3,4-Dichloro-1,2,5-thiadiazole: a commercially available electrophilic sulfur transfer agent and safe resource of ethanedinitrile

References

• Steudel R. The chemistry of organic polysulfanes R-S(n)-R (n > 2). Chem Rev. 2002;102(11):3905–3945. doi:https://doi.org/10.1021/cr010127m
   PubMed Web of Science ®Google Scholar
• Block E. The organosulfur chemistry of the genus allium–Implications for the organic chemistry of sulfur. Angew Chem, Int Ed Engl. 1992;31:1135–1178. doi:https://doi.org/10.1002/anie.199211351
   Web of Science ®Google Scholar
• Wijaya CH, Nishimura H, Tanaka T, et al. Influence of drying methods on volatile sulfur constituents of caucas (Allium victorialis L.). J Food Sci. 1991;56:72–75. doi:https://doi.org/10.1111/j.1365-2621.1991.tb07978.x
   Web of Science ®Google Scholar
• Casnati G, Ricca A, Pavan M. Sulla secrezione defensiva delle glandole mandibolariPaltothyreus tarsatus (Fabr.). Chem Ind (Milan). 1967;49:57–61. .
   Google Scholar
• Miller A, Scalan RA, Lee JS, et al. Volatile compounds produced in sterile fish muscle (sebastes melanops) by Pseudomonas putrefaciens, Pseudomonas fluorescens, and an achromobacter species. Appl Microbiol. 1973;26:18–21. doi:https://doi.org/10.1128/am.26.1.18-21.1973
   PubMedGoogle Scholar
• Yasuhara A, Fuwa K. Odor and volatile compounds in liquid swine manure. II steam-distillable substances. Bull Chem Soc Jpn. 1977;50:3029–3032. doi:https://doi.org/10.1246/bcsj.50.3029
   Web of Science ®Google Scholar
• Nielsen RW, Tachibana C, Hansen NE, et al. Trisulfides in proteins. Antioxid Redox Signal. 2011;15:67–75. doi:https://doi.org/10.1089/ars.2010.3677.
   PubMed Web of Science ®Google Scholar
• Nicolau KC, Hummel CW, Nakada M, et al. Total synthesis of calicheamicin gamma.1I. 3. The final stages. J Am Chem Soc. 1993;115:7625–7635. doi:https://doi.org/10.1021/ja00070a006.
   Web of Science ®Google Scholar
• Nicolau KC, Dai WM. Chemistry and biology of the enediyne anticancer antibiotics. Angew Chem, Int Ed Engl. 1991;30:1387–1416. doi:https://doi.org/10.1002/anie.199113873
   Web of Science ®Google Scholar
• Kohama Y, Lida K, Itoh S, et al. Increase of cytochrome b mRNA by bis(2-hydroxyethyl) trisulfide in J774A.1 cells. Biol Pharm Bull. 1996;19:876–878. doi:https://doi.org/10.1248/bpb.19.876.
   PubMed Web of Science ®Google Scholar
• Katrizky AR, Zhao X, Hitchings GJ. The synthesis of bis(N,N-disubstituted amino) trisulphides. Synlett. 1990: 473–476. doi:https://doi.org/10.1055/s-1990-21132.
   Google Scholar
• Wu M, Cui Y, Bhargav A, et al. Organotrisulfide: A high capacity cathode material for rechargeable lithium batteries. Angew Chem Int Ed. 2016;55:10027–10031. doi:https://doi.org/10.1002/anie.201603897.
   PubMed Web of Science ®Google Scholar
• Kuo WW, Wang WJ, Tsai CY, et al. Diallyl trisulfide (DATS) suppresses high glucose-induced cardiomyocyte apoptosis by inhibiting JNK/NFκB signaling via attenuating ROS generation. Int J Cardiol. 2013;168:270–280. doi:https://doi.org/10.1016/j.ijcard.2012.09.080.
   PubMed Web of Science ®Google Scholar
• Munday R. Harmful and beneficial effects of organic monosulfides, disulfides, and polysulfides in animals and humans. Chem Res Toxicol. 2012;25:47–60. doi:https://doi.org/10.1021/tx200373u.
   PubMed Web of Science ®Google Scholar
• Zhu SJ, Ying HZ, Wu Y, et al. Design, synthesis and biological evaluation of novel podophyllotoxin derivatives bearing 4β-disulfide/trisulfide bond as cytotoxic agents. RSC Adv. 2015;5:103172–103183. doi:https://doi.org/10.1039/C5RA12837D.
