Synthesis, crystal structures and antimicrobial activities of 3-methyl and 3-bromo substituted benzo[b]thiophene based thiosemicarbazones

References

• Padhye S, Kauffman GB. Transition metal complexes of semicarbazones and thiosemicarbazones. Coord Chem Rev. 1985;63:127–160. doi:10.1016/0010-8545(85)80022-9
   Web of Science ®Google Scholar
• Joule JA, Mills K, Smith GF. Heterocyclic chemistry. Chichester: CRC Press; 2020.
   Google Scholar
• Quin LD, Tyrell JA. Fundamentals of heterocyclic chemistry: importance in nature and in the synthesis of pharmaceuticals. Hoboken, New Jersey: John Wiley & Sons; 2010.
   Google Scholar
• Katritzky AR. Advances in heterocyclic chemistry. New York and London: Academic Press publishes; 2002.
   Google Scholar
• Vicini P, Zani F, Cozzini P, et al. Hydrazones of 1, 2-benzisothiazole hydrazides: synthesis, antimicrobial activity and QSAR investigations. Eur J Med Chem. 2002;37(7):553–564. doi:10.1016/S0223-5234(02)01378-8
   PubMed Web of Science ®Google Scholar
• Mendes IC, Teixeira LR, Lima R, et al. Structural and spectral studies of thiosemicarbazones derived from 3- and 4-formylpyridine and 3- and 4-acetylpyridine. J Mol Struct. 2001;559(1-3):355–360. doi:10.1016/S0022-2860(00)00729-8
   Web of Science ®Google Scholar
• de Oliveira RB, de Souza-Fagundes EM, Soares RP, et al. Synthesis and antimalarial activity of semicarbazone and thiosemicarbazone derivatives. Eur J Med Chem. 2008;43(9):1983–1988. doi:10.1016/j.ejmech.2007.11.012
   PubMed Web of Science ®Google Scholar
• Hong WS, Wu CY, Lee CS, et al. Novel iron carbonyl complexes from thiophene-2-carboxaldehyde thiosemicarbazone. J Organomet Chem. 2004;689(2):277–285. doi:10.1016/j.jorganchem.2003.10.012
   Web of Science ®Google Scholar
• Teoh SG, Ang SH, Fun HK, et al. Synthesis, crystal structure and biological activity of thiophene-2-carboxaldehyde thiosemicarbazone and its tin complexes. J Organomet Chem. 1999;580(1):17–21. doi:10.1016/S0022-328X(98)01099-7
   Web of Science ®Google Scholar
• Osmaniye D, Kurban B, Sağlık BN, et al. Novel thiosemicarbazone derivatives: in vitro and in silico evaluation as potential MAO-B inhibitors. Molecules. 2021;26(21):6640, doi:10.3390/molecules26216640
   PubMed Web of Science ®Google Scholar
• Kayed SF, Farina Y, Simpson J, et al. Structural, spectral studies and antimicrobial activity of Zinc (II). Cadmium (II) and Nickel (II) complexes of: 2-acetylbenzothiophene-3-thiosemicarbazone and 2-acetylbenzothiophene-4-ethyl-3-thiosemicarbazone. Inorg Chem Commun. 2022;146:110138.
   Web of Science ®Google Scholar
• Kayed SF, Farina Y, Simpson J, et al. Spectral studies of Zinc (II) complex of 2-Acetylbenzothiophene 3-Thiosemicarbazone. In: Prosiding Seminar Kimia Bersama UKM-ITB VIII. Bnagi, Selangor, Malaysia: Institut Teknologi Bandung; 2009;9(11): 567.
