Synthesis, identification and antimicrobial activity of substituted thiazolines and 1,3,4-thiadiazines from dehydroacetic acid

References

• Ghannoum, M. A. Candida: A Causative Agent of an Emerging Infection. J. Investig. Dermatol. Symp. Proc. 2001, 6, 188–196. DOI: 10.1046/j.0022-202x.2001.00047.x.
   PubMedGoogle Scholar
• Chate, A. V.; Tathe, A. G.; Nagtilak, P. J.; Sangle, S. M.; Gill, C. H. Efficient Approach to Thiazolidinones via an One‐Pot Three‐Component Reaction Involving 2‐Amino‐1‐Phenylethanone Hydrochloride, Aldehyde and Mercaptoacetic Acid. Chinese J. Catal. 2016, 37, 1997–2002. DOI: 10.1016/S1872-2067(16)62536-6.
   Web of Science ®Google Scholar
• Zhou, W.; Ni, S.; Mei, H.; Han, J.; Pan, Y. Cyclization Reaction of N-Allylbenzothioamide for Direct Construction of Thiazole and Thiazoline. Tetrahedron Lett. 2015, 56, 4128–4130. DOI: 10.1016/j.tetlet.2015.05.047.
   Web of Science ®Google Scholar
• Altıntop, M. D.; Kaplancıklı, Z. A.; Çiftçi, G. A.; Demirel, R. R. Synthesis and Biological Evaluation of Thiazoline Derivatives as New Antimicrobial and Anticancer Agents. Eur. J. Med. Chem. 2014, 74, 264–277. DOI: 10.1016/j.ejmech.2013.12.060.
   PubMed Web of Science ®Google Scholar
• Parker, P. D.; Ge, Y.; Pierce, J. G. Coupling of Thioamides with 4-Bromocrotonate Esters and Subsequent Conjugate Addition for the Rapid One-Pot Synthesis of Functionalized Thiazolines. Tetrahedron Lett. 2018, 59, 277–279. DOI: 10.1016/j.tetlet.2017.12.043.
   Web of Science ®Google Scholar
• Bae, S.; Hahn, H. G.; Nam, K. D.; Mah, H. Solid-Phase Synthesis of Fungitoxic 2-Imino-1,3-Thiazolines. J. Comb. Chem. 2005, 7, 7–9. DOI: 10.1021/cc049854w.
   PubMedGoogle Scholar
• Aridoss, G.; Amirthaganesan, S.; Kim, M. S.; Kim, J. T.; Jeong, Y. T. Synthesis, Spectral and Biological Evaluation of Some New Thiazolidinones and Thiazoles Based on t-3-Alkyl-r-2,c-6-Diarylpiperidin-4-Ones. Eur. J. Med. Chem. 2009, 44, 4199–4210. DOI: 10.1016/j.ejmech.2009.05.015.
   PubMed Web of Science ®Google Scholar
• Hargrave, K. D.; Hess, F. K.; Oliver, J. T. N-(4-Substituted-Thiazolyl) Oxamic Acid Derivatives, a New Series of Potent, Orally Active Antiallergy Agents. J. Med. Chem. 1983, 26, 1158–1163. DOI: 10.1021/jm00362a014.
   PubMed Web of Science ®Google Scholar
• Tsuji, K.; Ishikawa, H. Synthesis and anti-Pseudomonal Activity of New 2-Isocephems with a Dihydroxypyridone Moiety at C-7. Bioorg. Med. Chem. Lett. 1994, 4, 1601–1606. DOI: 10.1016/S0960-894X(01)80574-6.
   Web of Science ®Google Scholar
• Elliott, G. T.; Nagle, W. A.; Kelly, K. F.; McCollough, D.; Bona, R. L.; Burns, E. R. In Vitro Antiproliferative Activity of 4′ Substituted 2′-(2-Hydroxyphenyl)-2′-Thiazolines on Murineleukemia Cells. J. Med. Chem. 1989, 32, 1039–1043. DOI: 10.1021/jm00125a018.
