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Chemical Compound Review

Ethenyl     ethene

Synonyms: ethylenyl, Vinyl, Vinyl radical, AC1L3VZX, AR-1L8183, ...
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Disease relevance of ethylene

  • Recombinant Escherichia coli was able to oxidize different aryl vinyl and aryl ethenyl compounds to their corresponding optically pure epoxides [1].
  • The effect of a newly synthesized leukotriene antagonist, (E)-2,2-diethyl-3'-2-2-(4-isopropyl) thiazolyl ethenyl succinanilic acid (MCI-826), on liver injury and nephritis in mice was studied [2].
  • However, subsequent steps lead not only to analogues of styrene metabolites but also to oxidation of the second ethenyl group leading to compound(s) which may contribute to the toxicity of 1, e.g. to the aldehyde 5 [3].

High impact information on ethylene


Biological context of ethylene

  • Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group [9].
  • Several compounds, which could arise from biotransformation of both ethenyl groups in the molecule of 1, were detected but not identified unequivocally [10].
  • The corresponding ethenyl derivatives 8a and 8b and ethyl derivatives 9a and 9b were prepared by catalytic hydrogenation of 7a and 7b, respectively [11].
  • In the present study we synthesized aza-analogs of 8-styrylxanthines, in which the ethenyl bridge is replaced by an imine, amide, or azo function, in order to investigate structure-activity relationships of the 8-substituent of A2A-selective xanthine derivatives [12].

Associations of ethylene with other chemical compounds

  • The redox wave splitting mediated by dppa containing an ethynyl group (C triple bond C) is found to be more extensive than that by dppen containing an ethenyl (C=C) one [13].
  • Five days after planting, the plants were treated against the root fly by pouring onto soil around the plant stem an emulsion of chlorfenvinphos [2-chloro-1-(2,4-dichlorophenyl) ethenyl diethyl phosphate] in water [14].
  • The intramolecular cyclization reaction of ethyl 2-ethynylphenylcarbamates, which have an ethenyl part in the ethynyl group, was also used to produce carbazole derivatives [15].
  • We also found that introduction of an ethyl group to the 1-position of the ethenyl group in 1a gave the ET(A) selective antagonist (6u) with an oral endothelin antagonistic activity in rats [16].
  • The vinyl radical and the allyl radical are formed promptly from the 193 nm photolysis of their respective trichlorosilane precursors [17].
  • Bis(trimethylsilyl)chloromethane undergoes a rapid and selective metalation with s-BuLi, yielding the nucleophilic bis(trimethylsilyl)methyl anion and providing a straightforward general entry to vinyl silanes from aromatic, aliphatic and vinyl aldehydes [18].

Gene context of ethylene

  • However, a classical vinyl radical-like lies only 2-4 kcal/mol higher [19].
  • Novel C-2 substituted carbapenem derivatives. Part III. Synthesis and biological activity of 2-(functionalised ethenyl, oxyiminomethyl and alpha-[hydroxy]benzyl)-carbapenems [20].
  • Further studies on ethenyl and ethynyl-4-phenylamino-3-quinolinecarbonitriles: identification of a subnanomolar Src kinase inhibitor [21].
  • C-2 Ethenyl carbapenems showed moderate antibacterial activity but poor stability to DHP-1, C-2 Oxyiminomethyl carbapenems demonstrated variable activity and stability C-2 alpha-(Hydroxy)benzyl carbapenems were the most promising and showed good potency and DHP-1 stability [20].
  • The analysis of the individual group contributions (aij) shows the importance of the presence of an ethenyl moiety at position 8 on the xanthine ring for obtaining selective A2a antagonists [22].