   Google Scholar
• Bao B, Bai S, Fan J, et al. A novel and durable photochromic cotton-based fabric prepared via thiol-ene click chemistry. Dyes Pigm. 2019;171:107778, doi:10.1016/j.dyepig.2019.107778
   Web of Science ®Google Scholar
• Qiao Y, Che Y, Yu Y, et al. Solid-state photochromic properties, mechanism and electrospun membranes of (E)-2-(benzo[b]thiophen-2-ylmethylene)-N-ethylhydrazine-1-carbothioamide. Dyes Pigm. 2018;156:326–331. doi:10.1016/j.dyepig.2018.04.013
   Web of Science ®Google Scholar
• Şen B, Kalhan HK, Demir V, et al. Crystal structures, spectroscopic properties of new cobalt(II), nickel(II), zinc(II) and palladium(II) complexes derived from 2-acetyl-5-chloro thiophene thiosemicarbazone: anticancer evaluation. Mater Sci Eng: C. 2019;98:550–559. doi:10.1016/j.msec.2018.12.080
   PubMed Web of Science ®Google Scholar
• Rodríguez-Argüelles MC, Tourón-Touceda P, Cao R. Complexes of 2-acetyl-γ-butyrolactone and 2-furancarbaldehyde thiosemicarbazones: antibacterial and antifungal activity. J Inorg Biochem 2009;103(1):35–42. doi:10.1016/j.jinorgbio.2008.08.015
   PubMed Web of Science ®Google Scholar
• Berrade L, Aisa B, Ramirez MJ, et al. Novel benzo [b] thiophene derivatives as new potential antidepressants with rapid onset of action. J Med Chem 2011;54(8):3086–3090. doi:10.1021/jm2000773
   PubMed Web of Science ®Google Scholar
• Jianqi LI, Kai GAO, Na LV. Benzothiophene alkanol piperazine derivatives and their use as antidepressant. WO Patent. 2010; 198: A1.
   Google Scholar
• Jeong SJ, Higuchi R, Miyamoto T, et al. Bryoanthrathiophene, a new antiangiogenic constituent from the bryozoan Watersipora subtorquata (d’Orbigny, 1852). J Nat Prod. 2002;65(9):1344–1345. doi:10.1021/np010577+
   PubMed Web of Science ®Google Scholar
• Kelly TR, Fu Y, Sieglen JT, et al. Synthesis of an orange anthrathiophene pigment isolated from a Japanese bryozoan. Org Lett 2000;2(15):2351–2352. doi:10.1021/ol006127a
   PubMed Web of Science ®Google Scholar
• Fakhr IM, Radwan MA, El-Batran S, et al. Synthesis and pharmacological evaluation of 2-substituted benzo[b]thiophenes as anti-inflammatory and analgesic agents. Eur J Med Chem. 2009;44(4):1718–1725. doi:10.1016/j.ejmech.2008.02.034
   PubMed Web of Science ®Google Scholar
• Jagtap VA, Agasimundin YS. Synthesis and preliminary evaluation of some 2-amino-n’-[substituted]-4, 5, 6, 7-tetrahydro-1-benzothiophene-3-carbohydrazide as antimicrobial agents. J Pharmacy Research. 2015;9(1):10–14.
   Google Scholar
• Mourey RJ, Burnette BL, Brustkern SJ, et al. A benzothiophene inhibitor of mitogen-activated protein kinase-activated protein kinase 2 inhibits tumor necrosis factor α production and has oral anti-inflammatory efficacy in acute and chronic models of inflammation. J Pharmacol Exp Ther. 2010;333(3):797–807. doi:10.1124/jpet.110.166173
   PubMed Web of Science ®Google Scholar
• Sweidan K, Engelmann J, Abu Rayyan W, et al. Synthesis and preliminary biological evaluation of new heterocyclic carboxamide models. Lett Drug Des Discovery. 2015;12(5):417–429. doi:10.2174/1570180812666141201222527
   Web of Science ®Google Scholar
• Martorana A, Gentile C, Perricone U, et al. Synthesis, antiproliferative activity, and in silico insights of new 3-benzoylamino-benzo[b]thiophene derivatives. Eur J Med Chem. 2015;90:537–546. doi:10.1016/j.ejmech.2014.12.002
   PubMed Web of Science ®Google Scholar
• Loidreau Y, Deau E, Marchand P, et al. Synthesis and molecular modelling studies of 8-arylpyrido [3′, 2′: 4, 5] thieno [3, 2-d] pyrimidin-4-amines as multitarget Ser/Thr kinases inhibitors. Eur J Med Chem. 2015;92:124–134. doi:10.1016/j.ejmech.2014.12.038
   PubMed Web of Science ®Google Scholar
• Rao GK, Subramaniam R. Synthesis, antitubercular and antibacterial activities of some quinazolinone analogs substituted with benzothiophene. Chem Sci J. 2015;6(2):1, doi:10.4172/2150-3494.100092
   Google Scholar
• Banerjee T, Sharma SK, Kapoor N, et al. Benzothiophene carboxamide derivatives as inhibitors of plasmodium falciparum enoyl-ACP reductase. IUBMB Life. 2011;63(12):1101–1110. doi:10.1002/iub.553
   PubMed Web of Science ®Google Scholar
• Moinet G, Leriche C, Kergoat M. U.S. Patent No. 7,375,130. Washington (DC): U.S. Patent and Trademark Office; 2008.