   PubMed Web of Science ®Google Scholar
• Hutchinson, I.; Jennings, S. A.; Vishnuvajjala, B. R.; Westwell, A. D.; Stevens, M. F. G. Antitumour Benzothiazoles. Synthesis and Pharmaceutical Properties of Antitumour 2-(4-Aminophenyl) Benzothiazole Amino Acid Prodrugs. J. Med. Chem. 2002, 45, 744–747. DOI: 10.1021/jm011025r.
   PubMed Web of Science ®Google Scholar
• White, J. D.; Kim, T.-S.; Nambu, M. Synthesis of Curacin A: A Powerful Antimitotic from the Cyanobacterium Lyngbya Majuscule. J. am. Chem. Soc. 1995, 117, 5612–5613. DOI: 10.1021/ja00125a034.
   Web of Science ®Google Scholar
• Lai, J.-H.; Yu, J.; Mekonnen, B.; Falck, J. R. Synthesis of Curacin A, an Antimiotic Cyclopropane-Thiazoline from the Marine Cyanobacterium Lyngbya Majuscule. Tetrahedron Lett. 1996, 37, 7167–7170. DOI: 10.1016/0040-4039(96)01616-4.
   Web of Science ®Google Scholar
• Saeed, A.; Mahmood, S. U.; Rafiq, M.; Ashraf, Z.; Jabeen, F.; Seo, S. Y. Iminothiazoline-Sulfonamide Hybrids as Jack Bean Urease Inhibitors; Synthesis, Kinetic Mechanism and Computational Molecular Modeling. Chem. Biol. Drug Des. 2016, 87, 434–443. DOI: 10.1111/cbdd.12675.
   PubMed Web of Science ®Google Scholar
• Sondhi, S. M.; Singh, N.; Lahoti, A. M.; Bajaj, K.; Kumar, A.; Lozach, O.; Meijer, L. Synthesis of Acridinyl-Thiazolino Derivatives and Their Evaluation for anti-Inflammatory, Analgesic and Kinase Inhibition Activities. Bioorg. Med. Chem. 2005, 13, 4291–4299. DOI: 10.1016/j.bmc.2005.04.017.
   PubMed Web of Science ®Google Scholar
• Kim, D. S.; Jeong, Y. M.; Park, I. K.; Hahn, H. G.; Lee, H. K.; Kwon, S. B.; Jeong, J. H.; Yang, S. J.; Sohn, U. D.; Park, K. C. A New 2-Imino-1, 3-Thiazoline Derivative, KHG22394, Inhibits Melanin Synthesis in Mouse B16 Melanoma Cells. Biol. Pharm. Bull. 2007, 30, 180–183. DOI: 10.1248/bpb.30.180.
   PubMed Web of Science ®Google Scholar
• Kazmi, M.; Zaib, S.; Amjad, S. T.; Khan, I.; Ibrar, A.; Saeed, A.; Iqbal, J. Exploration of Aroyl/Heteroaroyl Iminothiazolines Featuring 2,4,5- Trichlorophenyl Moiety as a New Class of Potent, Selective and in Vitro Efficacious Glucosidase Inhibitors. Bioorg. Chem. 2017, 74, 134–144. DOI: 10.1016/j.bioorg.2017.07.012.
   PubMed Web of Science ®Google Scholar
• Betz, A.; Yu, L.; Reiher, M.; Gaumont, A.-C.; Jaffrès, P.-A.; Gulea, M. (N, N) versus (N, S) Chelation of Palladium in Asymmetric Allylic Substitution Using Bis (Thiazoline) Ligands; a Theoretical and Experimental Study. J. Organ. Met. Chem. 2008, 693, 2499–2508. DOI: 10.1016/j.jorganchem.2008.04.044.
   Web of Science ®Google Scholar
• Reddy, G. R.; Thompson, W. C.; Miller, S. C. Robust Light Emission from Cyclic Alkylaminoluciferin Substrates for Firefly Luciferase. J. Am. Chem. Soc. 2010, 132, 13586–13587. DOI: 10.1021/ja104525m.
