The Experts below are selected from a list of 6900 Experts worldwide ranked by ideXlab platform
Alireza Foroumadi - One of the best experts on this subject based on the ideXlab platform.
-
Synthesis and In Vitro Antibacterial Activity of New 2-(1-Methyl-4-nitro- 1H-imidazol-5-ylsulfonyl)-1,3,4-Thiadiazoles BAHRAM LETAFAT
2020Co-Authors: Negar Mohammadhosseini Ş, Ali Asadipour, Alireza ForoumadiAbstract:Abstract: In the present study we report the synthesis and antibacterial activity of a new series 2-(1-methyl-4-nitro-1H-imidazol-5-ylsulfonyl)-1,3,4-Thiadiazoles (6a-c). Compounds 6a-c were tested in vitro by the conventional agar dilution method against a panel of microorganisms including gram-negative and gram-positive bacteria. Compound 6b with 5-(5-nitrofuran-2-yl)-residue on 1,3,4-Thiadiazole scaffold have shown promising antibacterial activities against gram-positive bacteria including Staphylococcus aureus, Staphylococcus epidermidis and Bacillus subtilis
-
Synthesis and Biological Evaluation of Novel Benzyl Piperazine Derivatives of 5-(5-Nitroaryl)-1,3,4-Thiadiazoles as Anti-Helicobacter Pylori Agents
BioMed Central, 2013Co-Authors: Negar Mohammadhosseini, Alireza Foroumadi, Parastoo Saniee, Ameneh Ghamari Pour, Hassan Aryapour, Farzaneh Afshar, Najmeh Edraki, Farideh Siavoshi, Abbas ShafieeAbstract:Background and the purpose of the study Helicobacter pylori is recognized as the main cause of gastritis and gastroduodenal ulcers and classified as class 1 carcinogen pathogen. Different 1,3,4-Thiadiazole derivatives bearing 5-nitroaryl moiety have been shown considerable anti- H. pylori activity. In attempt to find new and potent derivatives of described scaffold, a new series of 1-(substituted benzyl)-4-(5-(5-nitroaryl-2-yl)-1,3,4-thiadiazol-2-yl)piperazine derivatives were synthesized and evaluated against three metronidazole-resistant isolates of H. pylori using paper disk diffusion bioassay test.Methods:The title compounds were prepared through the reaction of 1-(5-(5-nitroaryl-2-yl)-1,3,4-thiadiazol-2-yl) piperazine 5a-b and substituted benzyl chloride in DMF. The inhibitory activity of the new derivatives 6a-q against three metronidazole-resistant isolates of H. pylori was evaluated by the disc diffusion method and compared with the commercially available standard drug metronidazole.Results and discussion:The results of SAR study indicated that the potency and anti-H. pylori activity profile of synthesized derivatives is mainly attributed to the substituted nitroaryl moiety at the C-5 position of 1,3,4-Thiadiazole ring. Most of 1,3,4-Thiadiazole derivatives bearing 5-nitrofuran moiety at C-5 position of central Thiadiazole ring, demonstrated more promising anti-H. pylori than the 5-nitrothiophen counterpart.Conclusion:The most potent nitrofuran derivative containing 3-methoxybenzyl piperazine pendant at the C-2 position of 1,3,4-Thiadiazole ring (compound 6i), demonstrated strong anti-H. pylori potential at studied concentrations 100-25 mug/disk (IZD > 20 mm) against all studied metronidazole- resistant isolates of H. pylori
-
Cell death features induced in Leishmania major by 1,3,4-Thiadiazole derivatives
Experimental Parasitology, 2012Co-Authors: Sussan Kabudanian Ardestani, Fatemeh Poorrajab, Sepideh Razmi, Behnaz Gharegozlou, Soheila Ajdary, Alireza Foroumadi, Mina Behrouzi-fardmoghadamAbstract:Under a variety of stress conditions, Leishmania species display some morphological and biochemical features characteristic of mammalian programmed cell death or necrosis. Nitroheteroaryl-1,3,4-Thiadiazoles induce cell death in Leishmania major (L. major). Putative mechanisms of action of these compounds were investigated in vitro at cellular and molecular levels. We used colorimetric assay to measure acid phosphatase activity which is an indicator of cell viability in the promastigotes. The mode of toxicity was determined by detection of phosphatidylserine translocation to the surface, evaluation of cell membrane integrity, and in situ dUTP nick end-labeling assay. We also determined poly-ADP-ribose polymerase-like protein (PARP) level in the parasites after treatment. A significant reduction of acid phosphatase level, one of the most crucial and virulent factors of the parasite was found in parasites treated with 1,3,4-Thiadiazole derivatives. In addition, 1,3,4-Thiadiazole derivatives induced loss of plasma membrane integrity, DNA breakage, proteolysis of PARP and necrotic-like death in the parasites.