   Google Scholar
• Malamas MS, Sredy J, Moxham C, et al. Novel benzofuran and benzothiophene biphenyls as inhibitors of protein tyrosine phosphatase 1B with antihyperglycemic properties. J Med Chem 2000;43(7):1293–1310. doi:10.1021/jm990560c
   PubMed Web of Science ®Google Scholar
• Çakmakçı ES, Subaşı E, Öztürk E, et al. Cobalt(II), nickel(II), palladium(II) and zinc(II) metallothiosemicarbazones: synthesis, characterization, X-ray structures and biological activity. Inorganica Chim Acta. 2023;551:121462, doi:10.1016/j.ica.2023.121462
   Web of Science ®Google Scholar
• APEX2. Bruker AXS Inc. Madison Wisconsin USA (2013).
   Google Scholar
• CrysAlisPro Software System. Version 1.171.42.79a. Oxford: Rigaku Corporation; 2022.
   Google Scholar
• Sheldrick GM. SHELXT-integrated space-group and crystal-structure determination. Acta Cryst. 2015;A71:3–8. doi:10.1107/S2053273314026370
   Google Scholar
• Sheldrick GM. A short history of SHELX. Acta Cryst. 2008;A64:112–122. doi:10.1107/S0108767307043930
   Web of Science ®Google Scholar
• Sheldrick GM. Crystal structure refinement with SHELXL. Acta Cryst. 2015;C71:3–8. doi:10.1107/S2053229614024218
   Google Scholar
• Dolomanov OV, Bourhis LJ, Gildea RJ, et al. OLEX2: a complete structure solution, refinement and analysis program. J Appl Crystallogr. 2009;42:339–341. doi:10.1107/S0021889808042726
   Web of Science ®Google Scholar
• Spek AL. Single-crystal structure validation with the program PLATON. J Appl Crystallogr. 2003;36:7–13. doi:10.1107/S0021889802022112
   Web of Science ®Google Scholar
• Tarafder MTH, Islam MAAAA, Crouse KA, et al. (E)-4-(Benzyloxy)benzaldehyde thiosemicarbazone, H.-K. Fun. Acta Cryst. 2008;E64:o988–o989. doi:10.1107/S1600536808012671
   Google Scholar
• Şen Yüksel B. Spectroscopic characterization (IR and NMR), structural investigation, DFT study, and Hirshfeld surface analysis of two zinc(II) 2-acetylthiophenyl-thiosemicarbazone complexes. J Mol Struct. 2021;1229:129617, doi:10.1016/j.molstruc.2020.129617
   Web of Science ®Google Scholar
• Arfan A, Rukiah M. Crystal structures of crotonaldehyde semicarbazone and crotonaldehyde thiosemicarbazone from X-ray powder diffraction data. Acta Cryst. 2015;E71:168–172. doi:10.1107/S2056989015000663
   Google Scholar
• Sajitha NR, Sithambaresan M, Kurup MRP. Crystal structure of 2-[(E)-4-benzyloxy2-hydroxybenzylidene]-N-cyclohexylhydrazinecarbothioamide acetonitrile hemisolvate. Acta Cryst. 2014;E70:o987–o988. doi:10.1107/S1600536814017905
   Google Scholar
• Kayed SF, Farina Y, Simpson J. 1-Benzothiophene-2-carbaldehyde 4-ethylthiosemicarbazone. Acta Cryst. 2009;E65:o180–o181. doi:10.1107/S1600536808042797
   Google Scholar
• Kumbhar A, Sonawane P, Padhye S, et al. Structure of anti-tumor agents 2-acetylpyridinethiosemicarbazone hemihydrate and 2-acetylpyridinethiosemicarbazone hydrochloride. J Chem Crystallogr. 1991: 533–539. doi:10.1007/bf02576444
   Google Scholar
• Li MX, Zhang D, Zhang LZ, et al. Synthesis, crystal structures, and biological activities of 2-thiophene N(4)-methylthiosemicarbazone and its unusual hexanuclear silver(I) cluster. Inorg Chem Commun. 2010;13:1268–1271. doi:10.1016/j.inoche.2010.07.012
   Web of Science ®Google Scholar
• Latheef L, Manoj E, Kurup MRP. Salicylaldehyde 4,4 000 -(hexane-1,6-diyl)-thiosemicarbazone. Acta Cryst. 2006;C62:o16–o18. doi:10.1107/S010827010503564X
   Google Scholar
• Kose Yaman P, Şen B, Karagoz CS, et al. Half-sandwich ruthenium-arene complexes with thiophen containing thiosemicarbazones: synthesis and structural characterization. J Organomet Chem. 2017;832:27–35. doi:10.1016/j.jorganchem.2017.01.013
   Web of Science ®Google Scholar