   PubMed Web of Science ®Google Scholar
• Sun, Y.-Q.; Liu, J.; Wang, P.; Zhang, J.; Guo, W. Analogues: A Multicolor Toolbox for Bioluminescence Imaging. Angew. Chem. Int. Ed. 2012, 51, 8428–8430. DOI: 10.1002/anie.201203565.
   PubMed Web of Science ®Google Scholar
• Karabasanagouda, T.; Adhikari, A. V.; Ramgopal, D.; Parameshwarappa, G. Synthesis of Some New 2-(4-Alkylthiophenoxy)-4-Substituted-1, 3-Thiazoles as Possible anti-Inflammatory and Antimicrobial Agents. Ind. J. Chem. 2008, 47, 144–152.
   Google Scholar
• Amir, M.; Kumar, H.; Khan, S. A. Synthesis and Pharmacological Evaluation of Pyrazoline Derivatives as New anti-Inflammatory and Analgesic Agents. Bioorg. Med. Chem. Lett. 2008, 18, 918–922. DOI: 10.1016/j.bmcl.2007.12.043.
   PubMed Web of Science ®Google Scholar
• Nassar, E. Synthesis, (In Vitro) Antitumor and Antimicrobial Activity of Some Pyrazoline, Pyridine and Pyrimidine Derivatives Linked to Indole Moiety. J. Am. Sci. 2010, 6, 463–471.
   Google Scholar
• Sokolenko, T. M.; Davydova, Y. A.; Yagupolskii, Y. L. Efficient Synthesis of 5’-Fluoroalkoxy Thiazoles via- Bromo- Fluoroalkoxy Acetophenones Hantzsch Type Cyclization with Thioureas or Thioamides. J. Fluorine Chem. 2012, 136, 20–25. DOI: 10.1002/chin.201233145.
   Web of Science ®Google Scholar
• Singh, S. P.; Tarar, L. S.; Kumar, D. A Facile Route for the Synthesis 1-[5-Hydroxy-3-Methyl-1-(2-Thiazolyl)-4-Pyrazolyl]-1,3-Butanediones from Dehydroacetic Acid. Synth. Commun. 1993, 23, 1855–1861. DOI: 10.1080/00397919308011286.
   Web of Science ®Google Scholar
• Bikobo, D. S. N.; Vodnar, D. C.; Stana, A.; Tiperciuc, B.; Nastasă, C.; Douchet, M.; Oniga, O. Synthesis of 2-Phenylamino-Thiazole Derivatives as Antimicrobial Agents. J. Saudi. Chem. Soc. 2017, 21, 861–868. DOI: 10.1016/j.jscs.2017.04.007.
   Web of Science ®Google Scholar
• Srinivasan, S.; Girija, R. Microwave Assisted Synthesis, Characterization and Biological Studies on 1, 3, 4-Thiadiazinan-5-One Derivatives. Int. J. Mod. Sci. Technol. 2016, 1, 121–128.
   Google Scholar
• Gökşen, U. S.; Kelekçi, N. G.; Göktaş, Ö.; Köysal, Y.; Kılıçn, E.; Işık, Ş.; Aktay, G.; Özalp, M. 1-Acylthiosemicarbazides, 1,2,4-Triazole-5 (4H)-Thiones, 1,3,4-Thiadiazoles and Hydrazones Containing 5-Methyl-2-Benzoxazolinones: Synthesis, Analgesic-anti Inflammatory and Antimicrobial Activities. Bioorg. Med. Chem. 2007, 15, 5738–5751. DOI: 10.1016/j.bmc.2007.06.006.
   PubMed Web of Science ®Google Scholar
• Sahin, G.; Palaska, E.; Kelicen, P.; Demirdamar, R.; Altinok, G. Synthesis of Some New 1-Acylthio-Semicarbazides, 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles and 1,2,4-Triazole-3-Thiones and Their anti-Inflammatory Activities. Arzneim. Forsch, Drug Res. 2001, 51, 478–484. DOI: 10.1055/s-0031-1300066.
