Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 13
179
Views
5
CrossRef citations to date
0
Altmetric
Articles

Tandem synthesis and antibacterial screening of novel thieno[2,3-b]thiophene-linked bis(thiazole) hybrids

ORCID Icon, ORCID Icon &
Pages 1982-1993 | Received 13 Jan 2021, Published online: 27 Apr 2021

References

  • Lee, W.; Shin, C.; Park, S. E.; Joo, J. M. Regio- and Stereoselective Synthesis of Thiazole-Containing Triarylethylenes by Hydroarylation of Alkynes. J. Org. Chem. 2019, 84, 12913–12924. DOI: 10.1021/acs.joc.9b01619.
  • de Andrade, V. S.; de Mattos, M. C. One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid. Synthesis. 2018, 50, 4867–4874. DOI: 10.1055/s-0037-1610243.
  • Xiabing, M.; Ablajan, K.; Obul, M.; Seydimemet, M.; Ruzi, R.; Wenbo, L. Facial One-Pot, Three-Component Synthesis of Thiazole Compounds by the Reactions of Aldehyde/Ketone, Thiosemicarbazide and Chlorinated Carboxylic Ester Derivatives. Tetrahedron. 2016, 72, 2349–2353. DOI: 10.1016/j.tet.2016.03.053.
  • Sanad, S. M. H.; Ahmed, A. A. M.; Mekky, A. E. M. Synthesis, in-Vitro and in-Silico Study of Novel Thiazoles as Potent Antibacterial Agents and MurB Inhibitors. Arch Pharm. 2020, 353, e1900309. DOI: 10.1002/ardp.201900309.
  • Sun, N.; Lu, Y. J.; Chan, F. Y.; Du, R. L.; Zheng, Y. Y.; Zhang, K.; So, L. Y.; Abagyan, R.; Zhuo, C.; Leung, Y. C.; Wong, K. Y. A Thiazole Orange Derivative Targeting the Bacterial Protein FtsZ Shows Potent Antibacterial Activity. Front. Microbiol. 2017, 8, 855. DOI: 10.3389/fmicb.2017.00855.
  • Mohammad, H.; Reddy, P. N.; Monteleone, D.; Mayhoub, A. S.; Cushman, M.; Hammac, G. K.; Seleem, M. N. Antibacterial Characterization of Novel Synthetic Thiazole Compounds against Methicillin-Resistant Staphylococcus pseudintermedius. PLOS One. 2015, 10, e0130385. DOI: 10.1371/journal.pone.0130385.
  • Li, J. R.; Li, D. D.; Wang, R. R.; Sun, J.; Dong, J. J.; Du, Q. R.; Fang, F.; Zhang, W. M.; Zhu, H. L. Design and Synthesis of Thiazole Derivatives as Potent FabH Inhibitors with Antibacterial activity. Eur. J. Med. Chem. 2014, 75, 438–447. DOI: 10.1016/j.ejmech.2013.11.020.
  • Singh, I. P.; Gupta, S.; Kumar, S. Thiazole Compounds as Antiviral Agents: An Update. Med. Chem. 2020, 16, 4–23. DOI: 10.2174/1573406415666190614101253.
  • Dawood, K. M.; Eldebss, T. M.; El-Zahabi, H. S.; Yousef, M. H. Synthesis and Antiviral Activity of Some New Bis-1,3-thiazole Derivatives. Eur. J. Med. Chem. 2015, 102, 266–276. DOI: 10.1016/j.ejmech.2015.08.005.
  • Ayati, A.; Emami, S.; Moghimi, S.; Foroumadi, A. Thiazole in the Targeted Anticancer Drug Discovery. Future Med. Chem. 2019, 11, 1929–1952. DOI: 10.4155/fmc-2018-0416.
  • de Santana, T. I.; de Oliveira Barbosa, M.; de Moraes Gomes, P. A. T.; da Cruz, A. C. N.; da Silva, T. G.; Leite, A. C. L. Synthesis, Anticancer Activity and Mechanism of Action of New Thiazole Derivatives. Eur. J. Med. Chem. 2018, 144, 874–886. DOI: 10.1016/j.ejmech.2017.12.040.
