrared spectroscopy, proton nuclear magnetic resonance and mass spectral data. The compounds were screened for their antibacterial and antifungal activity. Ciprofloxacin derivatives with thiadiazoles 7c showed good antibacterial as well as antifungal activities, whereas 13c and 13e showed antibacterial and antifungal activity respectively. Sparfloxacin derivative 8c showed both antibacterial and antifungal activity. Sparfloxacin derivatives 14b and 14e showed antibacterial and antifungal activity respectively.
Synthesis and evaluation of the trypanocidal activity of a series of 1,3,4-thiadiazoles derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones
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.
, p. 1193 - 1203 (2016/07/06)
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