-
synthesis and anti leishmanial activity of 5 5 nitrofuran 2 yl 1 3 4 thiadiazol 2 amines containing n 1 benzyl 1h 1 2 3 triazol 4 yl methyl moieties
European Journal of Medicinal Chemistry, 2012Co-Authors: Azar Tahghighi, Sepideh Razmi, Sussan Kabudanian Ardestani, Abbas Shafiee, Saeed Emami, Farzad Kobarfard, Siavoush Dastmalchi, Mohammad Mahdavi, Parham Foroumadi, Alireza ForoumadiAbstract:Abstract A novel series of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines were synthesized by introducing N -[(1-benzyl-1 H -1,2,3-triazol-4-yl)methyl] moiety as a new functionality on the C-2 amine of Thiadiazole ring via click chemistry. The title compounds namely, N -[(1-benzyl-1 H -1,2,3-triazol-4-yl)methyl]-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines ( 3a – n ) were characterized by IR, NMR and MS spectra. These compounds were evaluated for their in vitro anti-leishmanial activity against promostigote form of the Leishmania major . Most compounds exhibited good anti-leishmanial activity against the promastigote form of L. major . The most active compound against promostigotes was found to be 4-methylbenzyl analog 3i , which significantly decreases the number of intracellular amastigotes per macrophage, percentage of macrophage infectivity and infectivity index.
-
synthesis and antileishmanial activity of novel 5 5 nitrofuran 2 y1 1 3 4 Thiadiazoles with piperazinyl linked benzamidine substituents
European Journal of Medicinal Chemistry, 2011Co-Authors: Azar Tahghighi, Sepideh Razmi, Javid Shahbazi Mojarrad, Sussan Kabudanian Ardestani, Abbas Shafiee, Saeed Emami, Farzane Rezazade Marznaki, Farzad Kobarfard, Siavoush Dastmalchi, Alireza ForoumadiAbstract:In order to optimize the antileishmanial activity of piperazinyl-linked 5-(5-nitrofuran-2-yl)-1,3,4-Thiadiazoles, we synthesized a series of 5-(5-nitrofuran-2-y1)-1,3,4-Thiadiazoles with piperazinyl-linked benzamidine substituent as scaffold found in pentamidine related antiprotozoals. The structure of target compounds was confirmed by IR, 1H NMR, 13C NMR and Mass spectral data. All compounds were tested for in vitro activity against the promastigote and amastigote forms of Leishmania major. From the results, we found that the substitution on amidine nitrogen has profound role in the biological activity of these compounds. The 5-nitrofuran-2-yl-1,3,4-Thiadiazoles having n-propyl, n-butyl and benzyl side chain on benzamidine (as in compounds 2d, 2e and 2g, respectively) showed very good activity in both forms of promastigote and amastigote. The most active compound was N-propyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl) benzamidine hydrochloride (2d) with IC50 value of 0.08 μM in promastigote model. This compound showed a very low level of toxicity against macrophages (CC50=785 μM), with the highest selectivity index (SI=78.5) among the tested compounds.
Saeed Emami - One of the best experts on this subject based on the ideXlab platform.