  • Jain, S.; Pattnaik, S.; Pathak, K.; Kumar, S.; Pathak, D.; Jain, S.; Vaidya, A. Anticancer Potential of Thiazole Derivatives: A Retrospective Review. Mini Rev. Med. Chem.. 2018, 18, 640–655. DOI: 10.2174/1389557517666171123211321.
  • Turan-Zitouni, G.; Altıntop, M. D.; Özdemir, A.; Kaplancıklı, Z. A.; Çiftçi, G. A.; Temel, H. E. Synthesis and Evaluation of Bis-Thiazole Derivatives as New Anticancer Agents. Eur. J. Med. Chem. 2016, 107, 288–294. DOI: 10.1016/j.ejmech.2015.11.002.
  • Luzina, E. L.; Popov, A. V. Synthesis and Anticancer Activity of N-bis(trifluoromethyl)alkyl-N'-thiazolyl and N-bis(trifluoromethyl)alkyl-N'-Benzothiazolyl Ureas. Eur. J. Med. Chem. 2009, 44, 4944–4953. DOI: 10.1016/j.ejmech.2009.08.007.
  • Kamat, V.; R.; Santosh, B.; Poojary, S. P.; Nayak, B. K.; Kumar, M.; Sankaranarayanan, Faheem, S.; Khanapure, D. A.; Barretto, S. K. Vootla, Pyridine-and Thiazole-Based Hydrazides with Promising ANTI-INFLAMMATORY and Antimicrobial Activities along with Their in Silico Studies. ACS Omega. 2020, 5, 25228–25239. DOI: 10.1021/acsomega.0c03386.
  • Deb, P. K.; Kaur, R.; Chandrasekaran, B.; Bala, M.; Gill, D.; Kaki, V. R.; Akkinepalli, R. R.; Mailavaram, R. Synthesis, anti-Inflammatory Evaluation, and Docking Studies of Some New Thiazole Derivatives. Med. Chem. Res. 2014, 23, 2780–2792. DOI: 10.1007/s00044-013-0861-4.
  • Rostom, S. A.; El-Ashmawy, I. M.; Abd El Razik, H. A.; Badr, M. H.; Ashour, H. M. Design and Synthesis of Some Thiazolyl and Thiadiazolyl Derivatives of Antipyrine as Potential Non-Acidic anti-Inflammatory, Analgesic and Antimicrobial Agents. Bioorg. Med. Chem. 2009, 17, 882–895. DOI: 10.1016/j.bmc.2008.11.035.
  • Muhammad, Z. A.; Masaret, G. S.; Amin, M. M.; A. Abdallah, M.; Farghaly, T. A. Anti-Inflammatory, Analgesic and anti-Ulcerogenic Activities of Novel Bis-Thiadiazoles, Bis-Thiazoles and Bis-Formazanes. Med. Chem. 2017, 13, 226–238. DOI: 10.2174/1573406412666160920091146.
  • Pember, S. O.; Mejia, G. L.; Price, T. J.; Pasteris, R. J. Piperidinyl Thiazole Isoxazolines: A New Series of Highly Potent, Slowly Reversible FAAH Inhibitors with Analgesic Properties. Bioorg. Med. Chem. Lett. 2016, 26, 2965–2973. DOI: 10.1016/j.bmcl.2016.02.061.
  • Kasralikar, H. M.; Jadhavar, S. C.; Goswami, S. V.; Kaminwar, N. S.; Bhusare, S. R. Design, Synthesis and Molecular Docking of pyrazolo [3,4d] Thiazole Hybrids as Potential anti-HIV-1 NNRT Inhibitors. Bioorg. Chem. 2019, 86, 437–444. DOI: 10.1016/j.bioorg.2019.02.006.