   Google Scholar
• Kiesel AV, Stan SD. Diallyl trisulfide, a chemopreventive agent from allium vegetables, inhibits alpha-secretases in breast cancer cells. Biochem Biophys Res Commun. 2017;484:833–838. doi:https://doi.org/10.1016/j.bbrc.2017.01.184.
   PubMed Web of Science ®Google Scholar
• Xu W, Xi B, Wu J, et al. Natural product derivative bis(4-fluorobenzyl)trisulfide inhibits tumor growth by modification of β-tubulin at Cys 12 and suppression of microtubule dynamics. Mol Cancer Ther. 2009;8:3318–3330. doi:https://doi.org/10.1158/1535-7163.MCT-09-0548.
   PubMed Web of Science ®Google Scholar
• Wu T, Huang Y, Chen Y, et al. Antibacterial effect of (2E,2E)-4,4-trisulfanediylbis(but-2-enoic acid) against staphylococcus aureus. PLoS One. 2018;13:e0197f348. doi:https://doi.org/10.1371/journal.pone.0197348.
   Web of Science ®Google Scholar
• Yang Y, Sun B, Zuo S, et al. Trisulfide bond–mediated doxorubicin dimeric prodrug nanoassemblies with high drug loading, high self-assembly stability, and high tumor selectivity. Sci Adv. 2020;6:eabc1725), doi:https://doi.org/10.1126/sciadv.abc1725.
   PubMed Web of Science ®Google Scholar
• Pluth MD, Bailey TS, Hammers MD, et al. Natural products containing hydrogen sulfide releasing moieties. Synlett. 2015: 2633–2643. doi:https://doi.org/10.1055/s-0035-1560638.
   Google Scholar
• Bhattacherjee D, Sufian A, Mahato SK, et al. Trisulfides over disulfides: highly selective synthetic strategies, anti-proliferative activities and sustained H2S release profiles. Chem Commun. 2019;55:13534–13537. doi:https://doi.org/10.1039/c9cc05562b.
   PubMed Web of Science ®Google Scholar
• Ong CL, Khaligh NG, Juan JC. Recent catalytic advances in the synthesis of organic symmetric disulfides. Curr Org Chem. 2020;24:550–581. doi:https://doi.org/10.2174/1385272824666200221111120.
   Web of Science ®Google Scholar
• Vineyard BD. Mercaptan—Sulfur reaction. Alkyl Trisulfides. J Org Chem. 1966;31:601–602. doi:https://doi.org/10.1021/jo01340a511.
   Web of Science ®Google Scholar
• Zysman-Colman E, Harpp DN. Optimization of the synthesis of symmetric aromatic tri- and tetrasulfides. J Org Chem. 2003;68:2487–2489. doi:https://doi.org/10.1021/jo0265481
   PubMed Web of Science ®Google Scholar
• Banerji A, Kalena GP. A new synthesis of organic trisulfides. Tetrahedron Lett. 1980;21:3003–3004. doi:https://doi.org/10.1016/0040-4039(80)88021-X.
   Web of Science ®Google Scholar
• Harpp DN, Steliou K, Chan TH. Organic sulfur chemistry. 26. Synthesis and reactions of some new sulfur transfer reagents. J Am Chem Soc. 1978;100:1222–1228. doi:https://doi.org/10.1021/ja00472a032
   Web of Science ®Google Scholar
• Derbesy G, Harpp DN. A simple method to prepare unsymmetrical di-, tri- and tetrasulfides. Tetrahedron Lett. 1994;35:5381–5384. doi:https://doi.org/10.1016/S0040-4039(00)73505-2.
   Web of Science ®Google Scholar
• Ali D, Hunter R, Kaschula CH, et al. Unsymmetrical organotrisulfide formation via low-temperature disulfanyl anion transfer to an organothiosulfonate. J Org Chem. 2019;84:2862–2869. doi:https://doi.org/10.1021/acs.joc.8b03262.
   PubMed Web of Science ®Google Scholar
• Soleiman-Beigi M, Mohammadi F. Simple and Green method for synthesis of symmetrical dialkyl disulfides and trisulfides from alkyl halides in water; PMOxT as a sulfur donor. J Sulfur Chem. 2017;38:134–141. doi:https://doi.org/10.1080/17415993.2016.1253696.