-
synthesis and anti leishmanial activity of 5 5 nitrofuran 2 yl 1 3 4 thiadiazol 2 amines containing n 1 benzyl 1h 1 2 3 triazol 4 yl methyl moieties
European Journal of Medicinal Chemistry, 2012Co-Authors: Azar Tahghighi, Sepideh Razmi, Sussan Kabudanian Ardestani, Abbas Shafiee, Saeed Emami, Farzad Kobarfard, Siavoush Dastmalchi, Mohammad Mahdavi, Parham Foroumadi, Alireza ForoumadiAbstract:Abstract A novel series of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines were synthesized by introducing N -[(1-benzyl-1 H -1,2,3-triazol-4-yl)methyl] moiety as a new functionality on the C-2 amine of Thiadiazole ring via click chemistry. The title compounds namely, N -[(1-benzyl-1 H -1,2,3-triazol-4-yl)methyl]-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines ( 3a – n ) were characterized by IR, NMR and MS spectra. These compounds were evaluated for their in vitro anti-leishmanial activity against promostigote form of the Leishmania major . Most compounds exhibited good anti-leishmanial activity against the promastigote form of L. major . The most active compound against promostigotes was found to be 4-methylbenzyl analog 3i , which significantly decreases the number of intracellular amastigotes per macrophage, percentage of macrophage infectivity and infectivity index.
-
synthesis and antileishmanial activity of novel 5 5 nitrofuran 2 y1 1 3 4 Thiadiazoles with piperazinyl linked benzamidine substituents
European Journal of Medicinal Chemistry, 2011Co-Authors: Azar Tahghighi, Sepideh Razmi, Javid Shahbazi Mojarrad, Sussan Kabudanian Ardestani, Abbas Shafiee, Saeed Emami, Farzane Rezazade Marznaki, Farzad Kobarfard, Siavoush Dastmalchi, Alireza ForoumadiAbstract:In order to optimize the antileishmanial activity of piperazinyl-linked 5-(5-nitrofuran-2-yl)-1,3,4-Thiadiazoles, we synthesized a series of 5-(5-nitrofuran-2-y1)-1,3,4-Thiadiazoles with piperazinyl-linked benzamidine substituent as scaffold found in pentamidine related antiprotozoals. The structure of target compounds was confirmed by IR, 1H NMR, 13C NMR and Mass spectral data. All compounds were tested for in vitro activity against the promastigote and amastigote forms of Leishmania major. From the results, we found that the substitution on amidine nitrogen has profound role in the biological activity of these compounds. The 5-nitrofuran-2-yl-1,3,4-Thiadiazoles having n-propyl, n-butyl and benzyl side chain on benzamidine (as in compounds 2d, 2e and 2g, respectively) showed very good activity in both forms of promastigote and amastigote. The most active compound was N-propyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl) benzamidine hydrochloride (2d) with IC50 value of 0.08 μM in promastigote model. This compound showed a very low level of toxicity against macrophages (CC50=785 μM), with the highest selectivity index (SI=78.5) among the tested compounds.
-
Synthesis and biological activity of 5-nitrofuran-containing (1,3,4-thiadiazol-2-yl)piperazine moieties as a new type of anti-Helicobacter pylori heterocycles
Serbian Chemical Society, 2011Co-Authors: Abbas Shafiee, Farideh Siavoshi, Saeed Emami, Eskandar Alipour, Maryam Omrani, Mohsen Vosooghi, Maryam Nakhjiri, Seyed Esmaeil Sadat-ebrahimi, Azadeh Yahya-meymandi, Mohammad Hassan MoshafiAbstract:In order to find new and potent drug candidates for the treatment of Helicobacter pylori infections‚ in this study attention was focused on the synthesis and anti-H. pylori activity of a series of 5-(5-nitrofuran-2-yl)-1,3,4-Thiadiazoles containing piperazinyl functionality at the C-2 position of the 1,3,4--Thiadiazole ring. The synthesis of 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2--yl]piperazine derivatives 3a–h and pyrrolidine derivative 3i was achieved with a versatile and efficient synthetic route via 2-chloro-5-(5-nitrofuran-2-yl)-1,3,4--Thiadiazole. The inhibitory activity of the new derivatives 3a–i against twenty clinical H. pylori strains was evaluated by the disc diffusion method and compared with the commercially available standard drug metronidazole. Resulting biological data indicated that most compounds exhibited strong inhibitory activity even at doses lower than 2 μg/disc (average zone of inhibition >20 mm) while metronidazole had little or no growth inhibition at this dose. Compound 3c containing the N-benzoylpiperazin-1-yl moiety showed the most potent inhibitory activity
-
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
Bioorganic & Medicinal Chemistry, 2008Co-Authors: Mina Behrouzifardmoghadam, Fatemeh Poorrajab, Sussan Kabudanian Ardestani, Abbas Shafiee, Saeed Emami, Alireza ForoumadiAbstract: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.