  • Khan, M-U-H.; Hameed, S.; Akhtar, T.; Al-Masoudi, N. A.; Al-Masoudi, W. A.; Jones, P. G.; Pannecouque, C. Synthesis, Crystal Structure, anti-HIV, and Antiproliferative Activity of New Oxadiazole and Thiazole Analogs. Med. Chem. Res. 2016, 25, 2399–2409. DOI: 10.1007/s00044-016-1669-9.
  • Kavitha, K.; Srikrishna, D.; Dubey, P. K.; Aparna, P. An Expedient One-Pot Tandem Method for the Synthesis of 3-(2-(Phenylamino)Thiazol-4-yl)-2H-Chromen-2-Ones under Green Conditions. J. Iran. Chem. Soc. 2019, 16, 1913–1921. DOI: 10.1007/s13738-019-01661-y.
  • Iino, T.; Tsukahara, D.; Kamata, K.; Sasaki, K.; Ohyama, S.; Hosaka, H.; Hasegawa, T.; Chiba, M.; Nagata, Y.; Eiki, J. I.; Nishimura, T. Discovery of Potent and Orally Active 3-Alkoxy-5-phenoxy-N-Thiazolyl Benzamides as Novel Allosteric Glucokinase Activators. Bioorg. Med. Chem. 2009, 17, 2733–2743. DOI: 10.1016/j.bmc.2009.02.038.
  • Oslob, J. D.; Romanowski, M. J.; Allen, D. A.; Baskaran, S.; Bui, M.; Elling, R. A.; Flanagan, W. M.; Fung, A. D.; Hanan, E. J.; Harris, S.; et al. Discovery of a Potent and Selective Aurora Kinase Inhibitor. Bioorg. Med. Chem. Lett. 2008, 18, 4880–4884. DOI: 10.1016/j.bmcl.2008.07.073..
  • Clark, R. F.; Zhang, T.; Wang, X.; Wang, R.; Zhang, X.; Camp, H. S.; Beutel, B. A.; Sham, H. L.; Gu, Y. G. Phenoxy Thiazole Derivatives as Potent and Selective acetyl-CoA Carboxylase 2 Inhibitors: Modulation of Isozyme Selectivity by Incorporation of Phenyl Ring Substituents. Bioorg. Med. Chem. Lett. 2007, 17, 1961–1965. DOI: 10.1016/j.bmcl.2007.01.022.
  • Kim, D. K.; Choi, J. H.; An, Y. J.; Lee, H. S. Synthesis and Biological Evaluation of 5-(pyridin-2-yl)thiazoles as Transforming Growth Factor-Beta Type1 Receptor Kinase Inhibitors. Bioorg. Med. Chem. Lett. 2008, 18, 2122–2127. DOI: 10.1016/j.bmcl.2008.01.084.
  • Giri, R. S.; Thaker, H. M.; Giordano, T.; Williams, J.; Rogers, D.; Sudersanam, V.; Vasu, K. K. Design, Synthesis and Characterization of Novel 2-(2,4-Disubstituted-Thiazole-5-yl)-3-aryl-3H-Quinazoline-4-one Derivatives as Inhibitors of NF-kappaB and AP-1 Mediated Transcription Activation and as Potential Anti-Inflammatory Agents. Eur. J. Med. Chem. 2009, 44, 2184–2189. DOI: 10.1016/j.ejmech.2008.10.031.
  • Rehman, M. Z.; Choudary, J. A.; Ahmad, S. An Efficient Synthesis of 2-Alkyl-4-Hydroxy-2H-1,2-Benzothiazine-3-Carboxamide-1,1-Dioxides. Bull. Korean Chem. Soc. 2005, 26, 1771–1775. DOI: 10.1002/chin.200614169.
  • Mabkhot, Y. N.; Kheder, N. A.; Farag, A. M. Synthesis and Antimicrobial Activity of Some New Thieno[2,3-b]Thiophene Derivatives. Molecules. 2013, 18, 4669–4678. DOI: 10.3390/molecules18044669.