   Web of Science ®Google Scholar
• Kertmen A, Lach S, Rachon J, et al. Novel and efficient methods for the synthesis of symmetrical trisulfides. Synthesis. 2009;9:1459–1462. doi:https://doi.org/10.1055/s-0028-1088161.
   Google Scholar
• Lach S, Witt D. Efficient synthesis of functionalized unsymmetrical dialkyl trisulfanes. Synlett. 2013;24:1927–1930. doi:https://doi.org/10.1055/s-0033-1338966
   Web of Science ®Google Scholar
• Xu S, Wang Y, Radford MN, et al. Synthesis of unsymmetric trisulfides from 9-fluorenylmethyl disulfides. Org Lett. 2018;20:465–468. doi:https://doi.org/10.1021/acs.orglett.7b03846.
   PubMed Web of Science ®Google Scholar
• Guillanton GL. Electrochemical activation of sulfur in organic solvents—new syntheses of thioorganic compounds with a sacrificial carbon-sulfur electrode. Sulfur Rep. 1992;12:405–431. doi:https://doi.org/10.1080/01961779208048949.
   Google Scholar
• Berberova NT, Smolyaninov IV, Shinkar EV, et al. Electrosynthesis of biologically active dicycloalkyl di- and trisulfides involving an H2S-S8 redox system. Russ Chem Bull. 2018;67:108–113. doi:https://doi.org/10.1007/s11172-018-2044-4.
   Web of Science ®Google Scholar
• Berberova NT, Smolyaninov IV, Shinkar EV, et al. Electrosynthesis of polysulfides R2Sn (n = 2–4) based on cycloalkanes and S8 via bromide-mediated oxidation of H2S. Int J Electrochem Sci. 2019;14:531–541. doi:https://doi.org/10.20964/2019.01.15.
   Web of Science ®Google Scholar
• Hou Y, Abu-Yousef IA, Doung Y, et al. Sulfur-atom insertion into the S–S bond—formation of symmetric trisulfides. Tetrahedron Lett. 2001;42:8607–8610. doi:https://doi.org/10.1016/S0040-4039(01)01897-4
   Web of Science ®Google Scholar
• Vorlander D, Mittag E. Über Triphenyl-thiocarbinol. Chem Ber. 1913;46:3450–3460.
   Google Scholar
• Ren YL, Sarwar M, Wright EJ. Development of cyanogen for soil fumigation. Ann Int Res Conf MB Alt Em Red. 2002;63:1–4.
   Google Scholar
• Lee BH, Park CG, Ren YJ. Evaluation of different applications of ethanedinitrile (C2N2) in various fumigation chambers for control of monochamus alternatus (Coleoptera: Cerambycidae) in naturally infested logs. J Econ Entomol. 2017;110:502–506. doi:https://doi.org/10.1093/jee/tox052
   PubMed Web of Science ®Google Scholar
• Ren YL, Lee BH, Padovan BJ. Penetration of methyl bromide, sulfuryl fluoride, ethanedinitrile and phosphine into timber blocks and the sorption rate of the fumigants. Stored Prod Res. 2011;47:63–68. doi:https://doi.org/10.1016/j.jspr.2010.04.006.
   Web of Science ®Google Scholar
• Park CG, Son JK, Lee BH, et al. Comparison of ethanedinitrile (C2N2) and metam sodium for control of bursaphelenchus xylophilus (Nematoda: Aphelenchidae) and monochamus alternatus (coleoptera: Cerambycidae) in naturally infested logs at low temperatures. J Econ Entomol. 2014;107:2055–2060. doi:https://doi.org/10.1603/EC14009
   PubMed Web of Science ®Google Scholar
• Jessup AJ, Golding JG. Qfly proof of concept for ethane dinitrile (EDN) fumigation. Sydney: Horticulture Australia Pty Ltd.; 2012.
   Google Scholar
• Lee BL, Yang JO, Beckett S, et al. Preliminary trials of the ethanedinitrile fumigation of logs for eradication of bursaphelenchus xylophilus and its vector insect Monochamus alternatus. Pest Manag Sci. 2017;73:1446–1452. doi:https://doi.org/10.1002/ps.4476.
   PubMed Web of Science ®Google Scholar
• Baotong L, Limei T, Zhonghua X. Adsorption and degradation of cyanogen in different cereals. Chin J Pestic Sci. 2015;17:735–740. doi:https://doi.org/10.3969/j.issn.1008-7303.2015.06.014.