Abbas Shafiee - One of the best experts on this subject based on the ideXlab platform.
-
Synthesis and Biological Evaluation of Novel Benzyl Piperazine Derivatives of 5-(5-Nitroaryl)-1,3,4-Thiadiazoles as Anti-Helicobacter Pylori Agents
BioMed Central, 2013Co-Authors: Negar Mohammadhosseini, Alireza Foroumadi, Parastoo Saniee, Ameneh Ghamari Pour, Hassan Aryapour, Farzaneh Afshar, Najmeh Edraki, Farideh Siavoshi, Abbas ShafieeAbstract:Background and the purpose of the study Helicobacter pylori is recognized as the main cause of gastritis and gastroduodenal ulcers and classified as class 1 carcinogen pathogen. Different 1,3,4-Thiadiazole derivatives bearing 5-nitroaryl moiety have been shown considerable anti- H. pylori activity. In attempt to find new and potent derivatives of described scaffold, a new series of 1-(substituted benzyl)-4-(5-(5-nitroaryl-2-yl)-1,3,4-thiadiazol-2-yl)piperazine derivatives were synthesized and evaluated against three metronidazole-resistant isolates of H. pylori using paper disk diffusion bioassay test.Methods:The title compounds were prepared through the reaction of 1-(5-(5-nitroaryl-2-yl)-1,3,4-thiadiazol-2-yl) piperazine 5a-b and substituted benzyl chloride in DMF. The inhibitory activity of the new derivatives 6a-q against three metronidazole-resistant isolates of H. pylori was evaluated by the disc diffusion method and compared with the commercially available standard drug metronidazole.Results and discussion:The results of SAR study indicated that the potency and anti-H. pylori activity profile of synthesized derivatives is mainly attributed to the substituted nitroaryl moiety at the C-5 position of 1,3,4-Thiadiazole ring. Most of 1,3,4-Thiadiazole derivatives bearing 5-nitrofuran moiety at C-5 position of central Thiadiazole ring, demonstrated more promising anti-H. pylori than the 5-nitrothiophen counterpart.Conclusion:The most potent nitrofuran derivative containing 3-methoxybenzyl piperazine pendant at the C-2 position of 1,3,4-Thiadiazole ring (compound 6i), demonstrated strong anti-H. pylori potential at studied concentrations 100-25 mug/disk (IZD > 20 mm) against all studied metronidazole- resistant isolates of H. pylori
-
synthesis and anti leishmanial activity of 5 5 nitrofuran 2 yl 1 3 4 thiadiazol 2 amines containing n 1 benzyl 1h 1 2 3 triazol 4 yl methyl moieties
European Journal of Medicinal Chemistry, 2012Co-Authors: Azar Tahghighi, Sepideh Razmi, Sussan Kabudanian Ardestani, Abbas Shafiee, Saeed Emami, Farzad Kobarfard, Siavoush Dastmalchi, Mohammad Mahdavi, Parham Foroumadi, Alireza ForoumadiAbstract:Abstract A novel series of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines were synthesized by introducing N -[(1-benzyl-1 H -1,2,3-triazol-4-yl)methyl] moiety as a new functionality on the C-2 amine of Thiadiazole ring via click chemistry. The title compounds namely, N -[(1-benzyl-1 H -1,2,3-triazol-4-yl)methyl]-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines ( 3a – n ) were characterized by IR, NMR and MS spectra. These compounds were evaluated for their in vitro anti-leishmanial activity against promostigote form of the Leishmania major . Most compounds exhibited good anti-leishmanial activity against the promastigote form of L. major . The most active compound against promostigotes was found to be 4-methylbenzyl analog 3i , which significantly decreases the number of intracellular amastigotes per macrophage, percentage of macrophage infectivity and infectivity index.
