5351-83-7Relevant academic research and scientific papers
Novel inhibitors of tyrosinase produced by the 4-substitution of TCT
Xu, Jian,Liu, Jing,Zhu, Xinqi,Yu, Yanying,Cao, Shuwen
, p. 1530 - 1538 (2017)
We synthesized a series of 4- or 5-functionalized TCT derivatives (1?12) and investigated their inhibitory activities and mechanisms on tyrosinase by using Spectrofluorimetry, 1H and 13C NMR titration and IR spectra. The results of the fluorescence spectr
Design and development of ((4-methoxyphenyl)carbamoyl) (5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl)amide analogues as Mycobacterium tuberculosis ketol-acid reductoisomerase inhibitors
George, Shilpa E.,Guddat, Luke W.,Krishna, Vagolu Siva,Nallangi, Radhika,Rekha, Estharla Madhu,Sai Prasad, D. V.,Sriram, Dharmarajan,Zheng, Shan
, (2020/03/19)
Based on our previous finding that the titled compound possesses anti-tuberculosis activity, a series of novel ((4-methoxyphenyl)carbamoyl) (5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl)amide analogues have been synthesized. Amongst the 22 compounds synthesized and tested, 5b, 5c and 6c showed potent inhibitory activity with Ki values of 2.02, 5.48 and 4.72 μM for their target, Mycobacterium tuberculosis (Mt) ketol-acid reductoisomerase (KARI). In addition, these compounds have excellent in vitro activity against Mt H37Rv with MIC values as low as 1 μM. The mode of binding for these compounds to Mt KARI was investigated through molecular docking and dynamics simulations. Furthermore, these compounds were evaluated for their activity in Mt infected macrophages, and showed inhibitory activities with up to a 1.9-fold reduction in growth (at 10 μM concentration). They also inhibited Mt growth in a nutrient starved model by up to 2.5-fold. In addition, these compounds exhibited low toxicity against HEK 293T cell lines. Thus, these compounds are promising Mt KARI inhibitors that can be further optimized into anti-tuberculosis agents.
Discovery of a novel nitroimidazolyl-oxazolidinone hybrid with potent anti Gram-positive activity: Synthesis and antibacterial evaluation
Khalaj, Ali,Nakhjiri, Maryam,Negahbani, Amir Soheil,Samadizadeh, Marjaneh,Firoozpour, Loghman,Rajabalian, Saeed,Samadi, Nasrin,Faramarzi, Mohammad Ali,Adibpour, Neda,Shafiee, Abbas,Foroumadi, Alireza
scheme or table, p. 65 - 70 (2011/02/25)
A number of linezolid analogues containing a nitroaryl-1,3,4-thiadiazole moiety, were prepared and evaluated as antibacterial agents against a panel of Gram-positive and Gram-negative bacteria. Among synthesized compounds, nitrofuran analogue 1b exhibited more potent inhibitory activity, with respect to other synthesized compounds and reference drug linezolid. The target compounds were also assessed for their cytotoxic activity against normal mouse fibroblast (NIH/3T3) cells using MTT assay. The results indicated that compound 1c exhibit potent antibacterial activity against Gram-positive bacteria at non-cytotoxic concentrations.
Synthesis and antiinflammatory activity of novel 2,5-disubstituted thiophene derivatives
Ibrahim Badr, Sahar Mohamed
experimental part, p. 131 - 143 (2011/12/05)
New series of 2,5-disubstituted thiophenes were synthesized. Thiosemicarbazones 1a-b were reacted with various reagents, such as diethyl-2-bromomalonate, ethyl-2-chloroacetoacetate, thioglycolic acid, 4-substituted phenacyl bromides, and acetic anhydride,
Synthesis and in vitro anti-leishmanial activity of 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl]- and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines
Behrouzi-Fardmoghadam, Mina,Poorrajab, Fatemeh,Ardestani, Sussan Kaboudanian,Emami, Saeed,Shafiee, Abbas,Foroumadi, Alireza
, p. 4509 - 4515 (2008/09/21)
The synthesis and anti-leishmanial activity of nitroheteroaryl-1,3,4-thiadiazole-based compounds including 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines were described. Most of the synthesized compounds exhibited potent anti-leishmanial activity against both promastigote and amastigote forms of Leishmania major at non-cytotoxic concentrations. In general, 5-nitrofuran derivatives were more active than the corresponding 5-nitrothiophene analogues.
Synthesis and anti-Helicobacter pylori activity of 5-(nitroaryl)-1,3,4-thiadiazoles with certain sulfur containing alkyl side chain
Foroumadi, Alireza,Rineh, Ardeshir,Emami, Saeed,Siavoshi, Farideh,Massarrat, Sadegh,Safari, Fatemeh,Rajabalian, Saeed,Falahati, Mehraban,Lotfali, Ensieh,Shafiee, Abbas
scheme or table, p. 3315 - 3320 (2009/04/11)
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.
Synthesis and antimycobacterial activity of some alkyl [5-(nitroaryl)-1,3, 4-thiadiazol-2-ylthio]propionates
Foroumadi, Alireza,Kargar, Zahra,Sakhteman, Amirhossein,Sharifzadeh, Zahra,Feyzmohammadi, Robabeh,Kazemi, Mahnoush,Shafiee, Abbas
, p. 1164 - 1167 (2007/10/03)
Two series of 2- and 3-[5-(nitroaryl)-1,3,4-thiadiazol-2-ylthio, sulfinyl and sulfonyl] propionic acid alkyl esters were synthesized and screened for antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. The MIC values for the compounds showing more than 90% inhibition were determined. The result of comparison between two groups of data exhibited that among the synthesized derivatives, the compound propyl 3-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-ylthio]propionate was the most active one (MIC = 1.56 μg ml-1).
Synthesis and in vitro leishmanicidal activity of 2-(5-nitro-2-furyl) and 2-(5-nitro-2-thienyl)-5-substituted-1,3,4-thiadiazoles
Foroumadi, Alireza,Pournourmohammadi, Shirin,Soltani, Fatemeh,Asgharian-Rezaee, Mitra,Dabiri, Shahriar,Kharazmi, Arsalan,Shafiee, Abbas
, p. 1983 - 1985 (2007/10/03)
A series of 2-(5-nitro-2-furyl) and 2-(5-nitro-2-thienyl)-5-substituted-1, 3,4-thiadiazoles (5a-d and 6a-j) were synthesized and evaluated against Leishmania major promastigotes using 3H-thymidine incorporation. Most of the compounds showed activity better than the reference drug sodium stibogluconate (Pentostam). The most active compound was 6c (IC50 = 0.1 μM).
Synthesis and in vitro antibacterial evaluation of N-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-yl] piperazinyl quinolones
Foroumadi, Alireza,Mansouri, Shahla,Kiani, Zahra,Rahmani, Afsaneh
, p. 851 - 854 (2007/10/03)
A series of N-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-yl]piperazinyl quinolones (7a-c) were synthesized and evaluated for in vitro antibacterial activity against some Gram-positive and Gram-negative bacteria. The antibacterial data revealed that compounds 7a-c had strong and better activity against tested Gram-positive organisms than the reference quinolones such as ciprofloxacin, norfloxacin and enoxacin. However, all three compounds were nearly inactive against Gram-negative bacteria. Compound 7a (ciprofloxacin analogue) was the most active compound against Gram-positive bacteria (MIC=0.008-0.015 μg mL-1).