Analytical, diagnostic and therapeutic context of ethylene


  1. A new biocatalyst for production of optically pure aryl epoxides by styrene monooxygenase from Pseudomonas fluorescens ST. Di Gennaro, P., Colmegna, A., Galli, E., Sello, G., Pelizzoni, F., Bestetti, G. Appl. Environ. Microbiol. (1999) [Pubmed]
  2. Effect of a newly synthesized leukotriene antagonist, (E)-2,2-diethyl-3'-2-2-(4-isopropyl) thiazolyl ethenyl succinanilic acid (MCI-826), on immunological liver injury and nephritis in mice. Nagai, H., Kitagaki, K., Miura, T., Shimazawa, T., Koda, A. Prostaglandins Leukot. Essent. Fatty Acids (1992) [Pubmed]
  3. Biotransformation of diethenylbenzenes. I. Identification of the main urinary metabolites of 1,4-diethenylbenzene in the rat. Linhart, I., Hanus, V., Novák, J., Smejkal, J., Pech, P. Xenobiotica (1989) [Pubmed]
  4. Cardiotonic agents. 9. Synthesis and biological evaluation of a series of (E)-4,5-dihydro-6-[2-[4-(1H-imidazol-1-yl)phenyl]ethenyl]-3 (2H)-pyridazinones: a novel class of compounds with positive inotropic, antithrombotic, and vasodilatory activities for the treatment of congestive heart failure. Sircar, I., Steffen, R.P., Bobowski, G., Burke, S.E., Newton, R.S., Weishaar, R.E., Bristol, J.A., Evans, D.B. J. Med. Chem. (1989) [Pubmed]
  5. A study of vinyl radical cyclization using N-alkenyl-7-bromo-substituted hexahydroindolinones. Padwa, A., Rashatasakhon, P., Ozdemir, A.D., Willis, J. J. Org. Chem. (2005) [Pubmed]
  6. Free radical-mediated vinyl amination: access to N,N-dialkyl enamines and their beta-stannyl and beta-thio derivatives. Prabhakaran, E.N., Nugent, B.M., Williams, A.L., Nailor, K.E., Johnston, J.N. Org. Lett. (2002) [Pubmed]
  7. Theoretical study on the reaction mechanism of vinyl radical with formaldehyde. Xie, H.B., Ding, Y.H., Sun, C.C. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
  8. The vinyl + NO reaction: determining the products with time-resolved Fourier transform spectroscopy. Zou, P., Klippenstein, S.J., Osborn, D.L. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
  9. Application of peptidyl radicals into a new radical cascade leading to unsaturated gamma-lactams. Andrukiewicz, R., Loska, R., Prisyahnyuk, V., Staliński, K. J. Org. Chem. (2003) [Pubmed]
  10. Biotransformation of diethenylbenzenes, V. Identification of urinary metabolites of 1,2-diethenylbenzene in the rat. Linhart, I., Weidenhoffer, Z., Sedmera, P., Polásekj, M., Smejkal, J. Xenobiotica (1996) [Pubmed]
  11. New neplanocin analogues. VIII. Synthesis and biological activity of 6'-C-ethyl, -ethenyl, and -ethynyl derivatives of neplanocin A. Shuto, S., Obara, T., Saito, Y., Yamashita, K., Tanaka, M., Sasaki, T., Andrei, G., Snoeck, R., Neyts, J., Padalko, E., Balzarini, J., De Clercq, E., Matsuda, A. Chem. Pharm. Bull. (1997) [Pubmed]
  12. Aza-analogs of 8-styrylxanthines as A2A-adenosine receptor antagonists. Müller, C.E., Sauer, R., Geis, U., Frobenius, W., Talik, P., Pawlowski, M. Arch. Pharm. (Weinheim) (1997) [Pubmed]
  13. Syntheses, structures, and redox properties of dimeric triruthenium clusters bridged by bis(diphenylphosphino)acetylene and -ethylene. Chen, J.L., Zhang, L.Y., Chen, Z.N., Gao, L.B., Abe, M., Sasaki, Y. Inorganic chemistry. (2004) [Pubmed]
  14. Influence of cow manure and composts on the effects of chlorfenvinphos on field crops. Rouchaud, J., Gustin, F., Benoit, F., Ceustermans, N., Gillet, J., Van de Steene, F., Pelerents, C. Arch. Environ. Contam. Toxicol. (1992) [Pubmed]
  15. Synthesis of 2,3-disubstituted indole using palladium(II)-catalyzed cyclization with alkenylation reaction. Yasuhara, A., Takeda, Y., Suzuki, N., Sakamoto, T. Chem. Pharm. Bull. (2002) [Pubmed]
  16. Synthesis and structure-activity relationships in a series of ethenesulfonamide derivatives, a novel class of endothelin receptor antagonists. Harada, H., Kazami, J., Watanuki, S., Tsuzuki, R., Sudoh, K., Fujimori, A., Tokunaga, T., Tanaka, A., Tsukamoto, S., Yanagisawa, I. Chem. Pharm. Bull. (2001) [Pubmed]
  17. Ultraviolet photochemistry of trichlorovinylsilane and allyltrichlorosilane: vinyl radical (HCCH2) and allyl radical (H2CCHCH2) production in 193 nm photolysis. DeSain, J.D., Jusinski, L.E., Taatjes, C.A. Physical chemistry chemical physics : PCCP. (2006) [Pubmed]
  18. Rapid and efficient entry to vinyl silanes from aldehydes employing a novel metalation-Peterson sequence. McNulty, J., Das, P. Chem. Commun. (Camb.) (2008) [Pubmed]
  19. Binuclear homoleptic copper carbonyls Cu(2)(CO)(x) (x = 1-6): remarkable structures contrasting metal-metal multiple bonding with low-dimensional copper bonding manifolds. Li, Q., Liu, Y., Xie, Y., King, R.B., Schaefer, H.F. Inorganic chemistry. (2001) [Pubmed]
  20. Novel C-2 substituted carbapenem derivatives. Part III. Synthesis and biological activity of 2-(functionalised ethenyl, oxyiminomethyl and alpha-[hydroxy]benzyl)-carbapenems. Clear, N.J., Davies, J.S., Eglington, A.J., Fell, S.C., Hinks, J.D., Hird, N.W., Hunt, E., Moss, S.F., Pearson, M.J. J. Antibiot. (1997) [Pubmed]
  21. Further studies on ethenyl and ethynyl-4-phenylamino-3-quinolinecarbonitriles: identification of a subnanomolar Src kinase inhibitor. Barrios Sosa, A.C., Boschelli, D.H., Wu, B., Wang, Y., Golas, J.M. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  22. De novo analysis of receptor binding affinity data of 8-ethenyl-xanthine antagonists to adenosine A1 and A2a receptors. Dalpiaz, A., Gessi, S., Varani, K., Borea, P.A. Arzneimittel-Forschung. (1997) [Pubmed]
  23. Identification of a plasma metabolite of 5-(2-bromo-E-ethenyl)-2'-deoxyuridine. Robinson, Y., Gerry, N., Brownsill, R.D., Vose, C.W. Biomed. Mass Spectrom. (1984) [Pubmed]
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