  • Kheder, N. A.; Mabkhot, Y. N. Synthesis and Antimicrobial Studies of Some Novel Bis-[1,3,4]Thiadiazole and Bis-Thiazole Pendant to Thieno[2,3-b]Thiophene Moiety. Int. J. Mol. Sci. 2012, 13, 3661–3670. DOI: 10.3390/ijms13033661.
  • Litvinov, V. P. The Latest Achievements in Thienothiophene Chemistry. Russ. Chem. Rev. 2005, 74, 217–248. DOI: 10.1070/RC2005v074n03ABEH000889.
  • Jarak, I.; Kralj, M.; Piantanida, I.; Suman, L.; Zinić, M.; Pavelić, K.; Karminski-Zamola, G. Novel Cyano- and Amidino-Substituted Derivatives of Thieno[2,3-b]- and Thieno[3,2-b]thiophene-2-Carboxanilides and thieno[3',2':4,5]thieno- and thieno[2',3':4,5]thieno [2,3-c]quinolones: Synthesis, Photochemical Synthesis, DNA Binding, and Antitumor Evaluation. Bioorg. Med. Chem. 2006, 14, 2859–2868. DOI: 10.1016/j.bmc.2005.12.004.
  • Mabkhot, Y. N.; Barakat, A.; Al-Majid, A. M.; Alshahrani, S.; Yousuf, S.; Choudhary, M. I. Synthesis, Reactions and Biological Activity of Some New Bis-Heterocyclic Ring Compounds Containing Sulphur Atom. Chem. Cent. J. 2013, 7, 112. DOI: 10.1186/1752-153X-7-112.
  • Egbertson, M. S.; Cook, J. J.; Bednar, B.; Prugh, J. D.; Bednar, R. A.; Gaul, S. L.; Gould, R. J.; Hartman, G. D.; Homnick, C. F.; Holahan, M. A.; et al. Non-Peptide GPIIb/IIIa Inhibitors. 20. Centrally Constrained Thienothiophene Alpha-Sulfonamides are Potent, Long Acting in Vivo Inhibitors of Platelet Aggregation. J. Med. Chem. 1999, 42, 2409–2421. DOI: 10.1021/jm980722p.
  • Li, Z.; Ono, R. J.; Wu, Z.; Bielawski, C. W. Synthesis and Self-Assembly of Poly(3-Hexylthiophene)-Block-Poly(Acrylic Acid). Chem Commun. 2011, 47, 197–199. DOI: 10.1039/C0CC02166K.
  • Gather, M. C.; Heeney, M.; Zhang, W.; Whitehead, K. S.; Bradley, D. D. C.; McCulloch, I.; Campbell, A. J. An Alignable Fluorene Thienothiophene Copolymer with Deep-Blue Electroluminescent Emission at 410 nm. Chem. Commun. 2008, 2008, 1079–1081. DOI: 10.1039/B716510B.
  • Heeney, M.; Bailey, C.; Genevicius, K.; Shkunov, M.; Sparrowe, D.; Tierney, S.; McCulloch, U. Stable Polythiophene Semiconductors Incorporating Thieno[2,3-b]Thiophene. J. Am. Chem. Soc. 2005, 127, 1078–1079. DOI: 10.1021/ja043112p.
  • McCulloch, I.; Heeney, M.; Chabinyc, M. L.; DeLongchamp, D.; Kline, R. J.; Cölle, M.; Duffy, W.; Fischer, D.; Gundlach, D.; Hamadani, B.; et al. Semiconducting Thienothiophene Copolymers: Design, Synthesis, Morphology, and Performance in Thin‐Film Organic Transistors. Adv. Mater. 2009, 21, 1091–1109. DOI: 10.1002/adma.200801650.
  • Melucci, M.; Favaretto, L.; Bettini, C.; Gazzano, M.; Camaioni, N.; Maccagnani, P.; Ostoja, P.; Monari, M.; Barbarella, G. Liquid‐Crystalline Rigid‐Core Semiconductor Oligothiophenes: Influence of Molecular Structure on Phase Behaviour and Thin‐Film Properties. Chemistry. 2007, 13, 10046–10054. DOI: 10.1002/chem.200701368.
