- Synthesis and antituberculosis activity of new acylthiosemicarbazides designed by structural modification
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Acylthiosemicarbazides 8a–n were designed by structural modification of lead Compound 7. The syntheses of 8a–n involve a five-step procedure starting from carboxylic acids. Compounds 8a–n were tested against three Mycobacterium tuberculosis strains to measure their inhibitory antituberculosis activities. These activities could be explained according to the presence or absence of the chlorine substituent in the aromatic ring of the amide joined to the thiosemicarbazide core. Thiosemicarbazide derivative 8n is a candidate for the development of novel antitubercular agents. Ongoing studies are focused on exploring the mechanism by which these compounds inhibit M. tuberculosis cell growth.
- Martínez, Roberto,Espitia-Pinzón, Clara I.,Silva Miranda, Mayra,Chávez-Santos, Rosa María,Pretelin-Castillo, Gustavo,Ramos-Orea, Aldahir,Hernández-Báez, ángela M.,Cotlame-Pérez, Sandra,Pedraza-Rodríguez, Rogelio
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p. 350 - 355
(2019/12/03)
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- Identification of 1,2,4-triazoles as new thymidine phosphorylase inhibitors: Future anti-tumor drugs
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Thymidine phosphorylase (TP) is over expressed in several solid tumors and its inhibition can offer unique target suitable for drug discovery in cancer. A series of 1,2,4-triazoles 3a–3l has been synthesized in good yields and subsequently inhibitory potential of synthesized triazoles 3a–3l against thymidine phosphorylase enzyme was evaluated. Out of these twelve analogs five analogues 3b, 3c, 3f, 3l and 3l exhibited a good inhibitory potential against thymidine phosphorylase. Inhibitory potential in term of IC50 values were found in the range of 61.98 ± 0.43 to 273.43 ± 0.96 μM and 7-Deazaxanthine was taken as a standard inhibitor with IC50 = 38.68 ± 4.42 μM. Encouraged by these results, more analogues 1,2,4-triazole-3-mercaptocarboxylic acids 4a–4g were synthesized and their inhibitory potential against thymidine phosphorylase was evaluated. In this series, six analogues 4b–4g exhibited a good inhibitory potential in the range of 43.86 ± 1.11–163.43 ± 2.03 μM. Angiogenic response of 1,2,4-triazole acid 4d was estimated using the chick chorionic allantoic membrane (CAM) assay. In the light of these findings, structure activity relationship and molecular docking studies of selected triazoles to determine the key binding interactions was discussed. Docking studies demonstrate that synthesized analogues interacted with active site residues of thymidine phosphorylase enzyme through π-π stacking, thiolate and hydrogen bonding interactions.
- Shahzad, Sohail Anjum,Yar, Muhammad,Khan, Zulfiqar Ali,Shahzadi, Lubna,Naqvi, Syed Ali Raza,Mahmood, Adeem,Ullah, Sami,Shaikh, Ahson Jabbar,Sherazi, Tauqir Ali,Bale, Adebayo Tajudeen,Kuku?owicz, J?drzej,Bajda, Marek
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p. 209 - 220
(2019/01/10)
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- A useful synthesis of 2-acylamino-1,3,4-oxadiazoles from acylthiosemicarbazides using potassium iodate and the discovery of new antibacterial compounds
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A useful method for the synthesis of 2-acylamino-1,3,4-oxadiazoles was developed. By using potassium iodate as an oxidant in water at 60 ?C, a wide range of 2-acylamino-1,3,4-oxadiazoles were afforded in moderate to excellent yields within two
- Li, Tianlei,Wen, Gang,Li, Jishun,Zhang, Wenxuan,Wu, Song
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supporting information
(2019/05/02)
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- Application of N-substituted aryl (arylformamido)-N'-substituted arylformyl thiourea compound in inhibition of blue alga growth
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The invention relates to an application of an N-substituted aryl (arylformamido)-N'-substituted arylformyl thiourea compound in inhibition of blue alga growth. The N-substituted aryl-N'-substituted arylformyl thiourea compound with a general formula I and
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Paragraph 0092; 0093; 0094; 0095; 0096
(2017/09/01)
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- Intramolecular hydrogen bonding and anion binding of N-benzamido-N′- benzoylthioureas
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(Chemical Equation Presented) N-(p-Dimethylamino)benzoyl-N′- phenylthiourea as an N-acylthiourea is known to be unable to bind anions due to a strong intramolecular hydrogen bond (IHB). We show here that by inserting an amido group in the N′-phenyl side the newly designed N-benzamido-N′- benzoylthioureas, despite this IHB too, bind strongly to anions with binding constants on the order of 106-107 mol-1 L. Results suggest that potential anion receptors or organocatalysts could be developed on the basis of this framework with a wide structural diversity.
- Liu, Wen-Xia,Jiang, Yun-Bao
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p. 1124 - 1127
(2008/09/18)
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- Antimicrobial activity and structural study of disubstituted Thiourea Derivatives
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The antimicrobial activity of six N-phenyl- and fourteen N-benzoylthiourea derivatives were evaluated from their Minimal Inhibitory Concentration (MIC) values using the microdilution procedure against ten microorganisms. Most of the compounds exhibited selective activity against fungi and Gram-positive bacteria, which were very effectively inhibited by some of the tested thioureas. Additionally, SAR considerations and four novel X-ray diffraction structures of N-benzoylthioureas are included. Springer-Verlag 2007.
- Cunha, Silvio,MacEdo Jr., Fernando C.,Costa, Giselle A. N.,Rodrigues Jr., Manoel T.,Verde, Rosival B. V.,De Souza Neta, Lourdes C.,Vencato, Ivo,Lariucci, Carlito,Sa, Fernando P.
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p. 511 - 516
(2008/02/03)
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- New access to pyrazole, oxa(thia)diazole and oxadiazine derivatives
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1,4-Disubstituted thiosemicarbazides 1b-f reacted with ethenetetracarbonitrile (5) in dimethylformamide with formation of 2-substituted 5-phenyl-1,3,4-thiadiazoles 2a-f and 2-substituted 5-phenyl-1,3,4-oxadiazoles 4a-f. Upon addition of 5 to 1c-e in chlorobenzene, 3-amino-2-benzoyl-4,5,5- tricyano-2,5-dihydro-1H-pyrazole- 1-[N-(4-tricyanovinyl)phenyl]carbothioamide (12), 5-benzylamino-, and 5-allylamino-4-benzoyl-2,3-dihydro-[1,3,4]thiadiazol- 2,2-dicarbonitrile (13a,b) and 5-amino-1-benzoylpyrazole-3,4-dicarbonitrile (14) as well as 2-phenyl-4H-[1,3,4]-oxadiazine-5,6-dicarbonitrile (15) were formed. Rationales for the role of the solvent and the conversions observed are presented.
- Hassan, Alaa A.,El-Shaieb, Kamal M.,Shaker, Raafat M.,Doepp, Dietrich
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