-
synthesis and antileishmanial activity of novel 5 5 nitrofuran 2 y1 1 3 4 Thiadiazoles with piperazinyl linked benzamidine substituents
European Journal of Medicinal Chemistry, 2011Co-Authors: Azar Tahghighi, Sepideh Razmi, Javid Shahbazi Mojarrad, Sussan Kabudanian Ardestani, Abbas Shafiee, Saeed Emami, Farzane Rezazade Marznaki, Farzad Kobarfard, Siavoush Dastmalchi, Alireza ForoumadiAbstract:In order to optimize the antileishmanial activity of piperazinyl-linked 5-(5-nitrofuran-2-yl)-1,3,4-Thiadiazoles, we synthesized a series of 5-(5-nitrofuran-2-y1)-1,3,4-Thiadiazoles with piperazinyl-linked benzamidine substituent as scaffold found in pentamidine related antiprotozoals. The structure of target compounds was confirmed by IR, 1H NMR, 13C NMR and Mass spectral data. All compounds were tested for in vitro activity against the promastigote and amastigote forms of Leishmania major. From the results, we found that the substitution on amidine nitrogen has profound role in the biological activity of these compounds. The 5-nitrofuran-2-yl-1,3,4-Thiadiazoles having n-propyl, n-butyl and benzyl side chain on benzamidine (as in compounds 2d, 2e and 2g, respectively) showed very good activity in both forms of promastigote and amastigote. The most active compound was N-propyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl) benzamidine hydrochloride (2d) with IC50 value of 0.08 μM in promastigote model. This compound showed a very low level of toxicity against macrophages (CC50=785 μM), with the highest selectivity index (SI=78.5) among the tested compounds.
-
Synthesis and biological activity of 5-nitrofuran-containing (1,3,4-thiadiazol-2-yl)piperazine moieties as a new type of anti-Helicobacter pylori heterocycles
Serbian Chemical Society, 2011Co-Authors: Abbas Shafiee, Farideh Siavoshi, Saeed Emami, Eskandar Alipour, Maryam Omrani, Mohsen Vosooghi, Maryam Nakhjiri, Seyed Esmaeil Sadat-ebrahimi, Azadeh Yahya-meymandi, Mohammad Hassan MoshafiAbstract:In order to find new and potent drug candidates for the treatment of Helicobacter pylori infections‚ in this study attention was focused on the synthesis and anti-H. pylori activity of a series of 5-(5-nitrofuran-2-yl)-1,3,4-Thiadiazoles containing piperazinyl functionality at the C-2 position of the 1,3,4--Thiadiazole ring. The synthesis of 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2--yl]piperazine derivatives 3a–h and pyrrolidine derivative 3i was achieved with a versatile and efficient synthetic route via 2-chloro-5-(5-nitrofuran-2-yl)-1,3,4--Thiadiazole. The inhibitory activity of the new derivatives 3a–i against twenty clinical H. pylori strains was evaluated by the disc diffusion method and compared with the commercially available standard drug metronidazole. Resulting biological data indicated that most compounds exhibited strong inhibitory activity even at doses lower than 2 μg/disc (average zone of inhibition >20 mm) while metronidazole had little or no growth inhibition at this dose. Compound 3c containing the N-benzoylpiperazin-1-yl moiety showed the most potent inhibitory activity
-
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
Bioorganic & Medicinal Chemistry, 2008Co-Authors: Mina Behrouzifardmoghadam, Fatemeh Poorrajab, Sussan Kabudanian Ardestani, Abbas Shafiee, Saeed Emami, Alireza ForoumadiAbstract: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.
Sussan Kabudanian Ardestani - One of the best experts on this subject based on the ideXlab platform.