  • Mekky, A. E. M.; Mohamed Ahmed, M. S.; Sanad, S. M. H.; Abdallah, Z. A. Bis(Benzofuran-Enaminone) Hybrid Possessing Piperazine Linker: Versatile Precursor for Microwave Assisted Synthesis of Bis(Pyrido[2',3':3,4]Pyrazolo[1,5-a]Pyrimidines). Synth. Commun. 2021, 51(7), 1085-1099, DOI: 10.1080/00397911.2020.1867745.
  • Sanad, S. M. H.; Mekky, A. E. M. Efficient Synthesis and Characterization of Novel Bis(Chromenes) and Bis(Benzo[f]Chromenes) Linked to Thiazole Units. Synth. Commun. 2021, 51(4), 611-624. DOI: 10.1080/00397911.2020.1846748.
  • Mekky, A. E. M.; Sanad, S. M. H. Synthesis and Antibacterial Evaluation of Novel Mono- and Bis(2H-Chromen-2-Imine) Hybrids Linked to Heteroarene Units. Mendeleev Commun. 2020, 30, 762–764. DOI: 10.1016/j.mencom.2020.11.024.
  • Mekky, A. E. M.; Sanad, S. M. H. Synthesis and in Vitro Study of New Coumarin Derivatives Linked to Nicotinonitrile Moieties as Potential Acetylcholinesterase Inhibitors. J. Heterocyclic Chem. 2020, 57, 4278–4290. DOI: 10.1002/jhet.4134.
  • Sanad, S. M. H.; Mekky, A. E. M. Novel Nicotinonitrile-Coumarin Hybrids as Potential Acetylcholinesterase Inhibitors: Design, Synthesis, In Vitro and In Silico Studies. J. Iran. Chem. Soc. 2021, 18(1), 213-224, DOI: 10.1007/s13738-020-02018-6.
  • Sanad, S. M. H.; Mekky, A. E. M. Novel Nicotinonitriles and Thieno[2,3-b]Pyridines as Potent Biofilm and COX-2 Inhibitors: Synthesis, In Vitro and In Silico Studies. ChemistrySelect. 2020, 5, 8494–8503. DOI: 10.1002/slct.202001208.
  • Sanad, S. M. H.; Mekky, A. E. M. Synthesis, Cytotoxicity and in Vitro Antibacterial Screening of Novel Hydrazones Bearing Thienopyridine Moiety as Potent COX-2 Inhibitors. J. Iran. Chem. Soc. 2020, 17, 3299–3315. DOI: 10.1007/s13738-020-01987-y.
  • Mekky, A. E. M.; Sanad, S. M. H.; Said, A. Y.; Elneairy, M. A. A. Synthesis, Cytotoxicity, in-Vitro Antibacterial Screening and in-Silico Study of Novel Thieno[2,3-b]Pyridines as Potential Pim-1 Inhibitors. Synth. Commun. 2020, 50, 2376–2389. DOI: 10.1080/00397911.2020.1778033.
  • Sanad, S. M. H.; Ahmed, A. A. M.; Mekky, A. E. M. Efficient Synthesis and Molecular Docking of Novel Antibacterial Pyrimidines and Their Related Fused Heterocyclic Derivatives. J. Heterocyclic Chem. 2020, 57, 590–605. DOI: 10.1002/jhet.3789.
  • Mekky, A. E. M.; Sanad, S. M. H. Microwave Assisted Synthesis of Novel Bis(Thiazoles) Incorporating Piperazine Moiety. J. Heterocyclic Chem. 2019, 56, 1560–1566. DOI: 10.1002/jhet.3531.
  • Sayed, O. M.; Mekky, A. E. M.; Farag, A. M.; Elwahy, A. H. 3,4-Dimethyl-2,5-Functionalized Thieno[2,3-b]Thiophenes: Versatile Precursors for Novel Bis-Thiazoles. J. Sulfur Chem. 2015, 36, 124–134. DOI: 10.1080/17415993.2014.975131.