   PubMed Web of Science ®Google Scholar
• Palaska, E.; Sahin, G.; Kelicen, P.; Durlu, N. T.; Altinok, G. Synthesis and Anti-Inflammatory Activity of 1-Acylthiosemicarbazides, 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles and 1,2,4-Triazole-3-Thiones. Farmaco 2002, 57, 101–107. DOI: 10.1016/S0014-827X(01)01176-4.
   PubMedGoogle Scholar
• Mullican, M. D.; Wilson, M. W.; Conner, D. T.; Kostlan, C. R.; Schrier, D. J.; Dyer, R. D. Design of 5-(3,5-di-Tert-Butyl-4-Hydroxyphenyl)-1,3,4-Thiadiazoles, -1,3,4-Oxadiazoles and -1,2,4-Triazoles as Orally-Active, Nonulcerogenic anti Inflammatory Agents. J. Med. Chem. 1993, 36, 1090–1099. DOI: 10.1021/jm00060a017.
   PubMed Web of Science ®Google Scholar
• Collins, C. H.; Lyne, P. M.; Grange, J. M.; Falkinham, J. O. Collins and Lyne’s Microbiological Methods; Arnold Publishers: Butterworth, London, 1970.
   Google Scholar
• Moghimi, S.; Shiri, M.; Heravi, M. M.; Kruger, H. G. A Novel and Easy Route to 1,3,4-Thiadiazine Derivatives via the Three-Component Reaction of Phenylhydrazine, α-Bromo Aryl Ketones and Aryl Isothiocyanates. Tetrahedron Lett. 2013, 54, 6215–6217. DOI: 10.1016/j.tetlet.2013.09.008.
   Web of Science ®Google Scholar
• (a) Stoltefuss, J, Braunlich, G.; Logers, M.; Schmeck, C.; Nielsch, U.; Bechem, M.; Gerdes, C.; Sperzel, M.; Lustig, K.; Strumer, W. PCT Int. Appl. WO 2001188, 2001. Chem. Abstr. 2001, 134, 91128.
   Google Scholar
  (b) Jonas, R.; Wolf, M.; Beier, N. Ger. Patent 19604388, 1997. Chem. Abstr. 1997, 127, 220677.
   Google Scholar
• (a) Campaigne, E. E.; Selby, T. U. S. Patent 4254259, 1981. Chem. Abstr. 1981, 95, 25150.
   Google Scholar
  (b) Zenno, H.; Sugihara, H.; Ito, M. Jpn. Patent 8033, 1967. Chem. Abstr. 1967, 67, 54173k.
   Google Scholar
  (c) Dekeyser, M. A.; McDonald, P. T. Pesticidal Thiadiazines. PCT Int. Appl. WO Patent 9838181, 1998. Chem. Abstr. 1998, 129, 216630.
   Google Scholar
• Kudelko, A. Reactions of α-Mercaptocarboxylic Acid Hydrazides with Triethyl Orthoesters: synthesis of 1,3,4-Thiadiazin-5(6H)-Ones and 1,3,4-Oxadiazoles. Tetrahedron 2012, 68, 3616–3625. DOI: 10.1016/j.tet.2012.02.071.
   Web of Science ®Google Scholar
• Nechak, R.; Bouzroura, S. A.; Benmalek, Y.; Salhi, L.; Martini, S. P.; Morizur, V.; Dunach, E.; Kolli, B. N. Synthesis and Antimicrobial Evaluation of Novel 4-Thiazolidinones Containing a Pyrone Moiety. Synth. Commun. 2015, 45, 262–272. DOI: 10.1080/00397911.2014.970278.
   Web of Science ®Google Scholar
• NCCLS, Performance standards for antimicrobial susceptibility testing. Twelfth informational supplement. NCCLS document M100-S12, Wayne, PA, 2012.
   Google Scholar
• Krasowska, M.; Kochel, A.; Filarowski, A. The Conformational Analysis of 2-Hydroxyaryl Schiff Thiosemicarbazones. Cryst. Eng. Comm. 2010, 12, 1955–1962. DOI: 10.1039/b921402j.
   Google Scholar