-
Cell death features induced in Leishmania major by 1,3,4-Thiadiazole derivatives
Experimental Parasitology, 2012Co-Authors: Sussan Kabudanian Ardestani, Fatemeh Poorrajab, Sepideh Razmi, Behnaz Gharegozlou, Soheila Ajdary, Alireza Foroumadi, Mina Behrouzi-fardmoghadamAbstract:Under a variety of stress conditions, Leishmania species display some morphological and biochemical features characteristic of mammalian programmed cell death or necrosis. Nitroheteroaryl-1,3,4-Thiadiazoles induce cell death in Leishmania major (L. major). Putative mechanisms of action of these compounds were investigated in vitro at cellular and molecular levels. We used colorimetric assay to measure acid phosphatase activity which is an indicator of cell viability in the promastigotes. The mode of toxicity was determined by detection of phosphatidylserine translocation to the surface, evaluation of cell membrane integrity, and in situ dUTP nick end-labeling assay. We also determined poly-ADP-ribose polymerase-like protein (PARP) level in the parasites after treatment. A significant reduction of acid phosphatase level, one of the most crucial and virulent factors of the parasite was found in parasites treated with 1,3,4-Thiadiazole derivatives. In addition, 1,3,4-Thiadiazole derivatives induced loss of plasma membrane integrity, DNA breakage, proteolysis of PARP and necrotic-like death in the parasites.
-
synthesis and anti leishmanial activity of 5 5 nitrofuran 2 yl 1 3 4 thiadiazol 2 amines containing n 1 benzyl 1h 1 2 3 triazol 4 yl methyl moieties
European Journal of Medicinal Chemistry, 2012Co-Authors: Azar Tahghighi, Sepideh Razmi, Sussan Kabudanian Ardestani, Abbas Shafiee, Saeed Emami, Farzad Kobarfard, Siavoush Dastmalchi, Mohammad Mahdavi, Parham Foroumadi, Alireza ForoumadiAbstract:Abstract A novel series of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines were synthesized by introducing N -[(1-benzyl-1 H -1,2,3-triazol-4-yl)methyl] moiety as a new functionality on the C-2 amine of Thiadiazole ring via click chemistry. The title compounds namely, N -[(1-benzyl-1 H -1,2,3-triazol-4-yl)methyl]-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines ( 3a – n ) were characterized by IR, NMR and MS spectra. These compounds were evaluated for their in vitro anti-leishmanial activity against promostigote form of the Leishmania major . Most compounds exhibited good anti-leishmanial activity against the promastigote form of L. major . The most active compound against promostigotes was found to be 4-methylbenzyl analog 3i , which significantly decreases the number of intracellular amastigotes per macrophage, percentage of macrophage infectivity and infectivity index.
-
synthesis and antileishmanial activity of novel 5 5 nitrofuran 2 y1 1 3 4 Thiadiazoles with piperazinyl linked benzamidine substituents
European Journal of Medicinal Chemistry, 2011Co-Authors: Azar Tahghighi, Sepideh Razmi, Javid Shahbazi Mojarrad, Sussan Kabudanian Ardestani, Abbas Shafiee, Saeed Emami, Farzane Rezazade Marznaki, Farzad Kobarfard, Siavoush Dastmalchi, Alireza ForoumadiAbstract:In order to optimize the antileishmanial activity of piperazinyl-linked 5-(5-nitrofuran-2-yl)-1,3,4-Thiadiazoles, we synthesized a series of 5-(5-nitrofuran-2-y1)-1,3,4-Thiadiazoles with piperazinyl-linked benzamidine substituent as scaffold found in pentamidine related antiprotozoals. The structure of target compounds was confirmed by IR, 1H NMR, 13C NMR and Mass spectral data. All compounds were tested for in vitro activity against the promastigote and amastigote forms of Leishmania major. From the results, we found that the substitution on amidine nitrogen has profound role in the biological activity of these compounds. The 5-nitrofuran-2-yl-1,3,4-Thiadiazoles having n-propyl, n-butyl and benzyl side chain on benzamidine (as in compounds 2d, 2e and 2g, respectively) showed very good activity in both forms of promastigote and amastigote. The most active compound was N-propyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl) benzamidine hydrochloride (2d) with IC50 value of 0.08 μM in promastigote model. This compound showed a very low level of toxicity against macrophages (CC50=785 μM), with the highest selectivity index (SI=78.5) among the tested compounds.
-
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
Bioorganic & Medicinal Chemistry, 2008Co-Authors: Mina Behrouzifardmoghadam, Fatemeh Poorrajab, Sussan Kabudanian Ardestani, Abbas Shafiee, Saeed Emami, Alireza ForoumadiAbstract: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.
Baoan Song - One of the best experts on this subject based on the ideXlab platform.