  • Mashraqui, S. H.; Sangvikar, Y. S.; Meetsma, A. Synthesis and Structures of Thieno[2,3-b]Thiophene Incorporated [3.3]Dithiacyclophanes. Enhanced First Hyperpolarizability in an Unsymmetrically Polarized Cyclophane. Tetrahedron Lett. 2006, 47, 5599–5602. DOI: 10.1016/j.tetlet.2006.05.098.
  • Mekky, A. E. M.; Elwahy, A. H. Synthesis of Novel Benzo‐Substituted Macrocyclic Ligands Containing Thienothiophene Subunits. J. Heterocyclic Chem. 2014, 51, E34–E41. DOI: 10.1002/jhet.2012.
  • Abd EL-Rahman, N. M.; Saleh, T. S.; Mady, M. F. Ultrasound Assisted Synthesis of Some New 1,3,4-Thiadiazole and bi(1,3,4-Thiadiazole) Derivatives Incorporating Pyrazolone Moiety. Ultrason. Sonochem. 2009, 16, 70–74. DOI: 10.1016/j.ultsonch.2008.05.001.
  • Farhat, M. F.; El-Saghier, A. M. M.; Makhlouf, M. A.; Kreddan, K. M.; Elmezoughi, A. B. Ketene N,S-Acetals in Heterocyclic Synthesis: Part 1: Synthesis of N-Phenyl-2-Ylidene and 2,5-Diylidene-4-Thiazolidinone Derivatives. J. Sulfur Chem. 2007, 28, 563–572. DOI: 10.1080/17415990701586823.
  • Bondock, S.; Fadaly, W.; Metwally, M. A. Synthesis and Antimicrobial Activity of Some New Thiazole, Thiophene and Pyrazole Derivatives Containing Benzothiazole Moiety. Eur. J. Med. Chem. 2010, 45, 3692–3701. DOI: 10.1016/j.ejmech.2010.05.018.
  • Mabkhot, Y. N.; Alharbi, M. M.; Al-Showiman, S. S.; Ghabbour, H. A.; Kheder, N. A.; Soliman, S. M.; Frey, W. Stereoselective Synthesis, X-Ray Analysis, Computational Studies and Biological Evaluation of New Thiazole Derivatives as Potential Anticancer Agents. Chem. Cent. J. 2018, 12, 1–9. DOI: 10.1186/s13065-018-0420-7.
  • Abdelhamid, A. O.; Afifi, M. A. Synthesis of Some New Thiazoles and Pyrazolo[1,5-a]Pyrimidines Containing an Antipyrine Moiety. Synth. Commun. 2010, 40, 1539–1550. DOI: 10.1080/00397910903100726.
  • Bakavoli, M.; Beyzaei, H.; Rahimizadeh, M.; Eshghi, H. Regioselective Synthesis of 2-[(E)-(Benzo[d]Thiazol-2(3H)Ylidene)(Cyano)Methyl]Thiazoles. Heterocycl. Commun. 2011, 17, 151–154. DOI: 10.1515/HC.2011.031.
  • Mekky, A. E. M.; Sanad, S. M. H. Novel Bis(Pyrazole-Benzofuran) Hybrids Possessing Piperazine Linker: Synthesis of Potent Bacterial Biofilm and MurB Inhibitors. Bioorg. Chem. 2020, 102, 104094. DOI: 10.1016/j.bioorg.2020.104094.
  • Mohammad, H.; Reddy, P. N.; Monteleone, D.; Mayhoub, A. S.; Cushman, M.; Seleem, M. N. Synthesis and Antibacterial Evaluation of a Novel Series of Synthetic Phenylthiazole Compounds against Methicillin-Resistant Staphylococcus aureus (MRSA). Eur. J. Med. Chem. 2015, 94, 306–316. DOI: 10.1016/j.ejmech.2015.03.015.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.