   Google Scholar
• Ren Y, Wang Y, Barak AV, et al. Toxicity of ethanedinitrile to Anoplophora glabripennis (Coleoptera: Cerambycidae) Larvae. J Econ Entomol. 2006;99:308–312. doi:https://doi.org/10.1093/jee/99.2.308.
   PubMed Web of Science ®Google Scholar
• Hall MKD, Pranamornkith T, Adlam AR, et al. Simulated commercial fumigation of sawn timber and logs to verify the sorption and desorption model of ethanedinitrile. Plant Food Res SPTS. 2014; New Zealand B3 Programme:No. 10152. 17 pp.
   Google Scholar
• Brotherton TK, Lynn JW. The synthesis and chemistry of cyanogen. Chem Rev. 1959;59:841–883. doi:https://doi.org/10.1021/cr50029a003.
   Web of Science ®Google Scholar
• Fierce WL, Sandner WJ. A new method for the synthesis of cyanogen. Ind Eng Chem. 1961;53:985–987. doi:https://doi.org/10.1021/ie50624a024.
   Google Scholar
• Gail E, Gos S, Kulzer R, et al. Cyano compounds, inorganic. Ullmann’s Encyclopedia Ind Chem. 2011;10:701–710.
   Google Scholar
• Ong CL, Heidelberg T, Juan JC, et al. Practical and efficient recyclable oxidative system for the preparation of symmetrical disulfides under aerobic conditions. J Sulfur Chem. 2021;42:281–294. doi:https://doi.org/10.1080/17415993.2020.1856849.
   Web of Science ®Google Scholar
• Ong CL, Titinchi S, Juan JC, et al. An overview of recent advances in the synthesis of organic unsymmetrical disulfides. Helv Chim Acta. 2021;104:e2100053. doi:https://doi.org/10.1002/hlca.202100053.
   Web of Science ®Google Scholar
• Sirakawa K, Aki O, Tsujikawa T, et al. S-Alkylthioisothioureas. I. Chem Pharm Bull. 1970;18:235–242. doi:https://doi.org/10.1248/cpb.18.235.
   Web of Science ®Google Scholar
• Harpp DN, Ash DK, Smith RA. Organic sulfur chemistry. 38. Desulfurization of organic trisulfides by tris(dialkylamino)phosphines mechanistic aspects. J Org Chem. 1980;45:5155–5160. doi:https://doi.org/10.1021/jo01313a026.
   Web of Science ®Google Scholar
• Buckman JD, Field L. Organic disulfides and related substances. XX. A novel preparation of symmetrical trisulfides using thiolsulfonates. J Org Chem. 1967;32:454–457. doi:https://doi.org/10.1021/jo01288a042.
   Web of Science ®Google Scholar
• Powolny AA, Singh SV. Multitargeted prevention and therapy of cancer by diallyl trisulfide and related allium vegetable-derived organosulfur compounds. Cancer Lett. 2008;269:305–314. doi:https://doi.org/10.1016/j.canlet.2008.05.027.
   PubMed Web of Science ®Google Scholar
• Subramanian MS, Nandagopal MSG, Nordin SA, et al. Prevailing knowledge on the bioavailability and biological activities of sulphur compounds from alliums: A potential drug candidate. Molecules. 2020;25(18):4111. doi:https://doi.org/10.3390/molecules25184111.
   PubMed Web of Science ®Google Scholar
• Greenwood NN, Earnshaw A. In Chemistry of the elements. 2nd ed. Oxford, Boston: Butterworth-Heinemann; 1997; pp. 320–321.
   Google Scholar
• Merschaert A, Boquel P, Gorissen H, et al. The ring opening of 3,4-dichloro-1,2,5-thiadiazole with metal amides. A new synthesis of 3,4-disubstituted-1,2,5-thiadiazoles. Tetrahedron Lett. 2006;47:8285–8288. doi:https://doi.org/10.1016/j.tetlet.2006.09.102.
   Web of Science ®Google Scholar
• Vest RD. 3,4-dichloro-1,2,5-thiadiazole and its preparation. 1963; US3115497A.
   Google Scholar
• Weinstock LM, Davis P, Handelsman B, et al. General synthetic system for 1,2,5-thiadiazoles. J Org Chem. 1967;32:2823–2829. doi:https://doi.org/10.1021/jo01284a040.
   Web of Science ®Google Scholar