• Subaşı E, Bulut Atalay E, Erdogan D, et al. Synthesis and characterization of thiosemicarbazone-functionalized organoruthenium (II)-arene complexes: investigation of antitumor characteristics in colorectal cancer cell lines. Mater Sci Eng. 2020;C 106:110152, doi:10.1016/j.msec.2019.110152
   Google Scholar
• Bernstein J, Davis RE, Shimoni L, et al. Patterns in hydrogen bonding: functionality and graph set analysis in crystals. Angew Chem Int Ed Engl. 1995;34:1555–1573. doi:10.1002/anie.199515551
   Web of Science ®Google Scholar
• Janiak C. A critical account on π-π stacking in metal complexes with aromatic nitrogen-containing ligands. J Chem Soc Dalton. 2000;21:3885–3896. doi:10.1039/b003010o
   Google Scholar
• Bondi AV. van der Waals volumes and radii. J Phys Chem. 1964;68(3):441–451. doi:10.1021/j100785a001
   Web of Science ®Google Scholar
• Mazik Arno M, Buthe C, Jones PG. C–H···Br, C–Br···Br, and C–Br···(interactions in the crystal structures of mesitylene- and dimesitylmethane-derived compounds bearing bromomethyl units. Tetrahedron. 2010;66:385–389. doi:10.1016/j.tet.2009.10.067
   Web of Science ®Google Scholar
• Koch N, Seichter W, Mazik M. Trimethyl-, triethyl- and trimethoxybenzene-based tripodal compounds bearing pyrazole groups: conformations and halogen-/hydrogen-bond patterns in the crystalline state. Cryst Eng Comm. 2017;19:3817, doi:10.1039/c7ce00577f
   Google Scholar
• Pahonțu E, Paraschivescu C, Ilieș DC, et al. Synthesis and characterization of novel Cu (II). Pd (II) and Pt (II) complexes with: 8-Ethyl-2-hydroxytricyclo (7.3. 1.02, 7) tridecan-13-one-thiosemicarbazone: antimicrobial and in vitro antiproliferative activity. Molecules. 2016;21(5):674, doi:10.3390/molecules21050674
   PubMed Web of Science ®Google Scholar
• Mendes IC, Moreira JP, Speziali NLN, et al. N(4)-tolyl-2-benzoylpyridine thiosemicarbazones and their copper(II) complexes with significant antifungal activity: crystal structure of N(4)-para-tolyl-2-benzoylpyridine thiosemicarbazone. J Braz Chem Soc. 2006;17:1571–1577. doi:10.1590/S0103-50532006000800013
   Web of Science ®Google Scholar
• de Araújo Neto LN, de Lima MDCA, de Oliveira JF, et al. Thiophene-thiosemicarbazone derivative (L10) exerts antifungal activity mediated by oxidative stress and apoptosis in C. albicans. Chem Biol Interact 2020;320:109028, doi:10.1016/j.cbi.2020.109028
   PubMed Web of Science ®Google Scholar
• Umamatheswari S, Balaji B, Ramanathan M, et al. Synthesis, stereochemistry, antimicrobial evaluation and QSAR studies of 2, 6-diaryltetrahydropyran-4-one thiosemicarbazones. Eur J Med Chem. 2011;46(4):1415–1424. doi:10.1016/j.ejmech.2011.01.029
   PubMed Web of Science ®Google Scholar
• Tyagi M, Chandra S. Synthesis, characterization, and biocidal properties of platinum metal complexes derived from 2, 6-diacetylpyridine (bis thiosemicarbazone). Inorg Chem. 2012;2(3):41–48. doi:10.4236/ojic.2012.23007
   Google Scholar
• Khan T, Raza S, Lawrence AJ. Medicinal utility of thiosemicarbazones with special reference to mixed ligand and mixed metal complexes: a review. Russ J Coord Chem. 2022;48(12):877–895. doi:10.1134/S1070328422600280
   Web of Science ®Google Scholar
• Clinical and Laboratory Standards Institute (CLSI). M02-A12 performance standards for antimicrobial disk susceptibility tests, 2015.
   Google Scholar
• Clinical and Laboratory Standards Institute (CLSI). M07-A10 methods for dilution antimicrobial susceptibility tests for bacteria, 2015.
   Google Scholar
• Clinical and Laboratory Standards Institute (CLSI). M27-A3 reference method for broth dilution antifungal susceptibility testing of yeasts, 2008.
   Google Scholar