-
antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt of 2 mercapto 5 substituted 1 3 4 oxadiazole Thiadiazole derivatives
Bioorganic & Medicinal Chemistry Letters, 2015Co-Authors: Pei Li, Xia Yang, Deyu Hu, Baoan SongAbstract:In this study, a series of 2-mercapto-5-substituted-1,3,4-oxadiazole/Thiadiazole derivatives were synthesized and evaluated for their antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt caused by Xanthomonas oryzae pv. oryzae ( Xoo ) and Ralstonia solanacearum ( R. solanacearum ) via the turbidimeter test in vitro. Antibacterial bioassays indicated that most compounds demonstrated appreciable antibacterial bioactivities against Xoo and R. solanacearum . Among the title compounds, compound 4i demonstrated the best inhibitory effect against Xoo and R. solanacearum with half-maximal effective concentration (EC 50 ) values of 14.69 and 15.14 μg/mL, respectively, which were even better than those of commercial agents Bismerthiazol and Thiodiazole Copper. In vivo antibacterial activities tests under greenhouse conditions revealed that the control efficiency of compound 4i against rice bacterial leaf blight and tobacco bacterial wilt were better than those of Bismerthiazol and Thiodiazole Copper. Meanwhile, field trials also indicated that compound 4i demonstrated appreciable control efficiency against rice bacterial leaf blight and tomato bacterial wilt.
-
antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt of 2 mercapto 5 substituted 1 3 4 oxadiazole Thiadiazole derivatives
Bioorganic & Medicinal Chemistry Letters, 2015Co-Authors: Li Shi, Xia Yang, Manni Gao, Wei Xue, Linhong Jin, Baoan SongAbstract:In this study, a series of 2-mercapto-5-substituted-1,3,4-oxadiazole/Thiadiazole derivatives were synthesized and evaluated for their antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt caused by Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (R. solanacearum) via the turbidimeter test in vitro. Antibacterial bioassays indicated that most compounds demonstrated appreciable antibacterial bioactivities against Xoo and R. solanacearum. Among the title compounds, compound 4i demonstrated the best inhibitory effect against Xoo and R. solanacearum with half-maximal effective concentration (EC50) values of 14.69 and 15.14μg/mL, respectively, which were even better than those of commercial agents Bismerthiazol and Thiodiazole Copper. In vivo antibacterial activities tests under greenhouse conditions revealed that the control efficiency of compound 4i against rice bacterial leaf blight and tobacco bacterial wilt were better than those of Bismerthiazol and Thiodiazole Copper. Meanwhile, field trials also indicated that compound 4i demonstrated appreciable control efficiency against rice bacterial leaf blight and tomato bacterial wilt.
-
design synthesis and antibacterial activity against rice bacterial leaf blight and leaf streak of 2 5 substituted 1 3 4 oxadiazole Thiadiazole sulfone derivative
Bioorganic & Medicinal Chemistry Letters, 2014Co-Authors: Pei Li, Xia Yang, Lei Yang, Xuewen Chen, Fang Wu, Weiming Xu, Ming He, Deyu Hu, Baoan SongAbstract:Abstract A series of 2,5-substituted-1,3,4-oxadiazole/Thiadiazole sulfone derivatives were synthesized and evaluated for their antibacterial activities against rice bacterial leaf blight and leaf streak caused by Xanthomonas oryzae pv. oryzae and Xanthomonas oryzae pv. oryzicolaby via the turbidimeter test in vitro. Antibacterial bioassay results indicated that most compounds demonstrated good inhibitory effect antibacterial bioactivities against rice bacterial leaf blight and leaf streak. Among the title compounds, compound 6c demonstrated the best inhibitory effect against rice bacterial leaf blight and leaf streak with half-maximal effective concentration (EC 50 ) values of 1.07 and 7.14 μg/mL, respectively, which were even better than those of commercial agents such as Bismerthiazol and Thiediazole Copper. In vivo antibacterial activities tests at greenhouse conditions demonstrated that the controlling effect of compounds 6c (43.5%) and 6g (42.4%) against rice bacterial leaf blight were better than those of Bismerthiazol (25.5%) and Thiediazole Copper (37.5%).
